Learnings from My Discussion with Jennifer Tejada, CEO of PagerDuty

On May 9th, I got the chance to animate a fireside chat with an incredible speaker, Jennifer Tejada, as part of another sold-out CEO Series event of the HBSANC and Harvard Club of San Francisco. Time flew by during a fantastic evening, packed with business learnings and life lessons. In addition to being the CEO of one of the most successful private B2B SaaS companies in the Silicon Valley, Jennifer is also one of its most visible female business leaders, and a vocal advocate for diversity and inclusion in the workplace, and gender equality. Jennifer is charismatic, fun and an original thought leader. I personally very much enjoyed conversing and hearing firsthand the advice from a great CEO, who happens to also be a very humble person. In this post, I am sharing just a few learnings from the 90mn discussion with Jennifer, illustrated by her actual answers. I hope that you will be encouraged to attend the next CEO Series event.

Jennifer’s unusual path

Jennifer’s background is very interesting. She very humbly states that she took “three left turns and ended up in technology somehow”. It is true that it is uncommon for a female liberal arts major who started her career in consumer goods to end up becoming the CEO of one of the most successful enterprise software companies currently. Because of that, observers have called Jennifer a “purple squirrel”. But as this segment shows, she had a strong interest in tech early on and she actually turned what’s different about her into areas of strengths, that she leveraged to build an impressive career and track record in the technology sector.

The state of leadership in the Silicon Valley

This topic was introduced by way of an observation regarding Jennifer’s first employer, Procter and Gamble. P&G is known, just like IBM or General Electric, for its strong leadership program which has produced generations of successful business leaders. The observation is that much of leadership in Silicon Valley is learned on the job and there isn’t as much foundational leadership training sponsored by leading companies here. Jennifer points out that gap and calls out some aspects of the business culture in the Valley, specifically the tendency to stay in jobs for a relatively short period of time, which makes it difficult for companies to justify an investment in leadership training as it is long-term oriented by nature. What’s impressive is what she decided to do about it.

PagerDuty

PagerDuty has become one of the most successful enterprise SaaS companies, growing in excess of 50% a year on average since inception. It is still a private company, so relatively unknown from the general public, but this is a good opportunity to learn about what is going to be a mainstream company, straight from the CEO. This segment covers a broad range of topics, from what the company does, to its drivers and a number of ways in which the company distinguishes itself. Most notably, PagerDuty has achieved a 50:50 male:female ratio in its executive team as well as its engineering leadership team, and even managed to achieve gender pay equity last year, which the company will maintain.

Challenges ahead

The company is late-stage but its CEO believes that PagerDuty is just getting started. PagerDuty’s mission has evolved to “elevate work to the outcomes that matter”, which is ambitious and oriented around helping people work better. Along the way, it will have to face both competitive challenges, which are addressed here, as well as the challenges of execution given the scale and increasing complexity. While other tech leaders may focus on a narrow strategic path or exit, this CEO contemplates the long-term future and building an enduring company.

Building a great culture

PagerDuty has received numerous awards and been recognized as a great place to work for by various industry publications. While it is clear that the company’s strong, inclusive culture has been built over time, the question we wanted Jennifer to address specifically is what she has done to maintain what works while continuing to evolve and change the culture. One particular take-away in this segment that I always find useful: don’t take yourself too seriously.

Fighting for diversity and equality

Jennifer is one of the most visible female leaders in the Silicon Valley. This segment addresses the very important question of how to change established cultural norms in the Silicon Valley to achieve greater diversity and inclusion in the workplace and gender equality, including equal pay, all causes that Jennifer is an outspoken advocate for. What PagerDuty has achieved shows that it is possible to build a balanced team. Note that this is the first time that we addressed these very important topics in such a comprehensive way as part of the CEO series, no doubt because Jennifer is one of our first female CEO guests. We will definitely have many more going forward.

Last but not least, the rapid fire questions section

This is always the most fun part of the evening. A series of questions to be answered in 60 seconds or less. We made an exception for one particular question based on the heartfelt, very personal answer that it brought. A fun moment to end this write-up.

If you liked this article, with its video excerpts, you will like even more being there in person the next time as you can meet the speaker and ask questions directly, as well as network with an interesting group of graduates from both Harvard and Harvard Business School while sipping a glass or wine or a cocktail. I certainly hope to see you at our next event.

Thanks for reading

JP Marcos
Twitter: @SignifAICEO

Originally published at blog.signifai.io on June 6, 2018.