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Help us revolutionize real estate services.
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 Brand and Digital Experience is responsible for defining, building and scaling Lessen’s brand and digital presence across every touchpoint. This role will own the Company’s brand strategy, visual identity, and the website content and operations to enhance brand presence, drive brand loyalty and revenue growth. The Director of Brand and Digital Experience will report to the SVP, Marketing.
Responsibilities
Brand Strategy & Governance
· Define and evolve Lessen’s brand architecture across Residential, Commercial, Marketplace, Lessen360, Lessen Pro, Direct, and emerging services
· Develop and maintain brand guidelines (visual system, tone, messaging alignment)
· Ensure brand consistency across sales enablement, campaigns, product launches, executive communications, and events
· Elevate Lessen from “property services provider” to our new positioning
· Partner with Product Marketing to translate vertical and persona-based messaging into compelling visual narratives Should specify the responsibilities, duties, tasks and requirements of the job
Website Ownership
· Owns Lessen.com as a strategic business platform. Responsibilities include:
o Leading full website redesign and ongoing optimization
o Defining UX, UI, information architecture, and conversion strategy
o Ensuring clear and differentiated AI storytelling (including Aiden)
o Structuring content around personas, verticals, and ICPs
o Partnering with Demand Gen on SEO, CRO, analytics, and performance optimization
o Managing developers, agencies, and external partners
o Maintaining release cadence aligned with product innovation cycles
· The website must function as:
o A demand generation engine
o A sales enablement tool
o A proof platform (case studies, ROI stories, vertical narratives)
o A brand signal of innovation and operational excellence
AI & Innovation Storytelling
· Translate technical differentiation into intuitive visual narratives
· Ensure consistent representation of AI capabilities and platform innovation
· Develop comparison visuals and proof frameworks
· Create compelling metrics storytelling (ROI, efficiency, automation impact)
· Support competitive differentiation through digital storytelling
Team & Cross Functional Collaboration
· Lead internal designers and creative contractors
· Scale team capabilities as company grows
· Collaborate closely with:
o Product
o Product Marketing
o Demand Generation
o Sales Leadership
o Executive Team
· Establish creative systems that support rapid product release cycles
Other Responsibilities
· Perform ad-hoc projects and other duties as assigned
· Lead, mentor, and develop a high-performing creative team aligned to Lessen’s objectives and values. Foster a culture of accountability, collaboration, innovation, and customer-centric thinking)
· 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.
Role Specific Skills
· Strategic thinker with hands-on execution capability
· Systems-oriented and operationally disciplined
· High creative standards
· Clear communicator and cross-functional collaborator
· Comfortable operating in high-growth, transformation environments
· Data-aware and conversion-focused
People Management Skills
· Advanced proficiency in all people management processes, including recruitment, performance management and reward
· Advanced proficiency in building, growing and developing a team; including department structure design and resourcing
· Advanced proficiency in coaching and developing individual team members to reach their potential
· Proficient in engaging multiple teams through communication, processes, personal impact and influence
Qualifications
Minimum Qualifications
· Bachelor’s degree in Marketing, business or related field
· 8–12+ years in brand, digital, or creative leadership roles
· Proven experience leading a website redesign as a strategic growth initiative
· Experience in B2B, SaaS, platform, or technology-enabled services companies
· Strong understanding of UX/UI and digital conversion strategy
· Experience building scalable brand systems
· Ability to translate complex product differentiation into compelling storytelling
· Experience collaborating with executive leadership
Other Relevant Qualifications
Preferred:
· Experience with AI-driven products or marketplaces
· Experience leading brand transformation or repositioning initiatives
· Video production and multimedia storytelling leadership
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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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
