The Role (Pacific Time Hours)

As Principal, Delivery, you are accountable for meeting customer deliverables as per contractual agreements (scope and time), and internal budget. The ideal candidate will drive and guide disciplined execution through the use of consistent methodologies, processes, and strong communication skills. You will be a passionate advocate for the League product and ensure the platform is implemented on time and with high quality to meet our clients’ business needs.

In this role, you are expected to:

• Manage, lead and oversee one or more client implementations and internal company and/or team initiatives simultaneously
• Implement the project governance structure, including delivery structure, change control and processes to support risk and issue escalation, decision making and program status 
• Lead the organization and deployment of League resources for implementation, the production of deliverables, and the oversight of timelines to ensure a seamless delivery of League products to clients
• Accountable for build and maintenance of end to end integrated program plans, resource assignments, budgets and performance against targeted implementation milestones for the implementation and teams
• Serve as escalation point for risks, issues, and decisions one or more implementations simultaneously
• Maintain a deep understanding of League’s product and platform to inform key business requirements and decisions during implementations
• Lead internal teams and the client on a successful change management plan by creating deliverables based on client pain points and objectives
• Collaborate on communication plans and drive accountability for obtaining final approvals on client deliverables
• Develop and manage a high performing team by providing direction and guidance both on the job and as a career coach to Implementation team members
• Coach and develop staff to have a deep understanding of implementation delivery methodology and the League’s product and platform
• Lead key internal initiatives to drive efficiencies and best practices for implementation processes, workflows, and tools
• Accountable for implementation client satisfaction scores and referenceable implementation clients
• Partner with Customer Strategy and Member Services teams to lead a smooth client transition from implementation to ongoing operations and account management
• Collaborate with the client lead from Customer Strategy to drive a smooth client transition from the sales cycle to implementation for the client and League teams

About You:

• Minimum 10 years in healthcare management, delivery and/or consulting experience
• 10+ years of client management and/or program management required
• Prior engagement management and/or team management experience serving as the primary interface with senior client executive sponsors
• Proven track record of strong client management and customer service skills
• Strong leadership skills and a drive to make a large impact on the company and its clients
• Excellent written and oral presentation skills, with the ability to engage, inspire, build credibility and engender trust across all levels of an organization.
• Strong business and technical acumen, and executive presence, combined with deep analytical and organizational skills
• Results-oriented individual with a history of setting and attaining goals and meeting aggressive timelines
• Confident, capable, enthusiastic self-starter with minimal need for direction
• Experience at a SaaS, health-tech company, and/or start-up company highly preferred  
• Experience with project management software and tools
• Bachelor’s degree or equivalent years of experience

What We Offer

• Comprehensive Health Benefits: We prioritize your well-being with complete medical, dental, and vision coverage
• Bonus Program: Be rewarded for your contributions with our performance-based bonus program
• Employee Stock Option Program: Become an owner and share in our success through our stock option program
• Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance
• Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts
• Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year
• Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement
• Mentorship Program: Benefit from guidance and support from experienced leaders in your field

Security-related Responsibilities

• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department and team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
• Compliance with Information Security Policies

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary

League is at an inflection point. We’re executing a delivery transformation — moving from reactive implementation to an AI-native, industrialized delivery model — at the same time as we’re scaling our most strategic enterprise accounts and standing up new delivery capabilities. This VP role is a defining hire: you’ll shape how engineering operates at League for the next five years, not just manage what exists today.

You are a seasoned engineering leader who leads with AI conviction — someone who doesn't just adopt AI practices but pulls the entire engineering organization forward through them. As VP Engineering, Apps & Solutions at League, you'll set the technical vision, own end-to-end delivery across a 50+ engineer organization, and drive an AI-native engineering transformation that makes League's delivery faster, more reliable, and more predictable. You'll own executive-level relationships with League's most strategic enterprise clients and be a defining voice in how League builds software for the next five years.

In this role you will:

• Lead the AI-native engineering transformation for Apps & Solutions — drive the adoption of micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions across all engineering pods; set a target of 40%+ AI-informed delivery decisions across the portfolio and build the operating model that makes it real, not aspirational
• Build and scale a world-class engineering organization — lead 50+ engineers through multiple Directors and Engineering Managers, manage through leaders of leaders, develop the EM cohort as a performance management discipline, and build the leadership bench that sustains delivery excellence through growth and change
• Set the technical vision and engineering standards — define the architecture direction for Apps & Solutions aligned with League's business objectives and product roadmap; champion CI/CD, observability, cloud-native engineering on GCP, and test automation practices that drive measurable quality improvement across all squads
• Own executive-level customer relationships — serve as the senior engineering sponsor for League's most strategic enterprise accounts; own escalation management, delivery confidence, and the executive relationships that determine whether clients stay, expand, or churn
• Partner at the company-wide level — work alongside the CTO, CPO, and CDO to shape technology strategy, architecture decisions, and go-to-market execution for enterprise customers; own P&L accountability for engineering delivery across the Apps & Solutions portfolio
• Drive cross-functional alignment at the leadership level — work closely with the CPO, CTO, and CDO to ensure engineering decisions are tightly coupled to product roadmap commitments and delivery capacity; own the relationship between engineering velocity and commercial feasibility before commitments leave the building.

About you:

• 15+ years of progressive software engineering experience, including 8+ years in senior leadership roles managing multiple engineering teams and leaders of leaders
• Demonstrated AI conviction — you lead AI-native delivery in practice, not just in aspiration; you have hands-on experience deploying AI-assisted engineering workflows (capacity matching, automated defect classification, PR review, agentic tooling) and a track record of pulling engineering organizations forward on AI adoption
• Proven track record scaling engineering organizations of 50+ engineers and delivering complex, enterprise-grade SaaS products in a B2B or B2B2C environment; health tech or enterprise healthcare SaaS experience strongly preferred
• Deep technical fluency in cloud-native architectures (GCP preferred), microservices, and full-stack development (Go, React, mobile) — you engage credibly with engineers on architectural trade-offs without losing your strategic altitude
• Exceptional executive presence with a demonstrated ability to build trust with C-suite stakeholders and enterprise customers; track record of owning high-stakes customer relationships at the account level, not just in QBRs
• Experience working within HIPAA, PIPEDA, or equivalent regulated data environments is required at this level — you understand the compliance obligations that come with handling PHI and have built engineering practices that treat security and data governance as foundational, not afterthought
• Demonstrated experience managing delivery partners, offshore teams, or hybrid internal/external engineering models; comfort holding external teams to the same quality bar as internal engineers

