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.
What You'll Do:
- 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 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
- 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
Process Standardization
GTM Sales Technology
Artificial Intelligence & Automation
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
- 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
Preferred Qualifications
Skills Required
- Bachelor's degree in Business, Information Systems, Finance, Economics, or a related field
- Experience designing, standardizing, and scaling go-to-market processes across sales, marketing, and customer success
- Deep hands-on expertise with Salesforce CRM, including architecture, automation, reporting, and data governance
- 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 front-office technology environments
- Strong written and verbal communication skills
- Experience transforming complex analysis into clear, actionable insights for senior leadership
- MBA or other advanced degree
- Experience in SaaS, technology, facility management, or real estate-focused industries
- Background in change management and project management
- Experience in a matrixed, multi-service, or multi-product B2B environment
What the Team is Saying
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Lessen LLC Compensation & Benefits Highlights
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Healthcare Strength — Health coverage is described as comprehensive, including medical, dental, vision, mental‑health support, and supplemental options like FSAs/HSAs and pet insurance. Feedback suggests plan quality can be a relative bright spot, with some reports of favorable employee‑only costs in recent years.
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Retirement Support — A 401(k) plan with employer matching is consistently highlighted in company materials and employee accounts. Feedback suggests the match (often cited as 50% up to a 4% employer contribution) makes retirement benefits a meaningful component of total rewards.
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Leave & Time Off Breadth — Paid parental leave, flexible or unlimited PTO for some roles, holidays, sick time, and paid volunteer days are part of the offering. Feedback suggests the breadth of time off appears strong on paper, though experiences can vary by position.
Lessen LLC Insights
What We Do
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. To learn more, visit Lessen.com.
Why Work With Us
We make caring for and improving properties simpler, faster, better. Powered by tech and perfected by people, we deliver best-in-class, transformational solutions to deliver assets to market faster, keep businesses up and running, and improve customer and resident experiences. We're property services, simplified.
Gallery
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Lessen LLC Teams
Lessen LLC Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
At Lessen, managers decide how teams work best—office, home, or hybrid. We value flexibility, connection, and outcomes, investing in tools that keep everyone aligned and focused on delivering great results together.
