Guild is seeking a Senior Software Engineer II to join our Member Experiences pillar, focused on enhancing the scalability, flexibility, and reliability of our client data onboarding and integration systems. In this role, you will design and deliver robust software solutions that serve the evolving needs of our Employer Partners and the employees they support.

We’re looking for a self-driven, product-minded engineer who thrives in fast-paced environments and is comfortable navigating ambiguity. You will collaborate cross-functionally with internal stakeholders to develop adaptable, high-impact systems that help our partners deliver seamless access to Guild’s education benefits and coaching services.

As a senior member of the team, you’ll contribute from day one; crafting high-quality, scalable solutions that can keep pace with Guild’s rapid growth and the dynamic volume of client and user needs.

As a Senior Software Engineer II, you will:

• Develop and maintain robust software systems that power core member experiences; ranging from user-facing applications to internal tools and supporting service layers; ensuring performance, maintainability, and adaptability.

• Partner with senior and staff engineers to design modular, observable, and secure architectures that scale with Guild’s growth and accommodate evolving business needs and high-volume client demands.

• Write clean, testable, and reusable code. Contribute to end-to-end development including testing, CI/CD pipelines, monitoring, and deployment, ensuring high availability and quality in releases.

• Lead by example in code quality, technical decision-making, and documentation practices. Create and contribute to design documents, architecture decision records (ADRs), and technical discussions that communicate trade-offs clearly.

• Work closely with product managers, designers, operations teams, and external client technical teams to translate business requirements into effective engineering solutions. Contribute to planning, estimation, and execution of product roadmap items.

• Use operational data; such as logs, metrics, and user feedback; to identify and implement enhancements in performance, reliability, and developer velocity. Take ownership of resolving issues and driving root cause analysis and sustainability.

• Improve internal development processes, tools, and workflows to enhance code quality, speed of delivery, and system security.

• Participate in on-call rotations and incident response. Provide constructive code reviews and mentorship to help elevate teammates and build a high-performing engineering culture.

You are a strong fit if you have:

• 5+ years of software development experience with: Python, TypeScript, Node.js, React, PostgreSQL, DynamoDB, and GraphQL

• Hands-on experience with: AWS services, including Lambda, Serverless Framework, Glue, API Gateway, and CDK or other Infrastructure-as-Code (IaC) tools

• A deep understanding of: the full software development lifecycle; from gathering technical requirements and selecting technologies to deploying and maintaining production systems

• AI Experience:  Utilizing AI-assisted development tools such as Cursor, GitHub Copilot, or similar; Experience integrating LLM APIs (e.g., OpenAI) and building AI-powered features, including assistants, summarization, RAG workflows, and vector search

Ideal Candidate Qualities:

• Demonstrated success working in a production AWS microservices environment

• Ability to write simple, clean, and maintainable code

• Brings thoughtful technical opinions, but remains open to new perspectives (“strong opinions, loosely held”)

• Willingness to take calculated risks and contribute vision and direction to both the team and Guild as a whole

• A mindset of continuous learning and improvement

• A genuine passion for Guild’s mission and long-term impact

• Excellent collaboration skills; able to work cross-functionally, share knowledge, and foster team alignment

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $160,000 - $195,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: May 4, 2026

*This role will stay open for a minimum of 3 days. 

*Please note this role is based in Denver, CO*

This role sits at the center of how Guild uses data to drive business decisions. As Senior Analyst, you'll own the KPI monitoring and insight generation that our executive team relies on to run the business, while also building the AI-powered tools and automated workflows that will enhance how the Analytics team operates for years to come. You'll bridge the gap between raw data and real decisions, partnering with Finance, Employer Partner Services, Product, and Marketing to ensure leaders can interpret, trust, and act on data with confidence. If you're excited about doing serious analytical work and building scalable systems that multiply the team's impact, this role was designed for you.

