Kari Kay

About

Kari

Specialization
B2B, B2B2C
Environment
Remote 95% of career
Leadership
Scaled in-house design as both manager and IC

I’m a collaborative design lead and systems thinker, passionate about building impactful brands.

I believe cross-team collaboration is what makes good work possible. Too many teams operate in silos, working from disjointed information, creating bottlenecks and wasted effort. Working closely with Customer Success, Support, Marketing, Engineering, Sales, and Product, I've seen how much stronger the outcome is when Design works with those teams, not alongside them—bringing clarity, and connecting business strengths to customer needs in ways no single team could do alone.

To me, the mark of good work is that it outlasts me. My goal is to inspire the people I work with, leave behind processes worth keeping, and deliver value that holds up well over time. Beyond deliverables, I bring the ability to ask productive questions that move the project forward, draw out different ways of thinking, and bring order to chaos. These are the qualities founders and hiring managers need from a trusted collaborator.

OVER THE PAST 20 YEARS ⋅ I’VE DESIGNED A LOT ⋅ 

Roles

  • Owned and managed a creative agency
  • Supported as a contract designer and consultant
  • Led Design as a full-time employee
  • Filled in Gaps as a Fractional Design Lead

Capabilities

  • End-to-end and iterative design
  • 0 → 1 product features
  • Enterprise-grade software and brand design
  • Complex B2B SaaS for technical audiences

Industries

  • Healthcare and wellness
  • Real estate and finance
  • Education and non-profits
  • Food & beverage, retail, and more

My Approach

As a Design Manager…

I optimize for clarity and each person's natural strengths, turning abstract problems into concrete deliverables.

  • Break down abstract concepts into approachable tasks so the team can move quickly and effectively
  • Hold weekly 1:1s with direct reports, with space to be heard, mentored, and supported in their career goals
  • I find that a mix of interactive work formats keeps designers motivated and in sync:
Skill-building Workshops
Learn new tools and processes that impact design choices
Jam Sessions
Engage collective input to sharpen ideas, check details, make decisions
Design Reviews
Present in-progress work for awareness and design feedback
“Kari is an engaged people manager that built strong loyalty to her as a leader, but was also very hands-on as an IC keeping close touch with the actual work and output. She regularly stepped in to disambiguate requests for niche technical features and was always proactive in gathering feedback while making thoughtful decisions to drive a collaborative process. There's no more role that's in the middle than product design, and Kari drove it like a pro.”
Keith SzotDirector of Innovation

As an Individual Contributor…

Before I build, I listen, orienting to the business and user problem before weighing solutions.

  • Pressure test ideas, build incrementally, gather feedback, and revise alongside team members and stakeholders so nothing gets lost in translation
  • Work quickly and thoughtfully, and teach others to do the same—in-line Figma annotations go a long way for handoffs, reminders and posterity in fast-paced environments
  • Turn stakeholder conversations into complete design requirements by the end of the discussion, and a prototype by the end of the day when needed
“Kari is without a doubt the best Design professional I have had the opportunity of working with. Her time navigating the ever-changing landscape of agency, paired with her deep knowledge of brand strategy, allow Kari to bring a fresh and unique perspective to Product. Perhaps what has amazed me most over the past two years of working with Kari is her ability to immerse herself at any level of the business and provide clear, concise thoughts on how to deliver iterative value that solves key customer pain-points.”
Cole JailletDirector of Product Management

For Scaling Companies…

Design is a tool. Its impact depends on when and how it’s welcomed into a scaling org.

  • Set expectations with leadership up front on how design will operate within constraints already built into the product
  • Operate as a seasoned design lead first, and build rapport with cross-functional teams and a streamlined process before scaling headcount
  • Allocate time to fix the most typical gaps in core flows so users don't need support to get unstuck: onboarding, thin error and empty states, and repeatable patterns
  • Establish a Design System and use AI to speed up tedious style and component swaps to reduce strain on Engineering time
“When Kari joined Esper we were in a phase of rapid growth. After just closing a $30M funding round–and another $60M shortly after that–she was forced to scale the design function rapidly. Throughout this time, Kari fostered a sense of collaboration and scrappiness that was unrivaled. Dealing with difficult constraints and high pressure demand from stakeholders, she was still able to grow her team and quickly onboard them to productivity. I remain impressed to this day by her ability to produce in the toughest of environments.”
Cole JailletDirector of Product Management