Director, Product Marketing

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. 

 

 

·         Define and evolve product positioning across:

o   Residential

o    Commercial

o   Marketplace

o   Lessen360

o   Lessen Pro

o   Aiden

o   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

 

·         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)

 

·         Build and maintain core sales assets:

o   Pitch decks

o   Battlecards

o   Objection handling

o   ROI narratives

o   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

 

·         Lead competitive research and narrative differentiation

·         Equip Sales with clear, defensible competitive positioning

·         Monitor industry trends in AI, property operations, marketplaces, and portfolio management

 

·         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

 

·         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

 

·         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.

 

·         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

 

·         Experience in AI-enabled platforms

·         Experience in property services or property management-related business

·         Experience building a PMM function from scratch