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