Dive Club 🤿 | Hannah Hearth – Design Careers in the Age of AI

Host: Ridd
Guest: Hannah Hearth, Head of Product Design at Vercel
Date: February 9, 2026

Overview

In this engaging episode, Ridd welcomes Hannah Hearth, newly appointed Head of Product Design at Vercel, for a deep dive into how AI-powered tools are radically transforming design careers, team structures, and leadership expectations. Their conversation traverses the changing nature of design hiring, evolving design leadership philosophies, hands-on technical expectations, portfolio and career strategy, and the future of tools and collaboration. Hannah offers candid stories and actionable insights, speaking both to junior designers entering the field and senior leaders navigating this fast-changing environment.

Key Discussion Points & Insights

1. The Changing Face of Design Leadership

(05:34–07:55)

• The traditional view: "Great managers hire smart people and get out of their way" is, according to Hannah, "farther from the truth" than ever before.
• Senior designers (staff/principal) now require close partnership, not less, due to the increased complexity and ambiguity of their projects.
• Modern design leaders must be present, hands-on collaborators—helping break down organizational silos, facilitating honest feedback, and focusing on shipping outcomes, not just beautiful artifacts.
  • Quote: "No designer wants to be an island. And a design leader can really help make you feel like you are part of a team and you have somebody that you can always go to..." (06:58, Hannah)

2. Team Size, Market Shifts & The Challenge of '10x'

(07:55–10:07)

• After pandemic hypergrowth, companies are entering a long-term "course correction"—leaner teams, more impact from fewer people, higher expectations for individual output.
• The myth of a return to overstaffed teams is dispelled—leaders must now ensure efficiency without burning out their teams.
• Pressure for designers to become "10x" contributors often overlaps with increased use of AI tooling; leaders are wrestling with maintaining sustainability alongside productivity.

3. AI Adoption: Philosophies and Realities

(10:07–13:15)

• On the spectrum from laissez-faire ("use AI if you want") to mandated daily AI usage, Hannah argues that enforced adoption may be a "necessary evil" to avoid disruption.
  • Quote: "Every single company of a certain size is going to be disrupted by AI. And the best way for you to disrupt yourself is for your own teams to be using the tools..." (10:55, Hannah)
• Encourages reframing: View AI adoption as a learning opportunity, not a burden.
• Junior designers are adopting tools and learning faster than any previous generation.
• Dedicated "builder days" and "hackathons" are essential for fostering experimentation without being swamped by the day-to-day.

4. Process, Collaboration, and the Disintegration of Old Frameworks

(15:30–18:59)

• Classic processes like the five-day design sprint have been "morphed": More asynchronous work, less synchronous time, faster prototyping (sometimes in a single day).
  • Quote: "Nobody is spending 5-8 hour days in a room together... Now it might be five days but you're actually only doing one hour of synchronous time in the morning..." (16:16, Hannah)
• The real risk in faster processes is NOT the loss of craft, but poor alignment on which problems to solve.
  • At companies that "breathe craft," high quality emerges naturally—but this isn't true everywhere.

5. Feedback, Craft, Alignment & Navigating Organizational Black Boxes

(18:59–22:58)

• Effective designers, regardless of seniority, share their work early and often—waiting for formal critique sessions is too late.
• High-fidelity prototypes have changed how and when feedback enters the process: "Fidelity is no longer as correlated to where we're at in the process."
• Handoff and collaboration are increasingly fragmented: AI prototypes, Figma files, Loom videos—industry tools haven’t caught up with this.
  • Quote: "What does handoff look like today... It's an AI prototype that's janky in some ways... I don't think design tooling has really solved the collaboration aspect of prototyping yet." (21:38, Hannah)

6. Designers Closer to Code & Shipping

(25:19–27:31)

• At Vercel, designers use Claude, Cursor, and other AI/code tools day-to-day—sometimes shipping design polish, sometimes delivering functional prototypes directly to engineers.
• The barrier for designers to code is dropping; having these skills can be optional, but offers more direct impact on shipped product.
  • Quote: "It's beautiful to be able to have that option when you have the skills, even if you don't want to use them all the time... to have the skills is really valuable." (25:53, Hannah)
  • Personal moment: Hannah recounts shipping a production bug-fix PR herself after just 5-6 weeks on the job.

