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 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:
  
  

oLeading full website redesign and ongoing optimization

oDefining UX, UI, information architecture, and conversion strategy

oEnsuring clear and differentiated AI storytelling (including Aiden)

oStructuring content around personas, verticals, and ICPs

oPartnering with Demand Gen on SEO, CRO, analytics, and performance optimization

oManaging developers, agencies, and external partners

oMaintaining release cadence aligned with product innovation cycles

• The website must function as:
  
  

oA demand generation engine

oA sales enablement tool

oA proof platform (case studies, ROI stories, vertical narratives)

oA 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:
  
  

oProduct

oProduct Marketing

oDemand Generation

oSales Leadership

oExecutive 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.

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.