Outbound Sales Development Manager at Fleetio

You're a seasoned sales leader with at least two years of experience managing SDR teams of six or more, and a solid background in full sales cycles. **What mak

Work type: remote

Location: Remote

Type: Full-time

Summary

You're a seasoned sales leader with at least two years of experience managing SDR teams of six or more, and a solid background in full sales cycles. **What makes it worth a look...** This fully remote, full-time Outbound Sales Development Manager role is with Fleetio, a modern software platform for fleet operations. They recently secured $450M in Series D funding. **You might be a good fit if you...** * Have proven experience scaling outbound SDR teams of 8-10 individuals. * Possess a deep understanding of outbound selling fundamentals and can coach from lived experience. * Have a track record of operational excellence and developing structured action plans. * Are comfortable presenting business results and strategic plans to senior leadership.

Job Description

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](https://rubyonrails.org/foundation)!

More about our team and company:

• Fleetio overview video: [https://www.youtube.com/watch?v=YoXyXTFWbkg](https://www.youtube.com/watch?v=YoXyXTFWbkg)

• Our careers page: [https://www.fleetio.com/careers](https://www.fleetio.com/careers)

Fleetio is seeking a high-impact Sales Development Manager (Outbound) 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

### 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

• 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

• 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

• 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

• 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

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