01 · Me

0 × 0

02 · Hello

0 × 0

03 · Photo

0 × 0

04 · Caption

0 × 0

05 · Smiley

0 × 0

06 · About

0 × 0

Hi, I’m Jessa Wolfe, a low-ego, high-impact Design Leader based in Charlotte, NC.

Over the last 15+ years, I’ve built a career around designing with empathy, collaborating across disciplines, and helping teams bring clarity to complexity.

As a designer, I lead with intention and curiosity, guiding designers to not just build great products, but to ask better questions, challenge assumptions, and always consider the “why” behind the work.

I think my superpower is that I don’t stop at the screen. I design how a product works, and then I keep going: I make it move, I set the art direction, and I draw the little things that make it feel like someone cared. Most teams hand those pieces off to different people. I like holding all of them at once, because that’s how the whole thing ends up feeling like one idea instead of a bunch of parts.

Over the last 15+ years, I’ve built a career around designing with empathy, collaborating across disciplines, and helping teams bring clarity to complexity.

Superpower

0 × 0

“I don’t just design how it works. I design how it moves, how it looks and how it feels.”

07 · What I believe

0 × 0

Fair warning: I have opinions.

Design is the invisible architecture of everything. People can’t always point at it, but they can feel when it’s off.

AI can assemble and remix what already exists. What it can’t do is care. That’s the work.

I care about three things: telling the truth about what’s broken, building things that actually serve people, and making room for people to be more of themselves, not less.

Good design isn’t “does it function.” It’s “does it respect the person using it.” Manipulative patterns are lazy design.

Teams aren’t headcount. They’re specific humans with specific stories, talents, and limits. I won’t lead by slogan or jargon.

No design theater. No leadership theater. I want outcomes you can feel in the room: less fear, more clarity, better work.

If I do my job right, the design disappears and the experience just feels right. The leadership disappears and people feel brave, trusted, and hungry to do the best work of their lives. That’s the bar.

Quote

0 × 0

“It isn’t how quickly you can build something. It’s if people love what you build.”

08 · Career

0 × 0

Full résumé →

09 · ACV Auctions

0 × 0

ACV Auctions / 2020 – Present

Head of Design

Built the design team from the ground up: rituals, critique culture, career ladders

Shaped design process with new technology and design systems

Shipped features used by 100k+ dealers nationwide

B2BB2CDesign SystemsSaaS

10 · ThreeSixty

0 × 0

ThreeSixty / 2016 – 2020

Creative Director

Owned the full creative process from strategy through final delivery

Reduced revision cycles about 30% with agency-wide review processes

Worked with over 200+ clients

B2BB2CCMSSaaSMarketingBranding

11 · Aurora Consulting

0 × 0

Aurora Consulting / 2012 – 2016

Lead Interactive Designer

Led design on Fisher-Price flagship microsites

Collaborated directly with Mattel brand teams

Hands-on development, CMS, and post-launch optimization

B2CMarketingBranding

12 · Specializing in

0 × 0

collaborationproblem solvingdesign thinkingresearchbuilding & shipping productsdelivering on business goalssystems thinkingcross-functional leadershipmentoring designersdesign strategyprototypingdesign systemsworkshop facilitationstorytellingvisual designaccessibility

13 · How I lead

0 × 0

Build the space.

Designers do their best work when they feel safe, autonomous, and clear on where they’re growing.

I make growth explicit. Every designer has a goal plan they own, reviewed each quarter. I track where each person wants to go next (senior, lead, or principal) and shape their work and visibility to move them there. Growth isn’t a year-end conversation; it’s a standing one.

I improve processes, not people. When something isn’t working, I look at the system around the person before the person. Most “performance problems” are really clarity, resourcing, or process problems wearing a costume.

I build rituals that compound. A recurring research-and-design journal where designers share work-in-progress for open feedback, a regular team reflection, and protected peer-review and working sessions. These aren’t status meetings. They’re how the team teaches each other and calibrates on quality.

I lead the team into new technology, not around it. As AI reshaped our field, my job was to make it learnable: strategy, onboarding, and new ways of partnering with product and engineering. The team grew with the change instead of bracing against it.

Work backwards from solutions.

A solution handed over is a starting point for questions, not the end of them.

With stakeholders. When a stakeholder, executive, or product partner arrives with a solution, I unpack the underlying problem, surface hidden opportunities, present on them, and facilitate the collaboration that turns a proposed answer into the right one. I do the same with my team.

At intake. I rebuilt how work enters the team and how UX partners with product and engineering. Problem-framing happens right at intake, so we collaborate on the problem before committing to a solution.

With AI-made designs. When product partners arrive with AI-generated solutions, the artifact gets interrogated instead of inherited. A designed artifact looks like an answer. It can quietly skip the question.

Think in years, not sprints.

Someone has to hold the long-range vision so the team has something to build toward.

A connected-marketplace product vision. A multi-year vision for the core wholesale marketplace, built on four principles: transparency in vehicle condition, pricing confidence, transaction speed, and simplicity for dealers of every size.

Bridging physical and digital auctions. A vision for how digital auction experiences extend the physical auction, letting buyers, sellers, and on-site staff move freely between the two worlds.

A unified “orders” experience. A vision reframing fragmented post-purchase touchpoints (won vehicles, invoices, transport, financing) into one coherent, e-commerce-style place to run a dealer’s business.

Evolving discovery as the model changed. What ties these together: each one starts with the whole journey, takes a big enough swing that people can “fight for great,” and is built to outlast any single roadmap cycle.

14 · A little more

0 × 0

15 · Talks

0 × 0