Senior Director (Head), Finance - Distributed / Remote

The Position

Do you thrive in a fast-paced startup style environment? Do you enjoy working on a small innovative team that is passionate about helping people solve problems? Are you a critical thinker with a love for innovative and scrappy solutions who loves to roll up their sleeves? We are seeking an experienced and highly results-driven Head of Finance to join our leadership team, and if that description resonates with you, you could be an excellent fit for our company.​

This hybrid role of hands-on doer and leader will oversee the strategy, operational processes, reporting, and team building needed to drive growth and decision making for both our B2B and consumer facing businesses. This senior leadership role will report directly to our President, and is expected to provide thoughtful leadership and support across our accounting and finance functions. You should also play a significant role shaping the company’s strategic planning. 

This is an executive level role, with commensurate responsibility and compensation. The anticipated salary range is $170,000 to $200,000 in addition to significant equity. Specific compensation will be determined based on your level of experience. We are a fully distributed team.

What You'll Do

Ultimately, you’ll be assisting an innovative travel start-up in reaching global scale by identifying opportunities to grow the business, maintaining financial rhythm and structure, communicating financial results and trends, and modeling complex scenarios. As Head of Finance you will define and drive financial performance, strategy, and execution. This role requires thought leadership and business partnership with the broader senior leadership team to drive performance, strategy and execution; we expect you to be a careful steward of the business and treat it as your own.

Key responsibilities will include:

  • Build and improve financial models that enable effective decision-making regarding the company’s revenue growth strategy, cost structure, and capital expenditures
  • Own the company’s three statement financial model
  • Develop ad-hoc analyses which enable strategic decision making and maximize ROI
  • Lead the planning processes including annual operating plan and rolling forecasts. Build calendar and milestones, target setting, and processes for planning. Track and report on performance relative to plan
  • Develop and communicate key financial and operating metrics to create transparency into financial performance and inform strategic and operational decisions
  • Communicate financial performance and trends simply and effectively to senior leadership, and board of directors; deliver insightful, actionable analysis beyond just reporting results
  • Serve as a leader in a potential fundraise, particularly by solidifying the long term financial model and supporting investor facing materials 
  • Improve operating teams’ understanding of financial levers, planning drivers, and performance with thoughtful and transparent analysis and partnership
  • Provide strategic thought leadership and analysis to identify actionable opportunities across the business 
  • Leverage systems, scalable processes and automation to increase time spent on value-add activities
  • Build and develop a high performing organization that is both a magnet for and a feeder of talent across the organization

What You Have

  • Minimum 10 years of experience, which can be a mix of relevant experience across finance and accounting
  • Experience leading FP&A function but coupled with commensurate accounting knowledge
  • Bachelor’s degree required. MBA preferred
  • Must possess excellent analytical, financial modeling and presentation skills with the ability to analyze raw data, draw conclusions, and develop actionable recommendations
  • Prior success in a scaling startup, preferably having led a Finance function through from early to mid stage
  • A knack for process optimization, with a strong ability to map and implement systems
  • Entrepreneurial spirit, with a high level of energy and unrelenting drive
  • Performance-oriented, with an interest in taking ownership of situations and a desire to roll up your sleeves
  • Previous experience in tech companies serving both businesses and consumers is a significant advantage
  • Experience building comprehensive reporting and dashboards and driving data-driven optimization and investment decisions
  • Demonstrated ability to build, mentor and develop a high performing team. 
  • A passion for building relationships with your team, other internal groups, and especially customers
  • Exceptional written and verbal communication skills, including handling virtual meetings, basic presentations, and managing Slack chatter
  • Tech savviness, and innate curiosity towards finding solutions that streamline processes or improve the day-to-day of your team
  • Strong interest and knowledge of travel industry, airline industry and/or credit card loyalty programs
  • Flexibility - we’re growing and evolving and we’re looking for folks to grow and evolve with us


Here at we’re devoted to bringing simplicity and clarity to a system that is intentionally opaque. And unlike traditional travel agencies, or even online booking services like Orbitz, Kayak, & Google, we don’t take a fee or commission from the airlines when someone books a flight.

Instead, is on the  side of our customers — we work directly for them! We’re an ally that uses our expertise and technology to ensure people travel better, and are never taken advantage of.

Our proprietary algorithm crawls the many hidden corners of the Internet, including those hard-to-search airline award websites to discover the clearest path to maximizing the value of loyalty and credit card points.

Benefits & perks

Join our growing team! Here at we believe in taking care of our team, so that our team can take care of our customers. All employees are offered the following:

  • Competitive salaries and meaningful equity
  • Comprehensive health care coverage
  • A 100% distributed workforce, so you can contribute from wherever you prefer
  • An open vacation policy, with a minimum of 15 days off each year
  • Team trips and outings

Given the nature of our business, we anticipate that all team members will be traveling from time to time, including company trips and off-sites, or meeting with strategic partners. As such, being fully vaccinated against COVID-19 is a condition of employment at We’ll ask you to send us a copy of your vaccination card in advance of your first day.

We respect the individual needs of employees and are an equal opportunity employer. Positions are remote, but you must be eligible to work in the United States.

Sound like a good fit? Let’s chat.