About the Role

The Vice President of Account Management (VP, AM) is responsible for building, leading, and scaling Take Command’s Account Management function. This role owns the strategy and execution behind client retention, renewals, and expansion across our employer portfolio.

The VP, AM will define what great Account Management looks like at Take Command—designing the team structure, establishing operating rhythms, and building a high-performing organization that delivers exceptional outcomes for clients and brokers.

This is a revenue-critical leadership role. The VP, AM is accountable for gross and net retention, renewal execution, and expansion growth, while ensuring a best-in-class experience for employers and their benefits consultants.

What You’ll Own

Account Management Strategy & Team Buildout
- Build and scale the Account Management organization, including hiring, onboarding, and development of Account Managers
- Define roles, responsibilities, and rules of engagement across AMs, Sales, and Client Success
- Establish team structure, segmentation, and book of business design aligned to company growth
- Create and refine playbooks for renewals, retention, and expansion
- Drive a performance culture with clear KPIs, accountability, and coaching

Renewals, Retention & Expansion
- Own company-wide renewal strategy and execution
- Ensure high on-time renewal rates and strong gross/net retention performance
- Develop frameworks for identifying and capturing upsell and expansion opportunities
- Oversee complex and high-value renewals, including executive-level client engagement
- Reduce renewal risk through proactive planning and standardized processes

Broker & Client Engagement
- Build strong relationships with key brokers, consultants, and enterprise clients
- Serve as an executive point of contact for high-priority accounts
- Partner with brokers and employers on strategic ICHRA plan design and long-term success
- Elevate the client experience through consistent, high-quality engagement
- Reinforce trust and credibility in the market through direct interaction and leadership presence

Account Health & Operational Excellence
- Define and track leading indicators of account health, retention risk, and growth opportunity
- Implement systems for proactive risk identification and recovery planning
- Ensure strong CRM hygiene, forecasting accuracy, and reporting consistency
- Minimize renewal compression and drive operational efficiency across cycles

Cross-Functional Leadership
- Partner with Sales on expansion strategy, account ownership, and deal support
- Collaborate with Client Success to ensure seamless implementation-to-AM handoffs
- Work closely with Product, Operations, and Finance to improve client outcomes and resolve systemic issues
- Provide feedback loops to leadership on market needs, product gaps, and client sentiment

What Success Looks Like
- Industry-leading gross and net retention rates
- High on-time renewal completion with minimal end-of-year compression
- Measurable expansion revenue driven through the AM team
- Strong broker and client satisfaction and trust
- A scalable, high-performing Account Management organization
- Clear visibility into account health, risk, and growth opportunities

Qualifications
- 8+ years of experience in account management, benefits consulting, HR tech, or insurance
- 3+ years of experience leading and scaling Account Management or Customer Success teams
- Proven track record of driving retention and expansion in a recurring revenue model
- Deep experience working with brokers and employer-sponsored benefits
- Strong executive presence and ability to engage senior stakeholders (clients and partners)
- Builder mindset with a passion for creating structure, process, and high-performing teams
- Exceptional communication, strategic thinking, and operational execution skills

About the Role: 

We're looking for a talented CRM & System Administrator to own, optimize, and scale the backbone of our go-to-market and customer operations. This isn't a "keep the lights on" role -- it's an opportunity to shape how a fast-growing healthtech company runs its most critical systems. If you're someone who gets excited about clean data, smart automation, and building systems that make people's jobs easier, you'll thrive here. 

About the Team: 

You'll sit at the intersection of Marketing, Sales, and Delivery Operations -- partnering with leaders across the business to solve real problems through technology. As an individual contributor, you'll have a high degree of ownership and autonomy, with direct visibility to leadership and the opportunity to shape how we scale our CRM and systems infrastructure as the company grows. 

What You’ll Do: 

Platform Management & Optimization 

• Maintain and optimize HubSpot Marketing, Sales, and Service Hubs 

• Build and refine workflows, automation, sequences, and lead routing 

• Create and manage custom properties, pipelines, dashboards, and reports 

• Conduct regular data audits to ensure accuracy, cleanliness, and governance 

Platform Ownership 

• Configure and maintain tickets, pipelines, SLAs, and customer feedback surveys 

• Partner with client-facing and back-office teams to streamline ticketing processes and improve response workflows 

• Build automation that enhances customer experience—ticket routing, escalation rules, satisfaction surveys, and follow-up sequences 

• Support campaign execution by building emails, landing pages, forms, and segmented lists 

Cross Functional Support 

• Collaborate with Marketing, Sales, and the Delivery Ops teams to translate business needs into scalable solutions 

