Lessen

Director, Brand and Digital Experience

Lessen

full-time

Posted on:

Location Type: Hybrid

Location: Chicago • Illinois • United States

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Salary

💰 $140,000 - $200,000 per year

Job Level

Lead

About the role

  • 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
  • Owns Lessen.com 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
  • 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)
  • Lead internal designers and creative contractors
  • Scale team capabilities as company grows
  • Collaborate closely with Product, Product Marketing, Demand Generation, Sales Leadership, Executive Team

Requirements

  • 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
Benefits
  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
UXUIinformation architectureconversion strategySEOCROanalyticswebsite redesignbrand guidelinesmetrics storytelling
Soft Skills
collaborationleadershipstorytellingcommunicationstrategic thinkingcreativityteam managementproblem-solvingadaptabilityorganizational skills
Certifications
Bachelor’s degree in MarketingBachelor’s degree in BusinessBachelor’s degree in related field