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“Bring your self.” With Tyler Gallagher & Jennifer Tejada

Bring your self. I don’t mean just to physically bring yourself to work. This is really about bringing and being your whole self when you come to work. There’s no reason and frankly, no time to put on airs or present myself in an artificial way I am “supposed to be.” Model authenticity, especially calling out your […]

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Bring your self. I don’t mean just to physically bring yourself to work. This is really about bringing and being your whole self when you come to work. There’s no reason and frankly, no time to put on airs or present myself in an artificial way I am “supposed to be.” Model authenticity, especially calling out your own failures, demonstrating both vulnerability and your willingness to learn FAST.


I had the pleasure of interviewing Jennifer Tejada is the CEO of PagerDuty, a global leader in digital operations management. Jennifer is a veteran software industry executive and business leader. Her 25 years of experience is unique, spanning mass consumer products to disruptive cloud and software solutions. She has a successful track record in product innovation, optimizing operations and scaling public and private enterprise technology companies.

Prior to her role at PagerDuty, Jennifer was the CEO of Keynote Systems where she led the company to strong profitable growth before its acquisition by Dynatrace in 2015. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at the enterprise software company Mincom leading its global strategy up to its acquisition in late 2011 by ABB. She has also held senior positions at Procter & Gamble and i2 Technologies (acquired by JDA Software.)

Jennifer was recently named “Entrepreneur of the Year — Norcal” by Ernst & Young in the category of Infrastructure & Operations. She is passionately invested in driving collective, actionable, metrics-driven strategies to increase diversity and inclusion across the technology industry.

She currently serves as a board member of The Estée Lauder Companies Inc. (NYSE: EL) and Puppet, Inc. She previously sat on the board of oOh Media. Jennifer holds a B.S. from University of Michigan.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

To be honest, I did not expect or plan to be a software executive, much less a CEO or board director, when I started my career. As an undergraduate student, I planned to go into healthcare to follow in the footsteps of my father, who was the CEO at our local hospital. But he was the person that encouraged me to forge my own path which eventually led me to begin my career at Procter & Gamble. Working there left an indelible impression on me. I learned classic principles around consumer marketing and research straight from the masters. Even 25 years later I still leverage many of these foundational, timeless lessons, whether I am defining our culture with intentionality, developing executive talent, or running experiments to refine our go-to-market fit. First and foremost, it’s about surrounding yourselves with people better and smarter than you, and striving to be a trusted servant and leader of these people, ultimately in service of your customers.

I then transitioned into the tech industry working for a series of high growth technology companies like i2 Technologies (which was eventually acquired by JDA Software), Mincom (now ABB) and Keynote Systems (now Dynatrace) where I joined as the CEO. By my mid-30s I had experience running sales, marketing, product, strategy and M&A and led global teams at high-growth tech companies. I also experimented with different industries from consumer goods, to telecommunications, gaming, and even hospitality and natural resources. Having functional depth and breadth is a key asset in career progression.

In addition, with every executive operating role, I have also served as an independent director on a separate private or public board. I find board work, not only helps you in exercising different brain muscles, it also gives you context that helps you see your own company in a different light. It creates empathy for your board and the unique position they are in.

By the time I joined PagerDuty in 2016, I felt as ready as I could feel and was excited to build and lead a high-growth, global technology company in the emerging space of digital operations management. That said, you are never done learning, and one of my favorite aspects of my job as a CEO is that there is always a new challenge and a need to build new mental muscles. I truly love the pace of the tech industry. My intellectual appetite is always fed, and there is no risk of boredom. The best part of my job hands-down is the fun of building teams and working with incredible people. Developing others is an immense privilege, and much like serving customers, is something I take very seriously.

Can you share the most interesting story that happened to you since you began leading your company?

When the opportunity to transition PagerDuty’s leadership from our founder, Alex Solomon, presented itself, I thought long and hard about how it could be successful. I thought about how we could change leadership but still give our employees an authentic, committed, passionate leadership and a mission they could adopt as their own. Alex has been a terrific partner and when we planned our transition, I spent many hours pressure-testing him and the board on whether he was truly ready to hand over “the con.” Over the past few years, we have built a trust and kinship that I am very proud of, and one that I think helped accelerate our teams’ ability to trust our handover and ultimately me as their leader.