Outcomes Expected to Achieve:

• Executive-grade KPI intelligence: Leaders across the organization have a reliable, proactive source of truth on business performance, with clear interpretation of trends, risks, and forward-looking signals
• AI-powered analytics at scale: The Analytics team and its cross-functional partners spend less time on manual, recurring work because you've built tools and automations that handle it
• Analytical enablement across the org: Business teams can independently contextualize and act on data because you've made forecasts, metrics, and insights accessible and interpretable

Skills/Competencies required:

• SQL proficiency: you're comfortable writing complex queries across multi-table data models; dbt and Omni (or comparable BI tools) experience strongly preferred
• Applied AI fluency: hands-on experience building AI-powered tools or automating analytics workflows, not just familiarity with the concepts
• Executive communication: ability to distill complex findings into clear, confident recommendations for non-technical audiences
• Builder's mindset: you proactively identify opportunities to automate, scale, and improve how data is used; you don't wait to be asked
• Stakeholder partnership: comfortable consulting with cross-functional partners on scope, feasibility, and tradeoffs; can manage competing priorities and expectations
• Quantitative rigor: 4+ years in analytics, data science, or a related field, with comfort working across complex, multi-source datasets

Here's what you will do in this role to achieve these outcomes:

• Monitor business KPIs, identify risks and trends proactively, and deliver data visualizations and narrative insights that drive meaningful engagement with executive-level stakeholders
• Partner with the Forecasting & Financial Analytics team to bridge forecast outputs to day-to-day decision-making, enabling cross-functional teams to interpret and act on data with confidence
• Build and deploy AI-powered analytic solutions - automated reporting pipelines, repeatable Skill frameworks, and scalable tools - that reduce manual effort across the Analytics team and its partners
• Consult with stakeholders on reporting feasibility and scope; produce metrics and data structures that best meet their actual decision-making needs
• Deliver ad hoc analyses on Guild's business trends, member behavior, and learner and employer outcomes
• Write and maintain complex SQL, work within dbt models, and leverage Omni to surface and communicate data; partner with Data Engineering on data quality and schema requirements
• Evaluate and implement emerging AI tools and techniques to improve analytic workflows and stay current on the applied AI landscape
• Translate data on member experience, learner outcomes, and employer outcomes into external-facing thought leadership that supports business growth

You are probably a strong candidate for this role if you've accomplished:

• Built or automated an analytics workflow - reporting, alerting, or data pipeline - that meaningfully reduced recurring manual work for yourself or your team
• Delivered an analysis or data narrative to senior or executive stakeholders that influenced a strategic decision
• Applied AI tools or techniques in a practical analytics context. Not just experimented, but shipped something that stuck
• Worked across multiple complex data models and navigated ambiguous, multi-table datasets to produce reliable outputs
• Translated technical findings into clear recommendations that non-technical audiences could act on

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $120,000 - $140,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date:

Thursday, April 23, 2026

*This role will stay open for a minimum of 3 days. 

Guild is hiring a Principal Product Operations Manager for our Grow product area. This is the most senior individual contributor Product Operations role at Guild. This role sits at the intersection of product strategy, technical execution, and operational excellence - owning the systems, workflows, and delivery infrastructure that make Grow run, while leading high-impact strategic initiatives end-to-end alongside Engineering and Product leadership.

Responsibilities

Strategic Product Initiative Leadership

• Lead high-impact, cross-functional product initiatives end-to-end - from aligning teams and clarifying technical trade-offs to driving execution and measuring outcomes.
• Translate product strategy into concrete execution plans by working closely with Engineering leaders on architecture boundaries, dependencies, sequencing, and technical trade-offs.
• Own launch and release readiness across all stakeholders: teams are informed, equipped, and ready before anything ships.

Operational Design, Optimization, and Impact

• Develop and refine operational systems, tools, and AI-enabled workflows to enhance the efficiency of Product, Engineering, Design, and Data teams.
• Conduct regular audits of Grow’s R&D processes to identify friction, map system dependencies, and drive scalable improvements with clear operational standards.
• Build and maintain operational playbooks, escalation frameworks, and governance models.
• Establish operating cadences for Grow, with a bias toward reducing coordination overhead and protecting time for high-value work.
• Design and continuously evolve the end-to-end product delivery system for Grow - intake, prioritization, planning cadences, release readiness, and delivery standards.
• Define and own delivery performance metrics and dashboards; use data to identify trends, diagnose systemic issues, and validate impact of improvements.

