ai-coaching
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Krishna Depura and the trouble with a good idea
Krishna Depura began with quizzes and virtual treasure hunts. Building Mindtickle meant learning when to keep playing, when to change the rules, and when a useful idea needed a harder question.
Think Fast, Talk Smart. Go off script.
A Stanford-born podcast turned everyday speaking anxiety into a global education business. Its next bet: listeners need somewhere to practice, not just another episode to hear.
Bravely: rehearse the conversation that could change your job
The difficult conversation is a workplace skill with remarkably little rehearsal time. Bravely sells employers a place for that rehearsal - and is now bringing an AI coach into the meeting itself.
Perceptyx wants your employee survey to earn its keep
For years, companies have asked employees what is wrong. Perceptyx is building a business around the more awkward question: what happens on Monday morning after the answers arrive?
The $10,000 Tennis Court Is Now a Phone
SwingVision took the machinery of elite tennis, squeezed it into one camera, and handed the argument over a line call to an iPhone. The trick was not merely teaching a phone to see. It was deciding what ordinary players would actually pay to know.
The School for Adults That Found Its Classroom at Work
LifeLabs Learning began with a slightly eccentric question: what if adults could practice the human skills nobody teaches in school? The answer became a global corporate classroom built around tiny behaviors, live rehearsal, and the useful discovery that a workshop is only the beginning.
Culture Amp wants your employee survey to have consequences
Thousands of companies use Culture Amp to ask employees what they think. Its next bet is AI that helps managers do something with the answers - while the company faces hard questions about its own workplace.
Multiverse wants your AI investment to earn its keep
The apprenticeship company that challenged university now teaches the existing workforce to put AI to work. Its real test is what happens after the lesson ends.
The $20,000 Mailer That Taught CallRevu to Listen
A Toyota dealer went looking for proof that his advertising worked and found something more useful: the conversations his store was mishandling. Two decades later, CallRevu is trying to turn every ring, pause and missed appointment into a dealership operating signal.
Cloverleaf Built an AI Coach Before Anyone Wanted One. Now the Office Has Caught Up.
In 2018, calling software a coach made buyers nervous. Cloverleaf renamed the idea, kept building, and waited for the market to learn its language.
Ian Gover Built Three HR-Tech Companies. His Latest Bet Is an AI Coach That Shows Up Before the Awkward Meeting
After 25 years in workplace technology, Gover stopped asking whether AI could replace a human coach. He asked what it could do for the millions of managers who never had one.
Talentism Turned Executive Confusion Into a Product - Now It’s Teaching AI to Ask the Hard Question
The Westport coaching firm built a business around a contrarian idea: confusion is data. Its next act combines veteran coaches, organizational diagnostics and an always-on AI advisor - but the useful part is a method any manager can test before buying anything.
The Stanford Dorm Algorithm That Turned a Spin Bike Into a Rhythm Game
freebeat took the music algorithm two Stanford students built in a dorm, wired it into a $599 bike, and bet that people will exercise longer if the workout scores them like a video game. So far the bet is holding.
Dima Syrotkin Is Teaching Companies to Hear What Change Sounds Like
At Pandatron, Dima Syrotkin is turning a founder’s long interest in self-awareness into an AI system for the awkward human work between corporate strategy and execution.
MasterClass Is Turning Celebrity Lessons Into a Career Stack
The company that taught millions to cook with Gordon Ramsay and write with Shonda Rhimes is widening its frame - from beautifully filmed inspiration to workplace training, AI rehearsal and credentials built for a changing job market.
The Campus Clinic That Never Closes
TimelyCare turned the overloaded campus counseling center into a 24/7 care network. Now its bet is that colleges will pay not only for access, but for proof that students get better - and stay enrolled.
Peloton Interactive
Peloton built a camera-ready fitness studio around a stationary bike. Now its higher-margin subscriptions, AI coaching and move into commercial gyms reveal the more durable idea underneath: fitness that feels scheduled, social and personal wherever you train.
MySivi
MySivi is a Bengaluru-based, AI-powered English-speaking practice app (Y Combinator W22) that helps Indian and global learners build spoken fluency through conversation with an AI teacher named Arya, real-time feedback on grammar and pronunciation, gamified lessons, and a peer-learning community. Originally launched as Speakify AI, it operates on a freemium model and has grown to millions of Android downloads.
Tim Regnier
Tim Regnier is the CEO and co-founder of Smart Access, a frontline performance management software company he started in Edmonton, Alberta in 2015 and now runs from San Francisco. After nearly a decade running retail-tech ventures, Regnier built Smart Access to solve the visibility gap for managers on warehouse, manufacturing, and store floors, turning static SOPs into living documents and pairing them with AI-driven observations, coaching, and analytics. His guiding belief that 'all truth is found on the floor' has shaped a platform used by top retail and logistics enterprises, and the company raised a $12M Series A in 2026.
Orum
Orum is an AI-powered live conversation platform for B2B sales teams. Its dialer automates the tedious parts of outbound calling - filtering out voicemails, bad numbers, and phone trees - so reps spend more time in live conversations. Layered on top is an AI coaching and enablement suite (scorecards, roleplay, live call visibility) that helps managers develop reps and shorten ramp time. Founded in 2018 by Jason Dorfman, the fully remote company has powered more than a billion calls and is used by over 1,200 revenue teams.
