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. 

·         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

·         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

·         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:

o   Product

o   Product Marketing

o   Demand Generation

o   Sales Leadership

o   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 developing individual team members to reach their potential

·         Proficient in engaging multiple teams through communication, processes, personal impact and influence

·         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 

Preferred: 

·         Experience with AI-driven products or marketplaces 

·         Experience leading brand transformation or repositioning initiatives 

·         Video production and multimedia storytelling leadership 

Compensation

$140,000.00 - 200,000.00 annually

Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.  

·        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