7. What Stands Out in Portfolios Now

(27:41–31:41)

• It’s now "table stakes" to demonstrate trying new tools/methods and experimenting with side projects.
• The emergence of "playground" or "experiments" tabs in portfolios is now seen as a gold star, signifying learning agility and curiosity.
• Time constraints are real—but "you can get really far in one hour on a Saturday."
• The era of the bland, process-heavy, case-study-only portfolio is over—make your portfolio "a little cringe; it’s fun."
  • Quote: "Cringe is in, right? So make your portfolio a little cringe. It's fun." (31:07, Hannah)

8. Designing Beyond Craft: Product Skills & Storytelling

(33:27–38:34)

• For designers less craft-centric and more product-minded: learn visuals and interaction, but don't be afraid to consider a pivot into product roles.
  • Advice: "Design today is more than UX... You need to figure out how to get those skills... The other option is: do you want to be a designer?" (34:05, Hannah)
• The most future-proof skills: adaptability, storytelling, and getting buy-in for what problems to solve.
• Outstanding ICs spot and articulate "the elephant in the room," and offer constructive solutions rather than complaints.

9. Hybrid Career Paths & Role Blending

(38:34–41:24)

• Senior designers increasingly operate across both engineering and product strategy tracks—those excelling at both are most resilient as roles blur.
• Interest in design systems is on the upswing, as LLM-powered tools yield exponential leverage when trained on robust design systems and documentation.

10. Trends from the Leadership Frontlines

(43:06–47:47)

• Senior managers and even VPs are opting to return to IC roles—the fastest-moving era in design history requires leaders to stay hands-on.
  • Quote: "It is very hard to be a design leader in this space if you don't have hands on experience with the tools. And honestly I don't think it's possible..." (43:58, Hannah)
• Onboarding is now "a sprint"—outcomes and trust-building are expected in weeks, not months.
  • Quote: "30, 60, 90 days... it doesn't work on that timescale anymore... If I did a listening tour for 30 days, people would be like, how do you still work here?" (46:14, Hannah)

11. Reflections on Leadership Style

(48:10–50:12)

• Hannah’s formative experience at Webflow: “Being in the weeds” with staff and senior designers—helping orchestrate cross-company collaboration is a hallmark of effective leadership, especially as companies grow and products bloat.
  • Quote: "There really wasn't somebody to string those beads... I think that's one of the biggest impacts that a design leader can make is that horizontally work..." (49:08, Hannah)

Notable Quotes & Memorable Moments

• On the new bar for portfolios:
  "Much more so than two to three years ago, showcasing in your portfolio in your hiring manager interview that you tried something new lately and you used a new tool or a new process. It’s like table stakes at this point..." (28:16, Hannah)

• On the pain and promise of AI:
  "You can choose to be a curmudgeon about it... You can also see it as an opportunity to learn something new... we love being uncomfortable. We love learning new things because... those are like, the best times of your career..." (11:47, Hannah)

• On rapid onboarding:
  "By week three, I was moving people... week four, making changes to how the whole design team works… If I did a listening tour for 30 days, people would be like, how do you still work here?" (46:14, Hannah)

• On leadership presence:
  "Every staff and senior staff designer that I worked with was so grateful that I was in their way all the time." (48:15, Hannah)

Timestamps for Important Segments

• Interviewing & Take-Home Assignments: 01:03–03:44
• Defining New Era of Design Leadership: 05:34–07:55
• Team Size/10x Designer Pressures: 07:55–10:07
• AI Adoption Spectrum: 10:07–13:15
• How Process is Changing (Design Sprints): 16:01–17:35
• Feedback, Alignment, Handoffs: 18:59–22:58
• Proximity to Code & Shipping: 25:19–27:31
• Portfolio Strategy in 2026: 28:16–31:41
• Design Systems & AI: 41:24–43:06
• Leadership Returning to IC Roots: 43:42–45:00
• Onboarding & Fast-Paced Change: 46:14–47:47
• Leadership Practices from Webflow: 48:10–50:12

Final Takeaways

• Adaptability, experimentation, and willingness to learn new tools are now baseline expectations for designers at all levels.
• Storytelling and navigating ambiguity are more vital than ever, especially as AI and product complexity rise.
• Leadership requires presence and empathy—not just delegating, but collaborating, unblocking, and guiding.
• Portfolios should be playful, real, and show learning—not just a bland museum of process.
• Expect the pace of change to accelerate—success (and survival) depends on thriving in continual discomfort and learning.
• Hybrid skills win: The most resilient designers are those who can flex across craft, product thinking, and technical implementation.

This episode is a must-listen for anyone navigating (or aspiring to) a modern design career—whether in the trenches, leading a team, or plotting the next move in a rapidly evolving landscape.