Desired Outcomes 

• Developer throughput and predictability: PR throughput per developer sustained at or above industry p75, with a clear trajectory toward p90
• Developer Experience Index (DXI): measurable quarter-over-quarter improvement, with named actions and owners
• Engineering quality: defect rate below p75 benchmark, high/critical incident rate below 10 per month, incident resolution SLA attainment at 100%
• Test automation coverage: 80%+ across the portfolio with quarterly delivery milestones
• AI-informed delivery: 40%+ of engineering delivery decisions AI-assisted within 12 months
• Customer satisfaction: NPS and CSAT scores for strategic enterprise accounts trending positive

AI Fluency (Core Competency)

• Lead the Apps & Solutions org through an AI-native delivery transformation — micro-sprints, agentic capacity management, AI-informed PR review and defect classification are operational realities under your leadership, not future-state aspirations
• Champion AI tooling adoption across engineering pods (Copilot, LLM-assisted workflows, AI-driven observability) and build a team culture where AI fluency is expected at every level of the engineering org
• Use AI actively in your own strategic work — synthesizing delivery data, accelerating architectural thinking, staying ahead of market and tooling evolution
• Define and own the org's posture on responsible AI adoption at scale — what to build with, what to evaluate carefully, and where human judgment must remain primary
• Integrate AI into your daily workflow, not just occasional use
• Maintain strong ownership and judgment over AI-generated outputs

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League's secure coding practice
• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary

League is at an inflection point. We’re executing a delivery transformation — moving from reactive implementation to an AI-native, industrialized delivery model — at the same time as we’re scaling our most strategic enterprise accounts and standing up new delivery capabilities. This VP role is a defining hire: you’ll shape how engineering operates at League for the next five years, not just manage what exists today.

You are a seasoned engineering leader who leads with AI conviction — someone who doesn't just adopt AI practices but pulls the entire engineering organization forward through them. As VP Engineering, Apps & Solutions at League, you'll set the technical vision, own end-to-end delivery across a 50+ engineer organization, and drive an AI-native engineering transformation that makes League's delivery faster, more reliable, and more predictable. You'll own executive-level relationships with League's most strategic enterprise clients and be a defining voice in how League builds software for the next five years.

In this role you will:

• Lead the AI-native engineering transformation for Apps & Solutions — drive the adoption of micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions across all engineering pods; set a target of 40%+ AI-informed delivery decisions across the portfolio and build the operating model that makes it real, not aspirational
• Build and scale a world-class engineering organization — lead 50+ engineers through multiple Directors and Engineering Managers, manage through leaders of leaders, develop the EM cohort as a performance management discipline, and build the leadership bench that sustains delivery excellence through growth and change
• Set the technical vision and engineering standards — define the architecture direction for Apps & Solutions aligned with League's business objectives and product roadmap; champion CI/CD, observability, cloud-native engineering on GCP, and test automation practices that drive measurable quality improvement across all squads
• Own executive-level customer relationships — serve as the senior engineering sponsor for League's most strategic enterprise accounts; own escalation management, delivery confidence, and the executive relationships that determine whether clients stay, expand, or churn
• Partner at the company-wide level — work alongside the CTO, CPO, and CDO to shape technology strategy, architecture decisions, and go-to-market execution for enterprise customers; own P&L accountability for engineering delivery across the Apps & Solutions portfolio
• Drive cross-functional alignment at the leadership level — work closely with the CPO, CTO, and CDO to ensure engineering decisions are tightly coupled to product roadmap commitments and delivery capacity; own the relationship between engineering velocity and commercial feasibility before commitments leave the building.

About you:

• 15+ years of progressive software engineering experience, including 8+ years in senior leadership roles managing multiple engineering teams and leaders of leaders
• Demonstrated AI conviction — you lead AI-native delivery in practice, not just in aspiration; you have hands-on experience deploying AI-assisted engineering workflows (capacity matching, automated defect classification, PR review, agentic tooling) and a track record of pulling engineering organizations forward on AI adoption
• Proven track record scaling engineering organizations of 50+ engineers and delivering complex, enterprise-grade SaaS products in a B2B or B2B2C environment; health tech or enterprise healthcare SaaS experience strongly preferred
• Deep technical fluency in cloud-native architectures (GCP preferred), microservices, and full-stack development (Go, React, mobile) — you engage credibly with engineers on architectural trade-offs without losing your strategic altitude
• Exceptional executive presence with a demonstrated ability to build trust with C-suite stakeholders and enterprise customers; track record of owning high-stakes customer relationships at the account level, not just in QBRs
• Experience working within HIPAA, PIPEDA, or equivalent regulated data environments is required at this level — you understand the compliance obligations that come with handling PHI and have built engineering practices that treat security and data governance as foundational, not afterthought
• Demonstrated experience managing delivery partners, offshore teams, or hybrid internal/external engineering models; comfort holding external teams to the same quality bar as internal engineers

Desired Outcomes 

• Developer throughput and predictability: PR throughput per developer sustained at or above industry p75, with a clear trajectory toward p90
• Developer Experience Index (DXI): measurable quarter-over-quarter improvement, with named actions and owners
• Engineering quality: defect rate below p75 benchmark, high/critical incident rate below 10 per month, incident resolution SLA attainment at 100%
• Test automation coverage: 80%+ across the portfolio with quarterly delivery milestones
• AI-informed delivery: 40%+ of engineering delivery decisions AI-assisted within 12 months
• Customer satisfaction: NPS and CSAT scores for strategic enterprise accounts trending positive

AI Fluency (Core Competency)

• Lead the Apps & Solutions org through an AI-native delivery transformation — micro-sprints, agentic capacity management, AI-informed PR review and defect classification are operational realities under your leadership, not future-state aspirations
• Champion AI tooling adoption across engineering pods (Copilot, LLM-assisted workflows, AI-driven observability) and build a team culture where AI fluency is expected at every level of the engineering org
• Use AI actively in your own strategic work — synthesizing delivery data, accelerating architectural thinking, staying ahead of market and tooling evolution
• Define and own the org's posture on responsible AI adoption at scale — what to build with, what to evaluate carefully, and where human judgment must remain primary
• Integrate AI into your daily workflow, not just occasional use
• Maintain strong ownership and judgment over AI-generated outputs

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League's secure coding practice
• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary

League is seeking an AVP, Engineering to join the Apps & Solutions engineering organization — a leader who brings deep technical credibility, strong delivery instincts, and the people leadership skills to build and sustain high-performing teams. Reporting directly to the VP, Engineering (Apps & Solutions), this role is the connective tissue between technical execution and enterprise delivery: you own the architecture and quality of member-facing applications, drive implementation excellence across your squads, and show up as a trusted engineering partner to League's most strategic clients.

