‘Software, At Your Service’ CEO Interview Series: Should I Hire A Chief Of Staff?

This post was first published by Nakulmandan.com on April 27, 2016. See the original article here.

In recent years, the number of chief of staff hires at early stage tech startups has gone up noticeably. While it may still not be a common hire, most CEOs I know who’ve worked with a chief of staff are big fans of having that role, and believe it can be transformational for the company. However, I haven’t come across many nuanced discussions around when is the right time for an early stage tech CEO to hire a Chief of Staff? Or, how to think about the role? I reached out to Nick Mehta, CEO of our portfolio company, Gainsight, about his thoughts on the role. Nick has a one-year rotational chief of staff position at Gainsight, with the idea that the chief of staff will get absorbed in a functional role at the end of the stint. It’s an interesting way to look at the role, and has worked great for Gainsight over the last 3 years. Here are his thoughts on the position:

Nakul: In recent years, we’ve seen a few tech CEOs hire a Chief of Staff for themselves. When did you first start thinking about it, and what was the motivation to hire one?

Nick: I kind of “fell into” having a Chief of Staff. A few years ago, I hired a very talented ex-BCG and Bain Capital professional (Allison Pickens) in a general “operations” role working for me. Allison contributed so much (in sales development, new markets and finance) that we quickly promoted her to VP Customer Success. I didn’t realize it at the time, but when I promoted Allison, I also lost my “chief of staff” in the process. While she didn’t have the formal title, Allison showed me the value of an “all-purpose athlete” working for the CEO.

As Allison was moving into the new role, she had hired an ex-Morgan Stanley investment banking analyst (Tyler Elkington) as our financial analyst and given her new role, she had Tyler report to me. I realized Tyler could do so much more than finance so I decided to take the plunge and make him my official “Chief of Staff.”

We are now on our third (fourth if you include Allison!)

Nakul: What does a Chief of Staff exactly do?

Nick: I look at the Chief of Staff role as being all about helping the CEO execute strategically. At any given point, a CEO has a few strategic priorities on her or his plate. The challenge is making progress on these amidst the inevitable flurry of emails and meetings. A Chief of Staff is a force multiplier for the CEO’s strategic value. At any given point, my Chief of Staff could be working on:

  • Driving the company’s strategic planning and budgeting process.
  • Coordinating a key exec meeting or offsite.
  • Prepping me for critical client or prospect meetings.
  • Project managing a strategic cross-functional initiative.

Nakul: Now that you’ve had a Chief of Staff for three years, what has been the biggest benefit you’ve derived from having that position filled?

Nick: I’m a believer now, having done it four times. In fact, I had a gap between my current Chief of Staff (Tim Hoag) and my previous (Nathan St. Martin) and felt the pain of not having one! At the most fundamental level, I can drive more parallel strategic initiatives with a Chief of Staff than without.

Nakul: At what stage of the company, should a SaaS CEO think about hiring a Chief of Staff?

Nick: It probably varies from company to company, and CEO to CEO. But in hindsight, here are some signs a CEO needs a Chief of Staff:

  • Your schedule is jam packed every week.
  • You have a growing list of strategic initiatives without an owner.
  • You are in a state where strategic initiatives tend to be cross-functional (hence not every one neatly falls under one exec).
  • You’re in a market that’s strategically growing and changing rapidly.

I also asked Nick’s current and last two chiefs of staff (Tim, Nathan and Tyler) as to how they thought about the role and where it fits in to their career aspirations, and here are their thoughts:

Nakul: What was the motivation to be a CEO’s Chief of Staff?

Tim: I wanted to be the Gainsight Chief of Staff specifically for two reasons — (1) the opportunity to lead/participate in cross-functional strategic initiatives and (2) to work directly for Nick.

As Chief of Staff, I’m able to work on (and many times lead) cross-organizational projects. So far, this includes the budget, employee success, growth/margin analysis, alignment with our partners, expense initiatives, TAM, product meetings and planning our annual “Pulse” conference.

