“Ask Me Anything” with CFO Lee Kirkpatrick Twilio (2012-2018)

A veteran CFO of multiple companies, Lee Kirkpatrick, guided Twilio to and through its IPO from 2012-2018.  Now an active board member and executive advisor to both venture-backed and public companies, Lee is eager to share his insights into what makes a successful CFO and leader.  

In this month’s installment of our “Ask Me Anything” Circle|Call series, Lee joined his CFO|Circle peers for an intimate conversation about his views and practices for exercising greater empathy and how these practices form the basis for being a strong leader in a company.  Here are the Takeaways from our conversation:

Preparing for Increased Responsibility and Scrutiny as a Public Company CFO

Lee kicked off the conversation by taking a look back, describing a few key points that he wishes he had known about leading a public company as CFO when he was still coming up.  In general, Lee explained how the increased public scrutiny that accompanies a public company amplifies the stakes of the CFO’s role and the roles of the entire executive team.  To better prepare oneself for the added public pressure and the inevitability that any mistake will fall back on the CFO, Lee recommended that fellow CFOs make sure that they get their controls and processes in place across all areas of the organization.  Finally, Lee discussed the necessity for a public company CFO to have some perspective on their role. They will likely receive too much-undeserved credit when things go well and too much unnecessary blame when things do not.        

The Importance of Empathy and Connectedness

Moving on to some of his thoughts on CFO leadership, Lee recalled one of his mentors told him early on in his career at Reuters: “Lee, the soft stuff is the hard stuff.”  While he balked at such a notion at first, Lee described how as he moved further in his career and gained more responsibility, the ‘soft’ areas, or how a leader connects and deals with people, become extremely important.  In particular, Lee discussed two soft skills, empathy and connectedness, and described instances where he leaned on these skills to add value to the company through his leadership.  

At Twilio, one of the leadership principles that guided Lee’s conduct was the question, “Are you waking up every day and making your colleagues better?”  While sometimes leaders will focus on making their specific team or their boss better, Lee stressed the importance of leveraging a CFO’s particular insight on the company’s operations to make each and every one of his colleagues better rather than tear them down.  

“Thinking about how you can make people better versus being the smartest person in the room and looking clever on your own is important.”  

Regarding navigating the tough situations where executives of a company and the board are not completely aligned on strategy, Lee described the art of taking a side while remaining civil and not allowing the situation to become too partisan.  To navigate these situations, Lee kept his approach firmly grounded in data and presented this data in a civil manner, ultimately helping all parties work through their differences together.  In scenarios where a debate carried particular importance, Lee advised maintaining a data-driven approach and ultimately taking a side if the CFO believes in the importance of the company’s future.  

While Lee knows that the demands of the CFOs role and the operations of a company can be stressful and time-consuming, he emphasized the importance of connecting with the members of both his own department as well as the other departments across the company.  Though finding the time to make these connections across the employee base can be incredibly difficult, Lee maintained that building these relationships can be immensely rewarding, especially during the COVID pandemic when most people are starving for a bit of personal connection.   

While finding the time to connect with employees across the company can be difficult or uncomfortable for some, Lee described how, in pre-COVID times, he would take simple steps like sitting down for a 30-minute lunch with engineers or sales reps that he wouldn’t otherwise interact with.  Indeed, Lee affirmed that, in the long run, the time spent with these engineers or sales reps would help to build a greater foundation of his knowledge of the company, develop relationships for success going forward, and ultimately create more value, both personally and professionally.

CFO Leadership Strategies

After spending so much time in the CFO role with multiple different companies, these days, Lee spends his time as an advisor or board member for six different companies.  Indeed, Lee described how the skillset one obtains by understanding the CEO, CFO, and executive team’s role is incredibly valuable for making the transition to an advisory role.  Understanding the particular industry, context, and big picture of company will help make an executive both a better CFO in the moment and a better board member down the line, as the board typically frames issues within the big picture context rather than focusing on every detail.  

Towards the end of the call, Lee answered some questions from his peers about his perspective and recommendations on different financial operations topics.  First, Lee described his strategy for building and scaling the finance team, noting how he eventually got comfortable with the assumption that no matter what, the finance team was probably under-resourced.  In building out his team, Lee focused on hiring those positions that the company needed to have on board to complete certain deals that would bring in potential revenue.  Further, Lee strongly urged his CFO peers to focus on hiring at all team levels, not just senior positions, as failing to fill secondary roles soon enough can result in significant lost time. 

Lee also talked about the decision to pursue one final round of funding before going public, this time targeting public investors.  Noting that a capital raise with these types of investors is very similar to an IPO roadshow, Lee appreciated how going after public investors allowed him to build relationships with certain investors that he then interacted with again while going public.  

To wrap up the conversation,  Lee shared a story from his time at Reuters, where he had to direct a turnaround of a company that he had advised Reuters to acquire.  Lee described how he implemented rigorous project plans, objectives, and incentives across the organization to really drive a financial turnaround to profitability.

Curious about the details shared in this conversation? You can be a part of the next one by joining The Circle, apply here.

Next up on the Ask Me Anything series:

Sandy Smith of Segment (ACQ. TWLO)

Dan Quinlan of Expanse (ACQ. PANW)

Yvonne Hao formerly of PillPack (ACQ. AMZN)

Jeff Epstein formerly of Oracle