Senior Director, Sales

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!

The Role

We're hiring a Sr. Director, Sales to lead our full sales organization (excluding Key Accounts). You'll own a team focused on net new SMB and mid-market business plus sales engineering, reporting directly to the CSO. This is a player-coach role with a build mandate. You inherit a team of seven (two mid-market AEs, three regional AEs, a regional sales manager, and a sales engineer) and will grow it significantly over the next 18 months. You will own the bookings number, run and improve the playbook, and build an AI-first sales team.

The Numbers

• Deal size: $20K to $400K ACV, majority of new logo volume in mid-market

• Quota-carrying reps: traditional enterprise SaaS quota of $700K to $1.25M in annual recurring subscription revenue, depending on segment and tenure

What You'll Own

• Bookings and forecast: own the team number with clean pipeline hygiene and tight commit accuracy

• SMB and Mid-market new logo growth: build a repeatable engine, improve conversion and velocity, shorten rep ramp

• Sales methodology: diagnostic-first, problem-anchored, ROI-driven selling; coach and improve the playbook weekly

• AI-first sales motion: build agentic workflows for research, business-case construction, deal scoring, and outreach

• People leadership: coach the existing team including front-line managers, performance-manage with clarity, and recruit A-players from outside your network

• Sales leadership: represent the sales department on the leadership team and in cross-functional and executive conversations

• Cross-functional partnership: work closely with Key Accounts, Marketing, CS, RevOps, and Product

What You'll Bring

• 10+ years in B2B SaaS sales, 5+ years leading sellers with a track record of hitting bookings numbers the majority of the time.

• Fluency in modern sales methodology (Winning by Design, MEDDPICC, Challenger Sale, or equivalent). You teach it, not just cite it

• Business case and cost-of-inaction selling. You've personally built quantified cases and coached reps to do the same

• Second-line leadership. You've coached and developed front-line managers, not just reps

• AI-first instinct. You've built or championed real AI-supported workflows inside a sales team

• Data-driven operator. You run your team off pipeline math and synthesize information fast

• High EQ and recruiting muscle. You make teams better and bring talent with you

Nice to Have

• PropTech, multifamily, real estate, or vertical SaaS Business solutions selling background.

• Experience selling alongside or against incumbents in property operations, ERP, procurement, or workflow categories.

• Pricing experience with tiered consumption, usage-based, or platform models.

• Have shipped a real, in-production AI agent or workflow inside a sales team, not a demo, not a pitch deck.

Interview Process

• Recruiter screen (30 min)

• Hiring manager interview with CSO (60 min)

• Sales leadership peers including Director of Key Accounts (60 min)

• Cross-functional panel: RevOps, Marketing, CS, Product (60 min)

• Working session: deal teardown and 30/60/90 plan (90 min)

• Executive conversation with CEO and President (45 min)

• References: manager, peer, direct report, cross-functional partner

Compensation & Logistics

• Location: Remote (US); strong preference for Chicago or Dallas

• Compensation: 60% base / 40% variable. We are deliberately weighted toward base. We are hiring a leader and operator, not a deal hunter.

• Equity: meaningful, commensurate with the level of impact and ownership of the role.

The Role

We're hiring a Sr. Director, Sales to lead our full sales organization (excluding Key Accounts). You'll own a team focused on net new SMB and mid-market business plus sales engineering, reporting directly to the CSO. This is a player-coach role with a build mandate. You inherit a team of seven (two mid-market AEs, three regional AEs, a regional sales manager, and a sales engineer) and will grow it significantly over the next 18 months. You will own the bookings number, run and improve the playbook, and build an AI-first sales team.

The Numbers

• Deal size: $20K to $400K ACV, majority of new logo volume in mid-market

• Quota-carrying reps: traditional enterprise SaaS quota of $700K to $1.25M in annual recurring subscription revenue, depending on segment and tenure

What You'll Own

• Bookings and forecast: own the team number with clean pipeline hygiene and tight commit accuracy

• SMB and Mid-market new logo growth: build a repeatable engine, improve conversion and velocity, shorten rep ramp

• Sales methodology: diagnostic-first, problem-anchored, ROI-driven selling; coach and improve the playbook weekly

• AI-first sales motion: build agentic workflows for research, business-case construction, deal scoring, and outreach

• People leadership: coach the existing team including front-line managers, performance-manage with clarity, and recruit A-players from outside your network

• Sales leadership: represent the sales department on the leadership team and in cross-functional and executive conversations

• Cross-functional partnership: work closely with Key Accounts, Marketing, CS, RevOps, and Product

What You'll Bring

• 10+ years in B2B SaaS sales, 5+ years leading sellers with a track record of hitting bookings numbers the majority of the time.

• Fluency in modern sales methodology (Winning by Design, MEDDPICC, Challenger Sale, or equivalent). You teach it, not just cite it

• Business case and cost-of-inaction selling. You've personally built quantified cases and coached reps to do the same

• Second-line leadership. You've coached and developed front-line managers, not just reps

• AI-first instinct. You've built or championed real AI-supported workflows inside a sales team

• Data-driven operator. You run your team off pipeline math and synthesize information fast

• High EQ and recruiting muscle. You make teams better and bring talent with you

Nice to Have

• PropTech, multifamily, real estate, or vertical SaaS Business solutions selling background.

• Experience selling alongside or against incumbents in property operations, ERP, procurement, or workflow categories.

• Pricing experience with tiered consumption, usage-based, or platform models.

• Have shipped a real, in-production AI agent or workflow inside a sales team, not a demo, not a pitch deck.

Interview Process

• Recruiter screen (30 min)

• Hiring manager interview with CSO (60 min)

• Sales leadership peers including Director of Key Accounts (60 min)

• Cross-functional panel: RevOps, Marketing, CS, Product (60 min)

• Working session: deal teardown and 30/60/90 plan (90 min)

• Executive conversation with CEO and President (45 min)

• References: manager, peer, direct report, cross-functional partner

Compensation & Logistics

• Location: Remote (US); strong preference for Chicago or Dallas

• Compensation: 60% base / 40% variable. We are deliberately weighted toward base. We are hiring a leader and operator, not a deal hunter.

• Equity: meaningful, commensurate with the level of impact and ownership of the role.

About HappyCoFounded 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!
Our HappyCo CultureHappyCo strives to build better communities. So naturally, we are dedicated to making our own community an enjoyable place that allows us 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, including stock options- 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.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!