Posted Jul 10, 2026

[Remote] Senior Director, Sales | SaaS / PropTech | Fully Remote (Chicago or Dallas Preferred) | Up to $400k OTE

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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 reputed company 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 reputed company, improve conversion and velocity, and shorten rep reputed company • 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 reputed company • Coach the existing team including reputed company-line managers, performance-manage with clarity, and recruit A-players from reputed company 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 reputed company-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 reputed company teams reputed company 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-reputed company flexibility. Company Overview • RET(Search) is a wholly owned subsidiary of August Hill, a leading Chicago-based investment and advisory firm. It was founded in 2021, and is headquartered in Chicago, Illinois, US, with a workforce of 2-10 employees. Its website is https://retsearch.com. Apply To This Job