Matthew Calkins, founder and CEO of Appian, built one of the most enduring low-code software companies by betting early on automation, workflow, and enterprise speed. Launching Appian in 1999, Calkins steered the company through multiple technology cycles, positioning it as a core platform for digital transformation across government and large enterprises. Under his leadership, Appian went public in 2017 and became a recognized leader in low-code development and process automation. Known for his long-term vision, intellectual rigor, and independent thinking, Calkins has maintained founder control while shaping how organizations build and deploy software at scale.

Joseph Liemandt, founder of Trilogy and ESW Capital, is one of the most discreet yet influential figures in enterprise software, building a vast portfolio of companies by acquiring and optimizing underperforming software assets. After becoming a young tech millionaire with Trilogy in the 1990s, he shifted to a buy-and-build strategy through ESW Capital, assembling hundreds of enterprise software businesses and implementing data-driven, remote-first operational models long before they became mainstream. Known for his anonymity, contrarian discipline, and rigorous process engineering, Liemandt has quietly shaped the economics of enterprise software while amassing one of the sector’s most substantial private fortunes.

John Sall, cofounder and executive vice president of SAS Institute, helped transform a university statistics project into the world’s largest privately held analytics software company. An expert in statistical methods and visualization, Sall led the development of JMP, SAS’s widely adopted exploratory analysis software used across science, engineering, and industrial research. Alongside cofounder Jim Goodnight, he has championed long-term, employee-centric management and reinvestment in research over short-term profit, making SAS a model of sustainable tech growth. A major philanthropist in education, nature conservation, and science innovation, Sall’s impact spans both the global analytics industry and public access to scientific literacy.

John Bicket, co-founder and CTO of Samsara, turned a PhD-level tech project at MIT into a multibillion-dollar industrial Internet-of-Things company. After earlier selling his first startup, Meraki, to Cisco for $1.2 billion, Bicket teamed up with Sanjit Biswas in 2015 to build Samsara—fusing sensors, AI, and cloud software to monitor fleets, equipment, and field operations across thousands of enterprises. With stakes valued at around $3 billion each post-IPO, Bicket reflects the rare path from academic research to top-tier tech billionaire, while steering product strategy, engineering culture, and long-term innovation at the heart of the connected-operations era.

James Scapa, founder, chairman, and CEO of Altair, has spent four decades building the company into a global leader in simulation, high-performance computing, and data analytics. Starting Altair in 1985 with a small engineering team, Scapa helped pioneer computer-aided engineering tools that transformed product design across automotive, aerospace, manufacturing, and technology industries. Under his leadership, Altair expanded into cloud computing, AI, and enterprise analytics, evolving into a multibillion-dollar publicly traded company. Known for his long-term vision and engineering-driven culture, Scapa remains one of the most respected leaders in applied simulation and computational science.

James Goodnight, cofounder and longtime CEO of SAS Institute, built one of the world’s largest privately held software companies by pioneering advanced analytics long before “data science” became a global discipline. Since 1976, he has led SAS with a distinctive focus on research, long-term product development, and a famously employee-centric culture that consistently ranks among the best workplaces in America. Under his guidance, SAS grew into a multibillion-dollar enterprise whose software powers decision-making for governments, corporations, and institutions worldwide, earning Goodnight recognition as a visionary architect of the modern analytics industry.

Jack Dorsey, tech entrepreneur and cofounder of Twitter and Block (formerly Square), has been a defining figure in the evolution of social media and digital finance. As Twitter’s cofounder and longtime CEO, he helped shape modern online communication, while at Block he revolutionized mobile payments and financial inclusion through technology. Known for his minimalist leadership style and focus on decentralization, Dorsey has increasingly turned his attention to Bitcoin and blockchain innovation, positioning himself at the intersection of technology, finance, and social change.

Jack Dangermond, founder and president of Esri, is a pioneering figure in geographic information systems (GIS) and digital mapping technology. Since founding the company in 1969 with his wife, Laura, he has transformed Esri into the global leader in GIS software, used by governments, businesses, and researchers in more than 100 countries. A landscape architect by training, Dangermond has combined environmental vision with technological innovation to help organizations make data-driven decisions about land use, sustainability, and urban planning. A dedicated philanthropist, he has donated hundreds of millions to environmental conservation and education.

