Lessen is the leading AI-powered, tech-enabled property services platform transforming how commercial and residential real estate services are delivered and managed at scale. Our platform provides data-driven insights that unlock growth opportunities, enhance operational efficiency, and reduce costs for investors, owners, managers, and service providers.

Powered by a network of over 30,000 vetted affiliates, Lessen supports clients with more than 1 million properties and completes over 3.5 million work orders annually across an expanding suite of services.

We are intentional about attracting, developing, and retaining exceptional talent from diverse backgrounds. We value teammates who are curious, motivated, empathetic, and collaborative, helping us amplify the inclusive culture that fuels innovation and growth.

The Enterprise Sales Director is a high-impact, quota-carrying sales hunter responsible for generating new business growth across one or more of Lessen’s key market verticals — including healthcare providers and veterinary care, K-12, distribution and logistics, retail, financial services, federal/state/local government, technology/data centers, foodservice, hospitality, industrial, and manufacturing.

This individual drives full-cycle enterprise sales engagements — from prospecting and territory planning through contract negotiation and close — while positioning Lessen’s AI-powered, end-to-end property service platform as a transformative solution that reduces operating costs, modernizes workflows, and elevates customer experience.

- Drive new business growth: Consistently exceed annual quota through proactive pipeline generation, strategic prospecting, and disciplined territory planning.

- Execute a targeted go-to-market plan: Build and manage a pipeline, leveraging market insights, vertical data, and multi-channel outreach to grow new accounts.

- Position the Lessen value proposition: Articulate and demonstrate how Lessen’s AI-driven platform improves customer experience, streamlines facilities management, automates workflows, and reduces the cost to maintain distributed assets at scale.

- Advise on digital transformation: Partner with clients to integrate AI into their operational, maintenance, and business processes, helping to redesign corporate workflows that enhance service delivery, improve workforce efficiency, and increase customer satisfaction.

- Lead C-Suite engagements: Build trusted relationships with CFOs, COOs, CIOs, and Heads of Real Estate or Facilities to influence strategic decisions and advocate for AI-enabled process modernization.

- Orchestrate cross-functional sales motions: Collaborate with Solutions Consultants, Product, Account Management, Marketing, Operations, and Channel Alliances to manage a team-selling process.

- Negotiate and close complex deals: Lead multi-stakeholder negotiations that meet financial, legal, and ethical standards while delivering measurable ROI for clients.

- Integrate technology and trades: Demonstrate how Lessen unites technology, AI, data intelligence, and field expertise across HVAC, electrical, plumbing, janitorial, and general maintenance trades to streamline service delivery at scale.

- Forecast with precision: Maintain CRM hygiene, ensuring pipeline accuracy and forecasting predictability.

- Represent Lessen externally: Participate in industry associations, conferences, and client forums to expand market presence and establish thought leadership.

- Travel: Up to 50% domestic travel for prospect meetings, industry events, and strategic presentations.

- Retail

- Financial Services

- Distribution and Logistics

- K-12

- Health Care Providers and Veterinary Care

- Technology/Data Centers

- Federal/State/Local government

- Foodservice

- Hospitality

- Manufacturing

- Industrial

- 8–10+ years of progressive experience in enterprise or solution sales, ideally within technology, SaaS, AI, or service platform environments.

- Demonstrated ability to convey how AI and automation can be integrated into customer maintenance, facilities operations, and other enterprise workflows.

- Proven experience leading or influencing workflow redesign initiatives that enhance customer experience, operational efficiency, or asset lifecycle management.

- Proven track record of exceeding multi-million-dollar quotas through net-new business acquisition.

- Expertise in selling to multi-site organizations (e.g., retail chains, financial institutions, logistics, or corporate real estate portfolios).

- Demonstrated ability to navigate complex, consensus-driven decision processes where multiple departments share ownership of budget and outcomes.

- Strong understanding of business process improvement, customer experience design, and technology-enabled transformation within corporate real estate or facilities operations.

- Exceptional executive communication skills with the ability to translate technical concepts into clear business value.

- Bachelor’s degree required; MBA or related advanced degree preferred.

- Background in software, AI, or platform sales

- Familiarity with PropTech, facilities management, or commercial real estate services.