Andrew Thompson on What Legal AI Can Learn From Software Engineering

Guest: Andrew Thompson

Role: CTO, Orbital

LinkedIn: https://www.linkedin.com/in/andrewmatthewthompson/

Website: www.orbital.tech (company) | www.andrewthompson.co (personal blog)

Most legal AI companies talk about accuracy. Almost none of them are willing to insure it.

Orbital decided to do both.

I spoke with Andrew Thompson, CTO of Orbital, the AI built for real estate legal that just raised a $60M Series B in January.

Andrew built the Caffè Nero app, ran product and tech at Appear Here, founded his own AI company, and now leads engineering, product and a team of in-house real estate lawyers at Orbital — which powered over 200,000 property transactions across the UK and US last year and now works with firms including Clifford Chance, Seyfarth Shaw, Vinson & Elkins and Mishcon de Reya.

We discussed:

→ Why accuracy, regulation and insurance are the three legs of any legal AI product — and why almost everyone in the market only talks about the first one.

→ The bet Andrew made in late 2022: walking away from years of classical ML work and going all-in on LLMs before it was obvious that was the right call.

→ Why portfolio diligence is the use case where AI changes the economics of real estate legal, not just the workflow.

→ Where frontier models still fall flat in real estate, and why it’s the visual layer (maps, surveys, plans) rather than the text.

→ Why legal is roughly 12-18 months behind software engineering, and how he thinks lawyers should be using that lag rather than denying it.

→ What “ship early and often” actually means inside a regulated industry, and how Orbital uses AI reliance insurance to make it work.

I hope you enjoy listening just as much as I did recording it.

Want to feature in the Best Practice podcast? Email george@georgehannah.com

Sources mentioned in the episode:

• Orbital’s $60M Series B (Jan 2026, led by Brighton Park Capital): https://tech.orbitalwitness.com/posts/2026-01-23-series-b-announcement/

• Caffè Nero (Andrew’s previous build): https://caffenero.com

• Appear Here (Andrew’s previous build): https://www.appearhere.co.uk

• Seedcamp (where Andrew was a startup mentor): https://seedcamp.com

• ElevenLabs (referenced re: agentic insurance): https://elevenlabs.io

• Legalweek New York 2026 (referenced throughout)

• McKinsey research on automatable legal work (referenced)

• OpenAI ChatGPT and GPT-4 (referenced as the inflection point)

• Anthropic Claude (referenced)

• Google BERT and T5 (Orbital’s pre-LLM stack)