Jobs at Fleetio

Conduct outbound lead generation through cold calls, email, and social outreach; research prospects, build lead profiles in Salesforce, qualify accounts, and schedule meetings and demos for Account Executives. The role focuses on creating qualified pipeline, educating prospects about Fleetio, and developing transferable software sales skills.

Lead and scale a team of 8–10 outbound SDRs, driving pipeline generation, funnel progression, coaching, accountability, and performance improvement. Develop outbound strategy, diagnose bottlenecks, partner with Sales, Marketing, and RevOps, and present pipeline and performance insights to senior leadership. The role requires sales leadership experience, full-cycle quota-carrying experience, strong coaching skills, and quarterly travel to Fleetio headquarters.

Draft and coordinate RFI, RFP, security questionnaire, and vendor assessment responses for commercial and public sector opportunities. Partner with Sales and cross-functional experts to create evaluator-ready answers, validate technical and contractual information, meet submission requirements, and manage deadlines. Track response outcomes, maintain the response library, use internal AI tools, and improve workflows, documentation, competitive framing, and pursuit processes.

Manage and scale AWS infrastructure and Ruby on Rails applications; improve reliability, performance, observability, and automation. Responsibilities include Infrastructure as Code, Kubernetes operations, monitoring, code review, production debugging, capacity planning, incident response, and partnering with feature engineering teams to deploy and operate services safely.

Own and optimize Fleetio’s outbound technology stack, including integrations, data quality, targeting, automation, AI-powered prospecting, and performance measurement. Partner with Sales, Marketing, Business Development, Enablement, and Data Engineering to improve outbound workflows, train teams, define KPIs, and scale effective GTM technologies.

Build and manage Fleetio’s reseller partner portfolio across fleet management companies, telematics providers, and VARs. Responsibilities include sourcing and closing new partner agreements, negotiating commercial terms, onboarding and enabling partners, driving account growth, managing joint business plans, supporting QBRs and co-selling, tracking pipeline and performance, and representing partner needs internally. The role requires extensive partnerships or channel sales experience, strong commercial skills, executive relationship management, and familiarity with B2B SaaS or fleet technology.

Scale and improve the reliability, performance, and scalability of Fleetio’s Ruby on Rails application and infrastructure. Responsibilities include observability, incident response, AI-powered automation, database capacity planning, disaster recovery, backups, documentation, performance analysis, code review, and on-call participation. The role collaborates with engineering teams to address bottlenecks and adopt AI-driven reliability practices.

Leads a mid-market B2B SaaS sales team by managing pipeline activity, forecasting, quota attainment, prospecting, negotiations, and performance. The role coaches account executives, drives outbound-sourced ARR growth, aligns execution with company goals, improves sales processes, manages hiring and performance, and develops team career paths. It collaborates with sales, marketing, business operations, and enablement leaders to achieve revenue objectives.

Leads Fleetio’s global brand strategy and expression across visual identity, content, thought leadership, social, video, PR, sponsorships, and experiential activation. Manages the in-house brand and content team, agency partners, creative operations, and brand standards. Drives narrative evolution, awareness, share of voice, content performance, executive visibility, and activation of Fleetio’s NASCAR partnership.

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.

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.