Knowing What to Hand to AI and What to Keep--Jessica Storry, CEO-Stockpress

Jessica Storry co-founded Stockpress in 2019 out of the web design agency she was running, drowning in files across Dropbox, Box, Google Drive and hard drives clients mailed them. They took a contract building on an open-source DAM, decided it was overcomplicated, pitched the customer on something simpler, got told no, and built it anyway -- on her promise that she'd sell it. She did. Stage 2 Capital invested, they closed the agency in 2020, and Stockpress now occupies the gap nobody was serving: a $9.99 Dropbox account on one side, a $2,500-a-month enterprise DAM on the other, nothing in between. The same instinct drove the decision that actually grew the business. They started out cloning the enterprise DAMs and charging less, and were still doing every onboarding by hand. So they re-architected around self-serve, lowered the price -- the only time it's ever gone down -- and replaced a product full of in-app pop-ups with a five-step onboarding checklist. "Maybe we don't give customers enough credit sometimes. They can figure it out if they if it's presented in the right way." She also tells the story of the Friday night she spent topping up tokens in Claude Design and ended with nothing to show: "I could have just designed that page myself in an hour and it would have been fine." WHAT WE COVER Arguing against an AI support agent, and being wrong: 72% of tickets closed by the bot What AI is allowed to write, and what has to be accurate enough that it isn't Wireframes straight to the dev team, and why nothing AI-made ships as final design Going self-serve: lowering the price and cutting the hand-holding The five-step checklist that beat in-app pop-ups 85% of customers leaving every AI feature switched on Buyers who arrive from ChatGPT having never seen the website Where AI burned money for an eight-person team and produced nothing CHAPTERS 0:00 Intro and sponsor: Common Room 1:16 What Stockpress is, and the founding story 4:23 Cutting the hand-holding, and lowering the price 7:59 The five-step checklist that replaced the pop-ups 10:28 AI inside the product, and the 85% who turn it all on 13:17 Arguing against Fin, and losing 15:36 Under three minutes, by hand, at any hour 18:02 Common Room, and how leads get attributed 19:07 Otterly and buyers who never see the website 19:59 Fifty prompts, and building content to show up against them 21:17 Narrowing the ICP after being "Stockpress for everyone" 23:38 Writing with AI, and the one thing she won't hand over 27:22 Claude Design for wireframes, straight to the dev team 28:46 AI in customer success, and the MCP server in progress 35:18 Her Friday night with no output 38:37 Rapid Fire Five Connect with Jessica Storry on LinkedIn, or learn more about Stockpress at stockpress.co. This episode is sponsored by Common Room (https://www.commonroom.io/?utm_source..., the AI GTM Intelligence Platform trusted by teams like Okta, Anthropic, and Fireworks AI. To hear more conversations like this one, subscribe to The GOATS of Growth on Spotify, Apple Podcasts, or YouTube.