This is not a platform role. You will be building and leading teams that deliver directly to end members; consumer health experiences that are fast, reliable, personalized, and clinically meaningful. You bring hands-on architectural judgment, a genuine bias for delivery, and the ability to represent engineering with conviction in executive and client-facing settings.

AI fluency is a core expectation of this role, not a bonus. You lead by example; integrating AI into your own engineering workflow, driving adoption across your teams, and building the culture and practices that make AI-native delivery a daily operational reality.

Why This Role, Why Now?

League is at an inflection point — executing a delivery transformation while scaling our most strategic enterprise accounts. This AVP role is a critical hire: you'll own the engineering execution that makes our delivery commitments real.

In this role you will:

Team Scope

• Direct reports: 3–5 Engineering Managers. Indirect reports: 25–35 engineers across web, mobile, and integration squads.

Technical & Architectural Leadership

• Own the technical direction for member-facing applications — define and enforce architectural standards, patterns, and guardrails across your squads; make trade-off calls with speed, quality, and scalability in mind
• Drive architectural reviews and decisions — lead design reviews for major features and platform integrations; ensure technical choices align with League’s roadmap, client commitments, and long-term platform health
• Maintain hands-on technical credibility — engage directly with engineers on architecture, code quality, and system design; you don’t need to be in the code daily, but you must be credible when you are

Implementation & Project Delivery

• Own end-to-end delivery accountability for your squads — from project scoping and estimation through to production release and post-launch stability; delivery commitments you make are commitments you keep
• Drive delivery predictability — implement the planning, tracking, and escalation practices that give the VP and CDO clear, real-time visibility into delivery health across your portfolio
•  Build and maintain delivery metrics — track PR throughput, defect rates, test automation coverage, and incident resolution SLAs; use data to drive continuous improvement, not just reporting

Client-Facing Engineering Leadership

• Serve as a senior engineering point of contact for strategic enterprise clients — represent engineering in client escalations, technical reviews, and delivery status conversations with the credibility and presence that builds lasting trust
•  Translate complex technical realities into clear client communication — own the narrative on delivery timelines, architectural decisions, and quality trade-offs in language that resonates with non-technical executive stakeholders

Member-Facing Application Ownership

•  Lead engineering delivery for consumer health experiences — own the quality, performance, and reliability of member-facing applications across web and mobile; you understand what ‘good’ looks like from a member’s perspective, not just an engineer’s

Cross-functional Collaboration

• Partner closely with Product Management and Design to translate roadmap commitments into realistic engineering plans;  own the technical scoping and estimation that makes delivery promises credible
• • Serve as the engineering point of contact within League's CDO delivery governance model; surface risks early and resolve cross-functional blockers before they become customer issues

People Leadership & Team Development

• Own performance management with rigor — set clear expectations for every EM, deliver candid feedback on a consistent cadence, and hold yourself accountable for developing the next tier of engineering leadership at League
•  Lead the hiring process for your squads — partner with Talent on sourcing strategy, conduct calibrated interviews, and make hiring decisions that raise the bar
•  Run structured calibration and career pathing — quarterly calibrations across your EM cohort; every engineer has a clear growth path and knows where they stand
•  Build inclusive, high-trust team culture — track engagement signals and act before attrition becomes a problem

AI-Native Engineering Leadership

•  Build the practices that make AI-native delivery real — micro-sprint methodologies, AI-informed delivery decisions, and AI-assisted defect classification are things your teams actually do       
• Maintain strong ownership and judgment over AI-generated outputs — your teams use AI confidently and responsibly; you set the standard for what that looks like in a regulated healthcare environment
•  Stay ahead of AI tooling evolution — continuously evaluate new capabilities and bring the right ones to your teams with a clear point of view on adoption

About you:

• 12+ years of progressive software engineering experience, including 5+ years in engineering leadership roles managing teams and engineering managers
• Proven track record owning end-to-end delivery of complex, enterprise-grade SaaS products in a B2B or B2B2C environment
• Deep experience building and shipping member-facing or consumer-facing applications — you understand this domain and have strong instincts for what quality looks like at scale
• Health tech or enterprise healthcare SaaS experience strongly preferred; experience working within HIPAA, PIPEDA, or equivalent regulated data environments is an asset
•  Strong architectural fluency in cloud-native systems (GCP preferred), microservices, and full-stack development (Go, React, mobile — Android and/or iOS
• Actively uses AI tools in engineering and leadership workflows
• Strong executive presence; you communicate with confidence and clarity in client escalations, executive reviews, and cross-functional forums
• Clear communicator who translates technical complexity into business language for non-technical stakeholders
• Experience managing delivery partners, offshore QA or development teams, or hybrid internal/external engineering models
• Familiarity with HIPAA, PIPEDA, or equivalent regulated data environments; understanding of what compliant engineering practice looks like in a healthcare SaaS context

Desired Outcomes 

• Delivery predictability: sprint commitments met at 85%+ with real-time visibility into delivery health
• PR throughput per developer at or above industry p75; trajectory toward p90 within 12 months
• Defect rate below p75 benchmark; high/critical incident rate below 10/month; incident SLA attainment at 100%
• Test automation coverage at 80%+ within 6 months of hire
• AI-assisted delivery decisions at 30%+ within 12 months
• Every EM has a current development plan; no unmanaged performance gaps older than 60 days

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League's secure coding practice
• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary

League is seeking an AVP, Engineering to join the Apps & Solutions engineering organization — a leader who brings deep technical credibility, strong delivery instincts, and the people leadership skills to build and sustain high-performing teams. Reporting directly to the VP, Engineering (Apps & Solutions), this role is the connective tissue between technical execution and enterprise delivery: you own the architecture and quality of member-facing applications, drive implementation excellence across your squads, and show up as a trusted engineering partner to League's most strategic clients.

This is not a platform role. You will be building and leading teams that deliver directly to end members; consumer health experiences that are fast, reliable, personalized, and clinically meaningful. You bring hands-on architectural judgment, a genuine bias for delivery, and the ability to represent engineering with conviction in executive and client-facing settings.

AI fluency is a core expectation of this role, not a bonus. You lead by example; integrating AI into your own engineering workflow, driving adoption across your teams, and building the culture and practices that make AI-native delivery a daily operational reality.

Why This Role, Why Now?

League is at an inflection point — executing a delivery transformation while scaling our most strategic enterprise accounts. This AVP role is a critical hire: you'll own the engineering execution that makes our delivery commitments real.

In this role you will:

Team Scope

• Direct reports: 3–5 Engineering Managers. Indirect reports: 25–35 engineers across web, mobile, and integration squads.

