Lead and scale a team of 8–10 outbound SDRs, driving predictable pipeline generation and improved funnel conversion. Develop outbound strategy, coach prospecting and objection handling, diagnose bottlenecks, enforce activity and quality standards, and partner with Sales, Marketing, and RevOps. Present performance and pipeline insights to senior leadership while building a culture of accountability, resilience, and continuous improvement.
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.
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What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
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