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 !

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 View phone number on hireskys.com.