Head of Finance

At TripWorks, we believe work should be meaningful, fast-paced, and a little bit adventurous. We're a fully remote team powering the experiences industry and helping tour, attraction, and activity operators grow their businesses with tools that actually work.

We value progress over perfection, action over ego, and results over buzzwords. Our team is small, scrappy, and serious about helping our customers win.

We're looking for a Head of Finance to partner directly with the CEO and leadership team to guide the company's financial strategy, planning, and decision making. This role combines strategic leadership with hands-on execution. You will help leadership allocate resources, improve visibility into performance, and ensure the company scales responsibly as we grow.

You will serve as the financial backbone of the company, connecting product, go-to-market, and operations teams through clear reporting, forecasting, and data-driven insight. We are especially interested in leaders who embrace AI and modern analytics tools to drive faster insights, improve forecasting accuracy, and automate financial processes as the company scales.

What You'll Do

• Partner directly with the CEO and leadership team to guide financial strategy, planning, and decision making.
• Lead company-wide financial planning, budgeting, forecasting, and long-term financial modeling.
• Build clear financial visibility into company performance through reporting, dashboards, and analytics.
• Partner closely with go-to-market leadership to improve visibility into pipeline, bookings, revenue, and retention while supporting forecasting and performance tracking.
• Collaborate with product and engineering leadership to evaluate investments, prioritize initiatives, and guide resource allocation across the business.
• Use AI and modern analytics tools to automate workflows, improve forecasting accuracy, and generate insights that drive better business decisions.
• Oversee financial operations including accounting oversight, reporting, and the development of scalable financial processes and controls.
• Maintain visibility into payment processing economics including fees, interchange, and margins, and help optimize the company's payment and revenue structure.
• Own and improve the finance systems and reporting infrastructure across tools such as QuickBooks Online, Stripe, HubSpot, Brex, Justworks, and AWS QuickSight.
• Serve as the financial partner across teams, translating data into actionable insight that drives accountability and informed decision making.
  
  

What You Bring

• 7+ years of experience in finance, FP&A, strategic finance, or related roles in high-growth technology companies.
• Experience partnering with founders or executive teams to support strategic decision making.
• Strong financial modeling, forecasting, and analytical skills.
• Experience building financial reporting that connects finance, go-to-market, and product performance.
• Familiarity with modern finance and data tools such as QuickBooks Online, Stripe, HubSpot, and business intelligence platforms.
• Experience using AI or advanced analytics tools to improve reporting, forecasting, or financial processes is a plus.
• Understanding of SaaS, marketplace, or payments-based business models.
• Experience analyzing payment processing economics such as fees, interchange, and margins is a plus.
  
  

What Makes You a Great Fit

• Strategic thinker who can translate financial insight into clear business decisions.
• Comfortable operating in a fast-paced startup environment with evolving priorities.
• Strong collaborator who works effectively across product, engineering, go-to-market, and operations teams.
• Analytical and curious, with a desire to deeply understand how the business works.
• Comfortable leveraging modern tools, automation, and AI to improve workflows and surface insights.
• Hands-on and pragmatic, able to move between strategic thinking and operational execution.
• Clear communicator who can simplify complex financial concepts for cross-functional teams.
• High integrity and accountability when handling sensitive financial information.
  
  

Why Join TripWorks?

• Remote-first with flexibility. We are a fully remote team with a hybrid option for those based near our New York City office.
• Values-driven culture. Our team operates with a strong sense of ownership and collaboration. We roll up our sleeves and get things done, support each other to win together, push beyond the status quo, and think like operators who care deeply about our customers' success.
• 401(k) with company match. TripWorks offers a 401(k) plan with a 3.5 percent company match.
• Flexible PTO. We trust employees to take the time they need to recharge and maintain balance.
• Team connection. We host a full-company retreat each year and create opportunities for teammates to connect in person throughout the year. Last year the team gathered in San Diego.
• High-impact role. Join a small, talented team where your work directly influences company strategy, product direction, and growth.