20VC PagerDuty CEO Jennifer Tejada on A Leader’s Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

In this episode of "20 Minutes VC," host Harry Stebbings interviews Jennifer Tejada, CEO of PagerDuty, discussing her journey in tech and leadership. Tejada shares insights from her career, starting at Procter & Gamble and moving through various executive roles leading to her current position. She emphasizes the importance of learning, personal growth, and clear career objectives. Tejada also delves into the challenges of decision-making with limited information, fostering a culture of healthy debate, and the significance of board composition and management. Additionally, she addresses the need for diversity in tech, treating it as a business imperative rather than a checkbox exercise. Throughout the conversation, Tejada underscores the value of mentorship, transparency, and the balance between risk-taking and self-doubt.

• Harry Stebbings introduces the podcast "20 minutes VC" and his excitement for enterprise.
• Jennifer Tejada, CEO of PagerDuty, is introduced as a guest, highlighting her achievements and the company's success, including its IPO and venture capital backing.
• Harry promotes several products and services including Carter, Brex, and Zoom prior to the interview.

This is the 20 minutes VC with me, Harry Stebbings, and I'm diving straight into the show today because all who know me know I love enterprise. And today I'm joined by one of the leading enterprise CEOs of our generation, Jennifer Tejada, CEO at PagerDuty.

Harry Stebbings expresses his enthusiasm for enterprise technology and introduces Jennifer Tejada as a prominent CEO in the field.

• Jennifer Tejada discusses her career journey, starting at Procter & Gamble and transitioning into technology.
• She emphasizes the importance of luck, hard work, and a clear vision in her career progression.
• Tejada's move to I2 Technologies was driven by her interest in disruptive technology and quantifiable value propositions.
• Her tenure at Keynote Systems and Mincom, leading to acquisitions, showcased her ability to build and grow companies.
• Tejada's strategic approach to networking and identifying growth opportunities led her to PagerDuty.

Some of it was luck, and some of it was hard work, and some of it was having the right network and being really clear about what I wanted.

Jennifer Tejada explains that her career success was a combination of luck, hard work, and a strong network, along with clear personal goals.

• Tejada sought a return to a growth-focused role, leading her to meet with prominent investors and analyze market opportunities.
• Despite considering a move towards consumer or B2B2C sectors, she was attracted to PagerDuty's platform and its impact on developers and enterprise customer experiences.
• She highlights the importance of being at the right place at the right time and having clarity on her desire to build and grow within a company.

I wanted to get back into building and growth because I had experienced that at I2 and I'd gradually gone to bigger and bigger companies and felt like I was improving things, but not really disrupting markets.

Jennifer Tejada expresses her desire to return to a role focused on building and growth, rather than just making incremental improvements in larger companies.

• Tejada recommends PagerDuty to graduates because of its explicit strategy around growth and development.
• She stresses the importance of investing in people's development, including technical, management, and leadership skills.
• Tejada warns of a potential future shortage of well-trained executives due to a lack of foundational training in the tech industry.
• She advises on the importance of gaining a broad range of experiences across different functions and roles to become a well-rounded leader.
• Tejada criticizes the rush to the top and the narrow functional expertise that results from not engaging in cross-functional training.

I worry that a lot of organizations in the tech industry are not investing in growth because they hire people off the street and expect them to be expert in coming and do what they need to do.

Jennifer Tejada expresses concern that tech companies may not be investing enough in the growth and development of their employees, leading to a potential future deficit in well-trained executives.

• Tejada highlights the value of management rotations and diverse assignments in developing leadership skills.
• She notes the trend of employees not being encouraged to cross-train and the industry's focus on rapid progression.
• Tejada emphasizes the need for CEOs to understand various functions within a company to effectively lead and coach their teams.

And I have to tell you that when you're the CEO, there's not a ton of time for on the job training. You really need to understand what you have in front of you and what you're working with.

Jennifer Tejada explains that as a CEO, there is limited time for learning on the job, thus understanding the different functions within the company is crucial for effective leadership.

• Understanding personal motivations is crucial for career development.
• Jennifer Tejada emphasizes the importance of being driven by intrinsic values rather than external rewards such as money, power, or public exposure.
• She advises focusing on learning and personal impact rather than external pressures or vanity metrics.
• Self-awareness and reflection on what truly inspires and fulfills an individual are key to making career decisions.
• Tejada shares her own experience of being motivated by learning and the impact she can have rather than conventional metrics of success.

