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Why Mailchimp never raised 📖
Ben Chestnut's reflections, framing the enteprise AI hammer, and B2B reels.
May 23
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Team Chargebee
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Why Mailchimp never raised 📖
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“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
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Team Chargebee
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“Don’t start a tech-enabled service” 👩💻
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April 2024
CEO -> CTO -> IC 🪃
Scratching a passionate itch, catching the PMF lightning twice, and an unlikely B2B brand bet.
Apr 25
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Team Chargebee
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CEO -> CTO -> IC 🪃
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The all-in-one niche 🍞
Really knowing the problem space, why Photoshop/Powerpoint stuck, and raising from a position of strength.
Apr 11
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Team Chargebee
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The all-in-one niche 🍞
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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
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Team Chargebee
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The transitional segment 🔄
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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
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Team Chargebee
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Avoiding enterprise “funny money” 🔮
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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
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Team Chargebee
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Who should own pricing? 💸
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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
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Team Chargebee
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Predicting SaaS waves 🌊
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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
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Team Chargebee
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Crazy, energy-draining 2021 🫠
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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
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Team Chargebee
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"..if you’re raising in 2024” ⏩
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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
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Team Chargebee
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Loom’s GTM stumbles 🚪
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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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Team Chargebee
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Founder-led-to-repeatable sales ⚙️
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