Garrett Camp, Canadian entrepreneur and investor, is best known as the cofounder of Uber and the founder of startup studio Expa. Before reshaping urban transportation with Uber, Camp created StumbleUpon, the pioneering web discovery platform acquired by eBay in 2007. At Uber, his vision helped scale the company from a niche car service into a global ride-hailing giant operating in hundreds of cities. Through Expa, he continues to back and build innovative startups, cementing his reputation as a tech visionary with a knack for disruptive ideas.

Frank Slootman, chairman and CEO of Snowflake, has earned a reputation as one of Silicon Valley’s most effective scale-up leaders, steering three companies to multibillion-dollar valuations. After leading Data Domain and ServiceNow through explosive growth and successful IPOs, he took the helm of Snowflake in 2019, guiding the cloud data platform to a record-breaking $33 billion IPO in 2020. Known for his no-nonsense leadership style and relentless focus on execution, Slootman has become a benchmark for operational excellence in the tech industry.

Ed Hallen is the co‑founder and Chief Product Officer (later Chief Strategy Officer) of Klaviyo, the Boston-based SaaS platform powering email/SMS marketing and customer data for over 100,000 brands, including Unilever and Citizen Watches  . A systems engineering graduate from UVA and MIT Sloan MBA, he previously led product at Applied Predictive Technologies and held roles at Google before launching Team Engine in 2018.

Devin Finzer is the American entrepreneur who co‑founded OpenSea in December 2017, becoming the largest global marketplace for NFTs. A Brown University alumnus in computer science and mathematics, he previously built Claimdog (acquired by Credit Karma) and worked at Pinterest, Flipboard, and Google on product growth. OpenSea’s rapid rise made him one of the first NFT billionaires in 2022, though its valuation has since declined amid market turbulence and regulatory pressures.

Bob Muglia is a veteran technology executive and cloud innovator, best known as the former CEO of Snowflake (2014–2019) and President of Microsoft’s Server & Tools division. A University of Michigan graduate, he brought Microsoft’s server & enterprise revenue from $9.7 B to $17.1 B and later led Snowflake’s rise from pre-revenue start-up to one of the largest enterprise software IPOs in history. He now invests and advises across AI-driven data and cloud companies.

Benoit Dageville is a French-American computer scientist and co-founder of Snowflake, the revolutionary cloud data platform. As President of Product, he steers the technical vision and innovation behind SQL performance and AI integration. A former Oracle architect with a PhD in parallel database systems, Dageville holds over 80 patents and helped grow Snowflake from stealth mode in 2012 to a multi‑billion‑dollar IPO in 2020. 

Anthony Wood is the English-born American billionaire and visionary behind Roku, the streaming-platform pioneer he launched in 2002. A self-taught engineer and entrepreneur, Wood previously created the DVR (ReplayTV) and later guided Roku to lead U.S. streaming with over 90 million households and a thriving ad-tech business. He also funds major philanthropy through his WoodNext Foundation.

Andrew Bialecki is the co‑founder and CEO of Klaviyo, the Boston‑based marketing automation unicorn. A Harvard‑trained engineer and physicist, he bootstrapped Klaviyo since 2012 and retained a rare ~38% ownership at IPO, guiding the company to a multibillion-dollar valuation through disciplined, data‑driven growth.

Alexis Le-Quoc is the co-founder and Chief Technology Officer of Datadog, a leading cloud monitoring and cybersecurity platform used by enterprises worldwide. With a background in engineering and infrastructure, Le-Quoc helped build Datadog into one of the most trusted tools for DevOps, enabling real-time observability across complex systems. His technical leadership has been central to the company’s rapid growth and global adoption.

Alex Shevchenko is the co-founder of Grammarly, the AI-powered writing assistant used by millions worldwide. With a background in computer science and a passion for language, Shevchenko helped build one of the most successful Ukrainian-founded tech companies, revolutionizing digital communication through intelligent writing tools. His work bridges technology and human expression at scale.

Alex Atallah is the co-founder of OpenSea, the world’s leading NFT marketplace, and a key architect of the decentralized web. A computer scientist and entrepreneur, Atallah helped shape the infrastructure of the digital collectibles economy, driving the rise of Web3 and blockchain-based ownership. Though he stepped back from daily operations, his influence continues to shape the future of NFTs and decentralized technology.

Alan Trefler is the founder and CEO of Pegasystems, a global leader in AI-powered business process automation and customer engagement software. A former chess prodigy and systems architect, Trefler has built Pegasystems into a multibillion-dollar enterprise serving Fortune 500 clients worldwide. He is also a thought leader in digital transformation and enterprise AI.