Jobs at Fleetio

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.

Manage outbound lead generation for Mid-Market: research and contact prospects via calls, email, and social; build CRM lead profiles; qualify accounts; schedule meetings and demos; support Account Executives and strategic efforts to create qualified sales opportunities.

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.

Lead and grow two Growth engineering squads to drive activation, adoption, and monetization via experimentation. Partner with Product, Design, Data to prioritize high-leverage work, run structured A/B tests, ensure quality instrumentation and analytics, coach engineers on engineering excellence, hire and develop talent, and translate experiment results into roadmap decisions.

Lead the Payments engineering team to build and maintain reliable, well-tested payment and billing systems. Partner with Product and Engineering leadership to prioritize roadmap work, guide technical tradeoffs, improve reliability and scalability, coach and grow engineers, recruit talent, and communicate progress, risks, and decisions to stakeholders.

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.

Lead and establish project management practices for Engineering, primarily supporting Solutions Engineering and Platform teams. Scope and drive SOW-based enterprise technical deliveries, track milestones and dependencies, manage risks, communicate status to executives, and partner with Customer Success. Implement tooling and cadence for consistent, timely delivery of complex cross-functional projects.

Lead and build Fleetio's product marketing and GTM commercialization function. Create repeatable launch frameworks, positioning, messaging, pricing, sales plays, and enablement. Align Product, Sales, Marketing, Customer Success, and Partners; hire and grow a commercialization team; establish operating rhythms, templates, and metrics to drive adoption, pipeline, and revenue.

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.

Lead Fleetio's telematics and connected-vehicle data strategy end-to-end. Own hardware and data partnerships, build a new product line from 0->1, standardize and activate real-time vehicle data, and drive partner integrations, mapping, vehicle health, and product launches across GTM, design, and customer teams.

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.