Heuristics and Hunches

Topic	Replies	Views	Activity
AI-Native PMF: "Why 90% of AI Tools Are Built Wrong for Enterprise", Pricing AI for a Buyer Too Comfortable with Seat-Based, and Hot Takes on AI for Sales Teams with Pocus' Alexa Grabell pmf , ai , ai-native Editor’s note: This new Relay by Chargebee series features field notes from AI-native SaaS founders as they tinker, build, and monetize their paths towards a new kind of product-market fit playbook. This post captures …	1	12	May 21, 2025
About the Heuristics and Hunches category	0	654	February 18, 2021
AI-Native PMF: Building an AI-Native CRM, Designing Human-in-The-Loop Workflows, and How "Customers Vote with Their Wallets" on Pricing Models with folk's Simo Lemhandez ai , product , pmf	0	36	April 12, 2025
AI-Native PMF: Question Base — AI's “Very Real” Cold Start Problem, Managing High-Stakes Hallucinations, and Balancing Adoption and Costs with a Freemium Strategy pricing , product , pmf , ai-native	0	286	February 7, 2025
AI-Native PMF: Differentiating Against Generic AI Tools, Lessons on Value and Margins from Three Pricing Model Evolutions, and Strong Hunches on AI-Native Building with Sudowrite’s Amit Gupta ai-native , product , pmf	0	143	April 7, 2025
Dropping Per-Seat Pricing after 14 Years, Creating a Customer-First Usage-Based Model, and Reckoning with an AI-Catalyzed Innovator’s Dilemma with Help Scout’s Nick Francis customer-centricity , ai , pricing , product , pmf	0	125	April 18, 2025
"I Psyoped Sam Parr" - BTS Notes on Winning Big Logos Early, Building in an Era When "SaaS Has Been Picked Over," and Why Community Is the Growth Channel of the Future with River's Co-Founder, Rae Lambert ai , operating-principles , product , pmf	0	66	March 7, 2025
“The State of the Market Matters More Than Its Size” and Other Notes From Building for an Always-Under-Pressure ICP with Goldcast’s Co-Founder, Palash Soni positioning , niches , product , pmf	3	132	October 7, 2024
Niching as a Learning Tool, Prioritizing Teams over Users, and Building at The Intersection of Technology and Culture with Flat’s Co-Founder, Seth Purcell niches , design , product , pmf	1	89	October 5, 2024
“I Don’t Think You Can Have a Great Product Unless It’s Freemium” and Other Notes on Growing in an Established SaaS Category with Loops’ Co-Founder, Chris Frantz crowded-markets , freemium , product	1	615	May 13, 2024
The Power of Intuitive Tech, “Juicing It” as a Usage (and Joy) Driver, and Other Notes on Shaping a Disciplined-Yet-Freeing Product Path with Arcade’s Co-Founder, Caroline Clark freemium , goal-setting , founders-self , product	2	559	April 18, 2024
Solving B2B Distribution with Viral, Persona-Focused Work Humor, Navigating Growth Plateaus, and Other Notes on Making Singular Bets with tl;dv’s Co-Founder, Raphael Allstadt founders-self , hiring , operating-principles , pmf , marketing-mix	1	460	April 2, 2024
“Sharing Our Experiences, Wins, and Lessons is Also Humbling. It Keeps Us Honest,” and Other Notes on Building a Customer-First, Bootstrapped Business with Canny’s Co-Founder, Sarah Hum culture , bootstrapping , product , operating-principles , pmf	0	612	February 9, 2024
Why the Lean Startup Approach Doesn't Work (as Often), Why PMF Surveys (Alone) Aren’t That Helpful, and Other Notes on Building Opinionated Software with June’s Co-Founder, Enzo Avigo product-led-growth , positioning , customer-research , product , pmf	2	927	January 26, 2024
“How Moving Away from Per-User Pricing Helped us 4X our Growth, Why We Were Moving Back, and Why We Won’t (For Now)” with Tability’s Co-Founder, Sten Pittet product , categories , pricing	12	1598	January 11, 2024
Solving a Truly Universal Problem, Competing with Software Built in The 80s, SMB Notes from Xero, and Other Observations with Tallyfor’s Co-Founders, Peter and Ben Wen hiring , operating-principles , churn , competitive-markets	2	397	December 23, 2023
