Finance Director



Remote (USA timezones)

About the role:

Scott’s Cheap Flights is a bootstrapped, profitable, travel tech startup that is on a mission to help people travel and experience the world. Our 55+ person team is fully distributed and has been for the past six years.

As the Finance Director, you will be accountable for managing both tactical and strategic aspects of the business. You will play a key role in supporting our growth across the entire organization. This role is the right fit for you if you aren’t afraid to get your hands dirty with some “junior” tasks all while stepping into a strategic role, owning our financial model, and working alongside leadership to make thoughtful financial decisions.

In the short term, you will:

  • Partner with an external finance firm to manage, maintain, and align our financial model
  • Define, and implement tools to support, and manage expenses and credit cards
  • Onboard vendors, contractors, and pay invoices
  • Reconcile monthly finances for accounting
  • Partner with the Data team to validate and identify the necessary reports and dashboards for the team to have access to
  • Lead sales tax, including, but not limited to, responding to inquiries from states, managing Avalara, and keeping registrations up to date
  • Define, implement, and manage functional budgets

In the long term, you will:

  • Own, iterate, and report on our financial model
  • Monitor and report on disputes and fraudulent charges
  • Streamline and simplify our accounts payable process, including implementing new tools
  • Work with outside counsel on corporate taxes, including R&D tax credits
  • Lead training for the entire organization on the business model and metrics.
  • Identify and manage a process to provide transparency to the organization on our model and metrics to motivate and support the team in doing their best work.
  • Partner with People Operations to scale our compensation philosophy and processes
  • Work closely with Marketing and Product on things like pricing, marketing spend, and LTV:CAC
  • Support the development of commission programs for advertisement and partnership sales
  • Manage KPI’s, reporting to leadership on a regular cadence

What you know:

  • You have excellent written and verbal communication skills.
  • You have experience working within a B2C model, ideally a subscription business, but B2B doesn’t intimidate you.
  • You’re an expert in FP&A, budget management, and GAAP accounting.
  • You love working both independently but also with a highly cross-functional team.
  • You can explain complex topics to a broad audience and enjoy teaching.
  • You’re excited to own the whole function and unafraid to get your hands dirty.
  • You have a bias towards action and are comfortable working through an ambiguous situation.
  • You get excited by improving processes, automating work, and finding “hacks” to make your and others' lives easier.
  • You have experience managing sales tax and registrations.


  • You’ve worked in a startup and understand the pace and broad scope of responsibilities.
  • You have experience with Quickbooks or other accounting software.
  • You have experience with outside fundraising. We’ve been bootstrapped for the past seven years and have no current intention of changing this, but we’re not closed-minded to the idea of bringing on outside capital.

Why you might love working here:

  • The annual salary for this position is $142,065 + stock options.
  • 100% remote work environment, so go ahead and bring your dog to work or wear your PJ's to the office!
  • $500/Quarter Remote Work Stipend
  • Open vacation policy, with a 3-week minimum!
  • Comprehensive health, vision, and dental insurance
  • 401(k) with a 5% match
  • Up to 12 weeks of paid family leave
  • No Meeting/Flex Fridays
  • Meetup stipend when you cross paths with a co-worker
  • Continuing education & development reimbursement
  • Yearly team retreat (In 2021, we went to Cabo San Lucas. In March, we went to Charleston.)
  • Challenging problems to solve and an awesome team to collaborate with every single day

A few things to note:

  • We have a company onsite at Zion National Park from September 5-9. We would love for you to join us, if possible.
  • While you will collaborate with a cross-functional team and have external support, you will be the only dedicated finance & accounting team member internally. We do not have plans to hire a second person to this team in the near future (12-18 months)

Who you’ll work with:

We want you to bring your authentic self to work every single day. We accept you for who you are and consider everyone on an equal opportunity basis without regard to ancestry; age; appearance; color; gender identity and/or expression; genetics; family or parental status; marital, civil union, or domestic partnership status; mental, physical, or sensory disability; national, social or ethnic origin; past or present military service; sexual orientation; socioeconomic status; race; religion or belief.

‍If you require reasonable accommodation or assistance for any part of the interview and employment process, please contact us at careers@scottscheapflights.com and let us know the nature of your request.