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

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)

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)