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

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.