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 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
Fully stocked kitchen with tons of drinks & snacks (BHM only)
Remote working friendly since 2012 #LI-Remote

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

Outbound Sales Development Manager

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