Director, Brand and Digital Experience

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 sen’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.

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.

• Define and evolve Lessen’s brand architecture across Residential, Commercial, Marketplace, Lessen
  360, 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

Owns  as a strategic business platform.

Responsibilities include:

• Leading full website redesign and ongoing optimization
• Defining UX, UI, information architecture, and conversion strategy
• Ensuring clear and differentiated AI storytelling (including Aiden)
• Structuring content around personas, verticals, and ICPs
• Partnering with Demand Gen on SEO, CRO, analytics, and performance optimization
• Managing developers, agencies, and external partners
• Maintaining release cadence aligned with product innovation cycles

The website must function as:

• A demand generation engine
• A sales enablement tool
• A proof platform (case studies, ROI stories, vertical narratives)
• A brand signal of innovation and operational excellence

• 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

• Lead internal designers and creative contractors
• Scale team capabilities as company grows
• Collaborate closely with:
  Product, Product Marketing, Demand Generation, Sales Leadership, Executive Team
• Establish creative systems that support rapid product release cycles

• 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.

• 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

• 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…