• Train internal teams on HubSpot features, processes, and best practices 

Systems Integration & Technical Ownership 

• Manage integrations between HubSpot and other business systems 

• Troubleshoot technical issues, identify root causes, and implement long-term fixes 

• Work with internal teams and external vendors on system enhancements and API based integrations 

Reporting & Insights 

• Build dashboards and reports that provide visibility into funnel performance, customer lifecycle, and service operations 

• Track KPIs across marketing, sales, and service to support data driven decision-making 

• Recommend improvements to processes, automation, and data structure based on insights 

What You Bring: 

• 3–5 years of hands-on CRM administration experience, with deep HubSpot expertise in a B2B environment 

• Deep expertise in HubSpot workflows, automation, lifecycle stages, and lead/ticket management 

• Experience supporting Customer Success or Support teams using Service Hub 

• Strong command of CRM data structures, segmentation, and reporting 

• Experience managing integrations between CRM platforms and third-party business systems, including tools like Intercom and Jira 

• Comfort working with custom-coded elements including troubleshooting scripts, custom workflows, or API-based logic 

• A systems thinker who can translate ambiguous business needs into clean, scalable solutions 

• Excellent communication skills and the ability to simplify complex processes 

Bonus Points: 

• HubSpot certifications (Marketing Hub, Sales Hub, Service Hub)  

• Experience managing integrations between CRM platforms and third-party business systems 

• Background in healthcare, benefits, or a high-growth SaaS environment 

What Success Looks Like: 

A great HubSpot Administrator doesn't just maintain the system; they make it work harder for everyone. Success means a well-organized, scalable HubSpot instance built on clean, reliable data, smart automation that reduces manual work, and clear reporting that drives smarter decisions across marketing, sales, and service. 

Compensation: $92,000-$115,000

The Account Executive Role

As an Account Executive selling Individual Coverage Health Reimbursement Arrangement (ICHRA) to employers. Your primary objective will be to drive revenue growth by acquiring and retaining broker partnerships, who will partner with you to identify new employer opportunities. In addition, you will be responsible for identify employers who are interesting in ICHRA’s and working with their brokers, as needed, to close the deal. The following job description outlines the responsibilities and requirements for this role:

Responsibilities:

• Develop and execute a comprehensive sales strategy to establish and maintain relationships with health insurance brokers and employers in the target market.
• Generate leads through networking, referrals, and prospecting to build a robust pipeline of potential broker partners & employers.
• Conduct sales presentations, product demos, and trainings to brokers & employers on the benefits and features of ICHRA.
• Collaborate with marketing to develop and implement marketing campaigns that generate interest in ICHRA and drive lead generation.
• Negotiate sales contracts and pricing agreements with employers to close deals and ensure profitability.
• Provide exceptional customer service to employers and brokers to their satisfaction with ICHRA.
• Keep abreast of industry trends, regulations, and competitor activities to identify opportunities and threats.
• Monitor and report on sales performance to identify areas for improvement and adjust sales strategies accordingly.
• Lead and mentor junior sales executives to ensure they meet sales targets and effectively manage broker relationships.

Requirements:

• Bachelor's degree in Business Administration, Sales, Marketing, or related field.
• Proven track record of sales success for 3+ years in a B2B environment in the healthcare industry.
• In-depth knowledge of the health insurance brokerage industry, including brokers, carriers, and regulatory requirements.
• Excellent communication and interpersonal skills to build relationships with brokers and other stakeholders.
• Strong presentation skills to deliver compelling sales pitches and product demonstrations.
• Ability to work independently and collaboratively in a team environment.
• Strong problem-solving and decision-making skills to identify and resolve sales challenges.
• High level of organization and attention to detail to manage and document sales activities, pipeline progress, and contracts.
• Proficiency in MS Office and sales management software.
• Willingness to travel to meet with brokers & employers and attend industry conferences as needed.
• SaaS experience is a plus!

What it takes to join our team
At Take Command, we believe in three key traits that set up a foundation for success in all sales roles within our team:

• Coachability 
  • The health insurance industry is complex and constantly changing. We are looking for folks that are not only open to being coached to success but are able to take feedback and implement it quickly. The attitude of “Feedback is a gift” goes a long way!
• Work Ethic 
  • We are big believers in ‘‘Talent is overrated” and that those with True Grit will rise to the top quicker than those with an abundance of talent but fail to put in the necessary time to achieve their potential. You may  be familiar with Malcolm Gladwell's “10 000-hour rule,” asserting that the key to achieving true expertise in any skill is simply a matter of practicing, albeit in the correct way, for at least 10 000 hours. Do you have the hunger and desire to get to these 10,000 hours quicker than anyone else? 
• Attitude
  • Sales is full of setbacks and there will be more deals that don’t go your way, than close. Feeling comfortable failing with the attitude of “Failure is a steppingstone on the path to success” is what is needed to be successful in any sales role, especially in sales in a startup environment as we continue to learn from mistakes, iterate processes and continuously improve. We are looking for positive people to add to our team, that believe it isn’t success that leads to happiness, it’s happiness that leads to success.

