With it being Valentine's Day, it may feel like everyone is looking for that perfect relationship. And that includes in-house counsel. Sometimes it seems like the search for the in-house gig of their dreams will never end. Both in love and in the legal job search, chemistry can be a tricky matter.

In celebration of relationships in the law department world, Corporate Counsel talked to three top-notch legal recruiter/matchmakers: Nicole Lipman, a partner in the In-House Counsel Practice Group at legal executive search firm Major, Lindsey & Africa in San Francisco and Palo Alto; Lee Udelsman, who is managing partner of MLA's New York office and a leader in the firm's In-House Practice Group; and John Gilmore, managing partner and co-founder at BarkerGilmore, based in Fairport, New York. The conversations have been edited for clarity and length.

Nicole Lipman

Corporate Counsel: What is the No. 1 quality tech companies want in a GC?

Nicole Lipman: They want their GCs to be business partners and to be commercial. The days of a lawyer saying, “No, no, you can't do that.” are over. They want someone to figure out how to solve the business problem while appropriately protecting the company. And the best lawyers understand that. That can often be a hard transition coming from a law firm, but I think that is the No. 1 thing that all of our clients are asking for. They're also asking for “roll up your sleeves” lawyers. A lot of smaller companies need someone who can be a player-coach—you can't manage big teams and not get in the weeds on stuff.

How has the rise of small but quickly growing startups changed the GC search in tech?

You have to really make sure there is an alignment [between] the CEO's vision and appetite for risk and where the GC is comfortable operating. I think for a long-term fit that is really critical. We've seen some mismatches with that, and you really have to get that right for it to be a successful relationship.

And again, there's a lot of uncertainty in startups. It takes a certain type of person that's comfortable with that, with business models changing, with funding and financing. You need someone who's been there before and is comfortable guiding the company through that risk. There's a good reason people keep taking leaps of faith to go work at startups.

What should a young lawyer who wants to be a GC in tech someday start doing now to prep for the future?

Really broaden your skill set to try to check as many boxes as you can. You want to get some management [experience] under your belt. And I think training in one of Silicon Valley's top law firms is always a great building block. Building your network is really important. I've seen lots of GCs with deep networks have very successful career paths due to their investment in the relationships they're building along the way. And also knowing venture capitalists is super helpful, because they make a lot of introductions to the portfolio companies. Get to know them. It can really help.

Think about what business excites you the most and move toward it. If you're interested in regulatory, there's not enough lawyers to go around. So that's where I'd advise someone to focus their energy. And health care. We still don't see as many in-house opportunities in litigation, so I would advise maybe moving away from that and toward transactional work.

A lot of tech companies are entering markets where certain regulatory frameworks have not yet been made clear. How does that impact their search for a GC?

I think being creative and being flexible and helping solve interesting business problems through the law and at the frontier of the law, I think that's interesting for the lawyers in that they can add a huge amount of value. … That's super exciting for a lawyer to be able to do that. That's a huge contribution they can make.

—Carolline Spiezio

John Gilmore

Corporate Counsel: What have been the biggest changes you've seen in the GC search?

John Gilmore: I think the biggest change is that four or five years ago everyone was looking for, or I should say, [putting] a priority on what was on the resume, meaning what specific regulators [job candidates] worked with or what specific types of matters they were experts in. And it's really gotten away from that a bit where it's now focused on the person's leadership abilities, meaning, how are they able to build the team, develop the others around them and earn the trust of everyone in the company? Also, the next component [is] business savvy. What is their financial acumen? Have they acted as a strategic business partner? Do they have exceptional judgment?

How can you start building business acumen early in your career?

I would say absolutely to start it's really [about] getting a good appreciation for how your company makes money, developing that financial acumen by … sitting with your CFO or your treasurer to really understand the inner workings of the business. That's absolutely critical.

The other component as far as that goes is having some direct exposure to higher-level people in the organization. Meaning, maybe it's a high-level business person where you really get a sense for what they need. What is it that they need to accomplish and how do they need to get there?

GC candidates with a combined MBA and JD must be really appealing.

What's more appealing is when they come in for an interview and they can really talk the talk, so when you speak to somebody that really has an appreciation for the business and its finances, it stands out, it separates them from the pack.

It's funny, after every search, I have to go back to the people who didn't get the job and tell them that they're not getting the job, and the first thing they always say to me is: What could I have done [differently]? And the reality is it's kind of like a dating game, how you came in and how you were received by that team … how you were able make the people on the other side of the table become confident that—one, you are qualified and capable, but two, you're someone they can really trust and would really want to work with on a day-to-day basis.

It's really not something that you can change a lot. I say it's kind of like “The Dating Game.” You can tell me you want 5 foot whatever and a tennis pro and a certain color hair, and I can bring you all that, but there's only going to be one person who has that special chemistry.

I'm sure there are some elements of that chemistry between company and GC that are tough to explain.

I track every person that I see that gets a new position, a new GC, and I study that and just get a sense for: Would I have presented this candidate? This was a finalist that was selected, and was this someone who I would have presented? And just looking at the resume, you might scratch your head and say: “I'm not sure why this person got this job. It doesn't look like they're the best possible person for the job.” But the reality is that person went into the interview and really got the attention of that executive team.

—Rebekah Mintzer

Lee Udelsman

Corporate Counsel: Do you think maybe, because there's more legal work staying in-house, that's driving the need for a business-oriented GC?

Lee Udelsman: The expectation is that the general counsel is going to be almost like a business partner, is going to be instrumental, not just in the execution of the legal strategy but also in the formulation of the business strategy.

So, correspondingly, the expectation is that the GC will manage her or his budget almost like a P&L, if you will. And part of that now is, what we've seen is a number of law departments are hiring legal operations managers to administer the budget. So therefore, the general counsel can really concentrate on what I call sort of the higher-value targets, formulating and executing the strategy along with the other people on the leadership team to drive the company's initiatives.

What other trends are going on out there in the world of legal departments?

What I've been able to identify [is a demand to fill] roles relating to privacy, marketing—including digital marketing—which makes a lot of sense, given the world in which we live, roles relating to import and export controls, again, which makes a lot of sense in the dangerous world in which we live, compliance and also cybersecurity. At some point this year, it seemed like every other week, another company was announcing a data breach. So not surprising is that there's an increase in hiring relating to cybersecurity-type roles.

Are those areas a focus mostly for lower level in-house lawyers, or are companies looking for GCs with expertise in the areas you mentioned?

Yeah, I mean frankly, these are areas of what are called functional subject matter expertise. So, it's not necessary that the GC be a subject matter expert relating to this but have some knowledge. And typically these would be people on the GC staff in a larger company who would have these responsibilities.

Do you see more companies hiring a general counsel and building a legal department who would not have otherwise had one?

Some of it varies by industry and how heavily regulated the company is within that particular industry but what happens is a company typically reaches a level of critical mass, and part of that … goes back to spend. And so somebody within the company, perhaps the CFO, is looking at what legal fees are as a result of external spend and then makes a determination that coupled with the fact that, you know, we're at a critical juncture in our business evolution or contemplating the filing of initial public offering. We've got a very significant piece of litigation in which we are a party. We've got a number of patents, if you will, that are about to be filed or they are about to expire that are mission critical. These are very significant events in the life cycle of a company, that typically compel the conclusion: You know what? We need to hire a general counsel.

—Rebekah Mintzer