Paul Williamson is a seasoned go-to-market leader and advisor best known for helping Plaid scale from $3M to $300M ARR. As Head of Revenue, he built and evolved Plaid’s go-to-market roadmap across product-market fit, upmarket expansion, and new verticals. With deep experience aligning GTM with product, he now advises founders on sequencing bets, building forward-compatible roadmaps, and scaling revenue organizations with intention.
Discussed in this Episode
- Why GTM roadmaps should be “forward-compatible”
- Iteration cycles in GTM vs. product roadmaps
- Early lessons from Plaid’s rudimentary qualification process
- Recognizing high-value clients vs. anti-patterns in inbound leads
- How daily standups created fast GTM learning loops
- Shifting from PLG to sales-led motions with SDRs and routing
- Sequencing GTM expansion: fintech → enterprise FSIs → embedded fintech
- Compensation design mistakes and their impact on sales behavior
Episode Highlights
00:00 — Why GTM roadmaps should be built “forward-compatible”
01:53 — How Plaid iterated through 9–10 GTM versions in the first year
05:12 — Plaid’s early qualification process: 4 simple questions
07:28 — Why most inbound leads weren’t equal—and how Plaid spotted patterns
10:01 — Using daily standups twice a day to refine GTM qualification
14:32 — How Plaid’s GTM roadmap evolved from monthly to yearly cycles
20:46 — Moving beyond partnerships to diversify top-of-funnel channels
24:53 — Scaling into enterprise financial institutions with tailored product needs
27:09 — Entering phase three: embedded fintech with customers like Tesla
30:00 — Compensation design mistakes that slowed deals and created risk
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The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