Account Executive Salary: $105,000-$115,000 OTE ($60,000-$70,000 + $45,000 variable)

About the Role

Enterprise Operations exists to ensure Take Command can scale efficiently and reliably by owning the internal systems, data, execution, and partnerships that power the business. We design, operate, and continuously improve the company’s internal operating model so teams can move faster, make better decisions, and scale with confidence.

We’re hiring a Director of Data & Business Intelligence to be a foundational leader within Enterprise Ops — someone who can build the data and BI muscle the company needs today while shaping how data, automation, and insight support scale over time.

This role is both hands-on and strategic. You’ll start by building core BI assets yourself, alongside a small team, and evolve into a leader who defines how data is governed, interpreted, and used across Operations, Finance, Product, and Go-To-Market teams. You’ll also play a key role in identifying opportunities to reduce manual work through automation and applied AI.

What You’ll Do

• Own the company’s business intelligence strategy, including KPIs, dashboards, and executive reporting

• Build and maintain core BI assets hands-on early (models, dashboards, metric definitions)

• Establish clear, lightweight data governance: definitions, documentation, and change management

• Partner closely with Engineering to ensure reliable, well-understood data flows without owning core platform infrastructure

• Design how insights are delivered so they drive action, not just visibility

• Identify opportunities to automate manual reporting, reconciliation, and operational workflows, including the thoughtful use of AI where it adds leverage

• Act as a strategic thought partner to leadership on performance, growth, and operational efficiency

• Gradually build and lead a small, high-impact data team

What You’ll Own

• Company KPIs and executive reporting

• Standard dashboards used across Operations, Finance, Support, and GTM

• Metric definitions and the data dictionary

• The BI and analytics layer (e.g., Looker, semantic models, reporting tools)

• Governance processes for introducing or changing metrics

• Identification and prioritization of automation and AI opportunities within data and reporting workflows

How You’ll Work (Enterprise Ops Principles in Practice)

• Build things that help everyone: You design data systems and reporting that scale beyond yourself and make the whole company better

• Seek clarity over comfort: You notice when numbers don’t line up, reduce ambiguity, and push toward clear decisions

• Own the outcome: You step in and move things forward, even when ownership or the path isn’t obvious

• Be technically grounded and customer-true: You understand the data, systems, and domain deeply and use that judgment to do right by the business and customers

• Stay curious and open-minded: You explore new approaches (including AI and automation), invite correction, and keep improving without losing attention to detail

Who You Are

• 8–12+ years experience in data, analytics, BI, or related fields

• Experience building or rebuilding a BI function in a growing company

• Comfortable operating as a player-coach — strategic, but willing to get into the weeds

• Strong business intuition; you understand how operational, financial, and go-to-market metrics fit together

• Confident influencing senior stakeholders and navigating ambiguity

• Pragmatic and execution-oriented — you know when “good enough” unlocks momentum

Nice to have

• Experience reducing manual operational work through automation or AI

• Background in fintech, healthcare, benefits, or other regulated environments

• Experience with modern BI stacks and semantic layers

What Success Looks Like

• Leadership trusts and uses a consistent set of metrics to run the business

• Teams spend less time reconciling numbers and more time acting

• Manual reporting and operational overhead decrease through automation

• BI is seen as a strategic partner within Enterprise Ops, not a reporting queue

• The data foundation is strong enough to scale without rework

Compensation: $158,000-$178,000 + 15% bonus

First 3 Months Deliverables

Month 1 — Clarity, Baseline, and Leverage Points

• Agreed-upon list of core company KPIs

• Documented definitions for the highest-impact metrics

• Inventory of existing dashboards, reports, pipelines, and manual data processes

• Identified 2–3 priority data or reporting issues to address first

• Identified top manual workflows (reporting, reconciliation, ops support) suitable for automation

• Initial draft of a data dictionary

Signal: understands the business, the data, and where automation will matter.

Month 2 — Standardization, Early Wins, and Automation Pilots

• Standardized definitions for core operational, financial, and GTM metrics

• 1–2 improved or newly standardized dashboards in active use

• Reduction or consolidation of duplicate/conflicting reports

• Published v1 data dictionary with named owners

• At least one manual workflow reduced or automated (reporting, reconciliation, or data QA)

• Defined lightweight process for requesting or changing metrics/reporting

Signal: delivers visible value and starts reducing operational drag.

