Outbound Sales Development Manager

Fleetio

5d•Remote

About The Position

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.

Requirements

Proven experience scaling teams of 8–10 outbound SDRs
Demonstrated ability to drive consistent attainment across a team
High standards for performance and accountability
Prior experience as an SDR or AE preferred
Deep understanding of outbound selling fundamentals
Ability to coach from lived experience, not theory
Exceptional ability to coach outbound prospecting
Strong understanding of full-funnel stage progression
Knows how to improve conversion from meeting → SQO → pipeline
Comfortable presenting business results and strategic plans in front of Senior Leadership
Data-driven storyteller with clear communication skills
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
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

Nice To Haves

Level up if you know a thing or two about cars and engines

Responsibilities

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, and 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

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)