Senior Director, Sales

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.