Head of Enterprise Sales

Role overview
 
You’ll define the strategy, sell the vision, land the deals, and build the infrastructure to scale.
As Our Client’s first Head of Enterprise Sales, you’ll lead the charge in building our enterprise GTM motion from the ground up—focusing on major players across SFR, STR, Commercial Multifamily, Retail, and Office sectors.
You’ll drive everything from identifying high-potential segments and shaping pilot programs to structuring complex deals and crafting compelling value narratives. You won’t be starting from zero: our product is already generating measurable impact with smaller clients.
 
Key Responsibilities

• Enterprise GTM Strategy Define ideal customer profiles, segment key accounts, design pilot frameworks, shape pricing models, and build a scalable land-and-expand approach.
• First $10M Enterprise Blueprint Map out what early traction turns into at scale—team structure, hiring priorities, success metrics, and operational rhythm.
• High-Stakes Deal Execution Personally own and close early-stage enterprise opportunities—navigating complex, multi-market, multi-year deals from first call to signed contract.
• Playbook Foundations Develop the core assets for enterprise sales: pitch flows, pilot formats, commercial frameworks, case studies, and enablement content.
• Narrative & ROI Positioning Work cross-functionally to craft a compelling value story that resonates with enterprise buyers—Ops leaders, CTOs, and heads of procurement.
• Customer-Driven Growth Partner with Customer Success and Product teams to transform early adopters into high-impact champions and scalable case studies.
• Field-to-Product Insights Loop Translate insights from prospects and clients into actionable feedback on features, integrations, packaging, and compliance needs.

You Might Be a Fit If:

• You’ve launched or revamped an enterprise sales motion from the ground up—either at an early-stage company or as part of a new vertical within a scaling business.
• You’ve sold complex SaaS, AI solutions, or industry-specific platforms into hands-on, operations-heavy sectors like PropTech, logistics, or facilities.
• You’re well-versed in value-based selling and skilled at building trust across executive teams, frontline operators, and technical stakeholders.
• You know how to design pilots that drive conversion—not just showcase features.
• You thrive in unstructured environments, take initiative naturally, and embrace the challenge of owning outcomes.
• You’re not afraid to get in the weeds—closing deals directly while building the repeatable systems that can scale beyond you.
• Bonus points if you’ve worked with or sold into real estate operators, REITs, large multifamily groups, or maintenance-focused tech teams.