Fleetio is seeking a high-impact Outbound Sales Development Manager to lead, coach, and scale a team of outbound SDRs. This leader will be responsible for driving pipeline generation, improving full-funnel stage progression, and instilling a culture of accountability and performance. This is a hands-on leadership role for someone who thrives in fast-paced environments, understands outbound at a tactical level, and can translate activity into measurable business outcomes. What You'll Do - Lead and scale a team of 8-10 outbound SDRs, driving consistent pipeline generation - Develop and execute outbound strategy aligned to company growth targets - Coach SDRs on: - Prospecting fundamentals - Messaging and objection handling - Multi-threading and authority mapping - Stage progression from meeting booked 12 SQO - Hold the team accountable to daily activity, quality standards, and conversion metrics - Diagnose funnel bottlenecks quickly and implement actionable improvement plans - Partner cross-functionally with Sales, Marketing, and RevOps to optimize performance - Present team performance, pipeline health, and strategic insights to Senior Leadership - Build a culture of ownership, resilience, and continuous improvement What We're Looking For Leadership & Scaling Experience - Proven experience scaling teams of 8-10 outbound SDRs - Demonstrated ability to drive consistent attainment across a team - High standards for performance and accountability Seller DNA - Prior experience as an SDR or AE preferred - Deep understanding of outbound selling fundamentals - Ability to coach from lived experience, not theory Coaching & Funnel Expertise - Exceptional ability to coach outbound prospecting - Strong understanding of full-funnel stage progression - Knows how to improve conversion from meeting 12 SQO 12 pipeline Executive Presence - Comfortable presenting business results and strategic plans in front of Senior Leadership - Data-driven storyteller with clear communication skills Operator Mindset - Track record of making sound decisions in fast-paced environments - Quickly diagnoses issues and builds structured action plans to fix them - Balances urgency with long-term team development What Success Looks Like - Predictable outbound pipeline generation - Improved conversion rates across funnel stages - Strong team morale paired with high accountability - Clear visibility and trust in reporting and forecasting - A culture where performance is owned, coached, and elevated consistently What You'll Bring - 2+ years of sales leadership experience, including leading a team of 6+ SDRs - 2+ years of full sales cycle experience with proven success in a quota-carrying role in the Mid-Market or Enterprise space - A track record of operational excellence and development - Exposure to coaching methodologies and techniques to drive performance & growth - Desire to build, combined with scrappiness and agility needed to scale an already robust SDR team - Ability to travel to Fleetio HQ for meetings quarterly - Level up if you know a thing or two about cars and engines Benefits - Multiple health/dental coverage options (100% coverage for employee, 50% for family) - Vision insurance - Incentive stock options - 401(k) match of 4% - PTO - 4 weeks (increases at year two!) - 12 company holidays + 2 floating holidays - Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid) - FSA & HSA options - Short and long term disability (short term 100% paid) - Community service funds - Professional development funds - Wellbeing fund - $150 quarterly - Business expense stipend - $125 quarterly - Mac laptop + new hire equipment stipend - Fully stocked kitchen with tons of drinks & snacks (BHM only) - Remote working friendly since 2012 #LI-Remote