The Role
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
· 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
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:
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
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.
What the Team is Saying
Jay Payne
Senior Strategic Initiatives Manager
Kirby Pumper
Director of Solutions Architecture • Process & Innovation
Maya Shea
Communications and Events Administrator
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Jay McKee
Founder and CEO
Jennifer Gordon
Manager of Talent Acquisition
Trevon
Director of Exterior Services
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Lessen LLC Compensation & Benefits Highlights
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Leave & Time Off Breadth — Time off is presented as generous, spanning paid holidays, sick time, bereavement leave, and paid volunteer time. For some roles, flexible or unlimited PTO adds additional latitude.
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Healthcare Strength — Core coverage includes medical, dental, and vision alongside mental‑health resources and FSAs. Pet insurance is also available, indicating breadth beyond standard medical plans.
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Parental & Family Support — Paid parental leave, family medical leave, childcare benefits, and onsite mother’s rooms are highlighted. These supports signal a family-oriented approach to benefits.
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The Company
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.
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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.
Typical time on-site:
3 days a week
