Shay Willard joined SamCart with an awesome mandate:

✅ Launch a brand-new product inside an established business

✅ Define its pricing & packaging from scratch

✅ Drive meaningful ARR and commercial value

Tackling pricing & packaging is usually scary and most product folks are learning how to do it on the fly.

Rather than guessing, Shay went deep into primary research. He conducted dozens of customer interviews, ran price sensitivity tests, and studied competitive benchmarks to land on a schema that worked.

What happened?

- The new product, CreatorU, grew to 80,000+ users in its first year

- It generated more than eight-figures in ARR in year one

- It attracted customers who weren’t even using SamCart creating a new funnel into the core product.

Key Takeaways from This Episode:

🔹 Pricing is a product decision -- Product managers who take ownership of pricing help ensure their products generate real commercial value.

🔹 Willingness to pay research is critical -- Instead of assuming, Shay got on calls, asked direct pricing questions, and shaped pricing around the willingness to pay of real customers & prospects.

🔹 Going multi-product requires clear positioning -- SamCart serves mature merchants. CreatorU serves beginners. Keeping them distinct—while enabling a natural upgrade path—was a critical decision.

𝗧𝗵𝗮𝗻𝗸𝘀 𝘁𝗼 𝗦𝗵𝗮𝘆 𝗳𝗼𝗿 𝘁𝗵𝗶𝘀 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻! 𝗧𝗵𝗶𝘀 𝗶𝘀 𝗼𝗻𝗲 𝗼𝗳 𝘁𝗵𝗲 𝗺𝗼𝘀𝘁 𝘁𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝗲𝗽𝗶𝘀𝗼𝗱𝗲𝘀 𝘄𝗲’𝘃𝗲 𝗱𝗼𝗻𝗲 𝗳𝗼𝗿 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗺𝗮𝗻𝗮𝗴𝗲𝗿𝘀.

If you’re thinking about pricing, monetization, or launching a new product, this conversation is worth your time.

Chapters:

00:00 – Intro & Welcome

01:15 – Shay’s career journey: From EdTech to SamCart

04:30 – How an MBA introduced Shay to pricing strategy

06:45 – When pricing & packaging became central to his PM role

08:10 – Joining SamCart to launch a new product

10:00 – Understanding the business opportunity & risks of multi-product expansion12:25 – Why SamCart needed a second product & who it was for

14:50 – Building a product for new creators vs. mature merchants

17:10 – Turning CreatorU into a revenue-generating business

19:05 – Finding product-market fit with a second product

20:45 – Early pricing decisions: When and how to monetize

22:30 – Learning pricing & packaging on the fly

24:00 – The power of primary research in pricing

26:10 – How Shay conducted willingness to pay interviews

28:00 – Pricing for adoption vs. maximizing revenue

30:15 – Pricing & packaging strategy: What worked and what didn’t

32:45 – CreatorU’s impact: 80,000+ users and $9–10M in ARR

35:10 – Why segmentation is crucial in pricing

37:00 – How SamCart positioned CreatorU separately from its core product

39:25 – How pricing decisions were made internally at SamCart

41:00 – The cross-functional approach to pricing & packaging

43:15 – How SamCart manages feature gating & entitlements

45:00 – The technical implementation of pricing (billing, CRM, access control)

47:20 – The importance of pricing & packaging as a PM skill

50:00 – Final takeaways: Why PMs should own pricing conversations

52:00 – Shay’s career-defining moment

54:00 – Where to find Shay & closing thoughts