AI Prototyping and Automation

• Identify where AI can be embedded across the product development lifecycle.Design and test AI-assisted workflows; validate impact before scaling broadly.
• Model responsible, high-leverage AI use for the broader P&E org.

Tool Evaluation

• Assess tooling gaps, lead vendor conversations, and ensure tools are appropriate, integrated, and adopted across Grow.

Cross-Functional Alignment

• Facilitate alignment across Product, Engineering, Design, Data, GTM, EPS, and Operations - ensuring priority clarity and seamless execution.
• Establish feedback loop infrastructure so customer, partner, and operational signals reach the roadmap systematically.
• Build communication norms and shared artifacts that scale across teams and reduce coordination overhead.

What We’re Looking For

• Systems thinking and technical acumen. You design operational systems that scale and understand how changes ripple across teams and platforms. Credible in rooms with engineers and architects - you understand architecture trade-offs, data flows, service dependencies, and when to go deep vs. zoom out to cross-team sequencing.
• AI-forward mindset. You have real opinions about where AI should and shouldn’t be applied in a product development lifecycle - and you’ve built or prototyped something with it. You don’t treat AI as a feature; you treat it as a lever.
• Ownership, not coordination. You drive outcomes. You step into gaps rather than route around them. When something is unclear, you make it clear.
• Executive communication. You distill operational and technical complexity for a VP without losing precision with an Engineering Director. You know what to escalate, what to absorb, and how to frame both.

Qualifications

• 12+ years of experience in Product Operations,Technical Program Management, Product Management, or a related role on Product Teams.
• Proven track record of designing and scaling product delivery systems across multiple teams or product areas.
• Experience leading cross-functional product initiatives end-to-end with accountability for outcomes.
• Hands-on experience designing or prototyping AI-assisted tools and workflows - not just familiarity with AI tools.
• Strong analytical mindset - you define metrics, build dashboards, and use data to drive decisions, not just report on them.
• Expertise with agile methodologies and associated tooling (Jira, Confluence, etc.).
• Experience operating autonomously at senior IC or staff level with demonstrated influence across engineering and product leadership.

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $180,000 - $215,000, a bonus and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: April 21

*This role will stay open for a minimum of 3 days. 

Principal Technical Program Manager - GROW

Guild is hiring a Principal Technical Program Manager for Grow Product, the most senior individual-contributor Technical Program Management role at Guild. In this role, you will drive execution across the technical foundations that support our multi-product organization while helping build the TPgM discipline from the ground up. This role combines deep technical leadership with program execution: leading critical company-wide initiatives, influencing architectural decisions across Guild’s technical stack, and shaping what technical program management means as we scale.

Responsibilities

• Assess the current state of Grow Product across business objectives, stakeholder needs, and delivery inhibitors, and translate findings into a long-term, multi-team execution roadmap in close partnership with Product and Engineering.
• Translate product strategy into concrete technical solutions and execution plans by working closely with engineering leaders to clarify architecture boundaries, dependencies, sequencing, and technical trade-offs.
• Own execution of the articulated roadmap by aligning teams, proactively managing dependencies, and ensuring predictable, high-quality delivery.
• Own launch and release readiness across all stakeholders, ensuring teams are informed, equipped, and ready before anything ships.
• Operate with full ownership across products, and programs. Proactively identify risks, blockers, decision gaps, and opportunities, resolving them directly or ensuring clear ownership and accountability.
• Help shape the TPgM craft at Guild by modeling technical excellence, strong ownership, and sound execution judgment, and by contributing to the standards and operating model as the function scales.
• Establish and evolve the operating cadences for Product and Engineering, including how teams plan, review, and align, with a bias toward reducing coordination overhead and protecting time for high-value work.
• Mentor TPgMs and Product and Engineering leaders, establish best practices, and scale program leadership capabilities across the Guild P&E organization.
• Champion AI adoption by identifying opportunities to embed AI into the Product Development Lifecycle and modeling effective, responsible use of AI tools.

