Images and Inspiration With AI: Pinterest’s Jeremy King
Jeremy King leads a team of 1,400 passionate engineers working on the continuous improvement of Pinterest’s image-driven platform. With a background that includes heading up a translation team at eBay and overseeing the technology behind Walmart’s U.S. retail stores and e-commerce business, Jeremy is now responsible for technology operations at Pinterest. To support the company’s mission to inspire people to “create a life that they love,” he and his team rely on advanced AI, machine learning, and a graph database to index and build a network of images so users can find inspiration — particularly when they aren’t completely sure what they’re looking for.
On this episode, Jeremy joins Sam and Shervin to talk about some recent advances Pinterest has made in the image-recognition space and shares his views on how generative AI will transform image-based content like Pinterest’s. Read the episode transcript here.
Me, Myself, and AI is a collaborative podcast from MIT Sloan Management Review and Boston Consulting Group and is hosted by Sam Ransbotham and Shervin Khodabandeh. Our engineer is David Lishansky, and the coordinating producers are Allison Ryder and Sophie Rüdinger.
Stay in touch with us by joining our LinkedIn group, AI for Leaders at mitsmr.com/AIforLeaders or by following Me, Myself, and AI on LinkedIn.
Guest bio:
Jeremy King is senior vice president of technology at Pinterest, where he leads the company’s technical vision and the engineering organization responsible for building and scaling a visual discovery engine.
Before joining Pinterest, he was CTO and senior vice president at Walmart, where he led the team responsible for the technology behind U.S. retail stores and e-commerce for Walmart and Jet, and oversaw customer, merchant, and supply chain technologies across cloud and data platforms. King has also held executive-level technology roles at Walmart Labs, LiveOps, and eBay.
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SaaS Product-Market Fit: 5 Founders Share What Worked
What if the fastest way to SaaS product-market fit was to walk into a train station and start asking strangers questions? That is exactly what Jeremy King did before building Attest into an eight-figure ARR business.
Five SaaS founders share hard-won lessons on customer discovery, product quality, monetization, and finding product-market fit - including Rahul Vora's product-market fit engine that helped Superhuman grow after two years of coding with no launch. Learn how to achieve SaaS product-market fit whether you are validating a new idea or measuring traction in an existing product.
Featured founders: Jeremy King (Attest, $1M ARR in 8 months), Melissa Kwan (eWebinar, $750K ARR bootstrapped), Christian Owens (Paddle, nearly $100M ARR), Trevor Kaufman (Piano, $80M ARR), and Rahul Vora (Superhuman, $125M+ raised).
Key Lessons
🎯 Validate by going to customers physically: Jeremy King interviewed 200 consumers at Waterloo Station before building Attest, proving demand existed beyond corporate research departments.
🛠️ Deep product experience beats surface research for SaaS product-market fit: Melissa Kwan did 1,000+ webinars before building eWebinar, knowing exactly what the product needed.
💰 Monetize from day one to compound growth: Christian Owens built every business to make money immediately, using revenue to reinvest rather than chasing distribution first.
📉 Conviction under pressure is not failure: Trevor Kaufman sold his house to keep Piano alive through years of market rejection before reaching $80M ARR.
🔄 Use the 40% benchmark for SaaS product-market fit: Rahul Vora's product-market fit engine asks users "How would you feel if you could no longer use the product?" and targets 40% answering "very disappointed."
Chapters
Introduction and episode overview
Preview of the five founder clips
Jeremy King - Attest: Zero to $1M ARR in 8 months
How Jeremy validated demand through customer discovery
Why Jeremy did the research for free
Overcoming skepticism from store managers
Melissa Kwan - eWebinar: Two years of building in silence
Why Melissa refused to launch before the product was ready
The cost of a bad first impression on early adopters
How 1,000+ webinars gave Melissa deep problem understanding
Managing competition anxiety while bootstrapped
Financial projections as the real urgency driver
Christian Owens - Paddle: Pragmatism and monetizing from day one
How Christian approaches SaaS product-market fit incrementally
Every business must be a real business from day one
Trevor Kaufman - Piano: Selling his house to survive
The belief that kept Trevor going through market rejection
Rahul Vora - Superhuman: The Product Market Fit Engine
How Sean Ellis's research inspired the PMF Engine
The four steps of the Product Market Fit Engine
Closing thoughts
Resources
Full show notes: https://saasclub.io/357
Join 5,000+ SaaS founders: https://saasclub.io/email
Startup Funding: He Got Customers to Call VCs For Him
Jeremy King had no product, no revenue, and a six-month deadline from his wife. Instead of pitching VCs the usual way, he convinced 15 potential customers to call investors and ask them to fund Attest so they could buy the product. That startup funding hack compressed two years of struggle into four months.
In this episode, Jeremy reveals how he used Series B investors to create warm intros to seed funds for his SaaS fundraising, why he interviewed 200 people at Waterloo train station to validate his idea, and how a subscription flip took Attest from pay-as-you-go users to $1M ARR in just 7.5 months. You will learn the specific startup traction tactics that helped Attest reach eight figures in ARR and $104 million in total early traction funding.
What You Will Learn
How Jeremy used customer demand as a startup funding proxy for revenue
Why pitching Series B investors shaped his seed-stage strategy
How flipping to annual subscriptions converted nearly all existing users
Why Attest's freemium experiment bombed despite strong user adoption
🔑 Key Lessons
💰 Use customer demand as a startup funding proxy for revenue: Jeremy got 15 potential customers to call VCs directly, replacing traction metrics with firsthand demand.
🧠 Pitch later-stage VCs to shape your startup funding strategy: Jeremy pitched Series B/C investors who gave milestone feedback and warm referrals to their preferred seed funds.
⚡ Compress timelines by engineering social proof loops: Customers, Series B investors, and seed VCs all reinforced confidence in Attest, compressing two years of SaaS fundraising validation into four months.
🔄 Force a subscription flip when usage proves recurring value: Attest moved all users to annual contracts, converting nearly everyone because the product had proven regular utility.
📉 High-ACV products can backfire with freemium: Giving away a $45,000-ACV product made users question data quality and reduced urgency for startup traction.
Chapters
Introduction
Jacques Cousteau quote and the science of curiosity
What Attest does and who it serves
From McKinsey consultant to SaaS founder
Desktop research and validating the TAM
Interviewing 200 people at Waterloo Station
Proving demand exists beyond corporate research teams
The Links of London area manager surprise
Zero to $1M ARR in 7.5 months
Compressing two years of startup into four months
Raising 650K pounds in seed funding
Meeting co-founder Tony Hunter at a startup event
Building the product for international scale
The November 2017 subscription flip
29-day sales cycle and $45K average contract value
Growing to 170 people and eight figures ARR
Why Attest's freemium experiment bombed
Competing against guesswork, not incumbents
Never hearing the term SDR until 18 months in
Lightning round
Resources
Full show notes: https://saasclub.io/331
Join 5,000+ SaaS founders: https://saasclub.io/email