VP of Sales – Regional, Player-Coach

This is a fully remote position, open to applicants in United States.

📋 Description

• Close intricate enterprise commercial real estate opportunities.

• Maintain a personal sales quota while managing a book of business, even when leading a team.

• Build and mentor a small team of three to four Account Executives, with potential growth to no more than six.

• Participate in deals, conduct debriefs, enhance discovery processes, and provide coaching to representatives in the CRE buying journey.

• Lead the most substantial and complex institutional opportunities.

• Engage with asset managers, ownership groups, and third-party property managers through multiple connections.

• Establish early relationships with economic buyers and nurture those connections.

• Collaborate with Finance and Operations to structure profitable deals, including revenue share models, capital expenditure considerations, management agreements, and pricing strategies.

• Take ownership of, forecast, defend, and achieve the regional sales targets.

• Keep accurate and up-to-date pipeline information in HubSpot.

• Work in tandem with the GTM AI Engineer, marketing, and growth teams on AI and automation initiatives.

• Report to the Head of Revenue while collaborating closely with the CEO.

• Travel regularly to customer locations, industry events, and team meetings.

⛳️ Requirements

• Currently meeting and exceeding an individual sales quota.

• Proven experience in personally closing enterprise-level deals.

• Familiarity with deals valued at $100K or more in annual contract value.

• Experience with sales cycles lasting four to six months or longer.

• Ability to manage opportunities that involve multiple stakeholders and committee decisions.

• Experience selling to commercial real estate owners and asset managers.

• Prior experience in CRE services, PropTech, or a related built-environment sector is strongly preferred.

• Background in mentoring individuals informally or in formally developing representatives.

• Formal training in MEDDPICC or a similar framework, applied in practice.

• Proficiency in deal structuring, including revenue sharing, capital expenditure amortization, management agreements, and unit economics.

• Strong forecasting discipline; familiarity with HubSpot is an advantage.

• Practical experience using AI in personal sales efforts.

• Willingness and capability to travel frequently.

• Existing connections with institutional owners, asset managers, or third-party property managers are a plus.

• Experience in selling a combined technology and services offering is a plus.

• Experience in a startup or high-growth environment is advantageous.

🏝️ Benefits

• Medical, dental, and vision insurance coverage.

• 401(k) plan with company matching contributions.

• Unlimited paid time off (PTO).

• Paid parental leave.

• Flexible, remote-first working environment.

• Support for learning and development, including conferences and certifications.

• Opportunities for retreats and team-building events.