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The Changemakers
Shaped By
Building brands at breakneck speed (and knowing when to pause): Alan Roll, LinkedIn
OCT 20, 202658 MIN
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Description
Alan Roll has built a career across culture-defining brands, high-growth tech, and deliberate time away. In this episode of Changemakers, he joins host Dave to reflect on a journey that began with fine arts and filmmaking at Washington University in St. Louis, and led to creative leadership roles at Gap, MTV, Interbrand, LendingClub, Opendoor, Airtable, and Deel.
Now Senior Creative Director of Brand at LinkedIn, Alan has a strong track record of building up brands from the agency side, from the inside, and at breakneck speed. And he’s learned that sometimes, stepping away matters as much as pushing on. In this episode, he unpacks:
The creative edge: Why judgment, taste, and courage will always outlast technical skill.
Agency vs. in-house: Eight years at Interbrand, then brand turnarounds from the inside - what each experience taught him, and how that experience compounded
Creating at speed: What hyper-growth at Airtable and Deel really demands of a creative leader.
The case for taking a break: Why intentional sabbaticals aren't a career pause, but a career move.
Starting out now: How to build a creative career when the old playbook no longer applies.
Whether you’re starting out in your creative career or ten years in, this is one to make time for. Listen today🎧
Timestamps
00:00 - Introductions
01:47 - Forging a self-taught path in fine arts and motion design at WashU
05:34 - Dynamic in-store media at Gap during the Mickey Drexler era
10:17 - Run-and-gun filmmaking, 9/11, and production detours
12:30 - Systems, technology, and early dual-screen experiences
15:30 - Interbrand: An 8-year masterclass in strategy, identity, and UX
21:24 - Embedded teams and LendingClub's post-IPO turnaround
27:15 - The art vs. science of team building
34:36 - Using sabbaticals to unpack lessons and avoid burnout
40:18 - What really makes a great creative
45:30 - Creative entrepreneurship, multi-threaded paths, and networking
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