Account Executive; on-site in Omaha, NE

Who We Are

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.

• 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.
• Hub Spot 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.