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 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 ho