The Life of a Technical Solutions Attorney with Sam Nickerson

Cockpit Counsel

The Life of a Technical Solutions Attorney with Sam Nickerson



There’s no shortage of ways to apply your JD, and more attorneys are going down alternative career paths. On this episode of Cockpit Counsel, Sam Nickerson joins Tim Parilla to talk about how she did just that by joining the team at LinkSquares as a Technical Solutions Attorney (TSA).


  • 00:00 Introduction
  • 00:57 What is your preflight ritual?
  • 01:32 Tell us a bit about your career path.
  • 04:52 How did you end up at LinkSquares?
  • 05:37 Talk a little bit about your day in and day out.
  • 07:05 How do you prepare for demos? Do you already have background knowledge on the company?
  • 13:03 Do most in-house legal teams utilize some type of legal technology?
  • 14:13 What is the number one reason people will leave their former legal tech tools/softwares?
  • 15:42 Within the TSA team, what do you think is the next development in how the team functions?
  • 17:58 How does the TSA team go about selecting which tools are appropriate for the customer?
  • 19:20 Do you have a regular feedback loop with the product team at LinkSquares? 
  • 21:54 How did you begin to build relationships with the account executives?
  • 25:42 What is a piece of advice for somebody considering a different career path with their legal background but isn’t sure where to start?
  • 29:15 What is your favorite LinkSquares feature to demo?
  • 31:16 What’s it like working at a legal tech company with a legal background, but not on the legal team


Tim Parilla Headshot
Tim ParillaChief Legal Officer, LinkSquares
Samantha Nickerson headshot
Samantha NickersonTechnical Solutions Attorney, LinkSquaresd

The sky’s the limit. Hey, why not get a demo?