Jobs at Fleetio

Lead the Leverage Engineering Pod to increase delivery velocity across Product & Engineering. Own strategy, roadmap, budget, and outcomes for shared frameworks, developer tooling, and partner delivery. Stand up Solutions Engineering, manage agency partners and SOWs, drive adoption of shared services, modernize the development lifecycle (AI-assisted to agentic), hire and develop leaders, and measure the Pod's multiplier effect on engineering throughput.

Drive new business for Fleetio by prospecting and closing mid-market customers. Conduct consultative sales, perform web-based demos, manage inbound and outbound pipeline, negotiate pricing, and collaborate cross-functionally to grow ARR. Role requires consistent follow-up and up to 20% travel.

Lead lifecycle marketing to move users from interest through activation, conversion, adoption, expansion, and retention. Design segmented, data-driven email and automation programs for PLG, mid-market, and enterprise motions. Partner cross-functionally to build scalable nurture, onboarding, and usage-based campaigns, measure lifecycle metrics, run experiments, and optimize funnel conversion and revenue outcomes.

Build and maintain Marketplace features that connect fleets and shops, handle scheduling, approvals, transactions, billing, and data entry. Collaborate with PMs, designers, and engineers, design architecture, deliver well-tested code, prototype solutions, and perform thorough peer code reviews.

Build and iterate product features that improve onboarding, adoption, and long-term engagement. Collaborate with PMs, designers, data and engineers to design, implement, test, and measure experiments and customer-facing full-stack functionality. Deliver maintainable, performant code and participate in code reviews and prototyping.

Own and scale paid search and paid social programs, manage six-figure media budgets and agency partners, lead SEO and organic growth initiatives, run experiments to improve CAC and pipeline, and coordinate integrated campaigns across product marketing, content, creative, and RevOps using analytics and AI-driven tools.

Sell Fleetio SaaS to small and medium businesses via inbound and outbound outreach. Conduct consultative web demos, qualify prospects, generate pipeline, negotiate pricing, and close deals while driving ARR growth and collaborating with cross-functional teams.

Lead product-led growth and self-serve initiatives to drive activation, adoption, monetization, retention, and expansion. Build growth loops, develop hypotheses, run experiments, analyze funnels, and partner cross-functionally to deliver measurable outcomes. Use quantitative and qualitative insights, prioritize roadmap work, and iterate on AI-enabled and product improvements to increase customer value and business growth.

Lead and scale a global accounting organization for a high-growth SaaS and payments company. Oversee monthly close, financial reporting, consolidations, audits, controls, tax, billing, collections, payroll and finance operations. Improve processes, automation, and cross-functional partnerships while building a high-performing team to support global, multi-entity operations and future strategic transactions.

Build and run growth-focused experiments and features to increase trial user engagement and adoption. Collaborate with Product, Design, Data Ops, and QA to design personalized onboarding, implement UX improvements, and measure outcomes to reduce churn.

Own and scale Fleetio's Deal Desk: manage deal review, approvals, discount policy, and exceptions; advise Sales/Partnerships/Finance on complex deals; analyze pricing and deal performance; build automation and AI-enabled workflows; define Deal Desk metrics and governance.

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 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%.