Technical & Architectural Leadership

• Own the technical direction for member-facing applications — define and enforce architectural standards, patterns, and guardrails across your squads; make trade-off calls with speed, quality, and scalability in mind
• Drive architectural reviews and decisions — lead design reviews for major features and platform integrations; ensure technical choices align with League’s roadmap, client commitments, and long-term platform health
• Maintain hands-on technical credibility — engage directly with engineers on architecture, code quality, and system design; you don’t need to be in the code daily, but you must be credible when you are

Implementation & Project Delivery

• Own end-to-end delivery accountability for your squads — from project scoping and estimation through to production release and post-launch stability; delivery commitments you make are commitments you keep
• Drive delivery predictability — implement the planning, tracking, and escalation practices that give the VP and CDO clear, real-time visibility into delivery health across your portfolio
•  Build and maintain delivery metrics — track PR throughput, defect rates, test automation coverage, and incident resolution SLAs; use data to drive continuous improvement, not just reporting

Client-Facing Engineering Leadership

• Serve as a senior engineering point of contact for strategic enterprise clients — represent engineering in client escalations, technical reviews, and delivery status conversations with the credibility and presence that builds lasting trust
•  Translate complex technical realities into clear client communication — own the narrative on delivery timelines, architectural decisions, and quality trade-offs in language that resonates with non-technical executive stakeholders

Member-Facing Application Ownership

•  Lead engineering delivery for consumer health experiences — own the quality, performance, and reliability of member-facing applications across web and mobile; you understand what ‘good’ looks like from a member’s perspective, not just an engineer’s

Cross-functional Collaboration

• Partner closely with Product Management and Design to translate roadmap commitments into realistic engineering plans;  own the technical scoping and estimation that makes delivery promises credible
• • Serve as the engineering point of contact within League's CDO delivery governance model; surface risks early and resolve cross-functional blockers before they become customer issues

People Leadership & Team Development

• Own performance management with rigor — set clear expectations for every EM, deliver candid feedback on a consistent cadence, and hold yourself accountable for developing the next tier of engineering leadership at League
•  Lead the hiring process for your squads — partner with Talent on sourcing strategy, conduct calibrated interviews, and make hiring decisions that raise the bar
•  Run structured calibration and career pathing — quarterly calibrations across your EM cohort; every engineer has a clear growth path and knows where they stand
•  Build inclusive, high-trust team culture — track engagement signals and act before attrition becomes a problem

AI-Native Engineering Leadership

•  Build the practices that make AI-native delivery real — micro-sprint methodologies, AI-informed delivery decisions, and AI-assisted defect classification are things your teams actually do       
• Maintain strong ownership and judgment over AI-generated outputs — your teams use AI confidently and responsibly; you set the standard for what that looks like in a regulated healthcare environment
•  Stay ahead of AI tooling evolution — continuously evaluate new capabilities and bring the right ones to your teams with a clear point of view on adoption

About you:

• 12+ years of progressive software engineering experience, including 5+ years in engineering leadership roles managing teams and engineering managers
• Proven track record owning end-to-end delivery of complex, enterprise-grade SaaS products in a B2B or B2B2C environment
• Deep experience building and shipping member-facing or consumer-facing applications — you understand this domain and have strong instincts for what quality looks like at scale
• Health tech or enterprise healthcare SaaS experience strongly preferred; experience working within HIPAA, PIPEDA, or equivalent regulated data environments is an asset
•  Strong architectural fluency in cloud-native systems (GCP preferred), microservices, and full-stack development (Go, React, mobile — Android and/or iOS
• Actively uses AI tools in engineering and leadership workflows
• Strong executive presence; you communicate with confidence and clarity in client escalations, executive reviews, and cross-functional forums
• Clear communicator who translates technical complexity into business language for non-technical stakeholders
• Experience managing delivery partners, offshore QA or development teams, or hybrid internal/external engineering models
• Familiarity with HIPAA, PIPEDA, or equivalent regulated data environments; understanding of what compliant engineering practice looks like in a healthcare SaaS context

Desired Outcomes 

• Delivery predictability: sprint commitments met at 85%+ with real-time visibility into delivery health
• PR throughput per developer at or above industry p75; trajectory toward p90 within 12 months
• Defect rate below p75 benchmark; high/critical incident rate below 10/month; incident SLA attainment at 100%
• Test automation coverage at 80%+ within 6 months of hire
• AI-assisted delivery decisions at 30%+ within 12 months
• Every EM has a current development plan; no unmanaged performance gaps older than 60 days

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League's secure coding practice
• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary:

We’re hiring a Demand Generation Specialist to join our Marketing Team and drive the execution of integrated, multi-channel demand generation programs. You will be the hands-on executor of full-funnel campaigns – translating strategy into targeted outreach, digital programs, and pipeline-driving plays. You’ll partner closely with Demand Gen, Campaigns, Product Marketing, Sales, and Marketing Ops to design and run campaigns that generate awareness, engagement, and pipeline for strategic payer accounts.

What you'll do: 

• Execute integrated demand generation programs across the full buyer journey (awareness → engagement → opportunity → expansion).
• Run multi-channel campaigns: email (Pardot), Demandbase programmatic, LinkedIn, digital ads, personalized landing pages/microsites, webinars/events and Qualified chat.
• Develop and implement targeted nurture programs aligned to buyer personas and funnel stages, including dynamic content and segment-specific messaging.
• Own the creative brief process: translate campaign goals into clear briefs for the creative team, managing feedback rounds and ensuring final assets are on-brand, on-message, and delivered on time.
• Measure & optimize: own campaign KPIs, engagement metrics, multi-touch and last-touch attribution, and ROI; iterate through structured testing and analysis.
• Support the execution of virtual events and webinars to drive awareness and engagement across key segments.
• Ensure compliance & governance: follow Legal/Privacy guidelines for U.S. healthcare data and consent (HIPAA awareness preferred).
• Operate with an Agile mindset: we work in two-week sprints to learn from results and iterate quickly.
• Security-related responsibilities: 
  • Compliance with Information Security Policies
  • Compliance with League’s secure coding practice
  • Responsibility and accountability for executing League's policies and procedures
  • Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violation

What we're looking for:

• 2 - 4+ years in B2B marketing in ideally in Demand Generation roles
• You love living in the tools!  Hands-on experience with Demandbase, LinkedIn Ad Manager, Pardot (Salesforce Account Engagement) and Salesforce (SFDC); experience with Webinar Hosting Platforms (Goldcast) and Qualified is a strong plus.
• Familiarity with account-based tactics.
• Solid grasp of full-funnel demand generation tactics: paid media, email nurture, content syndication, events, and webinars.
• Strong analytical skills – comfortable tracking campaign KPIs, building attribution reports, and making data-driven decisions.
• Strong project management, written communication and collaboration skills.
• Comfortable driving execution while liaising with the Campaign Owner and Sales.
• Comfortable working in Toronto in-office four days per week; occasional U.S. travel may be required.
• Comfortable with using AI tools like Claude, Chat GPT, Otter.ai, and Notebook LLM to support analysis, writing and daily workflow optimization. 

