Chief of Staff, Head of Product Strategy & GTM

Fleetio

13d•Remote

About The Position

A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide 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 our Series D funding round in March 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 About Fleetio & Auto Integrate Fleetio is a modern fleet operations platform used by thousands of organizations worldwide to manage vehicles, equipment, and drivers. Auto Integrate, acquired by Fleetio in 2025, is a leading global maintenance authorization network that supports fleets that choose to outsource their service, maintenance, and repair needs. The business is managed by a small, global team within Fleetio, combining the resources of a scaled SaaS company with the agility of a niche market leader. Who you are We are hiring a senior leader to serve as the chief of staff to the business unit president and to own product strategy and go-to-market for Fleetio’s Auto Integrate proprietary maintenance authorization network. This role reports to the president of the business unit and will operate in a small, entrepreneurial environment while being responsible for enhancing and appropriately pricing a service that supports many of the US’s largest fleets. You will support end-to-end product strategy, monetization, and go-to-market for all Auto Integrate products. You will partner closely with Sales, Product, Engineering, Finance, and Operations leadership to set the multiyear vision, define and execute pricing and packaging changes, and drive adoption of all new product functionality in the market. You must be located in Eastern Standard Time.

Requirements

7-10+ years of experience in a network business, B2B SaaS and/or payments across product, product marketing, strategy, or pricing/monetization; with meaningful experience successfully enhancing pricing and GTM decisions for a material product line.
Proven track record owning product strategy and roadmap for a material product line or business unit, ideally with network or transaction-driven models.
Deep pricing expertise, including usage-based models, transaction economics, and multiproduct monetization.
Strong product marketing and GTM experience; able to craft compelling narratives, launch products at scale, and enable sales to win in competitive markets.
Exceptional analytical and financial acumen, with the ability to build and interpret models, evaluate tradeoffs, and tie product decisions to P&L impact.
Must be located in Eastern Standard Time.
Entrepreneurial, low ego operating style, comfortable with ambiguity, and excited to run fast in a rapidly scaling business.

Nice To Haves

2+ years experience at a top-tier consulting firm advising on areas of product strategy and pricing preferred.
Experience in fleet, logistics, mobility, or other “physical economy” verticals is a plus, but not required.

Responsibilities

Define and evangelize the 3-year growth strategy for Auto Integrate, including segment, use case, and geographic expansion.
Lead pricing, packaging, and monetization strategy to appropriately balance customer value delivery with revenue maximization, while remaining simple and scalable.
Support product marketing, positioning, and go-to-market motions to drive new logo acquisition, product activation, and expansion/upsell.
Prepare materials and recommendations for executive team and board-level discussions on business unit strategy, including product, pricing, and market expansion.
Define and maintain executive dashboards, KPI frameworks, and leading indicators to monitor product performance, pricing impact, and GTM effectiveness.
Support setting the product vision and multiyear roadmap for Auto Integrate, working with executive leadership and Product to align on strategic bets and sequencing.
Define target customer segments, use cases, and vertical focus; clarify where we win versus competitors and adjacent solutions in fleet, logistics, and broader B2B SaaS.
In partnership with the product team. ensure market, customer, and competitive insights are translated into clear product requirements, investment cases, and prioritization frameworks.
Support ownership of the Auto Integrate and payments business model, including 3-year financial plans, scenario analyses, and investment cases for new initiatives.
Own the quantitative analysis underpinning pricing and packaging decisions for Auto Integrate, using customer cohort data, product usage, and transaction-level patterns to identify opportunities to improve revenue, margin, and adoption.
Build and maintain robust pricing and monetization models (e.g., unit economics, CLTV, payback, elasticity, sensitivity analyses) that directly inform changes to list pricing, discounting guardrails, value metrics, and packaging constructs.
Mine product and payments telemetry (e.g., active usage, feature adoption, TPV, invoice/transaction volume, interchange yield) to design and iterate on usage-based and transaction-based monetization levers.
Create clear, executive-ready pricing and monetization reporting: track and communicate key KPIs (ARPU, attach rate, adoption/activation, gross margin, churn/expansion by price point) and proactively flag risks and opportunities.
Maintain a source-of-truth pricing and packaging framework, ensuring that analytical logic, assumptions, and metrics are well documented, reproducible, and easy for stakeholders to understand and apply.
Support product marketing for Auto Integrate, including positioning, messaging, narrative, and sales enablement across self-serve, inside sales, and field motions.
Partner with Product to ensure launches and roadmap investments are deeply tied to monetization opportunities and measurable business outcomes.
Own integrated go-to-market plans for major launches and campaigns, partnering with Sales, Marketing, and Partnerships to hit pipeline, activation, and revenue targets.
Drive adoption and growth programs to increase Auto Integrate participation among existing Fleetio customers and expand usage within current accounts.

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)