"Harry, I think it's not so much a fast or slow thing, and it's more about being aware of what you're truly motivated by, like what you intrinsically are inspired by in your life and in your career."

This quote emphasizes the importance of understanding one's own intrinsic motivations over the pace at which one moves in their career.

• Jennifer Tejada describes herself as a natural risk-taker and encourages embracing risks as opportunities for learning.
• She suggests assessing risks by asking what the worst-case scenario is and how one could recover from it.
• Tejada stresses the importance of long-term thinking over short-term risk management, which can lead to fear-based decision making.
• Personal control over one's path and development is highlighted, with a focus on individual choices rather than societal expectations.

"My younger sister gave a toast at my wedding, and one of the things she referred to was me being the risk taker in the family."

This quote introduces Tejada's personal relationship with risk and sets the stage for her perspective on risk-taking and decision making.

• Jennifer Tejada finds solace and clarity in nature, which helps her isolate her decision making from external pressures.
• She practices walking one-on-ones with her team for more candid conversations and emotional engagement.
• Tejada also engages in activities like skiing and water sports to disconnect and reflect on decisions.
• She emphasizes the importance of self-reflection and processing with others, sometimes without them realizing they are aiding her thought process.
• Tejada also describes being provocative with her team to stimulate different thinking and to help her process challenges.

"I do walk every single day, and I do a lot of walking one on ones with my team."

This quote illustrates Tejada's approach to integrating physical activity and nature into her decision-making process and team interactions.

• Jennifer Tejada admits to frequently experiencing self-doubt and sees it as a natural part of leadership.
• She believes that expressing doubts openly can help in coming to terms with them.
• Tejada suggests that a lack of self-questioning in a leader could be concerning, indicating potential arrogance or narcissism.
• To manage self-doubt, she relies on data and analysis to understand business issues deeply, which gives her confidence in her decisions.

"I'm constantly doubting myself. I think anybody who runs a meaningfully sized company or is responsible for the employment of hundreds of people or has a duty of care in a leadership role is going to doubt themselves."

This quote acknowledges the prevalence of self-doubt among leaders and the importance of confronting and managing these feelings.

• Surrounding oneself with a great, experienced, and trustworthy team is crucial.
• The team should be experts in their fields, open to challenges, and not fear-based in their decision-making.
• Healthy debate and accountability within the team are necessary and require practice to develop.

"I'm surrounded by a phenomenal, experienced team, a team that I trust, a team who, each in their own right, are very good at their jobs and expert in what they do, but also open to new challenges and not afraid, not going to make fear based decisions, as opposed to sort of taking a leap every now and again."

This quote emphasizes the importance of having a supportive and skilled team that is open to taking calculated risks rather than making decisions out of fear.

"You have to build that muscle to be able to have an uncomfortable conversation within a team and being comfortable in holding each other accountable to goals and commitments that we've made."

The quote highlights the necessity of developing the ability to engage in difficult conversations and hold each other accountable within a team, which doesn't come naturally but must be built over time.

• Board work experience helps in making decisions with limited data.
• Crisis management experience teaches decisiveness under pressure and time constraints.
• Looking back on past decisions can reveal that decisions made with less information can be as good as, or better than, those made with extensive analysis.

"Being on board's got me comfortable making decisions with little information."

Jennifer Tejada explains that her experience as a board director has trained her to make informed decisions even with limited data.

"The truth about a crisis is it has a beginning and an end. And knowing that after having been through a couple gives you the peace of mind to, I think, be calm and weather that crisis as it's happening."

This quote reflects Jennifer's perspective on crisis management, suggesting that understanding the temporary nature of crises can help maintain calm and decisiveness during such events.

"Making any decision so that you're technically running an experiment and can learn something is better than waiting for more information."

Jennifer argues that making a decision, even with incomplete information, is preferable to inaction, as it allows for learning and progress.

• Building a strong foundation of trust within a team is essential for open communication and debate.
• Team culture and values need to be established to encourage progressiveness and accountability.
• Practicing healthy debate is necessary, and it can be challenging in a polite and non-confrontational environment.

"You have to have a foundation of trust. So I think it starts with making the investments in time, in money, whether it's off sites, it's one on ones."

Jennifer Tejada emphasizes the importance of investing in building trust within a team to enable open and honest communication.

"We will have a healthy debate, where we can disagree, where we can have a debate in a room, but then even if we don't all agree, in the end, we align, we sort of quote unquote disagree and commit."

