Senior Director, Sales

HappyCo

8d•Remote

About The Position

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.

Requirements

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)
Experience building quantified business cases and coaching reps to do the same
Second-line leadership experience (coached and developed front-line managers)
Experience building or championing real AI-supported workflows inside a sales team
Data-driven operator who runs their team off pipeline math and synthesizes information fast
High EQ and recruiting muscle

Nice To Haves

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
Shipped a real, in-production AI agent or workflow inside a sales team

Responsibilities

Own the team number with clean pipeline hygiene and tight commit accuracy
Build a repeatable engine, improve conversion and velocity, shorten rep ramp for SMB and Mid-market new logo growth
Coach and improve the playbook weekly using diagnostic-first, problem-anchored, ROI-driven selling methodology
Build agentic workflows for research, business-case construction, deal scoring, and outreach for an AI-first sales motion
Coach the existing team including front-line managers, performance-manage with clarity, and recruit A-players from outside your network
Represent the sales department on the leadership team and in cross-functional and executive conversations
Work closely with Key Accounts, Marketing, CS, RevOps, and Product