John Gleeson at SuccessVP

Another amazing Customer Success Meetup tonight with our friends @mondaydotcom! We talked consumption pricing with amazing CS leaders from Stripe, MongoDB and PeopleAI.

In a world where AI is reshaping discovery and traditional marketing channels are underperforming, community stands out as one of the most defensible channels. You need to be radically customer-centric to win vendor shortlists in 2025.

So many LPs get tricked by so-called deep tech GPs. “Deep tech” has become one of the most overused, underdefined terms in venture. It’s turned into a catch-all that often signals prestige without precision. Originally, deep tech was supposed to mean breakthroughs rooted in…

One thing that’s become increasingly clear to me while building SuccessVP is how important it is for funds not to outgrow their demand. I keep seeing an adverse selection dynamic—funds eager to invest in a company, but unable to secure meaningful ownership relative to their size.…

The more customers you visit in person, The more customers you close. The more revenue you retain. And the more they buy from you. As true in 2025 as it ever was.

Every minute I spend with @pejmannozad is a masterclass. Even at the top of the Midas Seed List 3 years running Pejman told me he still loses sleep over the deals he missed. His advice last night after the Pear AGM. “Venture is like a bus stop. You might miss a bus. But if you…

Newspapers are the original SaaS. This morning, I got a call from the SF Chronicle asking if I wanted to renew my subscription—months after I unsubscribed due to declining quality and a terrible offboarding experience. Here are 3 lessons for CS leaders: 1. Product is…

Pricing in the AI era needs a rethink: •Match your pricing model to how value is delivered •Ask: How do customers measure value? Can you predict usage? Do costs scale? •Best models combine a base fee + value-based scaling (usage, outcomes) Stable floor, unlimited upside.

Clay is really doing a great job of informing the future of packaging and pricing.

“At the app layer — you have to play out in 6 months — is it a wedge to something you believe in? That wasn’t the case in SaaS.” Jermey Kaufmann

“Over index on founders who really know their customers.” @MarHershenson

“Are your AE’s using AI to get better or to take short-cuts? I’m looking at AE’s who use it to make themselves better.” — Marc Wendling

In a world of experimental budgets and AI-driven buying, churn is everyone’s job. Value realization isn’t a post-sale function — it’s the core. “Make the value real.” Value realization is king in an AI world.

Every brand is trying to create community! In person events seem to be the only thing working for marketers these days.

Google search is up 9% but click through is down 25% because Gemini is answering the question. What does this mean for market? Great insight at the @scalevp Go To Market Summit.

Interesting insight from Thursday’s Customer Success Meetup: MongoDB, Stripe, Intercom, Clay, Notion, and PeopleAI are all hiring CSMs aggressively—some with 10+ open roles. They’re specifically looking for ex-consultants from firms like BCG and KPMG. While AI is driving…

“You can’t skimp on the voice of the customer and if you do you’re screwed!”

Early one Saturday morning, I arrived at @dougleone's home in Atherton with two vans full of Persian rugs. Doug, the charming Italian venture capitalist from Sequoia, knew exactly what he wanted—and none of my rugs matched his vision. As we talked, I offered to help @sequoia…

In-N-Out puts cash into fresh beef and well-paid people. McDonald’s feeds corporate overhead. Result? In-N-Out makes nearly double per store while making a far better product cheaper. I would always rather be In-N-Out.