Chat with Tilak Koilvaram, Lead Product Counsel @ Plaid

“Product counsel[ing] isn’t rocket science.” But “be a nerd about the business.”

Tilak’s path (snapshot)

• Law firm: Davis Polk (IP & Tech Transactions) for approx. 6 years.

• Pivot moment: Over 1-2 years, realized that the work he was doing at the law firm was not the work he wanted to do long‑term. Instead, Tilak wanted to be closer to building products and building the business.

“I probably could have left Big Law a couple of years earlier, but I stayed until I was close to burnout—not because I had a perfect plan.”

• First step in‑house: actually joined Plaid as Commercial Counsel.

• Evolution: Work shifted from commercial > hybrid commercial/product → majority product → Lead Product Counsel.

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TL;DR

1. Start career planning earlier than year 3–4*.* Use quiet weeks to zoom out.

2. Aim for a company where the legal team is small enough to let you try multiple hats.

3. Show real interest by matching your career goals to the company’s shape (product, team size, customer mix).

4. First 90 days = learn to communicate risk to non‑lawyers and adapt to tech‑forward workflows.

5. Be a product nerd: understand the APIs, flows, and user problems almost as well as the PMs/engineers.

6. Build your bench: peers, mentors, and communities so you’re never solving in isolation.

Tip 1: Plan earlier (as early as law school!)

1. Treat 2L–3L as exploration years: courses, clinics, talks across the university.

2. Don’t default to the on‑rails path. Ask: Which industries genuinely energize me? What work do I want in my day‑to‑day?

3. If you already suspect in‑house is your destination, back‑plan: skills, exposure, and networks to build now.

“Use downtime between deals to step back. That’s when the thoughtful planning happens.”

Tip 2: Find the right company fit

• What Tilak looked for:

  • Small/medium legal team → broader scope and experiments.

  • Infrastructure product (Plaid) → exposure to many sub‑sectors (payments, credit, budgeting, crypto, AI).

  • Day‑to‑day variety → fewer silos, more learning surface area.

• How he vetted Plaid as a fit:

  • Talked to alumni who'd gone in‑house at the company to understand culture. (Tip: ask about the Legal’s relationship with other departments like Product, Engineering, Marketing, Sales)

  • Searched for litigation and risks to sanity‑check ethical alignment.

  • “Vibe check” across 10–12 people across the company, including adjacent teams.

Tip 3: Show your passion (with limited domain history)

• Translate your goals to their world: Tilak explained that he didn’t come in with deep fintech or product experience, but he convinced Plaid by showing genuine alignment between his goals and what Plaid offered. He explained why his skills fit this size team, this product, this customer mix.

  • He was not interested in working at a massive bank or a giant legal team where he’d be siloed. Instead, he would thrive in a small/medium team where he could try different kinds of work.

  • He highlighted Plaid’s appeal as infrastructure: its product touched many areas (payments, credit, AI, budgeting), which meant day-to-day variety for a lawyer.

    
    

• Show you’ve done the homework: learn the ecosystem vocabulary (APIs, data flows, customers). Do your research to understand the issues critical to the business (i.e., for Plaid, he researched open banking and Plaid’s role as an intermediary bank data platform in the larger fintech industry).

  
  

• Show your interest (even passion): . talk about the times you climbed steep curves fast (new industries, new contracts, new regs).

“Once you know what you want—scope, team size, problem space—your enthusiasm reads as genuine in interviews. The details became fascinating once I saw what the product enabled.”

Tip 4: First 90 days — the transition in-house

• Audience shift: your “clients” are PMs, engineers, sellers—not lawyers. Build the muscle for crisp, business‑aware advice.

  
  

• Medium shift: using Slack, GDocs, tickets, PRDs; not Microsoft Word, version control databases.

  
  

• Pace + ambiguity: complex deals + fast timelines + divergent incentives. Your value becomes clarity under constraint; not perfect advice.

Skills to lean on:

• Critical thinking and detail orientation from big law.

• Structured issue spotting framed in product terms (privacy, payments, IP, contracts, AI).

“I didn’t know what an API was in law school. [But] product counseling isn’t rocket science—it’s issue spotting with context.”

Tip 5: From Commercial Counsel to Product Counsel

• Start in your strongest lane (e.g., commercial). Raise your hand for special projects with product teams.

• Deliver, debrief, and ask for the next product‑adjacent problem.

• Over time, your mix can evolve: commercial → hybrid → product.

  
  

Why product work can be addictive:

• You are embedded with PM/Eng/Design/Marketing.

• You are closer to business strategy and the actual product being built.

• You have constant variety; you’ll be a jack‑of‑many‑doctrines.

“I’m probably more of a product nerd than a legal nerd now—and that’s been a superpower.”

Tip 6: Don’t go it alone

• Inside: find thoughtful cross‑functional partners; cultivate healthy friction.

• Outside: peers at other companies, listservs, Slack groups, conferences.

“You don’t have to solve hard problems alone. Build your bench.”

Final Playbook

If you’re in big law and eyeing in‑house, here’s a rough guide:

1. Calendar a ‘zoom‑out’ during quiet weeks; write out your goal (target industries, role shape, skills to acquire).

   • Target industries that genuinely energize you (e.g., fintech, health tech, sports, etc.)

   • Role shape you want (e.g., small legal team, product vs. commercial focus, regulatory specialty, etc.)

   • Skills to acquire while still at the firm (e.g., privacy, payments, contracting, issue-spotting with non-lawyers)

   • Networking/alumni leads you want to reach out to

   • Indicators of readiness (e.g., “once I’ve seen X number of deals,” “once I’ve handled Y kind of contract,” “before burnout hits”)

2. Skill map your current deals to in‑house needs (privacy, payments, IP, AI, contracts, product counseling).

3. Shortlist 5 companies whose legal team size and product surface match your goals. Find alumni to decode reality.

4. Ecosystem primer: learn the vocabulary (e.g., open banking, APIs, data flows). Skim docs; diagram a feature.

5. Interview narrative: goals → company fit → ramp plan → examples of fast learning.

6. First‑90 plan: who to meet, what to read, how you’ll deliver fast wins (docs, templates, redlines, risk frameworks).

7. Community: join one peer group; set a monthly coffee with another in‑house counsel.

Thanks, Tilak, for the candor and the lessons!

If you’re a product or in‑house counsel with a perspective to share, reach out—I’d love to feature you. Reach out @ amyaixizhang@gmail.com.