SMB Account Executive - HappyCo

HappyCo is values-driven, offers a flexible, supportive culture, and is looking for a driven, coachable, and resourceful SMB Account Executive to help scale growth in the multifamily and property maintenance tech space.

Note: 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

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