Outbound Sales Development Manager - Fleetio

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!

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, objection handling, multi-threading, authority mapping, and stage progression from meeting booked to 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 to SQO to 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 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