“One of Our First Engineers Had Been Working in Tech for 30 Years” and Other Notes on Deliberately Hiring Senior People Early with Recast’s Co-Founder, Michael Kaminsky capital-efficiency , hiring , fundraising , pmf	1	423	December 12, 2023
"As We Scale, We Operate More Like a Typical (Horizontal) B2B SaaS Business Rather Than a Vertical One” and Other Lessons on Building an Ag-Tech SaaS with Regrow Ag’s Co-Founder, Anastasia Volkova hiring , pmf , vertical-saas , icp	2	455	December 11, 2023
Bootstrapping after 8 Years on the VC-Backed Path, Getting to Multi-Million ARR with a Team of 3, and Notes on PLG with Userflow’s Co-Founder, Esben Friis-Jensen capital-efficiency , product-led-growth , bootstrapping , founders-self	4	1024	November 22, 2023
How Selling 3K AppSumo Deals Proved Foundational, Not Niching Down, and Other Reflections on Scaling a Bootstrapped SaaS with Paperform’s Co-Founder, Dean McPherson niches , user-onboarding , differentiation , product-launches , bootstrapping	2	1373	November 6, 2023
How Atlassian Began in a Niche, Laddering to Scale, and Lessons from 2 Decades of Building for Development Teams with Released’s Co-Founder, Jens Schumacher dev-tools , product , niches	2	998	October 25, 2023
The Necessity and (Unceasing) Magic of Doing Thousands of User Onboarding Calls with Vimcal’s Co-Founder, John Li user-onboarding , freemium , product , retention	0	530	October 6, 2023
The Trouble with Building too Close to User Love, Why PLG Requires Balancing 4 Different Roadmaps, and Other Earnest Notes from Winding Down a Startup with Kairn’s Co-Founder, Patricia Bernasconi pivots , product-led-growth , pmf , founders-self , product	1	607	October 3, 2023
How Early Adopters Don’t Have to be Ideal Customers, Founder-Done Customer Support as a Growth Strategy, and Other Notes on Building with Reasonable Ambition with Missive’s Co-Founder, Philippe-Antoine Lehoux early-stage-growth , founders-self , bootstrapping , product	2	716	September 28, 2023
“It’s Tempting to Start Selling Something We’d Build 6 Months Down the Line” and Other Notes on Early Validation with Alphadoc’s Co-Founder, Job Rietbergen product-led-growth , customer-research , product , idea-validation	2	752	September 25, 2023
“No One Can Represent All Sides of an Argument Better Than You Can” and Other Instructive Notes on Early-Stage Product Marketing with Vanta’s VP of Marketing, Sarah Scharf customer-research , operators-series , operating-principles , product-marketing	2	862	September 8, 2023
“I Think I’m a Historian” — Pivots vs Hops, HubSpot’s Singular Self-Awareness, Why Bundling Gets Rebranded Every 3 Years, and Other Discerning Lessons with Nira’s Co-Founder, Hiten Shah pivots , enterprise , bundling , strategy , founders-self	2	681	August 23, 2023
Scaling an Open Source Tool While Running an Agency, Giving Back Control with On-Prem Deployments, and Bootstrapping Decisions with Flagsmith’s Founder, Ben Rometsch open-source , bootstrapping , fundraising , pmf , dev-tools	2	542	July 18, 2023
Prioritizing Engineering Momentum over Accurate Timelines and Building on the Merits of a Car When Users Might Want Faster Horses with Compose’s Co-Founder, Rami Kalai competitive-markets , metrics , operating-principles , pmf , product	2	552	July 4, 2023
How the Founder Persona Likely isn’t Your ICP, Why Biz Fundamentals Trump All Silicon Valley “Must-Haves”, and Other Recognitions with Basis’ Founder, Bebe Kim capital-efficiency , metrics , growth , pmf , founders-self	1	704	June 19, 2023

AI-Native PMF: "Why 90% of AI Tools Are Built Wrong for Enterprise", Pricing AI for a Buyer Too Comfortable with Seat-Based, and Hot Takes on AI for Sales Teams with Pocus' Alexa Grabell

pmf , ai , ai-native

Editor’s note: This new Relay by Chargebee series features field notes from AI-native SaaS founders as they tinker, build, and monetize their paths towards a new kind of product-market fit playbook. This post captures …