Archive - The SaaS Baton

Why Mailchimp never raised 📖

Ben Chestnut's reflections, framing the enteprise AI hammer, and B2B reels.

May 23, 2024 •

“Don’t start a tech-enabled service” 👩‍💻

The service/SaaS tightrope, why PMs made up for a uniquely difficult persona, and the beautiful utility of constraints.

May 9, 2024 •

April 2024

CEO -> CTO -> IC 🪃

Scratching a passionate itch, catching the PMF lightning twice, and an unlikely B2B brand bet.

Apr 25, 2024 •

The all-in-one niche 🍞

Really knowing the problem space, why Photoshop/Powerpoint stuck, and raising from a position of strength.

Apr 11, 2024 •

March 2024

The transitional segment 🔄

Why startups shouldn’t start with mid-market customers, deftly allaying platform risks, and observations from building an email platform.

Mar 28, 2024 •

Avoiding enterprise “funny money” 🔮

The virtues of subjective-but-informed-decisions, hard truths of founder-led sales, and where to start with enterprise deals.

Mar 14, 2024 •

February 2024

Who should own pricing? 💸

Deciding whether pricing strategy stays with product/GTM, the costs of pursuing foundational models, and positioning towards JTBDs not personas.

Feb 14, 2024 •

January 2024

Predicting SaaS waves 🌊

The criticality of market timing, why PMF is gradual and should be measured as such, and The (SaaS) Office.

Jan 17, 2024 •

Crazy, energy-draining 2021 🫠

Beyond growth frenzy, a top-down, all-hands AI excursion, and an org-building lesson on expectations and modelling.

Jan 3, 2024 •

December 2023

"..if you’re raising in 2024” ⏩

181 investor meetings, scaling with the user-buyer-developer persona, and deciding on experience over potential.

Dec 20, 2023 •

Loom’s GTM stumbles 🚪

Revisiting a SaaS cornerstone, how post-PMF growth isn’t necessarily linear, and shipping fast without shipping dates.

Dec 6, 2023 •

November 2023

Founder-led-to-repeatable sales ⚙️

A year of selling process-fully, how an AppSumo launch led to a bootstrapped “seed fund”, and a reminder on being more determinedly vocal about your…

Nov 22, 2023 •

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