Mid Market Account Executive

The Position

When properties perform better, people live better. That’s the HappyCo mission, and maintenance is where it starts. HappyCo is the industry’s leading maintenance platform, covering the full lifecycle of a residential community: acquisition, operations, improvements, and disposition. Companies of all sizes managing more than 20,000 communities rely on HappyCo to run their maintenance teams daily.

As a Mid-Market Account Executive, you’ll own a book of customers and prospects with 5 to 50 properties in your market. You’ll spend real time with operators onsite and run your book like your own business, owning new logos and expansion for the long term.

We hire trusted advisors who solve real problems for real operators. You’ll diagnose before you prescribe, advance deals on evidence the buyer has validated, and stay accountable for results well past signature. Do that well and you’ll grow your book and your career here.

What you’ll do

• Own your book of prospects and customers for as long as you hold it, and build new pipeline every week from signals, referrals, events, and outbound.
• Run the HappyCo Way. Use SPICED to map how work happens today and what it costs, so the demo confirms the fix.
• Open with a solution to the problem the operator has named, never an oversell, working alongside the PMS they already use (Yardi, RealPage, Entrata).
• Multithread across operations, maintenance, finance, and ownership to reach the people who sign.
• Meet operators at their offices, communities, and regional events. Expect roughly 30–50% travel.
• Keep Salesforce current and partner with Customer Success and Sales Engineering. We’re an AI-first sales team, so using agents, Gong, and HubSpot to move faster is standard practice here.

Why you’ll like it here

• A book you can win, with real ownership of your market. It’s built for entrepreneurial reps who are creative and love building relationships with operators.
• An offer built for this segment, with low-friction entry points that expand on results.
• A real selling system: the HappyCo Way, plus a 90-day certification ramp that gets you productive fast.

You may be a good fit if you have

• 5+ years of full-cycle B2B SaaS sales, with a record of hitting quota
• Deals closing in the $15K–$75K+ ACV range, including entry deals that grow into platform sales
• Experience selling multifamily, property management, or real estate operations software
• Operators in your market who know and trust you, or a history of building customers
• Training in a structured sales methodology, used on live deals
• Strong prospecting: you stay on top of your book, know your accounts and keep tabs on industry trends to engage at the right time
• Strong discovery: you map stakeholders, quantify impact, and build a business case the buyer owns
• Strong closer: you map impact to an investment thesis validated by your accounts stakeholders, navigating the legal, procurement and IT process like a pro
• Comfort demoing software, configuring systems, and delivering presentations
• You live in or near your market, travel regularly, and use AI in your daily workflow

Strong candidates may also have

• Winning by Design (SPICED) or MEDDPICC training
• Hands-on knowledge of multifamily maintenance, construction, or procurement workflows
• Experience with a major PMS (Yardi, RealPage, Entrata)