Jobs at Fleetio

Lead corporate FP&A for a multi-entity, high-growth SaaS business. Own board and executive reporting, consolidated financials, intercompany reconciliations, and acquisition integration. Drive process improvements, reporting automation, and FP&A systems modernization. Manage and develop one FP&A team member and partner closely with accounting and executives to ensure accurate, decision-useful financial narratives.

Build and iterate on AI-enabled, customer-facing product experiences across a Rails backend and React/TypeScript frontend. Design APIs, database-backed workflows, AI integration points, prompts, evaluation and observability; prototype and harden features; collaborate with Product, Design, Data, and Customer Success; mentor engineers on front-end and AI tooling.

Drive new business for Fleetio by prospecting and closing mid-market customers via consultative sales, web demos, strategic outreach, negotiation, and cross-functional collaboration to grow ARR.

Drive new business sales to government and education customers by prospecting, qualifying, and closing complex SaaS deals. Develop territory plans, navigate multi-stakeholder procurement processes, run POCs, collaborate with internal partners, and consistently meet ARR targets through data-driven ROI selling and repeatable sales strategies.

Manage strategic relationships with high-value enterprise fleet customers to drive expansion ARR and NRR through upselling, cross-selling, renewals, product demos, and partnership with Customer Success; travel to customer sites as needed to identify growth opportunities.

Own retention, expansion, and net revenue growth for a portfolio of mid-market Fleetio customers. Develop and execute strategic account plans, map stakeholders, drive upsell/cross-sell and renewals, partner with Customer Success to maximize adoption, present to executives, and achieve NRR targets. Travel ~25%.

Sell Fleetio's SaaS fleet-management product to small and medium businesses. Prospect and qualify leads, run web-based demos, negotiate pricing, and close deals. Generate pipeline through outbound outreach, manage inbound leads, coordinate with cross-functional teams, and own the sales process end-to-end to drive ARR growth.

Founding Staff Software Engineer for the Leverage team to design and build knowledge infrastructure that connects internal data to AI tools. Build secure, extensible integrations, identity/auth passthrough, and a context layer consumed by internal CLIs, SDKs, UIs, and agent tooling. Partner cross-functionally to prioritize integrations, define standards, improve CI/CD, measure AI adoption, and produce maintainable, well-tested systems to scale internal AI tooling adoption.

Build and maintain partner-facing frontend and backend systems for integrations. Design and implement integrations, handle high-volume data workflows, ensure performance and reliability, write tests, contribute to architecture, and mentor teammates.