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Chief Technical Officer

First Dollar
Austin, TX
  • Expired: May 26, 2022. Applications are no longer accepted.

First Dollar is building a health wallet for modern, member-driven plans. We power software-defined benefits that people love to use. Founded by a repeat founding team with prior exits to athenahealth and Expedia, First Dollar has ambitious plans to make healthcare work better by improving how people pay for it.

We're looking for a CTO to join our executive team. Reporting to the CEO and partnering with our co-founder & CPO, you'll be responsible for leading our technical strategy and continuing to expand our platform and infrastructure to meet the needs of our customers. At the nexus of fintech and healthcare, First Dollar's engineering team builds critical systems that need to work when people need them most.

In this role, you will:

  • Work closely with C-Suite stakeholders to develop and communicate a long-term, multi-horizon roadmap spanning 3-5 year time frame
  • Be a companion for the go to market strategy by communicating business impact and ROI of technical solutions
  • Lead the technical strategy of the roadmap at First Dollar and ensure release excellence
  • Work with product and the other functions of the business to prioritize features and requests based on estimated implementation costs versus business value
  • Inform and provide feedback to our senior engineers on the architecture of our system, ensuring we are rapidly meeting the needs of today with an eye towards the future
  • Represent First Dollar's engineering team in the sales cycle, interfacing directly with prospects and customers to help them understand our product and technology
  • Be a key stakeholder in setting the bar for security and compliance at First Dollar, including owning the technical portions of our compliance processes
  • Lead the procurement and evaluation process of key vendors, ensuring First Dollar is making sound multi-year decisions with the platforms we choose to partner with
  • Work with our VP of Engineering to retain and grow our engineering team, including recruiting great engineers to meet the demands of the business

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

  • Have experience in payments technology
  • Have previously led engineering teams for growth startups through Series C and beyond
  • Enjoy owning and understanding the details of our technology, but can yield autonomy of the implementation to our senior engineers
  • Enjoy being the external face of our engineering organization for our customers, prospects, and investors

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.
  • Healthcare 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. If you prefer to work from your home, we can accommodate that for most positions and locations across the United States via WeWork.

First Dollar


Austin, TX
78716 USA



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