In this episode of The Design Table Podcast, Tyler and Nick attempt something different: a live, real-time brainstorm where two senior product designers tackle an actual business problem — low feature adoption and poor upgrade conversion.

Companies keep shipping features that barely anyone uses. New tiers launch and… crickets. PMs blame “awareness” while designers blame “UX,” marketing blames “messaging,” and leadership wonders why revenue isn’t moving.

Tyler and Nick figure out why this happens, why most teams under-invest in feature communication, and how design, product, and marketing can work together to drive meaningful adoption without becoming sleazy or spammy.

They walk through upsell flow strategy, segmentation, in-app nudges, email sequencing, pricing psychology, ROI calculators, freemium tier traps, and how designers can get more comfortable with selling — because no one upgrades on accident.

If you work in SaaS, design for B2C or B2B, or you’ve ever launched a feature that landed with a sad thud… this episode is a must-listen.

Here is what is on the table in this episode:

🔸 Why “great features” still fail to get adoption
🔸 The biggest gap between feature design & feature awareness
🔸 How to avoid sounding salesy while still driving upgrades
🔸 Segmentation: who to upsell and when
🔸 The underrated power of email sequences for product teams
🔸 In-app education that actually works (and doesn’t annoy users)
🔸 How pricing, tiers, and value ladders influence upgrades
🔸 Why ROI calculators convert better than feature pages
🔸 What designers must learn from sales teams
🔸 How to build user advocates & power users intentionally

Chapters

00:00 Intro
00:32 The business problem we’re solving
01:54 B2C vs. B2B and how upgrades actually happen
03:50 Why awareness is the missing link
05:04 The disconnect between “we built it” and “users found it”
07:38 How to scorecard your adoption levers
10:07 The email sequencing mistake every product team makes
12:55 Building relationships vs. blasting announcements
17:00 Pricing tiers, value ladders & usage ceilings
21:56 When upgrades fail because value isn’t communicated
24:55 ROI examples (Zapier, time saved, etc.)
29:18 The role of in-app nudges, limits & locked features
34:57 Segmentation and timing your upsells
36:50 Avoiding pop-up overload
40:23 Webinars, product events & hype building
45:07 Discounts, loyalty, advocates & power-user programs
50:16 Stop being afraid to “sell” as a product designer
53:10 Next episode teaser: The Portfolio Mastermind

📢 Subscribe to The Design Table Podcast
👉 https://www.designtablepodcast.com/subscribe

👋 More about Tyler and Nick
Tyler: https://www.designtablepodcast.com/hosts/tyler-white
Nick: https://www.designtablepodcast.com/hosts/nick-groeneveld