With Gratitude Ep 6: Never Funded Holy Grails

What happens when the ideas that were never a no — just a never — are suddenly on the table?

Topics We'll Explore:

• What a systems thinker without a computer science degree could attempt in technology ten years ago versus today, and why that one gap explains who gets to lead this work now
• Why this isn't an efficiency play. One or two ideas tested on a six-month horizon became ten ideas on a three-month one, which changes what you ship, not just how fast
• The holy grail project: the thing everyone wanted and nobody could ever justify the people power for, and what happens to a team when it finally gets built
• What AI actually does for a design org, not moving the button two pixels, but freeing designers up for the architecture of design, and the governance that keeps it from drifting
• Designing for people who are never having a good day, because nobody opens a health plan app when things are going well
• The paradox of choice: when capacity stops being the constraint, judgment becomes the bottleneck and deciding when something is good enough is still yours

You'll hear Holly on fifteen years at Humana running the member-facing platform and then building the platform a payer buys, both sides of the equation, as she puts it. On the talk she gave for women in tech and the people she calls tech adjacent, who were kept out by a credential rather than an ability. On what a three-day hackathon produces now. And on what she'd say to someone who has spent a career standing just outside the room.