People Matter

Senior Director, Head of Product Design



Product, Design, Sales & Business Development
Chicago, IL, USA
Posted on Friday, January 5, 2024
Lessen is one of the fastest growing companies in the real estate services industry. Our proprietary technology platform provides clients with portfolio dashboards, the ability to review and approve project estimates, check in on project progress in real time and pay vendors all in one place! But we aren’t just a tech company. We are also a property service delivery company offering renovations, turns and maintenance to residential and commercial clients. Lessen recently acquired SMS Assist, an industry-leading facilities maintenance technology and delivery company. The new combined national footprint will serve more than 250,000 properties, facilitate approximately 2.5 million repair and maintenance orders, and complete nearly 20,000 renovation and turn projects per year. Lessen has quickly evolved from exciting startup to valued partner, delivering scalable and turnkey property services to our clients.
This role is based in Chicago, working in the office on Tuesday, Wednesday, and Thursday.
Job Summary
The Senior Director, Head of Design, is responsible for applying design thinking to Lessen product and operations for the purpose of transforming the property management industry and building sustainable advantage for the company. They are a key driver of human-centered design, a critical competence through the organization, and are charged with building up, nurturing and leading our team of user experience and visual designers, architects and researchers to accomplish this design transformation. They infect the whole organization in human-centered design thinking and doing, affecting this transformation with a high emotional intelligence and serving as a player-coach to model the desired behaviors.

What You'll Do

  • Recruit and coach a world-class team of UX and UI designers and researchers
  • Lead the team in the development and implementation of a comprehensive information architecture and design system that brings coherence and simplicity to the full end-to-end workflow for all of our user personas and lines of business
  • Help lead the organization in embracing and continuously improving its practice of dual-track scrum for the purpose of ensuring our development resources are efficiently applied to building the products customers most want and need
  • Serve as an individual contributor on strategic programs—providing hands-on design development, research, workshop facilitation as needed on high-profile projects
  • Develop a design workshop playbook of outlines, best practices, and tools for designers and product managers to leverage for organizing and executing high-impact, value-producing, delightful collaborative sessions with customers, affiliates and internal end-users
  • Directly facilitate design sessions involving senior executive customers or customer-prospects from multi-billion-dollar companies
  • Engage the larger organization, including operations teams, in the implementation of design-thinking as we streamline the human workflow in tandem with the digital workflow
  • Establish human-centered design as a widely recognizable Lessen core competence and source of sustainable advantage

What You'll Need

    Role Specific Skills
  • Expertise in a broad set of design-thinking frameworks, tools, methodologies such as persona development, journey-mapping, storyboard and wireframe development, immersion research, requirements discovery, longitudinal research, usability research, etc.
  • Demonstrated success in communicating and collaborating with C-Level executives; exudes a mix of humility, gravitas and credibility
  • Strong systems-thinking skills for driving an actionable information architecture and design system that supports top-level business objectives
  • Demonstrated emotional intelligence in support of mission of implementing transformational human-centered design practices in a larger organization
  • Strong communication skills—able to make the complex simple; can describe design decisions in terms of business implications and quickly translate business needs into design requirements; is known for great listening skills
  • 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
  • Minimum Qualifications
  • Bachelor’s degree in information architecture, human factors, computer human interaction, graphic art, psychology or related field;
  • 10+ years of experience with end-to-end software or process design
  • 5+ years of full-time experience managing and growing an in-house design team
  • Experience building and coaching multi-discipline design teams that are equipped to successfully collaborate in an agile/scrum discovery and development model
  • A track record of making sense out of chaos and leading teams to the highest and most productive use of their resources
  • Other Relevant Qualifications
  • Master’s Degree preferred
  • Experience working in and leading agile/scrum development teams; familiarity with dual-track scrum and jobs methodology
Why Lessen:
· Competitive compensation
· 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.