Outbound Sales Development Manager

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