ai-coaching
(15)
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.
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.
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.
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.
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.
Kirill Makharinsky
Kirill Makharinsky is the co-founder and CEO of Enki, an AI-powered work-skills coach used by professionals at companies that want their teams fluent in data, SQL, Python and the rest of the modern productivity stack. An Oxford mathematician who graduated top of the UK, he previously co-founded Quid (now NetBase Quid) and Emerging Travel Group (Ostrovok, RateHawk, ZenHotels), two companies whose combined revenues run into the hundreds of millions. He angel-invests on the side and has been on Forbes' 30 Under 30 Europe list.
Alexei Dunaway
Alexei Dunaway is the founder and CEO of Pinnacle, a New York and Palo Alto based startup building Pascal, an AI performance and career coach that lives inside Slack, Teams, and Zoom. A Stanford GSB graduate and Fulbright Scholar, he spent five years building an entrepreneur accelerator in Kenya before running an executive coaching practice for venture-backed founders. He now wants to give every worker the kind of coaching that used to be reserved for the C-suite. Pinnacle raised a $2.5M seed round in March 2025 led by eLab Ventures.
Jamie Albers
Jamie Albers is the co-founder and co-CEO of Mento, a Los Angeles career-health company that pairs people with coaches who blend 80% coaching and 20% hands-on mentorship from operators who have done the job before. A University of Pennsylvania grad who spent five years across Google and then ran growth and marketing at Jigsaw, she built Mento after her own executive coach reshaped how she led and felt at work. Mento has raised about $11.5M, including a $6M seed in 2023 backed by M13, and is now folding AI into coaching to make high-quality guidance affordable at scale.
Nick Deveau
Nick Deveau is the co-founder and CEO of Grotto AI, a New York startup building real-time AI coaching for apartment leasing teams. A Stanford-trained AI engineer who helped build the technology behind EvolutionIQ's $730 million sale, Deveau now bets that humans, not bots, close the deals that matter most. His platform, Guidance, listens to leasing calls and tours, decodes what makes top agents great, and whispers that playbook to everyone else in real time. In February 2026 Grotto raised a $10 million seed round led by ICONIQ Capital.
Rocky Collis
Rocky Collis is the co-founder and CEO of Mustard, a sports technology company that uses computer vision and AI to put world-class coaching in a phone. A former Cornell pitcher drafted by the Seattle Mariners, he detoured through Georgetown Law and big-firm litigation before teaming up with legendary throwing coach Dr. Tom House, mental-performance coach Jason Goldsmith, and his brother Luke to build an app that gives any kid the kind of mechanics analysis once reserved for Tom Brady and Nolan Ryan. Mustard has raised roughly $5.45M-$6M from backers including Mark Cuban, Ronnie Lott, and Justin Rose, and has expanded from pitching into golf through a partnership with Golf Digest.
Parker Mitchell
Parker Mitchell is the co-founder and CEO of Valence, the New York company behind Nadia, billed as the world's first enterprise AI coach. He spent two decades before that building Engineers Without Borders Canada, the charity he co-founded out of the University of Waterloo in 2000, and advising Fortune 500 leaders at McKinsey. In 2025 Valence raised a $50M Series B led by Bessemer Venture Partners, with Nadia deployed across companies like Delta, Experian, Kraft Heinz and General Mills, having logged more than a million coaching conversations.
Tom Griffiths
Tom Griffiths is the CEO and co-founder of Hone, a live, cohort-based talent development platform that trains managers at companies like Indeed, ConocoPhillips, and Aramark. Before Hone, he co-founded daily fantasy sports company FanDuel and ran product for a decade as Chief Product Officer, helping pioneer a new category and grow it into a billion-dollar business with millions of users. A Cambridge computer scientist who left a machine learning PhD in Edinburgh to chase a startup, he now builds technology that teaches human skills.
Will Foussier
Will Guillaume Foussier is the co-founder and CEO of AceUp, a Boston-based AI-powered team-transformation and leadership-coaching platform he launched out of the Harvard Innovation Labs. A former financial analyst who credits an executive coach with rerouting his own career, he set out to democratize coaching - turning a once-exclusive C-suite perk into a data-driven service deployed across more than 100 enterprises including LVMH, L'Oreal, IBM, BNP Paribas and John Deere. A Forbes 30 Under 30 honoree and EHL, Harvard and Techstars alumnus, he raised a $22.5M Series A in 2024 and runs the company on the conviction that everybody deserves a coach.
Alexi Robichaux
Alexi Robichaux is the CEO and Co-Founder of BetterUp, the human transformation platform he started in 2013 after a soul-searching walk along the Camino de Santiago. He built BetterUp from a two-person idea into a $5 billion company with 2,800 employees and over $628 million in total funding, pioneering digital professional coaching for enterprises including Google, Salesforce, and NASA. A former product executive at VMware who once struggled with imposter syndrome and public speaking anxiety, Robichaux turned his personal journey with coaching into a mission to make elite professional development accessible to everyone.
Ravi Swaminathan
Ravi Swaminathan is the co-founder and CEO of TaskHuman, a real-time 1:1 digital coaching platform that connects employees with live human coaches via video call across 1,000+ topics - from fitness and financial planning to leadership and emotional well-being. A seasoned technology executive with roots in semiconductor and enterprise storage, he built TaskHuman in 2017 after recognizing that no generic article or pre-recorded video could replace the power of an expert human conversation. The company has raised $35M+ in funding, grown ARR 700% between its Series A and B rounds, and now operates across nearly 50 countries with a network of 1,000+ coaches.