SMB Account Executive

SMB Account Executive

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!

We're looking for a driven, coachable, and resourceful SMB Account Executive to help scale HappyCo's growth in the multifamily and property maintenance tech space. This role is ideal for a seller who enjoys owning a territory end-to-end—from pipeline generation to close to long-term account growth.

If you're excited about solving real operational problems for multifamily operators, thrive in fast-paced environments, and want meaningful ownership over outcomes—not just deals—you'll feel right at home.

This is not a role for order-takers. We're looking for someone who builds pipeline proactively, leads with curiosity in discovery, moves with urgency, and can close multi-stakeholder, value-based SaaS deals, then expand those accounts over time.

If you're confident navigating C-suite conversations, fluent in selling SaaS platforms, and excited about AI, automation, and modernizing property operations—we should talk.

This position will cover the Mid-West Region of the United States and we are considering candidates in that geography only.

What You'll Do

• Own and grow a territory of Regional PMC accounts
• Manage the full sales cycle—from self-sourced and inbound discovery through close
• Lead strong discovery conversations that uncover operational, financial, and workflow pain
• Consistently generate pipeline through outbound prospecting, events & referrals
• Close $40K–$80K+ ACV deals, often involving multiple products and decision-makers
• Manage a full-funnel process using HappyCo's Sales Playbook and data-driven storytelling
• Identify and execute upsell and cross-sell opportunities within existing Regional accounts
• Forecast accurately & manage deal progression using Salesforce, Gong, Notion etc.
• Represent HappyCo at industry events, field meetings, and regional trade shows
• Champion modern, AI-driven workflows that improve how multifamily teams operate

What Sets You up for Success

• 2+ years of full-cycle SaaS sales experience, preferably in proptech, real estate, or operational software
• Proven ability to self-generate pipeline in a territory-based role
• Strong command of sales process—you can map stakeholders, align timelines, and drive decisions
• Track record of closing $40K–$80K+ ACV deals with meaningful deal complexity
• You've sold to technical, operational, or C-level buyers and know how to simplify complexity
• High sense of ownership—you treat your territory like a business
• Passionate belief in the HappyCo core values with unwavering commitment to quality and success
• Ability to travel - up to 30 - 40% - for field selling, industry events, and customer meetings
• You're comfortable evolving quickly—our market moves fast, and so do we

Bonus if You Have

• Experience selling into multifamily or property management companies
• Deep understanding of multifamily maintenance workflows (inspections, make-readies etc)
• Track record selling solutions that improve operational efficiency, NOI, or resident experience
• Training in a Sales Methodology (Winning By Design, Sandler, SPIN etc)

Why Join Us?

• Real ownership: You own your territory from first meeting through expansion
• Meaningful impact: Help operators reduce costs, increase visibility, and scale smarter
• Big vision: We're modernizing a lagging industry with smart, AI-powered tools
• Sales-forward culture: We value process, growth, and performance
• Visibility & influence: Work closely with leadership, product, & marketing to shape GTM
• Growth opportunity: Competitive comp, real opportunity to grow, and a supportive remote team

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!

HappyCo strives to build better communities. So naturally, we are dedicated to making our own community an enjoyable place that allows us to 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 careers page!

We Offer:

• Work from anywhere supported by a flexible company culture
• Opportunity to work for one of the fastest-growing technology companies in the PropTech industry
• Unlimited vacation time
• Generous paid parental leave
• Competitive and equitable pay
• Monthly stipends to support Wellness and Home Office expenses

Find out more about our US Employee Benefits here!

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 View email address on click.appcast.io