Nice-to-haves

• LinkedIn Ad-Manager / Pardot / Demandbase / Other ABM certifications
• Experience with paid media platforms, including LinkedIn Ad Manager and programmatic advertising tools (e.g., Demandbase, 6sense, or similar).
• Knowledge of the Healthcare and U.S. payer landscape — buyer roles, procurement cycles and regulatory considerations.

Position Summary

League is seeking a Senior ML Engineer to join our AI Models team, focused on advancing innovation in small language models (SLMs) and applied AI systems.

This role sits at the intersection of research and engineering, with a strong emphasis on experimentation, model development, and applied system design. You will work closely with AI leadership to explore, prototype, and operationalize new approaches to domain-specific language models that power League’s healthcare platform.

Unlike a traditional engineering role, this position is R&D-focused, designed for someone who can:

• Translate emerging research into practical implementations
  
  
• Rapidly experiment with model architectures and optimization techniques
  
  
• Leverage modern AI tools and frameworks to accelerate development

You will contribute to building League’s next generation of AI capabilities, while partnering with platform and product teams to bring high-impact innovations into production.

In this role, you will:

Model Development & Experimentation

• Design and implement experiments across fine-tuning, distillation, and optimization of small language models (1–10B parameters)
  
  
• Rapidly prototype and evaluate new approaches to model performance, efficiency, and reasoning quality
  
  
• Leverage modern tooling and AI-assisted workflows to accelerate iteration cycles

Applied AI & Systems Integration

• Build applied systems that connect models, data pipelines, and evaluation frameworks
  
  
• Focus on “wiring together” components across model training, evaluation, and deployment workflows
  
  
• Collaborate with engineering teams to transition promising experiments into production environments
  
  

Data & Training Strategy

• Contribute to training data design, including curation, labeling strategies, and synthetic data generation
  
  
• Work with data partners to explore AI-driven insights and improvements to model performance

Evaluation & Model Quality

• Define and run experiments to assess model performance across accuracy, reasoning, and safety dimensions
  
  
• Contribute to building lightweight evaluation frameworks and benchmarking approaches

AI-Native Development Practices

• Actively leverage AI tools (e.g., Copilot, LLM-assisted coding, research copilots) to improve productivity and experimentation speed
  
  
• Document and share workflows that improve how the team builds and evaluates models

Cross-Functional Collaboration

• Partner with Product, Platform Engineering, and AI Orchestration teams to integrate models into real-world use cases
  
  
• Communicate complex technical concepts clearly to cross-functional stakeholders

About you: 

• 5+ years of hands-on experience in applied ML/AI engineering, with a focus on language model development, fine-tuning, or NLP systems.
• Proven track record shipping fine-tuned or distilled LLMs/SLMs (1–10B parameters) to production.
• Deep expertise in PEFT techniques — LoRA, QLoRA, adapter tuning — and model quantization and distillation pipelines.
• Hands-on experience with RLHF/RLAIF, reward modeling, or safety alignment workflows.
• Strong background in data curation, labeling pipeline design, and synthetic data generation.
• Proficiency with model training frameworks and tooling: NeMo, Hugging Face Transformers, Axolotl, or equivalent.
• Experience with model serving stacks: vLLM, Triton, or similar; familiarity with inference optimization techniques.
• Comfort operating on cloud infrastructure (GCP, Vertex AI, AWS) and with GPU resource management.
• Solid understanding of healthcare data privacy and safety requirements: HIPAA, FHIR, clinical ontologies.
• Demonstrated ability to define and own evaluation frameworks — not just build models, but know whether they're working.
• Strong technical communication skills; able to present complex model decisions clearly to cross-functional and executive audiences.
• Bachelor's or graduate degree in Computer Science, Machine Learning, or equivalent experience.

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League’s secure coding practice
• Responsibility and accountability for executing League's policies and procedures
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

The role

League’s platform enables our customers to offer highly engaging and personalized health experiences to their users. The Apps and Solutions (A&S) Senior Product Manager is a customer-facing role that is instrumental in helping define the long term strategy and roadmaps of some of the most complex applications powered by League.

In this role you are responsible for building and maintaining strong relationships with client leaders and fellow PMs,   ensuring a deep understanding of their priorities,  smooth implementations and delivery of features, expert product solutioning, professional and timely client communication, and executing strong product judgment. 

In this role you may work with one or multiple customers or prospects and may move from customer to customer as League grows.  You will lean into solutions that leverage the broad range of capabilities in the League platform. When custom solutioning is required you will partner with design, engineering, strategy and your product peers to assure you are formulating solutions that are engaging, cohesive and help people lead healthier happier lives.

In this role you will closely track client metrics to track solution health and participate in organizational product reviews to lend your expertise to the solutions that other PMs are developing. 

 In this role, you will:

• Manage the roadmap for various A&S customers,  identifying opportunities to create new capabilities or optimizations of existing capabilities. 
• Develop the client relationship via offering, educating and delivering League solutions, and promoting the client’s vision and needs within League.
• Run product discovery, compile product requirements, and solicit engineering feedback to create solution definitions that are strategic and compelling
• Serve as a subject matter expert on League platform capabilities, and evangelize the value of the League platform to stakeholders.
• Proactively manage and prioritize the backlog of enhancements 
• Monitor engagement with the applications you are managing and identify opportunities to create value and exceed our goals
• Communicating effectively and clearly articulating trade-offs to internal and external leadership
• Define requirements and value proposition of custom features and complex capability deployments
• Define requirements and value proposition of custom features and complex capability deployments
• Monitor application performance and identify opportunities to create more value and exceed our goals
• Partner with Account Management to be the primary Product Management point of contact with our customer

About You:

• 5+ Years of Product Management experience
• Digital Healthcare experience, experience with the Payer market is preferred
• Exceptional client management skills — ensuring requirements are accurately captured, communication is clear,  and relationships are developed 
• Expert at balancing client requests with organizational goals.
• Expert level feature solutioning that includes soliciting internal stakeholder feedback
• Experience working with large engineering teams of different types including SI’s. 
• Experience working at a platform company, or on the implementation of platforms
• Agile expertise
• Believe in tightening every feedback loop regarding the product (e.g. release often, release early, talk to customers, Minimal Marketable Product, etc.)
• Experience working with large corporate clients and communicating with corporate leaders
• Strong Client Management skills — ensuring requirements are accurately captured, communication is clear, and expectations properly managed
• Excellent communication, presentation, interpersonal and analytical skills
• Demonstrated problem-solving skills and business acumen required
• Ability to quickly learn and gain proficiency in areas with limited experience
• Passionate about Generative AI and its potential to accelerate product workflows and improve customer experience.
• You thrive in a fast paced environment where priorities rapidly shift and needs often compete.

