Outbound Sales Development Manager

A 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 ! More about our team and company: Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg Our careers page: https://www.fleetio.com/careers 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 → 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 → SQO → 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