VP of Sales

Remote Full TimeAustin, TX, United States (Remote)First Dollar

First Dollar is a technology company that builds healthcare benefits infrastructure. Our health wallet platform gives benefit providers the tools they need to launch tax-advantaged accounts, supplemental benefits, or whatever they dream up next. Founded by a repeat founding team with prior exits to athenahealth and Expedia, First Dollar has ambitious plans to make healthcare better by improving how people pay for it.

We’re looking for a VP Sales to join our executive team. Reporting to the CEO and partnering with our co-founder & CPO, you’ll be responsible for leading our sales organization. You’ll be tasked with scaling the sales organization for a post product market fit Series A company. We have a validated ideal customer profile, run a surprisingly robust sales process for our stage, and believe there to be significant headroom given current pipeline & market demand. For the right candidate, this opportunity is a career maker.

You will:

  • Lead the sales organization, including our existing two senior sales executives. You’ll be immediately responsible for driving immediate expansion of this team in early 2023.
  • Deliver meaningful revenue growth to build upon an existing pipeline and defined ICP.
  • Develop a team of senior executives capable of full cycle enterprise software sales into healthcare and employer benefits verticals (health plans, TPAs, PEOs, HRIS/payroll, etc).
  • Hold the team accountable to an airtight sales process.
  • Engage with key organizational stakeholders to deliver market intelligence, fostering a continuous feedback loop.


You’ll be a good fit for this role if you:

  • Are a critical thinker with the ability to engage and inspire a new and growing team
  • Can demonstrate grit, team focus, and results oriented mentality
  • Have sales leadership experience in a healthtech or fintech startup.
  • Have demonstrated consistent performance in a high growth enterprise software startup environment.
  • Have experience with mentorship and proven ability to build and coach a team.
  • Have a strong understanding of healthcare finance and economics, with payor experience preferred


Benefits include:

  • Compensation: Competitive salary and meaningful equity. We take a data-driven approach to our compensation strategy so all employees are paid competitively and equitably.
  • Tax Advantaged Vehicles: Tax advantaged vehicles, including a 401(k) plan and a Health Savings Account (HSA) for eligible medical plans. We also provide a generous contribution to the HSA.
  • Benefits: Excellent medical, dental, and vision insurance. We cover 100% of employee medical premiums and 50% of family member medical premiums for employees enrolled in the HDHP. Plus, all employees receive a free One Medical membership.
  • Work-Life Balance: Progressive policies to support work/life balance, like our flexible paid time off and parental leave program.
  • Culture: A transparent and supportive culture. We keep employees up-to-date through monthly all-hands meetings, sprint demos, and regular check-ins where we discuss company goals, key updates, and more.
  • Office: A beautiful, convenient, and state-of-the-art office in downtown Austin for those who prefer an office setting.

Whenever possible, First Dollar wants to provide our team with the flexibility to work in the location that makes the most sense for them. For those that prefer an office setting, this role may be based in our Austin location with flexibility to work from the office/remote. If you prefer to work from your home, we can accommodate that for most positions and locations across the United States.

To apply for this job please visit apply.workable.com.

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