Private investment
Gatsby
Acquired by KlaviyoBacked a team building modern infrastructure for brand-to-customer engagement.
We help businesses put AI on real work.
O'Leary Good Company is a family-owned investment and operating company. Right now we help operators use Claude, Codex, ChatGPT, and other AI tools on the work that already eats their week—not as a demo, as part of how the business runs.
What we do
Find the messy workflow. Fix it. Make it stick.
We start with how you work today. Then we research it, recommend a practical fix, build a small working version, teach people to use it, and keep what works.
01
Workflow review
A focused working session and a written map of the messy process, the risks, and the places AI can actually help.
02
Practical fix design
We recommend a clear fix: who does what, which tools to use, what needs a person, and what done looks like.
03
Build sprint
We build one small working version—a shared knowledge base, internal tool, Claude or Codex workflow, or simple automation—and put it in people's hands.
04
Ongoing support
After launch we stay close: watch how people use it, fix friction, expand what works, and drop what does not.
OUR COMPANY FOCUS & TRACK RECORD
Where we invest, where we focus
Private investment
Reveal
Now part of CrossbeamBacked a company helping B2B teams grow through their partner ecosystems.
- B2B software and applied AI
- Businesses with real customers and real operators
- Long-horizon private positions
The team
Maria and Kaitlin lead. Dan backs them up.
A small family team. Maria runs the company and the client relationship. Kaitlin leads the technical work. Dan supports strategy and build behind the scenes.
Maria O'Leary
Operating Partner
Maria is a co-founder and Operating Partner at The O'Leary Good Company. She owns relationships, client intake, and follow-through. She turns conversations into clear next steps and keeps commitments moving.
Maria on LinkedIn
Kaitlin Klaum, M.S.
Principal, AI & Enterprise Solutions
Kaitlin has spent more than a decade in technical sales and solutions engineering, including leading Box's U.S. Public Sector Solutions Engineering team.
At The O'Leary Good Company she leads technical discovery and solution design: what to build, how it should work, and how people will use it. She brings experience from enterprise and public-sector environments, including regulated and FedRAMP work.
Next step
Book a discovery call.
Tell us how you work today, where it gets stuck, and what better would look like.
Book a discovery call
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