David Sclar, Principal Product Counsel at Babylist and Author: Captains of Industry Interview

David Sclar is a seasoned in-house counsel and Harvard Law School graduate who has spent a decade in-house as a Chief Privacy Officer and as the first or second full-time lawyer at startups, including his current role leading privacy at Babylist.

David spent his first seven years after law school clerking and working in BigLaw at Ropes & Gray and Cooley. He left to be a founding lawyer at Rally Health, a consumer health care startup that grew to $1B in annual revenue and was acquired by UnitedHealthcare.

David has also been in-house counsel at three large public international companies.

He is the author of the Amazon bestseller Workplace Strategies for Technology Lawyers, a book of essential skills for all in-house lawyers.  And he is an expert advisor on the platform Hubble.

Career Path & Transitions

Q: You’ve built a career at the intersection of technology, privacy, and healthcare. Tell me about that path and where you’re going?

A: I generally work in senior in-house counsel roles. But I like having a north star – at the intersection of technology, privacy, and healthcare, as you put it. So, I have worked for multiple companies that apply technology to consumer healthcare.

I handle the many demands of modern in-house lawyers – negotiating contracts, managing AI, informing leadership and the Board, and so on – and I leverage privacy and healthcare regulatory expertise to work at companies where technology meets healthcare through apps, telemedicine, and insurance benefits.

Working Effectively with Business Colleagues

Q: You wrote a short, practical book that I think many would benefit from reading, and I think you have valuable advice for anyone collaborating and communicating with business colleagues. Tell us about this book and your workplace strategies.

A: My book provides a set of practical tips that build on each other and collectively make you a force for getting things done, working with other teams.

It’s deliberately short. It will take an hour to read and keep at your desk. It’s called Workplace Strategies for Technology Lawyers.

As in-house lawyers, our performance day-to-day is determined by solving problems for or with other people.

You can issue spot all you want, but what really matters is what did you resolve? What got finished? What produced results?

Some might feel that’s unfair or beyond lawyers’ control. Maybe they didn’t go to law school to argue with a 25-year-old engineer who is a bit too arrogant while he pressures you to sign a SaaS contract with a vendor that claims they won’t accept redlines to their wildly unfavorable template.  And, oh yeah, he has already been storing our data in their software for the past six months after signing up for a free trial he never told you about.  Maybe he sarcastically calls you “Esquire.”

I strongly believe: 1) it’s fair and where you make your mark 2) the skills to solve this are teachable and 3) it’s not easy, but it’s really fun.

So, I wrote a book of tools for navigating the challenge of being a lawyer working with marketing, product, and engineering professionals while giving excellent legal advice.

I also do expert advising in 15-minute sprints with a company called Hubble. I advise current and aspiring in-house lawyers, as well as startup founders, law students, and law firm associates on privacy, regulatory, and business legal topics, as well as these kinds of “soft skills” for collaboration and communication.

Q: What’s one trick you use to communicate effectively with business colleagues?

A:I start nearly all my communications with “I recommend”. That’s what everybody wants to know. They’re asking, “What does legal want or need me to do?” So, I give them the bottom line upfront.

As a practical tip, the trick is to catch myself and revise my first draft before it goes out. My first draft of an email or a Slack message doesn’t always start with a simple, clear recommendation. Old law school IRAC habits die hard. (IRAC is “Issue, Rule, Application, Conclusion” if you have forgotten or repressed law school memories).

Others can do the same thing to stop and revise their first drafts to put their recommendations up top.

I want to elaborate on the benefits of recommendation–driven communication. Providing recommendations leads to closure, which is a theme in my book. With so many competing demands, in-house lawyers need to create their own closure wherever possible. So they can move on to the next thing.

Q: Looking back, what do you wish you had done differently—or earlier—to be successful as a lawyer or privacy lawyer?

A: I wish I could go back and be a BigLaw associate with the benefit of what I know now from being in-house. I would have been more engaged and proactive with my clients. I did a fine job of handling their legal questions, but I now realize I could have offered so much more.

Better understanding all of the context for their legal questions – including the nuances of their business and products, the client’s role and seniority, the personalities involved, and their underlying goals and pressures – would have made me irreplaceable as their outside lawyer, helped me build a book of business, and made me more marketable to go in-house.

When law firm lawyers often reach out to me on LinkedIn and on Hubble, my goal is to help them do more with their role than I knew how to do at the time.

Influencing Without Authority / Stakeholder Buy-In

Q: What would you share with someone trying to build credibility with business colleagues?

A: Good judgment builds credibility, and it’s the core skill of good lawyers.

Let’s take a situation you and I chatted about. You’re in the office at 11 pm and you see there’s a huge puddle of spilled milk by the coffee machine. Is it your job to mop it up and put up a “wet floor” sign? Of course it is. It’s not law, but you’re there to help the business and problem-solve.

But let’s take this a step further - and this is where additional judgment comes in. Suppose a colleague says, “We should shut down the entire floor. There could be mold. We could all get sick.”

Your job is to read the data: How old does the spill look?  Is it spilling into air ducts? Does the empty milk bottle on the floor next to the puddle have an expiration date from today or from six months ago? Then you: 1) make the judgment call about what’s necessary; and 2) come up with a reasonable solution that’s likely more appropriate and business-friendly than closing down the whole floor – whether just putting up a wet floor sign, contacting the facilities team to do a more thorough cleaning, or maybe closing off just that coffee station (and making sure there’s a backup coffee solution!).

That judgment earns you credibility and trust that you can solve others’ problems.

Q: Your book focuses on communication and influence. What’s one communication technique that helps lawyers connect more effectively with their business clients?

A: Here’s something I’m trying to do as an established in-house counsel when new business colleagues join the company. I get to know where they worked before, what they worked on, and how they worked with legal. It gives me a lot of context for how to work with them now. I know their expectations and points of reference.

It’s a two-for-one special because I also get to know them personally and build a relationship. Maybe they previously worked at a food delivery startup, and I’m a customer. I talk about my experience with my order.

But getting back to law, I also make it my mission to deliver for them in ways that the lawyers at their previous company didn’t. If they tell me what their previous lawyers did well and what they didn’t, I learn from that and respond.

Closing Question

Q: Any other closing thoughts you’d like to share?

A: I want to highlight one substantive privacy topic: Laws governing 1) sensitive personal information (SPI), as defined by state privacy laws like the CCPA/CPRA in California, and 2) consumer health data, as regulated by states like Washington, Nevada, Connecticut, and New York. There is a lot of work required to comply with these laws, and they reach so many companies, including companies handling health data outside of HIPAA.

Anyone with questions should reach out, and I’d love to discuss what companies or clients need to do around SPI or consumer health data.

Book:

Author of the Amazon bestseller Workplace Strategies for Technology Lawyers, a concise, practical guide for in-house lawyers focused on communication, judgment, and execution.

Link to book

Hubble:
Expert advisor on Hubble, offering 15-minute sessions on privacy, regulatory strategy, and effective collaboration for in-house lawyers and founders.
Link to Hubble