Senior Director, Sales (PropTech)

TL;DR

Senior Director, Sales (PropTech/SaaS): Leading the full sales organization for SMB and mid-market business with an accent on building an AI-first sales team and optimizing the sales playbook. Focus on driving net new logo growth, coaching front-line managers, and scaling a repeatable revenue engine.

Location: Remote (US); strong preference for Chicago or Dallas

Company

hirify.global builds mobile and cloud solutions to enable real-time property data, featuring a flagship product suite with over 5 million units on its platform.

What you will do

• Lead the full sales organization focused on net new SMB and mid-market business, including sales engineering.
• Own bookings, forecasting, and ensure tight pipeline hygiene and commit accuracy.
• Develop an AI-first sales motion by building agentic workflows for research, deal scoring, and outreach.
• Coach front-line managers and AEs using diagnostic-first and ROI-driven sales methodologies.
• Recruit top-tier talent to significantly grow the sales team over the next 18 months.
• Collaborate cross-functionally with Key Accounts, Marketing, Customer Success, RevOps, and Product.

Requirements

• 10+ years of experience in B2B SaaS sales, with 5+ years leading sales teams.
• Fluency in modern sales methodologies such as MEDDPICC, Winning by Design, or Challenger Sale.
• Proven track record in second-line leadership, having coached and developed front-line managers.
• Experience building or championing real AI-supported workflows within a sales organization.
• Strong data-driven approach to pipeline math and operational synthesis.
• Must be based in the United States.

Nice to have

• Background in PropTech, multifamily real estate, or vertical SaaS business solutions.
• Experience selling against incumbents in property operations, ERP, or procurement categories.
• Knowledge of tiered consumption, usage-based, or platform pricing models.
• Experience shipping production-ready AI agents or workflows within a sales team.

Culture & Benefits

• Flexible and supportive culture driven by values, without egos or politics.
• Meaningful equity ownership commensurate with impact.
• Compensation structure weighted toward base salary to prioritize leadership and operations.
• Environment focused on career growth and working with like-minded professionals.

Hiring process

• Initial recruiter screen and hiring manager interview with the CSO.
• Interviews with sales leadership peers and a cross-functional panel (RevOps, Marketing, CS, Product).
• Technical working session featuring a deal teardown and 30/60/90 day plan.
• Final executive conversation with the CEO and President, followed by reference checks.