Upwell is redefining order-to-cash automation in the logistics industry. Our AI-powered platform eliminates inefficiencies in billing, collections, and payments for freight brokers, trucking companies, 3PLs, and freight forwarders. Backed by deep industry expertise and cutting-edge technology, we help customers get paid faster, reduce errors, and improve cash flow.
We’re growing fast and looking for a proven freight tech seller to be our first Account Executive. This is an opportunity to make a massive impact, shape our go-to-market strategy, and earn at the highest levels in the company.
Who You Are- A top-performing freight tech or freight payments sales rep with a track record of closing deals and exceeding quotas.
- Deeply knowledgeable about TMS platforms, AR/AP automation, capital providers, and freight audit/payment firms.
- A natural storyteller and connector—you know how to build trust, sell a vision, and drive urgency.
- Competitive, money-motivated, and thrive in a high-stakes, fast-paced startup environment.
- Resilient, adaptable, and hungry to win—you know what it takes to get deals done.
- Experience selling SaaS, fintech, or freight automation solutions into logistics companies.
- Own the full sales cycle from prospecting to close, targeting mid-market and enterprise freight brokers, 3PLs, and carriers.
- Develop deep relationships in the TMS and freight payments ecosystem—you’ll be expected to bring (or build) a network.
- Sell consultatively, understanding customer pain points and crafting compelling solutions.
- Work alongside founders and leadership to shape pricing, positioning, and sales strategy.
- Drive revenue with a hunter mentality—no excuses, just results.
- Be the first of many—lay the foundation for Upwell’s future sales team.
- 3+ years of B2B sales experience in logistics or freight tech sectors, preferably in new logo acquisition.
- Proven track record of meeting and exceeding sales quotas.
- Deep understanding of the freight market and challenges facing freight brokers and logistics teams.
- Exceptional communication, negotiation, and presentation skills.
- HubSpot experience is a plus.
- Massive upside: Uncapped commissions + a chance to be the highest-paid person in the company.
- High-growth startup: Work directly with industry veterans and founders.
- Cutting-edge product: Be part of a game-changing solution that logistics companies need.
- No corporate BS: We’re a fast-moving, high-performing team that values action over talk.
- Be part of transforming an industry through technology
- Work on challenging problems that impact real businesses
- Clear career growth path as we scale
- Competitive salary range
- Comprehensive benefits including health, dental, and vision insurance
- 401(k)
- Flexible PTO policy
- Modern, collaborative workspace in Omaha
Experience matters, but attitude is everything. If you’re a freight tech sales killer who wants to be part of something big, let’s talk.
Top Skills
What We Do
Upwell uses artificial intelligence to automate and transform accounts receivable for transportation and logistics companies. Every dollar counts in this industry, but today’s landscape is too complex for companies to rely on back-office superheroes using manual processes and dated technologies. Many companies have thousands of dollars locked up in invoicing exceptions, and many don’t have reliable systems for knowing what’s been paid. Now there’s a better way. Upwell’s AI-powered platform empowers accounting and finance teams by improving cash flow, automating legacy processes, and enhancing the customer experience. Reinvent your accounts receivable and start the journey toward getting paid faster at upwell.com.
