Christopher Steiner

Chris has helped Cuesta build the leading data and AI consultancy for private equity portfolio companies.

Finding ROI Via Data

Chris helps companies solve business problems using technology and data. In 2012, he wrote a best-selling book on the coming (now here) wave of AI automation, and explained algorithms to a national audience on The Colbert Report. Chris has helped Cuesta build the leading data and AI consultancy for private equity portfolio companies.

Chris has a track record of unlocking value from technology for more than 15 years, helping build major incremental equity for clients. As a software engineer, Chris has also led hundreds of technology diligence processes, identifying the software, infrastructure and data plays that will lead to greater success during an investment hold period. One of Chris’ main focuses is assessing companies’ posture around AI and data to ensure they capture the greatest possible value on exit.

Experience + History

Y Combinator, Coinbase, Slack, Instacart & Gitlab

Chris’ technology investing background traces to Aisle50, a software/data startup he cofounded. Aisle50 was funded by Y Combinator in 2011 and acquired by Groupon in 2015. Steiner later served as an entrepreneur-in-residence at Northwestern University’s technology accelerator, The Garage. Chris also worked at Funders Club, a venture capital company with investments in Coinbase, Slack, Instacart and Gitlab.

New York Times Best-Selling Author

Chris is a New York Times Bestselling Author of two books, including Automate This, How Algorithms Came To Rule Our World. His writing on technology has appeared in The New York Times, The Wall Street Journal, Forbes magazine, and the MIT Technology Review.

Chris lives in Evanston, Ill., where his family tolerates him as a youth hockey coach and as an enthusiastic skier who insists on traipsing about the Rockies every winter. For skiers bent on being on the right snow at the right time—according to the data—Chris built ZRankings.com.

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Industry Insights by Chris Steiner

All industry insights

Data Strategy & Execution

Data-Driven Staffing Reduces $10K Monthly External Labor Costs for $1.5B Global Logistics Provider

Union labor planning at a major port relied on manual staffing methods, resulting in frequent over- and under-staffing. Cuesta introduced a data-driven Resource Demand Analytics solution using predictive models to forecast inbound volumes, targeting a reduction of 2 third-party hourly workers per week, or approximately $10K in monthly savings

Data Strategy & Execution

Master Data Management Program Delivers Trusted Customer Data for $1.5B Global Logistics Provider

Operating across 10+ Business Units without a centralized MDM function, the Client faced significant customer data duplication and fragmented reporting. Cuesta established an MDM foundation from the ground up, preventing most future duplicates, reducing CRM account volume, and introducing governance structures that enabled clean data, repeatable processes, and a clear path to in-house ownership

Data Strategy & Execution

Margin Analytics Unlocks $1M Profit Opportunity for $1.5B Global Logistics Provider

Client’s Finance and Sales teams relied on manual, weekly retroactive reporting with limited visibility into customer and transaction-level margin performance. Cuesta collaborated to design and deliver a transaction-level Margin Analytics dashboard that enables automated revenue and cost comparison and faster identification of low and negative margin transactions, supporting targeted profitability improvements up to $1M annually.