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 (roughly 5 to 6 deals per month at full ramp)25 to 35% sustained close rateAverage sales cycle under 30 daysForecast accuracy within 10% of committed pipelineClean, accurate HubSpot records with documented next steps at all timesHolds complex conversations with CFOs and Controllers without escalatingDrives next steps consistently -- the buyer is never the one deciding what happens nextCan articulate the AI-first differentiation clearly and confidently in any live conversation
Compensation
OTE: $250,000
Base Salary: $100,000 to $110,000Variable
Commission: $140,000 to $150,000 Uncapped upside with no earnings ceiling
Top performers significantly exceed OTE
How You Earn It. Your monthly quota is $30,000 to $40,000 in closed-won revenue. At an average deal size of $60,000 ACV and growing, that works out to roughly 5 to 6 deals per month to hit plan. That is a real number. It requires consistent execution across a full pipeline, and we are not going to pretend otherwise.
What makes it achievable: pipeline is provided. Inbound leads come in through paid media and SDRs are sourcing outbound on your behalf. You are not cold-calling your way to quota from a blank spreadsheet. You are closing a steady flow of qualified opportunities with a short sales cycle and a product that solves a problem prospects already know they have.
Hit your number and you earn your full variable. Exceed it and there is no ceiling. The structure rewards the reps who show up every month and close, not the ones who swing for a single big deal and coast.
Must-Have Experience
4 to 8 years of full-cycle closing experience in tech-enabled services, complex services, or financial services
Experience selling where the product has a meaningful service layer, implementation complexity, or operational depth -- this is not a pure software demo sale
SaaS experience is relevant if the sale involved multithreading across stakeholders and a complex, consultative buying process
Comfortable selling to CEOs, Owners, CFOs, Controllers, and COOs
Proven ability to run fast sales cycles (approximately 30 days) or compress longer ones
Minimum 1 year of HubSpot experience
Track record of contributing to and improving sales process, not just executing it
Strongly Preferred
Background in FinTech, Accounting Tech, Property Management SaaS, or Vertical SaaS
Experience selling outsourced or tech-enabled services where trust and skepticism are central to the win
Startup or high-growth company experience -- you know what it looks like to build while operating
Familiarity with MEDDIC, Challenger, or SPICED
The Competencies That Matter
Fast learner who makes complex things simple. You will need to get up to speed on the product and hold detailed conversations with skeptical CFOs and Controllers. If you cannot make hard things sound clear, you will lose credibility fast.
Active listener with controlled, confident communication. The best reps here are not high-energy pitchers. They are measured, sharp communicators who make buyers feel heard and run tight, purposeful conversations.
Creative pain discovery. Prospects will not always volunteer their problems. You know how to find the real pain through layered questions, genuine curiosity, and a working understanding of what operational dysfunction looks like in a property management business.
Quick on your feet. Buyers here are founders and executives who think fast and speak directly. You need to keep up, handle unexpected questions without defaulting to 'let me get back to you,' and keep deals on track when conversations shift.
Urgency without pressure. You move deals forward through timelines and business consequences, not desperation or discounting. When a deal goes quiet, you re-engage in a way that feels genuinely useful, not pushy.
Process discipline. You follow the sales process consistently and contribute to making it better. Clean CRM hygiene and accurate forecasting are not administrative tasks to you -- they are how a high-performance team operates.
Benefits:
Remote Work
Health insurance: 90% covered for employee, 75% for dependents (7 plan options)
Dental: 90% employee / 75% dependent coverage
Vision: 75% employee coverage
Life and AD&D Insurance: 1x annual salary, up to $500,000, employer-paid
401(k)
Unlimited PTO (beginning two months after start date)
Computer, monitor, and mouse provided
Monthly utility allowance ($30 USD)
One-time home office furnishing allowance (up to $200 USD)
Optional voluntary benefits: FSA, HSA, EAP, supplemental accident, critical illness, and hospital indemnity
Hiring Process
We use a PI Cognitive Assessment as part of our process. We weight cognitive aptitude and learning speed heavily, more so than educational background. A business, finance, or accounting degree is a plus, not a requirement.
Proper AI is an equal opportunity employer. We evaluate candidates based on competencies, capabilities, and potential.
