Director of Revenue Process and Technology
- Location
- Illinois or Arizona
- Work mode
- Hybrid
- Employment type
- Full-time
- Salary
- $1,50,000 – $1,65,000 / year-salary
About the job
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 management and real estate-focused industries
- Strong background in change management, project management
- Experience in a matrixed, multi-service or multi-product B2B environment is a plus
Why Lessen: · Competitive compensation · Health, Dental, Vision, Life, Disability options · 401K retirement savings plan · Paid vacation, federal and floating holidays · Maternity/Paternity Pay · Career advancement opportunities · All the tools you'll need to be successful
Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building. Lessen is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.
From Lessen's careers page (Lever), checked 10 Nov 2026.
How to apply
- Select Apply on lessen.com. It opens Lessen's own application form in a new tab, run on Lever.
- Fill in the form and upload your résumé there. Jobiwork never sees your application.
- Lessen will reply to you directly. No real employer asks you for money to apply.
Posted 10 Nov 2026 · checked 10 Nov 2026 · Report this job