Sales Director

About the TeamGreenlane is a fintech platform built for truckers. We collapse the complexity of running a small trucking business into a single product: fuel discounts, fleet capabilities, and a fintech product with a rewards loop. Our customers are owner-operators and small fleets (2-20 trucks) who want to run their business as efficiently as possible. We're a small team that ships fast, makes decisions on data, and treats trust as the core product.We're launching a fintech product this summer. This role exists to lead the sales motion that takes it to market.About the RoleWe're hiring a Director of Sales to run commercial sales across Greenlane, with Fleets and Fintech as the primary focus from day one. You'll inherit two reps, run their pipeline, coach them up, and carry your own bag alongside them. You'll partner closely with marketing to co-build the sales playbook and drive a shared account target.This is not a build-the-team role. It's a hands on, get-your-hands-dirty, run-the-team-and-the-motion role. Your leverage comes from getting involved and coaching the reps you have, building the playbook with marketing, and producing your own deals. If you want to spend year one hiring a team of 6, this isn't the role for you. If you want to own the GTM motion for a fintech launch in a vertical that's been ignored by tech for too long, keep reading.LocationThis role is remote or in-office, your call. We have an office for the team that wants one and we're fully set up for remote. What matters is output and presence when it counts, not where you sit.You're Excited About This BecauseYou'll influence the launch motion in a category that has been overlooked. Trucking is a $700B industry running on tools built in the 1990s. There's real money to be made and real operators to help.You'll bring go-to-market chops and field insight to influence positioning and messaging. No "sales vs. marketing" theater. If you've been frustrated by misalignment between the two functions at past companies, this is the model that fixes it.You're an owner. If you have a point of view, bring it. If we disagree, we'll fight it out and ship the answer.You'll coach a real team. You inherit two reps on day one. Your job is to make them better. If you love coaching as much as closing, you'll thrive here.You'll build the engine, not just run it. The CRM, the pipeline reporting, the forecasting rhythm, the playbook: you'll shape how all of it works. You're not inheriting a polished machine. You're building one.You'll sell something that matters. Truckers aren't broke. They're exposed. Every decline at the pump is an existential moment for a small fleet operator. We sell stability and control. The customer outcome is real.We're Excited About You BecauseYou have 5-10 years of sales experience in B2B or B2C technology. You've sold to SMB or mid-market, not just enterprise. You know what it's like to operate without an SDR team behind you.You've owned Sales Strategy and executed on it in partnership with other core functions. You're passionate about understanding ICPs deeply and what motivates them.You've helped build a sales playbook before, in partnership with marketing or product. You understand where positioning ends and motion design begins, and you operate well across that line.You're an owner, operator, and coach, not just a manager. You've trained reps, run deal reviews, and developed sellers who went on to outperform you. Or you're ready to.You live in the data and self-serve. You forecast accurately, run your own reports, and synthesize signal from noise. You don't wait for someone to build you a dashboard. You pull the numbers, find the truth, and act on it. On a lean team, the leader who answers their own questions moves faster than the one who files a ticket.You build and own the sales tech stack. You've set up or cleaned up a CRM (HubSpot or similar), defined the pipeline stages, and built the reporting that makes a motion repeatable. You treat clean data as table stakes, not an afterthought. You know good tooling is leverage and you'll build ours out as we scale.You're hungry. You want the next rung and you're willing to earn it. You were the #2 or #3 sales hire somewhere good, and you're ready to be the #1 somewhere that matters more.You communicate like an operator. Direct, concise, no consultant-speak. You can write a deal memo, present to leadership, and run a pipeline review with equal clarity.Bonus, not required: fintech, payments, trucking, logistics, fleet, or vertical SaaS experience. Fintech sales backgrounds are a strong callout given our product launch, but we can teach the industry. We can't teach operator-grade judgment.