ai-strategy
(18)
Chris Cummings Has Spent a Career Teaching Old Systems New Tricks
From storage efficiency to private-markets AI, Chris Cummings keeps arriving where established industries meet a new operating model. His method is equal parts category design, practical metrics, and impatience with waiting for perfect data.
Grant Belaire Has Spent 20 Years Turning Products Into Habits
From AOL's reinvention to sports-only newspaper subscriptions and consumer cybersecurity, Belaire has kept returning to the same problem: how to earn a direct, useful place in a customer's digital life. Now he is applying that discipline to MacPaw's shift from a suite of Mac apps to a connected AI ecosystem.
Rebecca Stone Wants the Data Clean - and the Customer Heard
After building pipeline at LiveRamp and speeding up marketing at Cisco, Rebecca Stone has taken on a wider brief at Plume: make every customer handoff carry context, and leave the difficult conversations to humans.
Daniel Stradtman Wants Companies to Stop Losing What They Know
After more than 25 years turning consumer research into corporate decisions, Bloomfire's CMO has a blunt diagnosis for the AI era: the cleverest system in the room is still only as useful as the knowledge people can trust.
Pam Cory Knows the Question That Gets a Room Moving
The INRIX chief marketing officer has spent decades translating complicated technology into useful choices. Her more revealing skill is simpler: asking the question that lets everyone else into the room.
Kristi Flores Built a C-Suite Career by Taking the Jobs No One Wanted
The Accruent executive began in sales support, learned her way across product and marketing, and discovered that the assignments other people sidestepped were often the ones with the longest runway.
Greg Shove Has Survived Seven Startups. Now He Wants to Rewire the Company.
After 30 years of pivots, exits, bruises and board meetings, the Section CEO is betting that AI will change companies only when their leaders change first.
Consello Is Building a Boardroom Without Walls
The young firm pairs former operators, athletes and dealmakers with an investment arm - a model designed to turn introductions and advice into measurable corporate action.
Jack Gierlich
Jack Gierlich is a Brooklyn-based growth marketing founder and fractional CMO who has spent 15+ years scaling healthcare, SaaS, and AI companies. He leads marketing and growth at Leal Health (formerly TrialJectory), an AI-powered platform that helps cancer patients find advanced treatment options, and he moderates several of the largest marketing and business communities on Reddit, reaching millions of readers a month. He describes his craft as building marketing systems that compound rather than one-off campaigns.
Workhelix
Workhelix is an enterprise AI-measurement company that breaks jobs down into individual tasks - hundreds of thousands of them per client - and scores each one for how much generative AI can actually help. Founded by economists Erik Brynjolfsson, Andrew McAfee, and Daniel Rock alongside CEO James Milin, the company pairs proprietary task-scoring software with data scientists to tell C-suite leaders where to deploy AI, how it is being adopted, and what return it is producing. It raised a $15M Series A in February 2025 and counts Wayfair, Coursera, Accenture, and BAYADA among its customers.
Quantum Rise
Quantum Rise is a Chicago-based AI transformation company founded in 2024 by serial entrepreneur Alex Kelleher. It sells what it calls 'Consulting 2.0' - a products-not-projects model that pairs an enterprise AI operating system (QR/OS), a repeatable methodology, and forward-deployed experts to help mid-market and enterprise clients turn AI into measurable revenue and cost savings. Backed by a $15M seed round from Erie Street Growth Partners, the company argues the traditional billable-hours consulting model is about to collapse under automation, and it aims to fill the gap between the Big Four giants and smaller boutique shops.
Cascade
Cascade is a strategy execution platform that pulls corporate strategy out of slide decks and boardrooms and turns it into a living, trackable system the whole organization can run on. It combines strategic planning, OKRs, projects, KPIs and outcome tracking - now layered with AI insights via its Tapestry suite - into one platform so leaders can see whether the plan is actually working. Founded in 2017 and used by thousands of teams across 100+ countries, from vaccine supply chains to Formula One teams.
Eric Berridge
Eric Berridge is a 23-year Salesforce ecosystem veteran and CEO of Coastal, a premier Salesforce consultancy he joined in 2020 and took the helm of in September 2023. He previously co-founded Bluewolf in 2000 - one of the first Salesforce-focused consulting firms - and built it to a major acquisition by IBM in 2016. A TED speaker, two-time author, and MFA-holder in creative writing who never studied computer science, Berridge argues that the humanities are tech's most underrated competitive advantage. Under his leadership, Coastal was acquired by Tata Consultancy Services (TCS) for $700 million in January 2026, the largest professional services acquisition in Salesforce ecosystem history.
Raj Gajwani
Raj Gajwani is Chief Business Officer at OpenArt AI, the San Francisco generative-AI creator suite for images and video. Before OpenArt he spent over a decade at Google, scaling DoubleClick's channel program to $1.3 billion in revenue and founding Orion Wifi, one of the most successful projects out of Google's Area 120 incubator (now part of Android). He also runs Day 0, an enterprise AI strategy consultancy, and serves as a board member, advisor, and angel investor across startups including Couchsurfing, MultiView, and the Wireless Broadband Alliance. A Harvard graduate who also studied at the London School of Economics, he sits at the intersection of frontier AI products and enterprise go-to-market.
Severence MacLaughlin
Severence MacLaughlin is the founder and CEO of DeLorean Artificial Intelligence, a Palm Beach-based company building predictive AI products for healthcare and sales. A Cornell-trained scientist with a PhD from the University of Adelaide, he ran AI and data science practices at Cognizant and Capgemini Invent before bootstrapping DeLorean AI with his own savings. The company says its Medical AI was the first to be biologically validated by two independent laboratories, trained on tens of millions of patient records and backed by seven patents. He advises the United Nations and World Health Organization on AI.
Lawrence Herman
Lawrence Herman is the Chief Financial Officer and AI Strategy Leader at Cents, the all-in-one operating system for laundromats and dry cleaners. A payments and fintech finance veteran, he has steered the books at Dwolla, Accrete, and Paxful, and logged earlier stretches at Mastercard, American Express, Dataminr, EY, Citi, Morgan Stanley, and Goldman Sachs. Harvard-trained in economics, he is known for calm during industry cycles, a preacher's zeal for financial literacy, and a habit of walking into every meeting with three discussion points and three asks.
Carrie Tharp
Carrie Tharp is the GTM COO & VP Customer Experience at Google Cloud, where she oversees end-to-end customer experience strategy and connects product innovation to customer outcomes across priority industries including Retail, Financial Services, and Manufacturing. A veteran of major retail and digital commerce transformations, she spent nearly three years as EVP and Chief Digital & Marketing Officer at Neiman Marcus Group before joining Google Cloud in 2019. With roots in a family bakery in Erie, Pennsylvania and an MBA from Kellogg, she has become one of the most prominent voices on generative AI adoption and agentic AI in enterprise commerce.
Kevin Scott
Kevin Scott is the Chief Technology Officer of Microsoft, where he has served since January 2017 under CEO Satya Nadella. A computer scientist from Gladys, Virginia, Scott rose from a working-class background to become one of the most influential technologists in the world, architecting Microsoft's landmark partnership with OpenAI, the Copilot suite, and the 'agentic web' vision. Before Microsoft, he held senior engineering roles at Google, AdMob, and LinkedIn, where he led the infrastructure overhaul known as 'Operation InVersion.' He is also a Wall Street Journal #1 bestselling author of 'Reprogramming the American Dream' (2020), which argues that AI must be harnessed to serve rural and working-class communities, not just coastal elites.