Month 3 — Trust, Operating Model, and Scale Readiness

• Finalized core KPI set actively used by leadership

• Executive reporting that ties together Ops, Finance, and GTM performance

• Established data governance rhythm (cadence, approvers, documentation)

• Clear roadmap for:

  • BI improvements

  • Data quality enhancements

  • Further automation and applied AI opportunities

• Defined team operating model (roles, responsibilities, near-term hiring)

Signal: the foundation is solid, trusted, and ready to scale.

Enterprise Account Executive

The Enterprise Account Executive Role

As an Enterprise Account Executive, you will be responsible for driving revenue growth by selling Individual Coverage Health Reimbursement Arrangements (ICHRA) to mid-market and enterprise employers through strategic broker partnerships and direct enterprise engagement.

In this role, you will manage complex, multi-stakeholder sales cycles, build relationships with national and regional brokerages, and work directly with C-suite and senior HR/benefits leaders at large organizations. You will partner closely with brokers to identify enterprise opportunities while also proactively sourcing and developing strategic employer relationships.

This role requires a consultative, strategic sales approach and the ability to navigate large organizations, educate stakeholders on the benefits of ICHRA, and drive consensus across multiple decision-makers.

Responsibilities

• Develop and execute a strategic enterprise sales plan focused on acquiring and expanding relationships with large employers and national/regional broker partners.

• Identify and pursue enterprise employer opportunities through broker networks, outbound prospecting, and industry relationships.

• Manage complex sales cycles involving multiple stakeholders including HR leaders, finance teams, benefits consultants, and executive leadership.

• Deliver executive-level sales presentations, product demonstrations, and educational sessions to brokers and enterprise employer decision-makers.

• Partner with brokers to position ICHRA as a strategic benefits solution for large employers transitioning from traditional group health plans.

• Build and maintain long-term strategic relationships with key brokerages, consulting firms, and enterprise clients.

• Collaborate with marketing to support enterprise-focused campaigns, events, and thought leadership initiatives that generate qualified opportunities.

• Lead contract negotiations and pricing discussions for enterprise deals, ensuring mutually beneficial outcomes while maintaining profitability.

• Serve as a trusted advisor to enterprise clients and broker partners throughout the evaluation, implementation, and expansion process.

• Stay informed on industry trends, regulatory developments, and competitive landscape to effectively position ICHRA in complex employer environments.

• Maintain accurate pipeline visibility and forecast enterprise deals within CRM systems (HubSpot).

• Partner with internal teams including sales leadership, partnerships, product, and customer success to ensure smooth deal execution and long-term client success.

Requirements

• Bachelor’s degree in Business Administration, Sales, Marketing, or a related field.

• 10+ years of B2B sales experience, with at least 2+ years selling to mid-market or enterprise organizations.

• Proven track record of closing complex, high-value deals with longer sales cycles.

• Experience working with or selling through health insurance brokers, benefits consultants, or HR leaders.

• Strong understanding of the health insurance or employee benefits ecosystem, including brokers, carriers, and regulatory dynamics.

• Exceptional executive communication and relationship-building skills.

• Ability to navigate large organizations and multi-thread deals across multiple stakeholders.

• Strong presentation and consultative selling skills.

• Highly organized with the ability to manage large pipelines, long sales cycles, and strategic accounts.

• Experience using CRM platforms (HubSpot preferred) and standard sales tools.

• Willingness to travel to meet with brokers, enterprise clients, and attend industry conferences.

• Employee benefits experience strongly preferred.

What It Takes to Join Our Team

At Take Command, we believe in three key traits that set a foundation for success across all sales roles:

Coachability

The health insurance industry is complex and constantly evolving. We look for individuals who actively seek feedback, implement it quickly, and view coaching as a pathway to continuous improvement. The mindset that “feedback is a gift” goes a long way.

Work Ethic

We believe that grit and persistence outperform raw talent. Those willing to put in the work, stay disciplined, and continually refine their craft will rise the fastest. As Malcolm Gladwell’s 10,000-hour rule suggests, expertise is built through consistent and intentional practice. We value individuals who bring the hunger to put in the hours required to master their craft.

Attitude

Sales inevitably comes with setbacks. Enterprise sales especially requires resilience, patience, and persistence. We look for individuals who embrace challenges, maintain a positive mindset, and believe that failure is simply a steppingstone toward success. At Take Command, we believe happiness fuels success — not the other way around.

Compensation

Enterprise Account Executive Salary:
$125,000 – $150,000 base + variable compensation (OTE dependent on experience)