Office Life: Making the Switch to a Legal Technology Company

I have never worked at a law firm. The closest I ever came was Winston & Strawn’s ‘Bring Your Daughter to Work’ Day, in which I helped faux-prosecute the case of Humpty Dumpty. (The exhibits really made our case.) However, I have worked at many large corporations, often collaborating closely with corporate counsel. As a result, I am familiar with the work environment that many lawyers experience day-to-day. If you are considering alternative legal careers - like the ones in legal technology that I recently described - you might wonder how that environment differs from what you’re familiar with. Here is what I experienced:

  • Your wardrobe may change: When I worked in the corporate world, my closet was a kaleidoscope of grey, black, and navy skirts, dress shirts, and sweaters. At a legal technology company, I can still wear all of those things, but I don’t have to; I can show up in jeans or a hoodie, and no one would care. In this photo from a recent team meeting, you can see everything from dress shirts to t-shirts. In other words, your dress code is generally your business (within reason, of course). The goal is to get the work done, not to itch to death in pantyhose.
  • Your level of input may change: At large corporations, my feedback was only requested in twice-yearly 360-degree team reviews. Moreover, it was focused on specific, day-to-day items considered to be in my purview. For instance, no one much cared to hear my thoughts about our office space, company name, medical plans, or strategic approach. At a smaller legal company, I have weighed in on all of those topics. Not only does that increase the chances of benefits and logistics that fit my needs, but it also opens up opportunities for cross-company collaboration. I can suggest an update to a developer, and she can give me an idea for a legal marketing program, enriching both company outcomes and my understanding of other fields.
  • Your water cooler talk may change: In large corporations, I often found myself discussing home remodels, children, and recent TV shows. All of these topics might still come up at my legal technology company, but so might more obscure ones. From discussions of ultimate frisbee or chess to homebrewing or Nabokov novels, the conversation at the office seems to be broader. We’ve even had office-wide Lunch and Learns, in which team members talk about something in which they have expertise, from world religions to whiskey tastings. As a result, I feel more connected to my co-workers - and to interests I didn’t even know existed!
  • Your reporting structure may change: At large companies, I always had a manager and another manager above her. The hierarchy was incredibly clear, and the career path was pretty much prescribed in advance of my arrival. At my legal technology company, I report to the CEO; not only is that true for me, but it is also true for team members with less than a year of work experience. Not all legal tech companies are small enough for this structure, but most make senior leadership accessible and career arcs flexible.

These are just some of the changes I discovered when moving from a large corporation to a smaller legal technology firm. Keep in mind that each company will have its own novel quirks and characteristics, and there are advantages and drawbacks to either type of work setting.  The key is to find the environment and culture that fits you - although knowing whether a hoodie is a good idea for your first day can’t hurt!


tanya f

This is great advice.  One of my friends is considering a change in this direction- now I have something to share with her


Very glad it was helpful, Tanya! If your friend wants to talk, she can always email me (ana @ everlaw).

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