The quote outlines the desired outcome of healthy debates within a team, where members can disagree but ultimately align and commit to a decision.

• Curating a board can be a significant opportunity for a CEO to align the board with the company's vision and strategy.
• Transparency and a no surprises policy are crucial in board management.
• Boards should be seen as partners rather than just overseers, and it's important to have a clear role for the board in the business.

"I think of the board as being for the company and for management, where often people think about the board as being governance and oversight."

Jennifer Tejada describes her view of the board as a supportive and integral part of the company, not just a governing body.

"We have a no surprises policy in my team and my board because bad news doesn't get better with age."

This quote highlights the importance of transparency and timely communication with the board, especially when it comes to sharing bad news or challenges.

"What is it about my background or my skill set that you think could uniquely bring value to this board today?"

Jennifer Tejada stresses the importance of understanding why one has been chosen for a board role, indicating the need for a board to have a well-thought-out composition of skills and experiences.

• Effective board members are characterized by their ability to listen actively and assess non-verbal cues.
• They ask insightful questions that provoke thought and provide new perspectives.
• Great board members serve as a sounding board for CEOs, offering a judgment-free space for discussion.
• Trust between a CEO and a board member is crucial and can be fostered by the board member's behavior in the boardroom.

"Good board members ask great questions, and they don't ask a lot of questions, to be honest."

This quote emphasizes the quality over quantity of questions asked by board members, highlighting that impactful questions are more valuable than numerous ones.

"I think great board members are great sounding boards."

Here, Jennifer Tejada explains that a board member's role includes being a supportive confidant for the CEO, indicating the importance of a trust-based relationship.

• Staying focused on the most impactful growth paths is a significant challenge in high growth companies.
• The key is to prioritize and narrow focus, which becomes more difficult as the company grows.

"Staying focused on the paths to growth that we think are going to have the biggest impact."

Jennifer Tejada notes the importance of maintaining focus on strategic growth areas, despite the temptation to pursue numerous opportunities.

• Resource allocation is an important skill for CEOs, but it may not be the primary characteristic of the best CEOs.

"The best CEOs are the best resource allocators agree or disagree with that being the primary characteristic."

This quote reflects the discussion on whether the primary trait of a successful CEO is being an adept resource allocator.

• Jennifer Tejada seeks mentorship for specific issues rather than relying on one person.
• Effective mentors challenge their mentees to think differently and focus on what matters.

"I think my best mentors are the ones that challenge me as opposed to ones that are constantly cheering me out."

This quote highlights the value of mentors who provide constructive challenges rather than just encouragement.

• Scott Cook, the founder of Intuit, is admired for his leadership and impact on the industry.

"Scott was at Procter Gamble and then was the founder of Intuit. And he's created such an incredible legacy of leaders."

Jennifer Tejada expresses her admiration for Scott Cook's legacy and his influence on leadership across various industries.

• There's a need for faster progress in increasing diversity in tech.
• Companies should treat diversity as a business initiative with measurable goals and dedicated resources.

"The diversity. I am tired of being one of the very few females in enterprise software, leading enterprise software companies."

Jennifer Tejada expresses her frustration with the slow progress in improving diversity within the tech industry.

"I think treating inclusion and diversity and access and equality as a business initiative, as opposed to some cultural or HR or corporate responsibility activity that we need to undertake, is part of driving change."

This quote emphasizes the need for a strategic and operational approach to diversity, rather than treating it as a mere formality or HR task.

• PagerDuty aims to evolve from a product company to a platform that manages time-sensitive work across various functions.
• The company is also focused on contributing to global healthcare and creating equitable communities.

"I'd like to think that in five years time, Pagerduty has not only delivered on that mission, but also on our commitment to improve time-sensitive global healthcare and access for people through pagerduty.org."

Jennifer Tejada shares her vision for PagerDuty's future contributions to healthcare and community equity.

• Transparency in reporting progress on diversity and inclusion can create peer pressure and advance the industry.

"The more transparent the industry and companies can be around reporting their progress on diversity and inclusion and things like pay equity, the more peer pressure we'll create to move the entire industry forward."

This quote suggests that openness about diversity efforts can lead to industry-wide improvements through increased accountability.

• Jennifer Tejada hopes to continue improving and contributing to PagerDuty's mission without rushing the process.

"Well, I hope I just continue to get smarter and better in myself and faster, but at the same time not have to do it in a hurry."

Here, Jennifer Tejada expresses her personal aspiration for growth alongside the strategic development of PagerDuty.