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.

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

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

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)

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

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