Enterprise Account Executive

Enterprise Account Executive

Dallas, Texas

Take Command is a start-up on a mission to improve the healthcare system, starting with health insurance. Pragmatically speaking, we help employers reimburse employees for individual insurance instead of offering a traditional one-size-fits-all group plan. We believe this model can empower employees (when they have the right support) to be savvy healthcare consumers and have a transformative impact on the entire healthcare system.

Let's be honest—health insurance is usually a confusing, frustrating, and even emotional experience for people. We want to fix that with a new model, great technology, and a superior user experience. We have made a great start, but we need your help to fully realize our long-term vision.

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)

We're excited to build a team and culture that reflects our values! We offer competitive pay and health benefits to share with this position.

• A generously funded ICHRA for medical, dental, and vision premiums and medical expenses. You get to use our own product and we think that's so exciting and rare!
• Unlimited personal vacation in addition to regular company holidays.
• 401(k): 90-day eligibility for 4% match that vests over 4 years with a one year cliff!
• We have two beautiful offices in Richardson, Texas (City Line) and Austin, Texas. The kitchen is well-stocked and we've designed the space to have lots of different areas to work--lounge on the couch, stand near your colleague at a kiosk desk or hole up in one of our phone rooms!
• Competitive parental leave for new parents.
• Up to two paid days of Paw-ternity leave. We recognize that pets are family too - and supporting life outside of work (including four-legged members) matters!
• ClassPass corporate membership with access to over 73,000 fitness and wellness options.
• Flexible on where you work – we believe in the power of connecting with intention! While we hope to see you around the office on a regular basis, you also have the ability to work from home some when you need to get focus work done.

More About Us

We secured our Series B funding in 2023 and are thrilled to be able to expand our team. Despite being a small startup in a land of health insurance giants, we're the recognized industry leader for what we do (health insurance reimbursements) and passionate about bringing it to market because we know we can help fix a broken system and improve our clients' wellbeing and health outcomes. We've been featured in The New York Times, The Wall Street Journal, The Dallas Morning News, and other national healthcare publications and are excited about our growth opportunities.

Take Command knows diversity and inclusion among our teammates is integral to our company's success and growth. Our vision is to recruit, develop, and retain the best team from a diverse candidate pool. This has mostly been about us, but we'd love to hear from you--we can't wait to hear your story!

*Take Command is an equal opportunity employer! We celebrate diversity and are committed to creating an inclusive environment for all employees.