Sean
I’ve spent twenty-five years building companies that big enterprises run on. Most evenings I’m with my family, or building smaller things just for me.
Things I’ve helped build
- IsomerSince 2025Co-founded. AI that reads everything an insurer receives and catches the risk buried in it.
- Catalytic2015–2022Co-founded. Automation for the work nobody wants to do by hand. Acquired by PagerDuty, where it now powers PagerDuty’s workflows.
- Fieldglass2000–2014Founding CTO. How big companies hire and manage their contractors and other outside workers. Acquired by SAP, and still a mainstay of large enterprises.
Tinkering with lately
- gumshoeWalks a beat over podcasts, blogs and newsletters and files what it finds into a vault.
- sitrepTurns that pile into briefs.
- Color palettesPalettes worth keeping, each with an Obsidian theme to match.
- opsigReads the plaintiff bar’s podcasts, newsletters and blogs so the defense side doesn’t have to. A daily brief, by invitation.
- dotfilesGeeking out on the command line and the config files that make it mine.
- ObsidianWhere everything lands. How I use it, written up.
Selected writing
All writing- Jan 2026Context is a state problemWhy the workflow, not the prompt, should hold what an AI knows.
- 2022My perilous journey through SaaS pricingNine pricing models in four years at Catalytic, and what each one broke.
- Nov 2016We never knew the name of the trendSaaS, mobile, and AI and bots, torn down, and six patterns in how we innovated without knowing what to call it.
- Nov 2015Fieldglass in five actsFourteen years from a dark office on Diehl Road to SAP, each act set against what tech and the economy were doing.
- Nov 2006Blue highways, gray skiesOur first RV trip, day by day from the journal I kept: half the country in a rented Sprinter with Jess and Simon.
- 2006How I fell in love with camper vansOur first trip in a rented Sprinter, thirteen days with Jess and Simon, and the start of a life of RVing.
Selected talks and press
- 2026Point of receipt: redefining claims risk detectionFireside chat at ITC Vegas with MSIG’s Prashant Hinge, moderated by Datos Insights’ Meredith Barnes-Cook.
- 2026Insurance Nerds: catching claims risk at the point of receiptWebinar with Datos Insights’ Meredith Barnes-Cooke, hosted by Nicholas Lamparelli. The full recording.
- 2025Introducing 9root, the vertical AI platform for insuranceEqual Ventures, on why they backed 9root, now Isomer.
- 2022PagerDuty to acquire CatalyticThe announcement.
- 2021Formulated AutomationWhere Catalytic came from and where it was going.
- 2021How 10 execs got their start in techCIO Dive. Starting in psychology, and learning the power of no.
- 2020Embrace Digital Transformation, episodes 31 and 32Intel’s show, with Darren Pulsipher, on back-office automation.
- 2020Supply Chain BrainWhen automation takes your job, is retraining the answer?
- 2017 & 2020Crain’s Tech 50Chicago’s list of the people moving tech, in 2017 and again in 2020.
- 2019A conversation with Justin BradyOn a hopeful future for AI.
- 2019Catalytic hauls in a $30M Series BTechCrunch. Intel led it.
- 2019Contingent Workforce Weekly, episode 413Back to where Fieldglass started.
- 2018What if you could automate the boring parts of your job?Crain’s Innovators. What’s left is the part people enjoy.
- 2017Passing the TorchCity Club of Chicago, with Howard Tullman.
- 2017Building AI: a software maker’s perspectiveCXOTalk, with Ed Sim.
- 2016Ex-Fieldglass CTO raises $11 million for new ventureCrain’s, on Catalytic’s first raise.
- 2014So we pitched each otherBuilt In Chicago. Jai Shekhawat on hiring me as Fieldglass’s first employee.
- 2013Lectures in Engineering EntrepreneurshipA dozen short clips at Illinois, from thick skin to setting your price.
- 20092009 Pros to KnowSupply & Demand Chain Executive, for helping clients manage supply chain risk through the downturn.
- 2002Are you more than just a techie?Monster.com: “The days of being a pure techie or a techie prima donna are gone.”