Tido Carriero has seen firsthand how pricing decisions can accelerate growth—or slow it down.

At Segment, he led engineering and product through massive pricing & packaging evolutions, including major shifts in their business model as they moved upmarket. Now, as founder & CEO of Koala, he’s applying those lessons to building one of the most delightful tools in the sales tech stack.

This episode is a masterclass in pricing & packaging for founders and product leaders.

Key Takeaways from Our Conversation:

🔹 Early-stage pricing mistakes can have long-term consequences.Segment’s initial pricing led to cannibalization, with customers realizing they could downgrade from $100K enterprise deals to a $500/month self-serve plan. Fixing it was a high-stakes challenge.

🔹 The right value metric matters more than the price itself.Segment originally metered on monthly tracked users, but in hindsight, a feature-based model would have created more stickiness. Tido shares why picking the right value metric is critical—and why listening to customers isn’t always enough.

🔹 Frequent pricing experimentation is essential.Segment made big pricing changes every two years, but struggled to test smaller, incremental pricing adjustments. In retrospect, Tido believes more frequent iteration could have driven significantly higher ARR.

🔹 Moving upmarket means shifting the entire pricing conversation.Segment had to reposition its core product as a low-margin acquisition channel while shifting revenue to higher-value products like customer data activation.

Tido and I also discuss:

🚀 The trade-offs of moving upmarket and why it changes everything

💡 Why pricing isn’t just a sales decision—it’s a product decision

🛠️ What he’s building at Koala to transform sales research

Chapters

00:00 – Intro & Welcome

01:10 – Tido’s background: Facebook, Dropbox, Segment, Twilio, and founding Koala

03:00 – The unexpected lesson from an "energy audit" on team dynamics

05:25 – The Segment journey: pricing, packaging, and scaling a multi-product SaaS business

07:00 – Chapter 1: Early-stage pricing challenges at Segment

08:40 – How early pricing led to cannibalization & churn risk

10:15 – The high-stakes decision to rework pricing & packaging in just two weeks

12:30 – Choosing the right value metric: Monthly tracked users vs. features15:10 – The long-term impact of early pricing decisions (still felt today)

17:30 – Chapter 2: Moving upmarket & launching new products

19:00 – Why Segment’s original pricing cut off new customer acquisition

21:20 – How Segment repositioned pricing to unlock enterprise revenue

24:10 – Creating higher-value products to shift away from build vs. buy conversations

26:50 – Chapter 3: The importance of pricing iteration

28:30 – Why Segment only made major pricing changes every two years

30:15 – The downside of infrequent pricing experiments

32:45 – What Tido would have done differently with pricing iteration

35:00 – Who should own pricing inside a SaaS company?

37:50 – The Koala story: Building the future of sales research

40:20 – What inspired Tido & his co-founders to start Koala

42:10 – The moment they realized Koala had strong product-market fit

44:30 – Koala’s early pricing strategy & lessons learned

46:45 – How Koala shifted from metered pricing to a simpler flat-fee model

49:15 – How they’re thinking about pricing & packaging today

52:00 – Tido’s biggest career inflection point & closing thoughts

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