SMB Account Executive
HappyCo
Job Description
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