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Episode 3: Allison Pickens, The New Normal Fund
In this Second Acts episode, Krish speaks with The New Normal Fund’s founder and GP, Allison Pickens; who draws on her time as the former COO of Gainsight and her work with several remarkable (pre-seed to pre-IPO) SaaS companies, to illuminate some of the foundations (across people, product, and GTM) necessary for scaling up.
Allison: “If you put… a great generalist in front of a customer and you say ‘make them successful’ they might again be able to use their heroics to make that customer successful. But those heroics may not be scalable because the product has a real gap. I think there was a period where the involvement of our generalists actually prevented the product from getting better, which is the opposite of what you would hope.”
—
Chapters:
(03:00) GTM-strategy-market fit
(03:38) Hiring for the scale phase
(04:58) Two reasons behind B2B’s recent (pre Gen AI) efficiency gains
(06:10) What generalists enable
(08:01) Charisma and playbooks
(09:22) Why great generalists can obscure the reality of a product
(10:41) Codifying all the hats that generalists wear
(13:30) Why one should map product features to actual customer processes
(17:55) Ego vs spirit
(22:26) Why Gainsight plateaued despite best-in-class growth and culture
(25:22) How well they understood the coming resurgence
(27:12) The four types of COOs
(31:37) The COO role that can best drive second acts
(33:21) The principles (and routines) that inform a successful CEO-COO relationship
(37:40) Shared context or why a founder should constantly download their brain
(39:27) The act two pitfalls that prevailing tech headwinds have exposed
(44:30) How some companies have revisited their playbooks post ZIRP
(46:38) How Gainsight helped create a new role (and an org structure)
—
Mentioned/Resources:
Why You Should Hire for Your Stage
Scaling Your Startup…Through Your Best Nature
Is Your Market Growing Fast Enough?
The Rise of the COO Role
The Customer Success Economy: Why Every Aspect of Your Business Model Needs A Paradigm Shift
—
Connect with Allison:
X
Allison Pickens' Newsletter
Connect with Krish:
X
—
About Chargebee:
Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.
View all episodes
By ChargebeeIn this Second Acts episode, Krish speaks with The New Normal Fund’s founder and GP, Allison Pickens; who draws on her time as the former COO of Gainsight and her work with several remarkable (pre-seed to pre-IPO) SaaS companies, to illuminate some of the foundations (across people, product, and GTM) necessary for scaling up.
Allison: “If you put… a great generalist in front of a customer and you say ‘make them successful’ they might again be able to use their heroics to make that customer successful. But those heroics may not be scalable because the product has a real gap. I think there was a period where the involvement of our generalists actually prevented the product from getting better, which is the opposite of what you would hope.”
—
Chapters:
(03:00) GTM-strategy-market fit
(03:38) Hiring for the scale phase
(04:58) Two reasons behind B2B’s recent (pre Gen AI) efficiency gains
(06:10) What generalists enable
(08:01) Charisma and playbooks
(09:22) Why great generalists can obscure the reality of a product
(10:41) Codifying all the hats that generalists wear
(13:30) Why one should map product features to actual customer processes
(17:55) Ego vs spirit
(22:26) Why Gainsight plateaued despite best-in-class growth and culture
(25:22) How well they understood the coming resurgence
(27:12) The four types of COOs
(31:37) The COO role that can best drive second acts
(33:21) The principles (and routines) that inform a successful CEO-COO relationship
(37:40) Shared context or why a founder should constantly download their brain
(39:27) The act two pitfalls that prevailing tech headwinds have exposed
(44:30) How some companies have revisited their playbooks post ZIRP
(46:38) How Gainsight helped create a new role (and an org structure)
—
Mentioned/Resources:
Why You Should Hire for Your Stage
Scaling Your Startup…Through Your Best Nature
Is Your Market Growing Fast Enough?
The Rise of the COO Role
The Customer Success Economy: Why Every Aspect of Your Business Model Needs A Paradigm Shift
—
Connect with Allison:
X
Allison Pickens' Newsletter
Connect with Krish:
X
—
About Chargebee:
Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.