Outbound Sales Development Manager

Fleetio · Remote · US

Open 268 days

New Business: you win brand-new customers.

Base: Not disclosed
OTE: Not disclosed
Posted: 8mo ago

Still open · checked 7h agoon Fleetio's careers page

Apply on Fleetio →

The job

What you'd do

Lead and coach a team of 8 to 10 salespeople who find new customers for a company that helps organizations worldwide run their vehicle fleets. The job is remote, with visits to the head office each quarter.

What you'd sell

Helps organizations run their vehicle fleets day to day

When a company runs a fleet of vehicles, there is a lot to keep track of across every truck and van. The problem is, each vehicle needs its own care and its own driver, and that gets hard to keep straight as the fleet grows. Fleetio is software that helps organizations manage their fleet operations, so the people in charge can stay on top of it all.

In plain English, from their own job posts. Something wrong? Tell me · More Industry-specific software companies →

Who you'd sell to

Organizations that manage fleet operationsIn their words: “helps thousands of organizations worldwide manage their fleet operations”

Where deals come from

Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle. Ask about all five.
Time on market: Open 268 days. Ask why it's been hard to fill.
Company hiring: 5 sales roles open, hiring at a steady pace.

Red lights

Pay. No pay listed at all.
Time on market. Open 268 days. Ask why it's been hard to fill.

Yellow lights

Open 90+ days. This role has been posted for three months or more. Ask why it's been hard to fill, and whether anyone left it.

Green lights

None spotted.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
This role has been open a while. What's made it hard to fill?
The answer tells you what candidates saw that made them walk.
2.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
3.
What are the base and the OTE for this role?
No point investing hours before you know the number.
4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
5.
What share of last year's closed deals did reps source themselves?

Before You Apply

Find out where you fit, and where you don't, before you hit submit.

Why I built it this way ↓

Most résumé tools try to make you look like a match. I'd rather help you find out if you are one.

Nothing made up.
Nothing goes on your résumé that you didn't do. If a line would need a number you didn't give me, I ask. I don't guess. On Braun Board it's checked in code, not just promised.
Curiosity before conclusions.
If the job wants something your résumé doesn't show, I ask before I assume. Plenty of sellers have done the thing and just never wrote it down.
Sorting, not selling.
Some jobs won't line up with what you've done. Finding that out before you apply isn't a loss. It's an hour back, spent on a job that fits.
No score.
A match score tells you how well you copied their words. It doesn't tell you whether you'd be good at the job, or happy there.

It's the same way I teach selling. We don't control who says yes. We do control where we spend our time, and whether everything we say is true.

Josh

1 Is the job worth it?

Ask hard questions. Too much is left unsaid. Make them answer before you invest.

No pay listed at all.
Open 268 days. Ask why it's been hard to fill.

Might be worth asking about these before you spend an hour on a tailored résumé.

See the full Braun Read

2 Where you fit

Upload once, see where you fit on any job.

What people say about working at Fleetio ↓

Got an offer from Fleetio? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Rather talk it through? Call or text me: 954-695-0844 (text)

Full posting

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 About the Role 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 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 Requirements - 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.

Apply →