Lessen · 2 months ago
Enterprise Sales Director
Chicago, IL
Full-time
Hybrid
Director/Executive
8+ years expLessen is a leading AI-powered, tech-enabled property services platform transforming real estate services. The Enterprise Sales Director will be responsible for generating new business growth across key market verticals, driving full-cycle enterprise sales engagements, and positioning Lessen’s platform as a transformative solution for clients.
Online PortalsProperty ManagementReal EstateRental Property
Responsibilities
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
Qualification
Required
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
Preferred
Background in software, AI, or platform sales
Familiarity with PropTech, facilities management, or commercial real estate services
Company
Lessen
Lessen is an online platform for managing properties and maintenance services.
501-1000 employees
Funding
Current Stage
Late StageTotal Funding
$735MKey Investors
Legacy KnightFifth WallNavitas Capital
2023-01-12Series Unknown· $500M
2023-01-12Debt Financing
2022-05-01Series B· $30M
Leadership Team
J
Jay McKee
Founder and CEO
Sean Miller
Chief Revenue Officer (CRO)
Recent News
www.finsmes.com
2026-01-09
General catalyst
2026-01-08
Business Wire
2025-11-11
Company data provided by crunchbase