What We’re Looking For

Technical Acumen and Cross-System Reasoning

• Working technical foundation with the ability to understand architecture, service boundaries, data flows, and technical trade-offs
• Demonstrated systems thinking: ability to reason about how changes ripple across teams and systems, and to think in sequences (e.g., dependency readiness, integration timing, and rollout order), not just individual projects
• Able to identify what needs to be measured and why, ensuring product data is trusted and actionable, and using data to surface risks and drive decisions
• Knows when to go deep and when to go broad, able to dive into technical details when a program is at risk, and zoom out to cross-team sequencing when alignment is the bottleneck

Ownership mindset and trust-building

• Proven track record of owning outcomes, not tasks.
• Proactively steps into ambiguity and execution gaps rather than routing around them.
• Builds credibility with Product and Engineering partners by understanding the “why,” anticipating issues, and acting as a true execution partner

Communication and Collaboration

• Communicates with precision across audiences — translates technical complexity for executives without losing credibility with engineers and architects
• Drives alignment in ambiguous, multi-stakeholder environments by creating clarity around decisions, owners, and sequencing
• Establishes feedback loop infrastructure that ensures customer, partner, and operational insights are systematically captured and inform product and roadmap decisions
• Establishes communication norms and shared artifacts that scale across teams and reduce coordination overhead

Qualifications

• 12+ years of experience on software teams as a Technical Program Manager, Engineering Manager, Product Manager, or similar role.
• Experience driving and delivering complex tech programs or products from inception to delivery
• Experience operating autonomously across multiple teams and functions, demonstrated critical thinking, and thought leadership
• Communication experience at executive level and experience influencing senior leadership and technical management teams to develop systems, solutions, and products
• Experience establishing work relationships across multi-disciplinary teams and multiple partners in different time zones
• Experience working with product teams to build and deliver end-to-end customer focused products with technical knowledge of the underlying platforms and technologies

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $180,000 - $215,000, a bonus and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: March 2, 2026

*This role will stay open for a minimum of 3 days. 

Guild is hiring a Senior Product Analytics Data Scientist. 

The Opportunity

Guild's product organization is at an inflection point—and we need a data scientist who can ensure we're building the right things, measuring what matters, and proving impact. As our Senior Product Analytics Data Scientist, you'll be the strategic analytics partner for Grow Core and Payments Network, with expanding scope into Academy and Navigator. Your work will directly shape product strategy by ensuring leaders have the insights they need to focus investments on high-return solutions, validate that launches actually drive impact, and create objective accountability across the business. Without this role, our product and engineering efforts risk operating without understanding how our work affects members and the bottom line. This is your chance to change that.

Here are the outcomes you will be expected to achieve:

• Focus product investments on the highest-return solutions by providing actionable insights that inform roadmap prioritization
• Validate that product launches actually drive impact through rigorous experimentation and causal inference
• Create objective measures of accountability by defining and operationalizing KPIs that align business and mission incentives
• Enable a self-sufficient, data-driven product culture where leaders can access the insights they need without bottlenecks

Here's what you will do in this role to achieve these outcomes:

• Proactively influence product strategy and roadmap decisions through narrative insights and recommendations
• Define logical KPI driver trees in partnership with Senior Directors of Product Management that drive aligned incentives
• Own and lead analytical standards for the product organization—driving rigor across experimentation, causal inference, and descriptive analytics using Optimizely, Segment, and Fullstory
• Deliver dashboards and workflows that consistently provide value, articulate performance, and support prioritization decisions
• Consult with stakeholders on the feasibility and scope of reporting requests, enabling self-service whenever possible
• Translate ambiguous questions into concrete analysis with clear narratives for non-technical audiences
• Manipulate and analyze complex datasets using Snowflake, dbt, Databricks, and Looker/Omni
• Partner with Data Engineering to flag data quality issues, request new events/metrics, and define data requirements for existing and new products

