Director of Revenue Process and Technology

Lessen•Illinois or Arizona, IL

1d•$150,000 - $165,000

About The Position

The Director of Revenue Process & Technology leads the standardization, automation, and technology strategy that powers Lessen’s go-to-market engine. The role owns consistent processes across sales, marketing, and account management; drives the roadmap for Lessen’s GTM technology stack, anchored by Salesforce; and leads adoption and utilization of AI and automation to make the sales cycle faster, more predictable, and more scalable. The position defines and enforces standardized revenue processes and data governance, identifies and removes friction across the revenue funnel, and delivers reporting and analysis for revenue productivity. It owns the revenue technology strategy, including Salesforce architecture, data models, automation, integrations, supporting GTM technologies, and Master Data Management. The role also drives system adoption through training, enablement, and change management, and serves as an escalation point for system usability and performance issues. The Director leads Lessen’s evolution toward an AI-enabled operating model across forecasting, pipeline management, account expansion, and renewals. They identify automation opportunities, partner with IT and Data teams to assess and deploy practical, secure AI-enabled tools, and translate emerging capabilities into a realistic, sequenced roadmap. Lessen is a tech-enabled property service provider serving commercial and residential real estate. It has a network of more than 30,000 vetted vendors, serves clients with more than 1 million properties, and completes more than 3.5 million work orders annually. The company is venture-backed and privately held, with offices in Scottsdale and Chicago.

Requirements

Bachelor’s degree in Business, Information Systems, Finance, Economics, or a related field.
Demonstrated success designing, standardizing, and scaling go-to-market processes across sales, marketing, and customer success.
Deep, hands-on Salesforce CRM expertise in 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.
Experience managing data at scale in common front-office technology environments.
Strong written and verbal communication skills, including experience translating complex analysis into clear, actionable insights for senior leadership.

Nice To Haves

MBA or other advanced degree.
Experience in SaaS, technology, facility management, or real estate-focused industries.
Strong background in change management and project management.
Experience in a matrixed, multi-service or multi-product B2B environment.

Responsibilities

Define, document, and enforce standardized sales processes, lifecycle stages, and definitions across Sales, Marketing, and Customer Success.
Identify revenue-funnel friction and redesign workflows to remove manual, redundant, or inconsistent steps from lead generation through renewals.
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 ProdTech, RevOps, Sales, and Marketing on architecture, data models, Salesforce automation and integrations with adjacent revenue systems.
Lead evaluation, selection, and deployment of supporting go-to-market technologies, including low/no-code platforms.
Lead Master Data Management and data governance strategy across go-to-market sales systems.
Drive technology adoption through training, enablement, and change management, and act as the escalation point for system usability and performance issues.
Lead the evolution toward an AI-enabled operating model across forecasting, pipeline management, account expansion, and renewals.
Identify and prioritize AI and automation opportunities to reduce manual work, including lead routing, lead scoring, and next-best-action recommendations.
Partner with IT and Data teams to evaluate and deploy practical, secure AI-enabled tools that improve seller productivity.
Monitor emerging AI and automation capabilities in RevOps and GTM technology and translate them into a realistic, sequenced roadmap.