Help build the commercial engine of a fast-moving fintech that’s redefining business banking for growing companies. Backed by founders with successful prior exits, the company combines business banking, payments, and spend management into one modern platform that helps businesses earn meaningful cashback on everyday operating expenses. This is a rare opportunity to work directly with the CEO and shape the sales playbook from the ground up. If you’ve built pipeline through cold outreach and personal networks, and sold commercial card, banking/payments/spend management software/SaaS or adjacent solutions and closed deals with CFO/controller or owner/operator personas across industries, you’re comfortable leading customers through operational change and you bring early-stage or founding AE energy, this could be an exceptional fit for you. The role is fully remote (or Chicago-based for those local) and offers a competitive base salary and benefits, meaningful equity in the company, and uncapped commission for ambitious sellers who thrive in high-ownership environments.

Overview:

As the founding Account Executive, you will own the full sales cycle. You will source your own pipeline, diagnose fit, tailor demos, navigate multi-stakeholder decisions, and close. You will work directly with the CEO, and your wins will build the playbook. This is not a seat-filler role; it’s for someone who can sell consultatively to CFOs, controllers, and founder-operators, who understands that switching a business bank is a trust decision as much as a product decision, and who is comfortable being one of the first voices customers hear.

Key Responsibilities:

Own the full sales cycle

• Run discovery, demos, pricing conversations, and close with CFOs, controllers, VPs of Finance, and owner-operators at companies with $10M to $50M in revenue
• Navigate multi-stakeholder deals involving finance, operations, and ownership, with typical ACVs of $30K to $250K
• Quarterback technical and operational questions by pulling in product, banking partners, and the CEO when needed
  

Build your own pipeline

• Own top of funnel end to end: build target account lists, run cold outbound across email, phone, and LinkedIn, and work referrals and warm network
• Develop a point of view on which of our target verticals (distribution, logistics, auto, healthcare, nonprofit, construction) convert best, and double down
• Use tools like Apollo, Sales Navigator, and your own creativity to get in front of the right CFOs, controllers, and owner-operators
• Build a personal presence on LinkedIn that warms up your outbound and opens doors. Thoughtful posts, visible engagement with prospects, and a profile that signals credibility to CFOs and operators
  

Shape the playbook

• Document what works: objection handling, discovery frameworks, demo flows, pricing conversations, and competitive positioning
• Feed customer objections and product gaps back to the CEO and product team
• Help hire, onboard, and eventually mentor the AEs who follow you
  
  

Ideal Background:

• A closer with 3+ years of full-cycle B2B sales experience, ideally selling into finance or operations leaders at SMB or lower mid-market companies
• Credible with middle-market operators, not just startup founders. You are comfortable across the table from the controller of a family-owned distributor, the CFO of a multi-location auto dealer group, or the COO of a growing construction firm. Tech-seller polish is optional. Credibility with hands-on finance leaders is not
• A network you can lean on. Former customers, operators, finance leaders, partners, or peers who will pick up when you call. This is a founding seat, and relationships you have built are day-one pipeline
• Comfortable prospecting and closing. You are happy to pick up the phone, run cold outbound, and self-source pipeline. Inbound-only sellers will not be a fit here
• Curious about how businesses run, especially the mechanics of money movement, cash management, and operating expense
• Organized enough to keep a pipeline clean without being told, and honest enough to forecast accurately when deals are not there
• Energized by ambiguity. You would rather help build the motion than inherit one
• Experience selling fintech, banking, payments, spend management, or treasury products
• Experience selling into CFOs, controllers, or owner-operators at SMB and lower mid-market companies
• A track record as an early or founding seller at a startup
• Network in one or more of our target verticals: distribution, logistics, auto dealer groups, healthcare, nonprofits, construction
  

Why This Role:

• Founding seller seat with ownership of the commercial motion
• Direct access to the CEO and the product team. Your feedback shapes what gets built
• A product that puts money back in customers’ pockets. Our 1.5% cashback on debit spend returns tens of thousands of dollars a year to a high-spend business, on expenses they were already making
• Competitive base, uncapped commission, and meaningful equity
  

What Success Looks Like:

• In 30 days, you are fluent in the company’s story, the product, and the target verticals, and you are running your own outbound and qualified demos
• In 90 days, you have built a pipeline, have active late-stage deals, and can point to a documented discovery and demo motion
• In 6 months, you are closing consistently and have contributed meaningful improvements to pricing, positioning, or segmentation
• In 12 months, you are the reference point for how the solution sells, and you are helping shape the team around you
• Key Metric: The primary measure of success in this role is closed revenue from customers that fit the target profile, measured against a ramping quota.
  

Contact:

Ian Horsted
605-275-8803
Ia*@********up.com
Schedule a Call with Ian