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Base pay: $150,000 - $175,000 AUD

Security-Related Responsibilities

• Compliance with Information Security Policies
• Compliance with League’s secure coding practice
• Responsibility and accountability for executing League's policies and procedures
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

The Role

As a Technical Delivery Project Manager, you support the successful execution of internal technical workstreams required for customer delivery. You serve as the day-to-day liaison between internal technical teams (e.g., Data Engineering, Data Science, Integrations, R&D) and the customer-facing delivery team. You coordinate technical requirements, gather inputs from customers, help translate requirements into internal technical tasks, manage supporting documentation, and ensure technical deliverables are completed on time.

In this role, you work closely with the Delivery Lead and functional technical leads to ensure alignment, visibility, and smooth execution of technical dependencies. You apply strong working knowledge of tools like Jira and foundational technical literacy to understand and communicate risks, issues, and timelines. You operate with growing independence while receiving guidance for complex or ambiguous matters.

One specific area of responsibility is to manage League’s customer-facing data product called Analytics Objects (AOs), which is a recurring data export of complex KPIs configured to meet a wide range of customer requirements. Your responsibilities include:

In this role, you are expected to:

Technical Workstream Coordination

• Coordinate technical tasks and dependencies across Data, Engineering, R&D, and other internal technical teams.
• Translate customer requirements into clear Jira tickets or internal work items.
• Maintain visibility into task progress, blockers, and timelines.

Manage Data Products 

• Coordinate launch of Analytics Objects (AOs) and other data products to customers.
• Manage the configuration of AOs and other data products to suit customer use cases.
• Manage customization requests and recommend existing solutions to customers as needed. Coordinate with product managers on custom solutions.

Customer Engagement & Requirements Gathering

• Attend customer-facing technical requirement meetings as a supporting point of contact.
• Document technical requirements and ensure internal technical teams understand expected outcomes.
• Communicate updates, risks, and next steps back to customer-facing stakeholders.

Jira & Tooling Ownership

• Support maintaining Jira boards, grooming tasks, updating statuses, and ensuring accurate workflow progression for tasks related to customer delivery.
• Support reporting on technical delivery progress and timelines.

Risk & Issue Management

• Identify and flag risks or blockers related to technical workstreams.
• Escalate issues to the Delivery Lead or technical leads as needed.

Technical Delivery Support

• Support internal test cycles, data validation activities, and technical documentation requirements.
• Understand and articulate the impact of deviations from standard practices.

Process & Documentation

• Maintain technical requirement documentation, task tracking, and workstream-level artifacts.
• Contribute feedback to help improve technical delivery processes and tooling.

About You:

• 3+ years in SaaS technical coordination, technical support, or data operations.
• Working knowledge of data platforms (Airflow, BigQuery, Looker, or similar).
• Strong proficiency with Jira for workflow tracking and ticket management.
• Foundational understanding of SaaS architectures, APIs, data pipelines, or ETL.
• Experience collaborating with Data teams, R&D, or technical SMEs.
• Experience managing projects with complex technical dependencies.

What We Offer

• Comprehensive Health Benefits: We prioritize your well-being with complete medical, dental, and vision coverage
• Bonus Program: Be rewarded for your contributions with our performance-based bonus program
• Employee Stock Option Program: Become an owner and share in our success through our stock option program
• Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance
• Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts
• Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year
• Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement
• Mentorship Program: Benefit from guidance and support from experienced leaders in your field

Security-related Responsibilities

• Compliance with Information Security Policies
• Compliance with League’s secure coding practice
• Responsibility and accountability for executing League's policies and procedures
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

Please note: We’re always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise.

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary: 

We're looking for a highly skilled and experienced Quality Assurance Lead to join our team. In this external client-facing role, you'll manage a small team of dedicated QA testers, overseeing all day-to-day test management activities, including planning, resource allocation, and crucial customer/UAT support. You'll be instrumental in ensuring the delivery of high-quality software solutions, leveraging your strong technical expertise in both automation and manual testing across diverse project methodologies, including Waterfall and Agile environments.

What you'll be doing:

• Leads day to day testing efforts for Internal testing
• Provides guidance and support to team members
• Provides testing estimates & dependencies required for test execution
• Performs resource allocation for testing activities
• Creates detailed test plans for testing projects, including function, end-to-end, back-end/API testing
• Reviews product requirements (internal & customer) 
• Supports External UAT cycles ; defines the process & tools. triages UAT defects and performs root cause analysis for escaped defects.
• Collaborate with engineers and product team to understand project scope & requirements 
• Reviews test cases for accuracy/coverageExpand & enhance test testing process; trains and mentors testers
• Monitors testing progress & results; raises risks/escalations to Project & Engineering managers
• Performs defect root cause analysis on escaped defects (Customer UAT & Production)
• Works closely with External Customers to understand project scope, identifies testing dependencies and performs 
• Identifies areas for continuous/process improvements with  focus and emphasis on improving testing quality and reducing defect leakage
• Provides input towards test automation approach
• Conducts test plan review & Customer UAT hand-off
• Work closely with the Engineering team; track development progress and identify risks and issues related to quality deliverables.
• Participates in Engineering / scrum ceremonies.
• Creates execution & defect dashboard reports.
• Security-related responsibilities: 
  • Compliance with Information Security Policies
  • Compliance with League’s secure coding practice
  • Responsibility and accountability for executing League's policies and procedures
  • Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violation

What we're looking for: 

• A Bachelor's degree in Computer Science, Engineering, or a related field.
• Progressive experience in Quality Assurance, with at least 3+ years in a dedicated Test Lead or similar leadership role.
• Expertise in both manual testing, including functional, integration, end-to-end (E2E), and regression testing.
• Proven hands-on experience in test automation, including running tests and analyzing results.
• Demonstrated ability to thrive and deliver in fast-paced, dynamic environments.
• Extensive experience working in external client-facing roles, with excellent communication and collaboration skills.
• Deep understanding and practical experience with both Waterfall and Agile delivery methodologies.
• Strong analytical skills with the ability to translate complex business requirements into comprehensive test scenarios, including both positive and negative testing.
• Experience with testing mobile applications 

Please note: We’re always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise.

