Enterprise Sales Director

Description

• Forecast with precision: Maintain CRM hygiene, ensuring pipeline accuracy and forecasting predictability.
• 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.
• 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.
• Orchestrate cross-functional sales motions: Collaborate with Solutions Consultants, Product, Account Management, Marketing, Operations, and Channel Alliances to manage a team-selling process.
• 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.
• Represent Lessen externally: Participate in industry associations, conferences, and client forums to expand market presence and establish thought leadership.
• 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.
• Negotiate and close complex deals: Lead multi-stakeholder negotiations that meet financial, legal, and ethical standards while delivering measurable ROI for clients.
• 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.
• Drive new business growth: Consistently exceed annual quota through proactive pipeline generation, strategic prospecting, and disciplined territory planning.

Requirements

• Exceptional executive communication skills with the ability to translate technical concepts into clear business value.
• Expertise in selling to multi-site organizations (e.g., retail chains, financial institutions, logistics, or corporate real estate portfolios).
• Familiarity with PropTech, facilities management, or commercial real estate services.
• Demonstrated ability to convey how AI and automation can be integrated into customer maintenance, facilities operations, and other enterprise workflows.
• Demonstrated ability to navigate complex, consensus-driven decision processes where multiple departments share ownership of budget and outcomes.
• 8–10+ years of progressive experience in enterprise or solution sales, ideally within technology, SaaS, AI, or service platform environments.
• Travel: Up to 50% domestic travel for prospect meetings, industry events, and strategic presentations.
• Strong understanding of business process improvement, customer experience design, and technology-enabled transformation within corporate real estate or facilities operations.
• Background in software, AI, or platform sales
• Proven experience leading or influencing workflow redesign initiatives that enhance customer experience, operational efficiency, or asset lifecycle management.
• Bachelor’s degree required; MBA or related advanced degree preferred.
• Proven track record of exceeding multi-million-dollar quotas through net-new business acquisition.

Benefits

• Financial Services
• $130,000.00 - 150,000.00 annually.
• Health Care Providers and Veterinary Care

Training + Development

Interview process

Visa Sponsorship

Security clearance