SMB Account Executive

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