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary: 

The Quality Assurance Analyst plays a critical role in ensuring product excellence by leading testing strategy and execution across functional, integration, and end-to-end systems. This individual serves as the primary QA partner on implementation initiatives, driving comprehensive test coverage, strengthening automation frameworks, and preventing critical defects from reaching customers. Through strong collaboration with Engineering and project teams, the Sr. QA Analyst safeguards release quality and ensures on-time, high-confidence deployments.

What you'll be doing: 

• Serve as primary tester on implementation projects.
• Develop and maintain test plans and test cases based on project and technical requirements.
• Creates and executes  functional , integration / E2E test cases to validate business systems.
• Ensures our products meet high quality standards.Conduct peer reviews of test cases to ensure depth and breadth of test coverage.  
• Reviews automated test case execution results; analyzing results to identify potential issues.
• Adds functionality to test cases using an automated test framework/suite.
• Identify, document and prioritize defects using JiraCollaborate with engineers and project team to understand requirements.
• Execute automated test scripts and analyze results to identify defects and report issues.
• Work closely with the Engineering team; track development progress and identify risks and issues related to quality deliverables.
• Security-related responsibilities: 
  • Compliance with Information Security Policies
  • Compliance with League’s secure coding practice
  • Responsibility and accountability for executing League's policies and procedures

What we're looking for: 

• Bachelor's degree in Computer Science, Engineering, or a related field.
• 5+ years experience in Quality Assurance. Ability to write test plans, test cases and follow processes.
• Expertise in manual testing including functional , integration, E2E and regression testing.
• Experience running test automation and reviewing results.
  Ability to understand business requirements and develop comprehensive test scenarios that include positive and negative testing.

Please note: We’re always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise.

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary: 

As Principal, Strategic Partnerships, you will be responsible for building and leading strategic partnerships on behalf of League and will report to the SVP of Customer & Partner Ecosystem.  You will manage partnerships within a single portfolio or combination of partnerships across System Integrator & Enterprise Technology, and/or Product/ISV segments.  You will be responsible for the strategy, execution, negotiation/contract management, and relationship management for your partnerships towards achievement of business objectives, prioritizing sourcing and influencing closed won revenue.

The ideal candidate will have demonstrated experience growing and managing partnerships with Systems Integrators, Cloud providers or ISVs & AI natives, with proven success in driving opportunities via complex partner networks. They will have shown the ability to think strategically, navigate complex partner ecosystems, and lead cross-functional teams to execute on revenue-generating KPIs.  The ideal candidate must have experience in healthcare/digital health.

In this role, you will: 

• Partnership strategy definition and alignment: Define success/KPIs, develop a plan to get there, and align support to achieve those targets independently (including cross functional stakeholders, external stakeholders, working team and leadership).
• Develop sales strategies and identify opportunities that align to League’s platform go-to-market segments (focus on payors by working closely with internal and external commercial teams. 
• Continuously educating and enabling partners on League’s unique positioning and value proposition, and enabling internal teams on new partnerships. 
• Collaborate with Product Marketing to develop ‘better together’ messaging for the partnership and enable our internal and partner commercial teams.
• Partner with Marketing on strategies to drive partnership awareness through joint blogs, podcasts, webinars, case studies, etc.
• Define and gain alignment on the partnership product roadmap internally and with the partner product development teams (e.g. technology integrations).
• Execution: Deliver on objectives at a high standard, on time, and meeting success criteria (e.g. partner-generated and partner-influenced KPI’s, sales qualified opportunities, revenue targets) independently. 
• Responsible for driving execution on the strategy from start to finish, internally & externally, cross functionally, and with all levels of leadership. 
• Effectively consider dependencies and mitigate risks when planning work.
• Manage partnerships to the partnership health framework.  
• Proactively raise and address issues, such that the resulting impact is minimized. 
• Partnership Structuring & Negotiation: Responsible for defining commercial models and negotiating contracts resulting in longstanding win-win partnerships independently. 
• Successfully navigate, identify, evaluate and prioritize risk to minimize negative impacts to the business. 
• Manage partnerships in alignment with contracts.
• Relationship Management: Ensure healthy partner relationships that both position the partnership for success in achieving objectives, and are aligned with League's core values.   
• Develop and nurture relationships at all levels (including senior executives) and across all applicable functions within the partner organization. Identify and collaborate with key decision-makers and influencers.
• Coordinate governance (e.g. QBRs) with key stakeholders to drive partnerships forward.
• Manage partnerships such that teams that are responsive, execute, make decisions, ideate well together, and trust each other.  If one of these tenants falls, you ensure that it is promptly addressed.
• Security-related responsibilities: 
• Compliance with Information Security Policies
• Responsibility and accountability for executing League's policies and procedures
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

We're looking for: 

• 5+ Years of partner or channel development/management, co-selling, and/or experience working with ISVs, Global System Integrators (e.g. Deloitte, Accenture - experience in digital transformation a bonus) and/or with a Cloud Provider (e.g. Google, Microsoft, AWS)
• 5+ years of partner management experience with revenue-generating KPIs
• Experience building partner evaluation frameworks, building and onboarding new partners, and ongoing execution of the partnership post-launch.
• 7+ years of experience in healthcare/digital health
• AI and agentic platform literacy

• Nice-to-have: 
• Consulting, investment banking, corporate development experience and/or MBA
• AI-native platform experience
• Entrepreneurial experience or experience building net new partner revenue lines at a hyper-growth organization
• Strong understanding of the payor market

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary:

League’s PaaS business, Powered by League, is rapidly scaling. Building on the proven success among our market-leading customers and partners including Medibank, Highmark Health, Google, Accenture, Manulife, and Shoppers Drug Mart - our Go-to-Market team is expanding and seeking a Director, Sales & Account Management to help us achieve this next phase of growth. 

As a Director, Sales & Account Management, you will be a core part of the Go-to-Market team working across priority segments including Private Health Insurers, Private Healthcare Providers, Public Sector Health Agencies, Retail Pharmacies, and Digital Health Innovators. You will be responsible for leading complex enterprise-scale business development and sales initiatives with prospects and carry a quota for Powered by League platform sales.  In addition, responsible for nurturing and growing existing client relationships, identifying new opportunities within these accounts, and ensuring the long-term success and satisfaction of League’s customers in Australasia.

Working in collaboration with other parts of the Go-to-Market team (including Solution Engineering, Partnerships and Product Marketing) as well as our Delivery & Product Management functions, you will identify, design, plan and deliver impactful customer partnerships that power the transformation of their digital consumer, member or patient experiences. 

