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 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 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