Outbound Sales Development Manager
At a glance
Mid-level Sales Development role at Fleetio. Remote, USA.
Pay not stated
Growth Roles summary, based on the employer's posting.
What you'll do
- Lead and expand an outbound SDR team while generating dependable pipeline
- Set outbound plans tied to growth goals and inspect daily activity, quality, and conversion
- Coach prospecting, messaging, objection handling, multi-threading, and authority mapping
- Find funnel weak points and improve movement from booked meetings through SQO
- Share team results, pipeline condition, and recommendations with senior leaders
What you bring
- At least two years managing sales teams, including a team of six or more SDRs
- At least two years carrying a quota in full-cycle Mid-Market or Enterprise sales
- A successful record of operational discipline, team development, and performance improvement
- Hands-on outbound selling knowledge, ideally built through prior SDR or AE experience
- Experience using coaching methods to improve performance and growth
Who this fits
You’ll suit a hands-on sales leader who can coach from direct selling experience, use data to make decisions, and balance urgency with long-term team development. The role is remote within the USA and requires travel to Fleetio HQ for quarterly meetings. It centers on leading and scaling an outbound SDR team while presenting results and plans to senior leadership.
From the employer
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
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
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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