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

Remote Worldwide Hiring now

Note: The job is a remote job and is reputed company 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 reputed company 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 reputed company 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 reputed company, and recruit reputed company 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 reputed company 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 reputed company or championed reputed company 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, reputed company 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 reputed company, 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 reputed company 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.

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