Jake Cronin
Jake Cronin is the founder and CEO of Siro, a New York based conversation intelligence platform that records and analyzes the face-to-face conversations of field sales reps and turns them into AI coaching. He learned the sales craft the hard way, selling Cutco knives door to door as a teenager and ranking among the company's top reps worldwide, then spent two years as a McKinsey business analyst before leaving in 2020 to code Siro's first product himself. The company has raised roughly $75 million, including a $50 million Series B led by SignalFire in 2025, and works with home services, telecom, and multifamily sales teams across the country.
Pandatron
Pandatron is an AI change-activation platform that helps large enterprises turn strategy into execution. Its conversational AI runs private, role-tailored coaching conversations with thousands of employees at once, then feeds leaders real-time behavioral intelligence on readiness, resistance and risk. Founded in Helsinki and now with a San Francisco presence, Pandatron works with Fortune 500 companies including SAP, Panasonic, Mitsubishi, Merck and Skanska to make coaching-driven change dramatically cheaper and more measurable.
Section
Section is a New York-based AI workforce-transformation company that helps enterprises turn expensive AI licenses into measurable behavior change. Founded in 2019 by NYU Stern professor Scott Galloway as the business-education startup Section4 and led by CEO Greg Shove, the company pivoted hard into AI in 2023. Its software - Section HQ, Section Coach and the ProfAI assistant - pairs certification, coaching and use-case discovery to move employees from 'I have a ChatGPT login' to actually applying AI on the job. Customers include Johnson & Johnson, Nike, Unilever, Okta and Horizon Media.
Shift Health
Shift Health is a San Francisco-based healthtech startup building a Human+AI behavioral care platform that keeps people supported between clinical visits. Its AI coach delivers 24/7, in-the-moment guidance across mental, physical, and behavioral health, while care teams set the protocols, tone, and clinical guardrails. Available as a consumer app ('Shift - AI Mental Health') and as an enterprise platform aimed at health systems, employers, and high-demand professions like first responders and veterans, the company frames good outcomes as coming from 'what happens between visits.'
Smart Access
Smart Access is an AI platform for frontline operations that closes the gap between how work is supposed to be done and how it actually gets done on the floor. Built for large retail, distribution, and logistics operations, it digitizes standard operating procedures, tracks frontline performance in real time, and turns floor-level observations into mobile coaching and skill-building for workers. Founded in 2015 by Tim Regnier and John White, the company raised a $12M Series A led by Lobby Capital.
Enki
Enki is a San Francisco-based edtech company building an AI-powered coaching platform that helps professionals and teams learn coding, data, and no-code tools faster. Founded in 2019 by Kirill Makharinsky and Bruno Marnette, Enki pairs on-demand 1:1 AI coaching with structured, role-specific exercises for tools like SQL, Python, Excel, Tableau, Looker, and Power BI. It began as a mobile app that grew to millions of users and 20,000+ five-star reviews, then pivoted toward enterprise upskilling, offering companies a way to raise data literacy and tool adoption across their workforce.
Grotto AI
Grotto AI builds an AI coaching platform for multifamily leasing teams, listening in on calls and tours and nudging agents in real time toward the behaviors - curiosity, rapport, a well-timed laugh - that its data shows actually close leases. Founded in 2025 by Nick Deveau and Ben Epstein, veterans of the AI-in-insurance startup EvolutionIQ, the company raised a $10 million seed round led by ICONIQ Capital in February 2026 and already runs on portfolios for operators like Weidner Apartment Homes.
Mento
Mento is a performance-coaching platform that pairs leaders and teams with 1:1 executive coaches, adds a lighter layer of mentorship, and uses AI to connect what happens between sessions. Built on an 80/20 coaching-to-mentorship methodology and staffed by former C-suite, VP, and director-level coaches, Mento sells leadership development to companies that want to grow and keep their highest performers. Co-founded in 2019 by Jamie Albers and Alex Marcus, the Los Angeles company counts Anthropic, Dropbox, Brex, Gusto, and Vercel among its clients.
Mustard
Mustard is a Los Angeles-area sports-tech company that puts elite athletic coaching in an app. Using AI and computer vision, it analyzes ordinary smartphone video of a pitcher's throwing motion or a golfer's swing, compares it against a decades-deep biomechanics database, and returns a report card plus a personalized drill plan. Co-founded by legendary throwing coach Dr. Tom House, the company aims to make world-class, data-driven coaching accessible to any athlete, starting with baseball and golf and expanding toward other sports.
Pelotero
Pelotero is a Player Intelligence Platform for baseball and softball that blends computer vision, bat-sensor data, and professional coaching expertise to deliver personalized player development. Using nothing more than a phone video, the app scores a hitter's swing across 50+ mechanical attributes, identifies the gap between current performance and potential, and turns that data into individualized training plans. Founded by former MLB player Chris Colabello and hitting coach Bobby Tewksbary and led by serial software entrepreneur Bennett Fisher, the company has assessed more than 10,000 players and works with 40+ organizations plus scouting service Perfect Game.