In this role you will:

• Be the first Growth & Customer employee on the ground in Australia, representing League in this important new growth market, and supporting our flagship customers (one each in Australia & New Zealand)
• Support League’s international growth -  working closely with our Growth Organisation including: Account Management and Sales Leadership.
• Lead and own the end-to-end sales process for target platform strategic accounts, including formulating sales strategy, driving revenue growth and developing new customer relationships.
• Develop and execute comprehensive account plans for League’s Australiasian customer base, outlining clear objectives, strategies, and tactics to drive revenue growth.
• Leverage your own relationships to build pipeline (both net new and up-sell / cross-sell of new solutions to existing customers), and work in partnership with the Business Development and Marketing teams to run account-based marketing campaigns that lead to closed revenue and quota attainment.
• Successfully achieve and exceed budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner.
• Negotiate complex software and professional services agreements from initial stages through to completion; and execute contract amendments and renewals
• Create demand by leveraging healthcare industry expertise and what the priorities from C-level executives are, uncovering business problems for prospects and customers and matching them to our solution.
• Work collaboratively with League Executives and Go-to-Market leaders to build the story and tailored materials for meetings with prospective accounts.
• Work with the Go-to-Market leadership team to create and improve sales processes and buyer journeys, especially in new industry verticals.
• Serve as the voice of the Australiasian customer base ensuring their needs and priorities are understood and addressed and proactively identify and communicate product needs of Powered by League prospects and industry verticals to executive and product leadership.
• Cultivate and maintain strong, trusted advisor relationships with key stakeholders within League’s customer base and establish and monitor key performance indicators (KPIs) for customer health, providing regular reporting and actionable insights to internal stakeholders. 
• Work with the Value Realization function to measure impact and ensure customers are consistently achieving their desired business outcomes and realizing the full value of League's platform and services.

Security-Related Responsibilities

• Compliance with Information Security Policies
• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/ team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

About you:

• 10 years of experience in ‘Platform as a Service’ (PaaS) or ‘Software as a Service’ (SaaS) sales and account management experience
• 5 years of healthcare industry experience in digital transformation and/or consumer & patient engagement sales required
• Strong knowledge of the Australian healthcare industry (Providers, Pharmacy Retailers) and/or health benefits industry
• A history of successful quota attainment in a complex sales environment
• Exceptional relationship-building and interpersonal skills, with the ability to establish rapport, build trust and win the support of key C-suite executives in large corporations
• Demonstrated ability to develop and execute strategic account plans that drive measurable results
• Excellent analytical and problem-solving skills, with the ability to interpret data and develop actionable insights
• Proficiency with Salesforce and sales acceleration tools
• Experience developing exceptional documentation for client presentations and webinars
• Bachelor's degree in Business or equivalent experience

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Position Summary:

Position Summary:

Position Summary:

Position Summary:

Position Summary:

Position Summary:

Position Summary:

The Role

We are seeking a Senior AI Engineer to join our AI & Data Group on the AI Orchestration team. This role is responsible for designing, building, operating and scaling the orchestration layer that powers League’s AI-driven healthcare experiences. 

Sitting at the intersection of AI systems design, ML productionization, and distributed software engineering, you will take the probabilistic capabilities of large language models and engineer them into reliable, measurable, and scalable product experiences.

This is a hands-on senior engineering role for a practitioner who moves beyond prototypes to own the hard problem of making AI work at scale. You will translate leading edge AI innovation into reliable, secure, and compliant systems. Your work will directly impact how AI is operationalized across League’s digital health ecosystem—ensuring systems are scalable, observable, performant, and safe in a regulated environment.

Position Summary: 

The solution consulting & sales engineering team is a critical part of League’s growth organization, focused on applying League’s platform capabilities to power new digital consumer experiences in healthcare.  

Through collaborating with League’s market development, strategic sales, customer, partner, product & implementation teams, Solutions Engineering partners with the world’s leading healthcare organizations to design new digital business models, products, and experiences.  League’s growth organization supports organizations across the Payer, Provider, Life Sciences, and Consumer Health markets (i.e., Pharmacy Retail).

As Principal, Solutions Engineering, you are a leader in League’s solution consulting & sales engineering team.  You take a leadership role in having a deep understanding of the League platform, and are able to connect customer business priorities with League’s technology capabilities - while helping to chart League’s broader strategy for how our platform delivers a better digital health experience for consumers.

Note: this is an Evergreen role as we are always building our talent pipeline. This is a recurring role on our team and we are always excited to meet talent who may be a fit now or in the future. 

In this role, you will: 

• As a Principal, Solutions Engineering, you are a leader on the pre-sales team at League, partnering with Strategic Account Directors to showcase League’s platform capabilities, understand prospective customers’ business & digital requirements, visualize League’s platform capabilities, and collaborate with customers to align their needs with League’s market-leading capabilities and solutions.
• Design Digital Consumer Experiences - you will partner with prospective customers, and their business, product, digital & IT teams to design ‘what’s possible’ in redefining the role of digital in delivering healthcare and benefits for millions of consumers
• Align Platform Capabilities to Business Value - you will demonstrate a deep knowledge and understanding of League’s platform and technology capabilities with the ability to architect solutions and articulate how those solutions connect to the key business drivers for our prospective customers (e.g., business growth, service automation, experience transformation, high engagement care delivery, population health, etc.)
• Visualize Best-in-Class Health Experiences - bring to life League’s platform capabilities through presentations, mock-ups, and demonstrations by partnering with League’s product & design teams
• Partner for Success - you will work cross-functionally at League with our customer, implementation, product and engineering teams to turn strategy, solutions and requirements into concrete action plans to build, launch & scale our customers’ new digital health experiences 
• Growth Team Alignment - you will work with Strategic Account Directors on RFP/RFIs, partner contracts and technical evaluations
• Security-related responsibilities:
  • Compliance with Information Security Policies
  • Compliance with League’s secure coding practice
  • Responsibility and accountability for executing League's policies and procedures
  • Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

What we're looking for: 

• 8+ years Solutions Engineering / Pre-Sales / Solutions Consulting experience
• 10+ years total professional experience
• Deep healthcare (specifically Payer) industry experience in sales, business development and/or strategy consulting
• Experience in leading solution architecture and software demonstrations for healthcare IT, digital health and/or patient engagement solutions
• Platform-as-a-Service or Software-as-a-Service experience 
• Excellent storytelling and communication skills, including presenting complex solutions, concepts & ideas to executive, technical and/or non-technical audiences
• Bachelor equivalent - minimum

Nice-to-Have

• Master equivalent
• Product Management experience