HappyCo is a company where people can grow their careers and work with like minded people, with no egos or politics. HappyCo is values driven and offers a flexible, supportive culture. Join HappyCo and Make Work Happy!

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)

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About HappyCo

Founded in 2011, HappyCo (happy.co) builds mobile and cloud solutions to enable real-time property data. Our flagship product suite 'Happy Property’ has more than 5 million units on its platform.

We’re everyday people with a shared purpose — improving the lives of others. Our team is made up of thinkers, talkers, planners, makers, builders and everything in between. Together, we’re turning our passions into happier communities!

When customers use our software, their communities get stronger. Our tools empower everyone in multifamily property management to improve their operations and maximize returns, which means they’re building better experiences for their residents. Learn more about our Product Vision here!

Our HappyCo Culture & Values

HappyCo strives to build better communities. So naturally, we are dedicated to making our own community an enjoyable place that lets us do our best work. We’re devoted to building an inclusive, supportive culture that empowers each HappyCo’er to succeed and grow. To learn more about our culture, check out our Glassdoor page and our careers page!

HappyCo’s culture is driven by our core values of Make Happiness, Better Together, Get Good Sh*t Done, Customer Obsessed and Kaizen - sounds great, right, but what does this mean for you?

We believe in supporting people to do their best work and thrive, and building a diverse, equitable, and inclusive company is core to our mission. Our goal is to ensure that HappyCo upholds an inclusive environment where all people feel that they are equally respected and valued, whether they are applying for an open position or working at the company. We welcome applicants of any educational background, gender identity and expression, sexual orientation, religion, ethnicity, age, citizenship, socioeconomic status, disability, and veteran status. HappyCo is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures.

A note to Recruitment Agencies: Please don’t reach out to us about our roles -- we’ve got it covered. We don’t accept unsolicited agency resumes and HappyCo is not responsible for any fees related to unsolicited resumes

A note on hiring scams: All legitimate communication from HappyCo about this role — including interview scheduling, offer letters, and any request for personal information — will come from an @happy.co email address. We will never conduct interviews over chat-only platforms (e.g., Telegram, WhatsApp, Skype) or ask you to pay for equipment, training, or background checks. If you receive an offer or interview request from any other domain, please don’t respond, and report it to us at recruitingscam@happy.co