Founding Account Executive

About Us CollectWise is a fast growing and well funded Y Combinator-backed startup. We’re using generative AI to automate debt collection, a $35B market in the US alone. Our AI agents are already outperforming human collectors by 2X, and we’re doing so at a fraction of the cost. With a team of five, we scaled to a $2 million annualized run rate in just a few months, and we are now hiring a Founding Account Executive to help us reach $10 million within the next year. Why Now For the past year, our founder has personally run every single sales call—hundreds of them. We’ve closed millions of dollars in revenue, and demand has remained overwhelming throughout. This is not a sales problem. It is a capacity problem. We are now ready to bring on a Founding Account Executive to help us catch up and scale forward to $10M ARR. What You’ll Do Own the full sales funnel from first touch through close Run a high volume of demos and sales calls with qualified prospects while still building significant pipeline yourself Consistently exceed quota and close large, high-ACV deals with a strong command of value-based, consultative selling Attend conferences, trade shows, and industry events to generate leads, build relationships, and create pipeline Manage the sales process end-to-end, including lead generation, follow-ups, demos, stakeholder coordination, objection handling, and closing Generate pipeline through outbound prospecting, relationship-building, email outreach, and creative hunting Lead compelling, high-conviction product demos that clearly communicate ROI and move buyers toward close Work directly with the founder to refine messaging, positioning, pricing, and demo flow so we can build a repeatable sales process as quickly as possible Navigate complex sales cycles across multiple stakeholders, including executives, operators, legal, compliance, and procurement, while helping drive implementations and escalations to get customers live. Who You Are 3+ years of experience as a front-line seller in enterprise or complex B2B sales You have closed millions of dollars in deals and ideally $5M+ in ARR at a SaaS, fintech, or AI company in an adjacent industry A proven track record of consistently exceeding quota, not just hitting it You have helped scale a company from roughly $1M or less in revenue to $10M or more You have experience selling at a startup or in a similarly high-growth environment You can run 8 to 12 demos a day without losing energy or sharpness You can build pipelines and expand GTM strategies. You want to build the playbook, not just follow one You are strong at consultative, ROI-driven selling and know how to sell outcomes, not just features You are ready to work hard because you are ambitious, hungry, and want to win Bonus Points If You Have experience selling in the ARM or debt collection industry Have experience selling into collection agencies, financial institutions, BPOs, or health systems Have built and scaled an end-to-end enterprise sales motion Have generated meaningful pipeline through conferences, events, and relationship-driven selling What You Get A chance to be a foundational sales hire at a fast-growing AI company High commission upside for a top performer Direct access to leadership and real influence over the company’s sales motion and growth Meaningful equity with real upside $300,000 to $375,000 OTE