Director, Product Marketing
Lessen, Chicago, IL, United States
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.
Summary The Director of Product Marketing will build and lead the product marketing function, including product positioning, messaging, go-to-market strategy, and sales enablement across multiple product lines. This role involves close collaboration with the sales and product development teams to ensure marketing strategies align with product capabilities and sales objectives. Initially this role will operate as a strategic individual contributor, and over time will build and scale a product marketing team. The Director of Product Marketing reports to the SVP, Marketing.
Responsibilities Positioning & Messaging Architecture – Brand Strategy & Governance
Residential
Commercial
Marketplace
Lessen360
Lessen Pro
Aiden
Emerging services
Lead development of messaging houses
Clarify ICPs, buyer personas, and vertical narratives
Translate complex capabilities (including AI differentiation) into clear business outcomes
Ensure consistency across website, decks, campaigns, and sales materials
Go-to-Market Strategy & Launch Excellence
Own GTM strategy for product launches and major releases
Partner with Product on roadmap communication and release planning
Develop launch messaging, sales tools, competitive positioning, and internal enablement
Create repeatable launch playbooks and processes
Align cross-functional stakeholders (Product, Sales, Demand Gen, Customer Success)
Sales Enablement & Commercial Support
Build and maintain core sales assets:
Pitch decks
Battlecards
Objection handling
ROI narratives
Competitive comparison
Develop vertical-specific messaging for priority segments (e.g., fitness, banking, medical, multi-family)
Partner with Sales leadership to identify gaps in messaging and tools
Support strategic deals with tailored positioning
Competitive & Market Intelligence
Lead competitive research and narrative differentiation
Equip Sales with clear, defensible competitive positioning
Monitor industry trends in AI, property operations, marketplaces, and portfolio management
AI & Innovation Narrative
Shape and scale the story around Aiden and Lessen’s proprietary data advantage
Ensure AI differentiation is consistently communicated and commercially relevant
Develop proof frameworks and metrics storytelling
Function Building & Leadership
Establish foundational product marketing processes
Create documentation standards and templates
Define future team structure and hiring roadmap
Mentor future PMM hires as the function scales
Other Responsibilities
Perform ad-hoc projects and other duties as assigned
Ensure confidentiality of internal and external data
Limited travel is expected, primarily to support marketing events, and to participate in team meetings at our Chicago or Scottsdale AZ offices.
Qualifications Minimum Qualifications
Bachelor’s degree in business, engineering, computer science, or a related field required
8–12+ years in B2B product marketing roles
Experience owning positioning and GTM strategy
Proven success launching products in SaaS, platform, marketplace, or technology-enabled services environments
Strong collaboration with Product and Sales leadership
Experience translating technical differentiation into outcome-driven messaging
Strong executive communication skills
Other Relevant Qualifications
Experience in AI-enabled platforms
Experience in property services or property management-related business
Experience building a PMM function from scratch
Compensation $140,000.00 - 200,000.00 annually
Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.
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.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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Summary The Director of Product Marketing will build and lead the product marketing function, including product positioning, messaging, go-to-market strategy, and sales enablement across multiple product lines. This role involves close collaboration with the sales and product development teams to ensure marketing strategies align with product capabilities and sales objectives. Initially this role will operate as a strategic individual contributor, and over time will build and scale a product marketing team. The Director of Product Marketing reports to the SVP, Marketing.
Responsibilities Positioning & Messaging Architecture – Brand Strategy & Governance
Residential
Commercial
Marketplace
Lessen360
Lessen Pro
Aiden
Emerging services
Lead development of messaging houses
Clarify ICPs, buyer personas, and vertical narratives
Translate complex capabilities (including AI differentiation) into clear business outcomes
Ensure consistency across website, decks, campaigns, and sales materials
Go-to-Market Strategy & Launch Excellence
Own GTM strategy for product launches and major releases
Partner with Product on roadmap communication and release planning
Develop launch messaging, sales tools, competitive positioning, and internal enablement
Create repeatable launch playbooks and processes
Align cross-functional stakeholders (Product, Sales, Demand Gen, Customer Success)
Sales Enablement & Commercial Support
Build and maintain core sales assets:
Pitch decks
Battlecards
Objection handling
ROI narratives
Competitive comparison
Develop vertical-specific messaging for priority segments (e.g., fitness, banking, medical, multi-family)
Partner with Sales leadership to identify gaps in messaging and tools
Support strategic deals with tailored positioning
Competitive & Market Intelligence
Lead competitive research and narrative differentiation
Equip Sales with clear, defensible competitive positioning
Monitor industry trends in AI, property operations, marketplaces, and portfolio management
AI & Innovation Narrative
Shape and scale the story around Aiden and Lessen’s proprietary data advantage
Ensure AI differentiation is consistently communicated and commercially relevant
Develop proof frameworks and metrics storytelling
Function Building & Leadership
Establish foundational product marketing processes
Create documentation standards and templates
Define future team structure and hiring roadmap
Mentor future PMM hires as the function scales
Other Responsibilities
Perform ad-hoc projects and other duties as assigned
Ensure confidentiality of internal and external data
Limited travel is expected, primarily to support marketing events, and to participate in team meetings at our Chicago or Scottsdale AZ offices.
Qualifications Minimum Qualifications
Bachelor’s degree in business, engineering, computer science, or a related field required
8–12+ years in B2B product marketing roles
Experience owning positioning and GTM strategy
Proven success launching products in SaaS, platform, marketplace, or technology-enabled services environments
Strong collaboration with Product and Sales leadership
Experience translating technical differentiation into outcome-driven messaging
Strong executive communication skills
Other Relevant Qualifications
Experience in AI-enabled platforms
Experience in property services or property management-related business
Experience building a PMM function from scratch
Compensation $140,000.00 - 200,000.00 annually
Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.
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.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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