When and How to Make Your Second Hire as GC at a Tech Startup

Startup life is often compared to being on a rocket ship. In your role as GC, you’re a key player in the cockpit, deftly navigating turbulence (and the occasional incoming asteroid). But when your company enters hyperdrive mode, it’s time for a co-pilot.

But tech companies in their nascent stages often have limited resources. So, how do you go about finding a reliable navigator when the stakes are sky-high?

Here’s a primer on when and how to make your next hire from the skilled executives in The L Suite network.

Key Takeaways

• When transitioning from being the sole legal linchpin to a team of two or more, understanding the company culture and its specific needs for both the short term and longer-term growth trajectory can help you identify the type of hire you need next.
• Evaluate the tasks you need completed over the next 18-24 months, then determine whether they are a better fit for a junior lawyer, a seasoned attorney, or a legal ops support role.
• In a high-growth environment, don’t be afraid to hire someone looking to stick around for one to two years instead of a decade; people who seek a future GC role themselves are highly motivated and willing to wear many hats.
• Resources like LinkedIn Recruiter and The L Suite's job board can be valuable resources in sourcing candidates.

When to Hire Your Go-To Number Two

Many companies loosely aim to staff one lawyer for every 100 employees — but in startup land, you may want to aim closer to one lawyer per 60-70 people, says Julia Shullman, General Counsel and Chief Privacy Officer at smart TV startup Telly. In highly regulated industries, this ratio might need to be even higher.

Devang Shah, General Counsel at biotechnology company Pivot Bio, Inc, said it’s prudent to consider timing in addition to numerical benchmarks — he suggested waiting at least three to six months after you start at an organization before diving into hiring. This gives you time to figure out the ins and outs of the culture, as well as your true needs.

“Sometimes when you first get [to an organization], people come to you for things that aren’t in your wheelhouse,” he said, citing his own prior experience at e-commerce platform Wish, where employees were asking him tax and stock admin questions in his first couple of months. Ultimately, this was because other teams hadn’t yet been fleshed out. “If I had quickly reacted to [those early days at the company], I might have hired in the wrong area.”On a related note, Shullman advised GCs to critically consider the resources they need specifically in legal, versus in other areas of the company. “For data-driven companies, really think long and hard about what resources you need in legal versus in engineering and other teams,” she said. “We’re lawyers, not empire builders.”

Junior Lawyer, Senior Attorney, or Legal Ops? Determining Who to Hire

Once you’ve decided it’s officially time to hire, the next step is to land on the type of candidate to look for — a junior lawyer who may be “moldable,” a seasoned attorney who can hit the ground running, or a legal ops support role. In a recent L Suite Braintrust conversation about this topic, one member was struggling with this exact conundrum. This GC, who works at a healthtech startup, was juggling duties like:

• Procurement work
• Compliance matters
• Employment matters
• Corporate governance
• Budgeting and department planning
• High-level strategy

In this instance, the majority of L Suite members suggested pursuing the seasoned attorney route. Several recommended hiring someone with at least a few years of healthcare experience.

Valerie Chianuri, General Counsel at software startup nTop, outlined the importance of hiring someone who understands both in-house and startup dynamics. “[You need somebody] who can ‘quarterback’ for you, irrespective of the role/title/seniority level,” she said. (Chianuri recently made such a hire successfully, opting for an attorney with about five years of in-house experience.)

Patrick Lytle, General Counsel at mental health app Headspace, suggested hiring someone with a mix of experience and willingness to expand their skill set. “This person will need to jump on things they are not 100% (or even 50%) comfortable handling… look at this as a win-win for both of you. It’s a huge opportunity for them to take on a wide range of new challenges in an interesting field,” he said.

Offering a different point of view, Kent Schoen, Chief Legal Officer and Chief Compliance Officer at ClarityPay, noted that a legal ops hire might make more sense depending on the company’s immediate needs. “Whatever you do, do not hire the best and most experienced healthcare attorney you can afford if you need them to do a ton of administrative, operational, and process work,” he said. “That lawyer is unlikely to be happy in that role… But if you hire the best legal ops person you can find, or maybe even a fantastic paralegal, they will thrive.”

Shah added that even if you’re committed to hiring a full-time employee, you don’t need to be thinking ten years out. “Don’t be afraid to hire somebody who only wants to stick around for a year or two; that can actually be a great solution,” he said, noting that often, people with aspirations to become a GC themselves are highly motivated and willing to wear many hats for the sake of experience. This strategy, he said, “gives you time to plan a year or two down the road for what the team would really look like as you evolve.”

How to Find the Perfect Fit

There are a few key elements to keep in mind when evaluating potential candidates for a new legal hire, says Seth Weismann, an executive coach and former Chief Legal Officer for Marqueta, including:

• IQ = the candidate's domain expertise relative to their years of experience. The "raw horsepower" part of the equation.
• EQ = personal and social competence. A mix of self-awareness and self-management, as well as of social awareness and relationship management.
• Fit = dependent on organizational needs and company culture. Includes traits like authenticity, humility, willingness to work on a team, likeability, and resilience.

Schoen advised creating a detailed skills matrix by analyzing the specific tasks required over the next 18-24 months: “Get ultra-detailed — not just ‘contract work,’ but ‘contract negotiation,’ ‘contract drafting,’ and contract administration’ — and include weighting for how much depth you need for each skill set. Then, create a shadow staff (AGC 1, Paralegal 1, Legal Ops 1, etc.) to fill out those needs. Be sure to include outside resources as part of your team.”

In terms of logistics of the talent search, Shah recommended working with HR to utilize LinkedIn Recruiter. He added that this tool can help you branch out from your personal network, which — though valuable in many contexts — can also be limiting. “It’s important to keep in mind that your network is going to have some bias in it,” he said.

L Suite members can also post on and peruse our job board, which compiles exclusive opportunities for GCs and other legal professionals. We also offer a members-only legal team budgeting and benchmarking survey that can be incredibly useful when looking to bring a co-pilot aboard — so you can take your startup to new, stratospheric heights.

Looking to expand your legal team? Want advice from fellow GCs who’ve been there, done that? Apply for L Suite membership today.

About The L Suite

Called “the gold standard for legal peer groups” and “one of the best professional growth investments an in-house attorney can make,” The L Suite is an invitation-only community for in-house legal executives. Over 2,000 members have access to 300+ world-class events per year, a robust online platform where leaders ask and answer pressing questions and share exclusive resources, and industry- and location-based salary survey data.

For more information, visit lsuite.co.