From a $875m exit to building again, the AI opportunity, pricing trade-offs, and more | Tracy Young

Описание: In this episode of Second Acts, Krish interviews TigerEye’s (previously PlanGrid’s) co-founder and CEO, Tracy Young.

Tracy talks about: her big insights from scaling one of the most formative vertical SaaS businesses (PlanGrid, acquired by Autodesk for $875m), winning with technological shifts (and where she sees TigerEye’s AI-native opportunity), how PlanGrid’s best-in-class pricing model was ultimately outplayed by a now-public competitor, the mid-market “no man’s land”, why to zealously slice TAM when growth stalls, and much more!

Tracy: “I think it’s really easy to increase prices…Changing the shape, and how you charge is much harder. And the reason it’s hard is because you have to look at what percentage of your current revenue that might not renew because of the new pricing. And you always want to protect every dollar of revenue. And that’s the hard trade-off, even if you know this is a better pricing for your customers and for the company.”

Krish: “…It is normally accepted that with scale your growth rate tends to fall. But what you are actually referring to [is] that by deliberately not just looking at an overall business, but slicing it in every dimension, you actually continue to think about the potential in each one of those segments to layer those S curves.”

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Chapters:
(01:06) Episode intro
(03:18) Tracy’s kind, founder-to-founder note of praise
(04:06) TigerEye’s founding premise
(06:58) Why Tracy started PlanGrid (a vertical SaaS pioneer that sold for $875m)
(07:56) Why Tracy chose a horizontal path with TigerEye
(10:10) Reimagining a competitive enterprise category with the AI shift
(12:17) There are (still) at least 10 good startup ideas in every enterprise category
(17:16) Why changing the shape of how you charge is much harder than changing price points
(18:37) How PlanGrid’s exceptionally successful (netting 130-140% NRR) seat-based motion was still bested by a different approach of a now-public competitor
(22:00) Tracy explains how (in the construction space between 2011-20) landing logos faster was more important than the average contract value
(22:55) PlanGrid’s freemium, mobile-SEO driven top of funnel
(23:25) Why Tracy picked a one-price-for-everything (including unlimited seats) for TigerEye
(25:20) How AI allows TigerEye to do things that don’t scale with the depth of best-in-class consulting firms; “insanely fast and at a fraction of the cost”
(28:04) How a painstakingly precise view of segments is critical for understanding where a business is struggling and where it’s headed
(31:40) The “gnarly” data issues PlanGrid encountered post the Autodesk acquisition and how that informed TigerEye
(33:24) Tracy’s three distinct flavours of mid-market (and why the classical definition of that segment fails most founders)
(37:20) Having built SaaS scale-ups in the past decade, Tracy and Krish reflect on the possibilities of building AI-native teams
(42:55) How Tracy sees AI-driven enterprise business models evolving over the next couple of years
(45:00) Why TigerEye is training their own tailored AI models

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Mentioned/resources:

American Dreamers: Tracy Young Has The Eye Of The Tiger: https://www.forbes.com/sites/joannech...
TigerEye: https://www.tigereye.com/
PlanGrid: https://en.wikipedia.org/wiki/PlanGrid
Tracy Young, Co-founder & CEO of PlanGrid (The Social Radars): https://open.spotify.com/episode/2EiW...
YC: https://www.ycombinator.com/
Procore: https://www.procore.com/en-sg
Part II: The failure points from $5m to $100m in ARR: https://tracy.posthaven.com/part-ii-t...
Mid-market is no man’s land: https://tracy.posthaven.com/mid-marke...
Do Things that Don’t Scale: https://paulgraham.com/ds.html
Cursor: https://cursor.com/
GitHub Copilot: https://github.com/features/copilot

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Connect with Tracy:

Tracy writes: https://tracy.posthaven.com/
LinkedIn:   / tracy-young-0a17441  

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Connect with Krish:

LinkedIn:   / krishs  
X: https://x.com/cbkrish

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more: https://www.chargebee.com/