Head Of Strategic Finance, GTM

We’re looking for a high-impact finance leader to join Fleetio’s Finance & Strategy team as the Leader of GTM Strategic Finance. This role will serve as a strategic partner to our Sales, Marketing, and Customer Experience organizations, focusing on driving smarter decisions, optimizing investment allocation, and enhancing execution capabilities across our GTM engine. A little about us…Fleetio is a modern software platform that helps thousands of organizations around the world manage their fleet operations. Transportation technology is a hot market and we’re leading the charge, with raving fans and new customers signing up every day. We raised $450M in Series D in June of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

More about our team and company:

Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU Our careers page: https://www.fleetio.com/careers Who you are The ideal candidate brings deep experience in B2B SaaS or enterprise GTM motions, combines analytical rigor with business acumen, and thrives in high-growth, fast-moving environments. This leader will help shape how we scale efficiently and make data-driven decisions that accelerate revenue growth and improve return on investment. Your impact Strategic Business Partnering Serve as the senior finance partner to Sales, Marketing, and Customer Experience leadership, providing insight, challenging assumptions, and influencing key decisions that drive top-line growth and operating efficiency Incorporate strategic priorities into rolling GTM financial forecasts and operational outcomes, ensuring alignment between GTM strategy and company objectives Performance Management & KPIs Build and refine performance management frameworks across teams and strategic initiatives (leading and lagging indicators of product adoption, customer engagement) Establish aggressive but achievable revenue targets, and partner cross-functionally to track progress, diagnose performance gaps, and enable rapid course correction GTM Efficiency & Economics Own GTM efficiency metrics and reporting, including CAC payback, LTV/CAC, segment-level profitability, and retention economics Deliver actionable insights to improve ROI on customer acquisition and expansion investments Strategic Alignment & Cross-Functional Collaboration Act as the connective tissue between Finance and GTM teams, working closely with Revenue Operations, Product, and Engineering to ensure that investment and resource allocation support our highest growing opportunities Lead cross-functional strategic projects that drive commercial effectiveness and scalable growth Process Improvement & Scalability Identify and operationalize improvements in forecasting, planning, and performance measurement Build systems and processes that improve decision velocity, scalability, and financial transparency across GTM functions. Your experience 6+ years of experience in B2B / Enterprise software investing, Strategic Finance, FP&A, or Business Operations roles, preferably supporting or working closely with GTM teams. Strong command of GTM metrics (ARR, pipeline, conversion, retention, LTV/CAC, CAC payback) Proven ability to translate data into narrative and influence senior executives. Track record of driving measurable improvements in revenue productivity, investment efficiency, or forecasting accuracy. High EQ, strong communication skills, and a collaborative leadership style Benefits Multiple health/dental coverage options (100% coverage for employee, 50% for family) Vision insurance Incentive stock options 401(k) match of 4% PTO - 4 weeks (increases at year two!) 12 company holidays + 2 floating holidays Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid) FSA & HSA options Short and long term disability (short term 100% paid) Community service funds Professional development funds Wellbeing fund - $150 quarterly Business expense stipend - $125 quarterly Mac laptop + new hire equipment stipend Fully stocked kitchen with tons of drinks & snacks (BHM only) Remote working friendly since 2012 #LI-REMOTE Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need. This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will. If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.