About Us & Careers — FleetSpring

Fleet safety, built for the rest of us.

FleetSpring exists for a specific kind of fleet operator — the owner of five to fifty trucks who answers their own phone, dispatches the morning runs, and worries about insurance, tool theft, and finding good drivers all in the same week. That operator has been overlooked by the enterprise fleet-technology market for a long time.

Enterprise fleet platforms weren't built for you. They're priced for hundreds-of-truck fleets, sold through multi-month procurement cycles, and configured by IT teams you don't have. We took the same class of hardware and AI those platforms use, and rebuilt the buying experience, the packaging, and the contracts around how SMB fleet operators actually work.

No multi-year lock-ins. No six-month integration sprints. Quotes in days, not months. Six pre-configured industry packs. One bundled hardware + cloud platform per pack. Fifteen minutes per truck to install. One supplier, one invoice, one number to call. That's the whole pitch.

Built for fleets of 5–50. Not the Fortune 500.

You don't have an IT team. You don't have a procurement department. You don't have time for six-month integration projects. You have trucks to run and a business to grow. That's exactly who we built this for.

One contract. Everything covered.

Dashcam, blind-spot, exterior asset camera, driver monitoring, sensors, platform — one supplier, one invoice, one number to call when something goes wrong. No more juggling three vendors.

Cancel-anytime contracts. No lock-ins.

No multi-year commitments. No camera-only deals. One bundle for hardware plus the safety platform. Add vehicle data activation and replace your existing tracker — save another $25–$35/month per truck on the contract you already have.

15 minutes per vehicle. Done.

Single cable into your OBD-II / J1939 port. AI auto-calibrates. 3–4 vehicles per hour per installer. A 30-truck fleet is fully deployed in a single day.

We're hiring people who'd rather build for the bakery than the boardroom.

The SMB fleet operator is the most overlooked customer in the trucking-tech world. Building for them means writing software that gets installed in fifteen minutes by a guy named Pete, not by a procurement department. It means legible contracts, 24-hour quote turnarounds, and a phone that rings into a real person. If that sounds like the kind of place you'd want to work, we'd love to talk.

"We didn't build FleetSpring to win a Fortune 500 RFP. We built it because there's an HVAC owner in Ohio losing a contract over compliance, a dairy hauler in Wisconsin getting a six-figure quote for fleet software, and a last-mile DSP in Texas whose insurance just went up 22%. They deserve enterprise-grade tools without the enterprise-grade buying ordeal. That's the gap we fill." — FleetSpring founding team

The values we hire for

Every culture pillar below is something we evaluate during hiring — and something we'd want our customers to be able to identify in any FleetSpring employee they meet.

⚒

SMB-first, always.

If a feature only makes sense at 500 trucks, we don't ship it. Every decision starts with: does this make the 12-truck operator's day easier? If not, we drop it — no matter how slick the demo would be.

⏱

Ship in days, not months.

Pre-configured packs. 15-minute installs. Quotes within 24 business hours. No 6-month integration projects, no "let's set up a discovery call." We deliver in the time other vendors spend scheduling kickoffs.

✓

Customer's side of the table.

Quotes in days, not months. Contracts are cancel-anytime. We earn the renewal every month — no auto-renew traps, no termination fees, no "managed contract" games. That's not marketing copy, it's policy.

▶

Show, don't tell.

Live demos beat slide decks. ROI calculators beat case studies. Public pricing beats RFP games. Internally we ship things you can poke at, click, break — never a roadmap deck. Externally, same standard.

☻

Built for the people behind the wheel.

Drivers are end users, not surveillance subjects. The Driver App is built to be useful to them — fair recaps, self-coaching, real bonuses. If a feature would make a driver hide their phone, we don't build it.

★

Earn the renewal every month.

The best moat in software isn't a contract — it's customers who'd be sad to lose you. We measure ourselves on whether customers would re-sign tomorrow if forced to. Anything less means we're coasting on lock-in.

Open roles

2 hiring now

Customer Success Manager

Full-time Remote · US Customer team

You own the post-install relationship for a portfolio of 30–60 SMB fleet customers (12–50 trucks each). The job is part trusted advisor, part outcomes coach: you make sure operators actually use FleetSpring to lower their insurance premium, recover their tools, and exonerate their drivers — and you renew them when the year is up.

3+ years in B2B customer success, ideally with SMB-segment owner-operators (not Fortune-500 buyers)
Comfortable on a phone with a small-fleet owner; comfortable in a spreadsheet walking through their fuel-savings numbers
Bonus points for any prior life in fleet ops, dispatch, insurance, or commercial telematics

Apply → Compensation: $85–115k base + 20% target bonus + equity

Solution Sales Representative

Full-time Remote · US Sales team

You own the top of the new-business funnel. Inbound leads from packaged demos, ROI-calculator runs, and the contact form come to you first — you qualify, demo, quote, and close, all in days, not months. Average deal cycle is 1–6 weeks. No 80-page RFPs and no procurement choreography — quotes go out within 24 hours and our contracts are cancel-anytime.

2+ years closing B2B SaaS or hardware deals, ideally to SMB operators
You write a tight follow-up email and you record a clean Loom video
Bonus: prior fleet, insurance, or field-service vertical experience

Apply → Compensation: $70–95k base + uncapped commission (OTE $130–180k) + equity

Don't see your role? Send a note to [email protected] — we hire opportunistically when good people show up.

About FleetSpring.