You are probably a strong candidate for this role if you've accomplished:

• Partnered directly with product leaders to define KPIs and measurement frameworks that shaped roadmap decisions
• Designed and analyzed A/B tests or other causal inference methods that validated (or invalidated) product bets
• Built dashboards or reporting infrastructure that product teams actually used for ongoing decision-making—not one-off analyses
• Translated messy, ambiguous business questions into structured analyses with clear, actionable takeaways
• Identified data quality issues or gaps and worked cross-functionally to resolve them

Here are the skills/competencies you have that will be needed to achieve the expected outcomes:

• Strong proficiency in SQL and experience with modern data tools (Snowflake, dbt, Databricks, Looker or similar)
• Expertise in experimentation design, causal inference, and statistical rigor
• Ability to define meaningful KPIs and connect them to business outcomes through logical frameworks
• Experience with product analytics tooling (Optimizely, Segment, Fullstory, Amplitude, or similar)
• Strong communication skills—able to craft clear narratives for non-technical stakeholders
• Consultative mindset: you scope requests, push back when needed, and deliver what stakeholders actually need
• Comfort with ambiguity and the ability to structure problems independently

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $120,000 - $140,000 and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: January 27, 2026

*This role will stay open for a minimum of 3 days. 

Guild is seeking a Senior Software Engineer to build scalable, reliable systems that empower our Employer Partners to administer education benefits and integrate employee data with Guild’s platform. You’ll play a pivotal role in developing tools and services that streamline eligibility processing, policy management, and data onboarding—ensuring employees get the most out of Guild’s career opportunity programs.

This role is ideal for product-minded engineers who are excited by cross-functional collaboration, thrive in a modern AWS serverless environment, and enjoy solving data and systems design challenges at scale.

As a Senior Software Engineer, you will:

• Design and build robust, scalable systems that power data onboarding, eligibility workflows, and benefit policy administration.
• Develop backend services, APIs, ETL pipelines, and internal tools using serverless architecture (AWS Lambda, Glue, S3, API Gateway).
• Create clean, testable, maintainable code in TypeScript/Node.js and Python following best practices and established patterns.
• Ensure system observability, security, and performance using tools like Datadog and CloudWatch.
• Collaborate closely with engineers, product managers, designers, internal ops, and customer technical teams to deliver high-impact features.
• Write and maintain comprehensive tests (unit, contract, BDD, and end-to-end) and support CI/CD pipelines for consistent delivery.
• Participate in Agile ceremonies and on-call rotations, with a focus on production readiness, system health, and issue resolution.
• Contribute to system architecture decisions, technical documentation, and mentoring of junior developers.
  
  

You are a strong fit if you have:

• 5+ Years Hands-on Experience with: TypeScript/Node.js, Python, React, PostgreSQL, DynamoDB, GraphQL, REST APIs.
• Experience with AWS tools: Lambda, Glue, API Gateway, S3, EventBridge, SQS, Secrets Manager, CDK, Serverless Framework.
• Knowledge of: ETL pipeline development, CSV/API data ingestion, data transformation, event-driven architecture.
• Testing & Tooling: Jest, Pact, Cypress, Gherkin, CI/CD pipelines, infrastructure as code (AWS CDK/CloudFormation).
• AI Experience: Experience integrating LLM APIs (e.g., OpenAI) and building AI-powered features such as virtual assistants, summarization tools, vector search, or retrieval-augmented generation (RAG) workflows. Proficient in using AI-assisted development tools (e.g., GitHub Copilot, Cursor) with a solid understanding of their application in production-grade environments.
• Strong communication, collaboration, and documentation skills.
• Ability to balance technical decisions with business goals and deliver pragmatic solutions.
• A passion for Guild’s mission to unlock opportunity through education and upskilling.

We are committed to equal pay for equal work and believe in compensation transparency. This role offers a competitive total compensation package, including a base salary of $150,000 - $180,000, and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: September 9th, 2025
*This role will stay open for a minimum of 3 days.