Senior Account Executive

Proper AI is the first AI-native accounting and operations platform built exclusively for the property management industry. We are growing fast, and expanding our sales team with people who want to be part of building something significant. This is a full-cycle closing role. You will own deals from first call to signed contract, selling into property management and real estate leadership: CEOs, CFOs, Controllers, Owners, and COOs. The product is complex, the buyers are sharp, and the sales cycle is short. That is by design. This is the kind of role that defines careers. If you want to sharpen your craft, close deals that matter, and help set the standard for how a high-performance sales team operates, this is the place. What You Are Selling Into Property management companies are sitting on a $20B accounting and operations problem. The traditional solution has always been in-house accounting staff, but that model is breaking down. Accounting talent is expensive, hard to hire, harder to retain, and increasingly difficult to train and manage at scale. Most operators are stretched thin and know it. Proper AI is a fundamentally different answer. We are not a staffing firm, not a bookkeeping vendor, and not a point solution bolted onto existing software. We pair top-tier accounting talent with purpose-built AI technology to deliver a level of accuracy, consistency, and scalability that in-house teams simply cannot match. Our service is geared directly with the property management systems our clients already use (Yardi, AppFolio, RealPage) and takes on the full scope of their accounting operations. There is no real competitor category here. You are not going up against other software companies. You are making the case for a new model entirely, one built for this era of AI, against the status quo of hiring, managing, and hoping your accounting department holds together. That is a compelling sell for the right person. The Sale This is a consultative, complex sale, not a transactional one. Prospects are executives and operators who think fast and ask detailed questions. They want to understand how the product actually works, how their team interacts with ours, and why this is different from what they have tried before. Many prospects have been burned by outsourced accounting vendors in the past. Others do not yet see us as anything more than a bookkeeper. Your job is to change that perception through genuine discovery, operational fluency, and a clear-eyed case for why Proper AI is a better path forward. You will not be starting from zero. Pipeline is generated through inbound leads and SDR-sourced outbound, and you will have support from day one. That said, this is not a role where everything is handed to you. The best AEs here bring their own instincts, help sharpen what is working, and occasionally build new ground when the opportunity is there. Sales cycles run approximately 30 days. What Success Looks Like at 6 Months Achieving monthly quota of $30K to $40K MRR (roughly 5 to 6 deals per month at full ramp) 25 to 35% sustained close rate Average sales cycle under 30 days Forecast accuracy within 10% of committed pipeline Clean, accurate HubSpot records with documented next steps at all times Holds complex conversations with CFOs and Controllers without escalating Drives next steps consistently -- the buyer is never the one deciding what happens next Can articulate the AI-first differentiation clearly and confidently in any live conversation