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: Our careers page: 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 prefer