Senior Director, Sales
HappyCo
Sales & Business Development
United States
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.