Job Description: Outbound Sales Development Manager at Fleetio

About the Role

Lead, coach, and scale a team of outbound SDRs (8 610 members).
Drive pipeline generation and improve full-funnel stage progression.
Instill a culture of accountability and performance.
Hands-on leadership in fast-paced environments with tactical outbound expertise.

Responsibilities

Lead and scale a team of 8 610 outbound SDRs to drive consistent pipeline generation.
Develop and execute outbound strategy aligned with company growth targets.
Coach SDRs on:
Prospecting fundamentals
Messaging and objection handling
Multi-threading and authority mapping
Stage progression from meeting booked to Sales Qualified Opportunity (SQO)
Hold team accountable to daily activity, quality standards, and conversion metrics.
Diagnose funnel bottlenecks and implement improvement plans.
Partner cross-functionally with Sales, Marketing, and RevOps.
Present team performance, pipeline health, and strategic insights to Senior Leadership.
Build a culture of ownership, resilience, and continuous improvement.

Qualifications / What They9re Looking For

Leadership & Scaling Experience

Proven experience scaling teams of 8 610 outbound SDRs.
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.

Coaching & Funnel Expertise

Exceptional coaching ability in outbound prospecting.
Strong understanding of full-funnel stage progression.
Knowledge on improving conversion from meeting 12 SQO 12 pipeline.

Executive Presence

Comfortable presenting business results and strategic plans to Senior Leadership.
Data-driven storyteller with clear communication skills.

Operator Mindset

Makes sound decisions in fast-paced environments.
Diagnoses issues quickly and builds structured action plans.
Balances urgency with long-term team development.

Success Metrics

Predictable outbound pipeline generation.
Improved conversion rates across funnel stages.
Strong team morale with high accountability.
Clear visibility and trust in reporting/forecasting.
Culture of owned, coached, and elevated performance.

Requirements

2+ years sales leadership experience leading a team of 6+ SDRs.
2+ years full sales cycle experience with quota success in Mid-Market or Enterprise space.
Track record of operational excellence and development.
Exposure to coaching methodologies for performance & growth.
Desire to build combined with scrappiness/agility for scaling SDR team.
Ability to travel quarterly to Fleetio HQ.
Bonus: knowledge about cars and engines.

Benefits

Multiple health/dental coverage options (100% employee coverage, 50% family).
Vision insurance.
Incentive stock options.
401(k) match of 4%.
PTO: 4 weeks (increases after year two).
12 company holidays + 2 floating holidays.
Parental leave: birthing parent (16 weeks paid), non-birthing (4 weeks paid).
FSA & HSA options available.
Short and long term disability (short term fully paid).
Community service funds; professional development funds; wellbeing fund ($150 quarterly).
Business expense stipend ($125 quarterly).
Mac laptop + new hire equipment stipend provided.
Fully stocked kitchen with drinks & snacks at Birmingham office only (BHM).
Remote working friendly since 2012.

Additional Information

Fleetio is an equal opportunity employer committed to diversity and inclusion. Employment decisions are based on qualifications, merit, and business need. Employment is at-will. Accommodations are available for applicants with disabilities upon request.