More importantly, I talked with many of Nick and my mutual connections. The feedback on him was similar across the board — super sharp, hard worker, handles himself well around investors, empowering, motivating, full grasp on everything going on in his organization, etc. So far he has been great to work for, a fantastic role model and always has a great perspective.

Tyler: When the opportunity for the role came by my desk, I thought it was a unique opportunity to learn from a well-regarded CEO of a fast growing SaaS company. It would also allow me to quickly diversify the Finance-heavy skill set that I developed from doing Investment Banking, and start developing some operational experience.

Nakul: Where do you think you provided the maximum leverage to Nick on his time?

Tim: The initiatives I mentioned above are all things Nick would have to do otherwise. Nick still wants to know everything that is going on, so I will usually email him outlines, clarifications, etc. so I don’t spin my wheels. But he usually lets me run with executing the analysis (90% of the project time).

In addition, I perform various “program management” tasks, including prepping Nick for client meetings, coordinate certain executive/product meetings, and one-off items Nick wants accomplished.

Nathan: The major project I did as Chief of Staff was working on our Series D financing. During this time, I was able to manage the aspects of the fundraising process that were not critical for Nick to be involved in. Since the diligence for later-stage rounds involves more quantitative analysis and metrics, I was able to handle these requests while Nick focused on telling the Gainsight story and meeting with investors. I was able to work with junior members of the investment teams that were looking into Gainsight in addition to managing the data room. All of this freed Nick up to meet with multiple investors and still work with the sales team and customers to exceed our targets for the quarter.

In addition to the fundraise, I was able to positively impact such things as weekly GM meetings and Nick’s trips outside of the Bay Area. For the weekly GM meetings and quarterly offsites, I worked on the agenda was able to build presentations and reports that helped Nick make decisions without having to search for the data. When Nick had trips scheduled, I worked with the AEs and CSMs that had customers/prospects in the area, so that Nick was able to meet with as many companies as possible and have the biggest impact with his time. The first project I ever did with Nick, I was able to set 20 meetings up with other executives at a conference; many of the companies were not opportunities at the time but since then, a number have become customers.

Nakul: In what areas has the position helped you grow professionally?

Nathan: The position allowed me to see every aspect of the business and howa CEO runs his company. Not many people get to experience the full fundraising experience like I did so early in their careers. The position also allowed me to gain confidence in what I have to say and made it so that I now will share my opinion with anyone and even challenge more senior people on their ideas. Being Chief of Staff allowed me to see so much more of Gainsight than just Finance or Strategy; I have now worked closely with every team and spent multiple months with Sales, Customer Success, and Marketing. Following my term as Nick’s Chief of Staff, I helped Nick find my replacement and moved into a Marketing role where I report directly to our amazing VP of Marketing.

In general though, building a good relationship with your CEO is great, so being able to spend 6 months with him and work with him on a daily basis was enough of a benefit for me to say it was worth it. Just seeing Nick work helped me learn so many things about being a good leader.

Tyler: The role gave me incredible insights into the different functions — sales, marketing, customer success — of a fast-growing tech company and how they all work together. It also has grounded into me to always keep the bigger picture in mind, to always think cross-functionally … It’s easy to get too focused on only the department in which you work. I’d highly recommend the role to anyone who is looking to work for the best and learn a ton about growing a business.

We’d love to hear from other tech CEOs who’ve had chiefs of staff about their thoughts on the role, and their advice to other CEOs who may be thinking of hiring a chief of staff.

Nick Mehta
Nick Mehta

As a huge sports fan, Nick thinks of his job as being like that of a head coach. His role is to help bring the right people together on the team and put them in the best position to win for our customers, partners, employees and their families. He’s a big believer in the Golden Rule and we try to apply it as much as we can to bring more compassion to our interactions with others. And he talks way too fast and overuses the word awesome like it’s going out of style. Before coming to Gainsight, Nick was the CEO of awesome leading Software-as-a-Service E-Discovery provider LiveOffice through its acquisition by Symantec and prior to that was a Vice President at VERITAS Software and Symantec Corporation.

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