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Responsibilities
What You’ll DoLead and scale a team of 8–10 outbound SDRs, driving consistent pipeline generationDevelop and execute outbound strategy aligned to company growth targetsCoach SDRs on:Prospecting fundamentalsMessaging and objection handlingMulti-threading and authority mappingStage progression from meeting booked → SQOHold the team accountable to daily activity, quality standards, and conversion metricsDiagnose funnel bottlenecks quickly and implement actionable improvement plansPartner cross-functionally with Sales, Marketing, and RevOps to optimize performancePresent team performance, pipeline health, and strategic insights to Senior LeadershipBuild a culture of ownership, resilience, and continuous improvementWhat We’re Looking ForLeadership & Scaling ExperienceProven experience scaling teams of 8–10 outbound SDRsDemonstrated ability to drive consistent attainment across a teamHigh standards for performance and accountabilitySeller DNAPrior experience as an SDR or AE preferredDeep understanding of outbound selling fundamentalsAbility to coach from lived experience, not theoryCoaching & Funnel ExpertiseExceptional ability to coach outbound prospectingStrong understanding of full-funnel stage progressionKnows how to improve conversion from meeting → SQO → pipelineExecutive PresenceComfortable presenting business results and strategic plans in front of Senior LeadershipData-driven storyteller with clear communication skillsOperator MindsetTrack record of making sound decisions in fast-paced environmentsQuickly diagnoses issues and builds structured action plans to fix themBalances urgency with long-term team developmentWhat Success Looks LikePredictable outbound pipeline generationImproved conversion rates across funnel stagesStrong team morale paired with high accountabilityClear visibility and trust in reporting and forecastingA culture where performance is owned, coached, and elevated consistentlyWhat You’ll Bring2+ years of sales leadership experience, including leading a team of 6+ SDRs2+ years of full sales cycle experience with proven success in a quota-carrying role in the Mid-Market or Enterprise spaceA track record of operational excellence and developmentExposure to coaching methodologies and techniques to drive performance & growthDesire to build, combined with scrappiness and agility needed to scale an already robust SDR teamAbility to travel to Fleetio HQ for meetings quarterlyLevel up if you know a thing or two about cars and enginesBenefitsMultiple health/dental coverage options (100% coverage for employee, 50% for family)Vision insuranceIncentive stock options401(k) match of 4%PTO - 4 weeks (increases at year two!)12 company holidays + 2 floating holidaysParental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)FSA & HSA optionsShort and long term disability (short term 100% paid)Community service fundsProfessional development fundsWellbeing fund - $150 quarterlyBusiness expense stipend - $125 quarterlyMac laptop + new hire equipment stipendFully stocked kitchen with tons of drinks & snacks (BHM only)Remote working friendly since 2012A 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!
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