Director of Revenue Process and Technology

Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed sen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services.

Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.

The Director of Revenue Process & Technology leads the standardization, automation, and technology strategy that powers Lessen’s go-to-market engine. This role owns the design and enforcement of consistent processes across sales, marketing, and account management; drives the roadmap for Lessen’s GTM technology stack, anchored by Salesforce; and leads the adoption and utilization of AI and automation to make the entire sales cycle faster, more predictable, and more scalable.

• Define, document, and enforce standardized sales processes, lifecycle stages, and definitions across Sales, Marketing, and Customer Success so every function operates from the same playbook
• Identify friction points across the funnel from lead generation through opportunity development, close, expansion, and renewal, and redesign of workflows to remove manual, redundant, or inconsistent steps
• Establish data quality, field-level, and process-adherence standards, and implement governance to maintain data integrity as the organization scales
• Deliver an end-state suite of reporting and analysis for revenue productivity measures

• Own the strategy and roadmap for Lessen’s revenue technology stack, with Salesforce CRM as the system of record for sales, marketing, and customer success
• Partner with Prod Tech, the Rev Ops Team, Sales and Marketing on architecture, data model, automation (Flows), and integrations between Salesforce and adjacent revenue systems (marketing automation, CPQ, forecasting, and reporting tools)
• Lead evaluation, selection, and deployment of supporting GTM technologies, including low/no-code platforms, to extend Salesforce’s capabilities without adding unnecessary complexity
• Lead the organization’s Master Data Management (MDM) and data governance strategy across the GTM sales systems
• Drive user adoption of the technology stack through training, enablement, and change management. Act as the escalation point for system usability and performance issues

• Lead Lessen’s GTM evolution toward an AI-enabled operating model, embedding intelligence across the revenue lifecycle, including forecasting, pipeline management, account expansion, and renewals
• Identify and prioritize opportunities to apply AI and automation to reduce manual work across the platform, from lead routing and lead scoring to next-best-action recommendations for sellers.
• Partner with IT/Data teams to evaluate and deploy AI-enabled tools (agentic workflows, predictive insights, revenue intelligence) that are practical, secure, and genuinely improve seller productivity — not adoption for its own sake
• Stay current on emerging AI and automation capabilities in the Rev Ops/GTM technology space and translate them into a realistic, sequenced roadmap for the organization

• Bachelor’s degree in Business, Information Systems, Finance, Economics, or a related field
• Demonstrated success in designing, standardizing, and scaling GTM processes across sales, marketing, and customer success
• De…