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 at scale. Lessen’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.

What You'll Do: Process Standardization

- 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

GTM Sales Technology

- 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 ProdTech, the RevOps 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

Artificial Intelligence & Automation

- 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 RevOps/GTM technology space and translate them into a realistic, sequenced roadmap for the organization

What You'll Need: - 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

- Deep, hands-on expertise with Salesforce CRM — architecture, automation, reporting, and data governance — with proven experience managing a broader revenue technology stack

- Technical experience applying AI and automation (including AI agents and low/no-code platforms) to revenue operations, and managing data at scale in common front-office technology environments

- Strong written and verbal communication skills, with experience transforming complex analysis into clear, actionable insights for senior leadership

Preferred Qualifications

- MBA or other advanced degree preferred

- Experience in SaaS, technology, or facility manag