Senior Director, Sales

HappyCo

Senior Director of Sales at HappyCo leading B2B SaaS sales organization focused on SMB and mid-market. Building an AI-first sales team and improving sales methodologies to drive revenue.

Posted 6/1/2026full-timeRemote • 🇺🇸 United StatesSeniorWebsite

About the role

Key responsibilities & impact

Lead the full sales organization (excluding Key Accounts)
Own a team focused on net new SMB and mid-market business plus sales engineering
Improve the playbook and build an AI-first sales team
Build a repeatable engine, improve conversion and velocity, shorten rep ramp
Coach the existing team and recruit A-players
Represent the sales department on the leadership team
Work closely with Key Accounts, Marketing, CS, RevOps, and Product

Requirements

What you’ll need

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)
Business case and cost-of-inaction selling
Second-line leadership
AI-first instinct
Data-driven operator
High EQ and recruiting muscle

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

B2B SaaS salessales methodologybusiness case sellingcost-of-inaction sellingdata-driven decision making

Soft Skills

leadershipcoachingrecruitinghigh emotional intelligence (EQ)team building