[Remote] Senior Director, Sales | SaaS / PropTech | Fully Remote (Chicago or Dallas Preferred) | Up to $400k OTE
Note: The job is a remote job and is open to candidates in USA. RET(Search) is a high-growth, values-driven SaaS company modernizing the multifamily property management industry. They are seeking a Senior Director, Sales to lead the sales organization, focusing on net-new SMB and mid-market business, while building and growing an AI-first sales team.
Responsibilities
- Own the team number with clean pipeline hygiene and tight commit accuracy
- Build a repeatable new-logo engine, improve conversion and velocity, and shorten rep ramp
- Drive diagnostic-first, problem-anchored, ROI-driven selling; coach and improve the playbook weekly
- Build agentic workflows for research, business-case construction, deal scoring, and outreach
- 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
Skills
- 10+ years in B2B SaaS sales, including 5+ years leading sellers, with a track record of hitting numbers the majority of the time
- Deep command of modern sales methodology (Winning by Design, MEDDPICC, Challenger, or equivalent) you teach it, not just cite it
- Proven experience building quantified, cost-of-inaction business cases and coaching reps to do the same
- Experience coaching and developing front-line managers, not only individual reps
- You have built or championed real AI-supported workflows inside a sales team
- You run your team off pipeline math and synthesize information quickly
- You make teams better and bring talent with you
- PropTech, multifamily, real estate, or vertical-SaaS 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
- A real, in-production AI agent or workflow shipped inside a sales team
Benefits
- Meaningful equity/stock options, commensurate with the level of impact and ownership of the role.
- Comprehensive medical, dental, and vision insurance.
- Unlimited vacation policy.
- Generous paid parental leave.
- Monthly Wellness and Home Office stipends.
- Work-from-anywhere flexibility.
Company Overview