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
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Deal size: $20K to $400K ACV, majority of new logo volume in mid-market
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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
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Bookings and forecast: own the team number with clean pipeline hygiene and tight commit accuracy
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SMB and Mid-market new logo growth: build a repeatable engine, improve conversion and velocity, shorten rep ramp
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Sales methodology: diagnostic-first, problem-anchored, ROI-driven selling; coach and improve the playbook weekly
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AI-first sales motion: build agentic workflows for research, business-case construction, deal scoring, and outreach
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People leadership: coach the existing team including front-line managers, performance-manage with clarity, and recruit A-players from outside your network
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Sales leadership: represent the sales department on the leadership team and in cross-functional and executive conversations
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Cross-functional partnership: work closely with Key Accounts, Marketing, CS, RevOps, and Product
What You'll Bring
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10+ years in B2B SaaS sales, 5+ years leading sellers with a track record of hitting bookings numbers the majority of the time.
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Fluency in modern sales methodology (Winning by Design, MEDDPICC, Challenger Sale, or equivalent). You teach it, not just cite it
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Business case and cost-of-inaction selling. You've personally built quantified cases and coached reps to do the same
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Second-line leadership. You've coached and developed front-line managers, not just reps
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AI-first instinct. You've built or championed real AI-supported workflows inside a sales team
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Data-driven operator. You run your team off pipeline math and synthesize information fast
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High EQ and recruiting muscle. You make teams better and bring talent with you
Nice to Have
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PropTech, multifamily, real estate, or vertical SaaS Business solutions selling background.
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Experience selling alongside or against incumbents in property operations, ERP, procurement, or workflow categories.
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Pricing experience with tiered consumption, usage-based, or platform models.
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Have shipped a real, in-production AI agent or workflow inside a sales team, not a demo, not a pitch deck.
Interview Process
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Recruiter screen (30 min)
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Hiring manager interview with CSO (60 min)
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Sales leadership peers including Director of Key Accounts (60 min)
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Cross-functional panel: RevOps, Marketing, CS, Product (60 min)
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Working session: deal teardown and 30/60/90 plan (90 min)
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Executive conversation with CEO and President (45 min)
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References: manager, peer, direct report, cross-functional partner
Compensation & Logistics
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Location: Remote (US); strong preference for Chicago or Dallas
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Compensation: 60% base / 40% variable. We are deliberately weighted toward base. We are hiring a leader and operator, not a deal hunter.
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Equity: meaningful, commensurate with the level of impact and ownership of the role.