It was not all smooth sailing in the beginning, and anyone who says it is, is lying or delusional. In my first 100 days at PagerDuty, I, with the help of our board and Alex, made significant changes in both leadership and our business model. We built what I thought was a reasonable plan for the next financial year and started executing quite well. Then we unexpectedly missed my second quarter with the business….BIG. When we missed that quarter, it was a combination of bad planning, a lack of understanding of important leading indicators, and a little complacency on the part of a team that had experienced many quarters of growth. At our company town hall shortly after, emotion got the better of me, and I publicly scolded myself, aired how I felt about my own failure and how disappointed I was that we hadn’t lived up to both our commitments and our potential. I couldn’t hide my frustration which was mostly with myself. The team found this open airing of failure, what I learned and what I thought we needed to change, refreshing and some even found it inspiring. In the following weeks it was like the company shifted into a different, higher gear, and we haven’t looked back since- or missed a quarter since.

Are you working on any exciting projects now? How do you think that will help people?

I am generally an excited human, so we have a lot of exciting projects in the works! On the product side, we’re making great progress in transitioning from a product-based company to a platform-oriented one. We are doing this by leveraging our huge, unique data sets that intersect human behaviors and machine signals to facilitate real-time operations for the most disruptive startups and the world’s largest companies. Sometimes I have to pinch myself- it’s our job to help people work more efficiently with the aid of AI and ultimately, with more purpose. Since I’ve come aboard, I’ve made it a goal to expand the business from a response-based tool to a predictive and proactive solution. All of these product innovations support our mission which is to enable our customers to focus on the work that matters in the micro moments that matter. When time is the most valuable asset, giving time back to users makes their lives better.

We are also expanding around the world and in choosing office locations, we’ve taken a less conventional approach than most companies who follow the herd. In our second US location, we sought out a city where we could create access to careers in the tech industry for underrepresented candidates. I am thrilled to share that PagerDuty is opening an office in Atlanta in order to better serve our customers with product, engineering, finance and go-to-market teams. (We are headquartered in San Francisco and have offices in Toronto, Seattle, London and Sydney.)

Inclusive leadership is not a strategic initiative for us. It’s the way we do things. Not only are we architecting a diverse board, leadership team and employee base, we are also raising the standards for our partners and managers to ensure we nurture an inclusive culture — one of belonging comprised of people from different backgrounds and with different perspectives. We know an inclusive culture produces better business outcomes and product innovation. Our Atlanta office gives us the opportunity to extend our inclusive culture and expand our access to diverse talent outside the highly competitive San Francisco Bay Area. We plan to hire up to 100 employees by the end of 2019 and more than 300 in the near future across all functions.

Additionally, Georgia Tech, located just nine miles from downtown Atlanta, produces more underrepresented minority degree holders and graduates more female software engineers than any other university in North America. This diverse community is further complemented by other nearby universities, including Georgia State, Emory, Morehouse, and Spelman.

Expanding our presence to Atlanta isn’t just about achieving hiring goals. I’ve made it a personal goal as a CEO to change the face and make up of what a typical technology company looks like. Diversity, inclusion and equity begins with leadership taking action and setting an example for other key stakeholders in the organization. Currently at PagerDuty, women make up approximately 40% of managers while underrepresented minorities (black, LatinX) make up 25% of managers. Also, our executive leadership team is 50% female. This is the example we want to set for our industry.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

There’s a lot to unwrap in that Forbes article. Unhappiness in one’s role can be caused by a myriad of reasons both professionally or personally.

My personal philosophy on happiness at work is underpinned by my own deep sense of accountability, responsibility and perseverance. I’ve always felt that it’s no one else’s job but mine to chart out my career and ensure my happiness. That said, I am happiest personally when I am empowered and enabled to do my best work and to bring myself, my whole self to work. I think most people intrinsically want to succeed. I am proud of our high ratings as a company with a 4.5 rating on Glassdoor, including a very positive outlook (89% confidence in our future) and tremendous support in my own leadership from our teams (100% approval). None of this happens by chance or luck.

We are investing well ahead of companies our size to empower and enable employees to do the best work of their lives and to have a career-making experience at PagerDuty. This includes simple, but difficult initiatives like designing and transparently communicating career architectures, surveying and measuring employee sentiments and feedback with resulting action plans and measurable goals. We have doubled down on management evaluation from performance-based to peer review and engagement surveys. When it comes to leadership development, we rolled out a comprehensive leadership program to complement our management training to ensure that those who lead at PagerDuty are ready to lead successful teams that grow.

When you’re running hard, work-life balance and burnout become real issues.We’ve worked very hard to create focused, simple strategies and goals that everyone can understand and interpret for their own roles while being empowered to lead in their own way. This freedom is more rare than you’d think.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

When it comes to productivity, we’ll know right away if productivity has gone down. Our success is based on our ability to innovate quickly. We are constantly being tested by our competitors and our customers who want something more, something better from us. If we aren’t productive, we can’t innovate. And if we can’t innovate, we can’t deliver for our customers. Innovation is critical to our company’s success. Disrupting ourselves is a core value we instill in each employee.

I think people generally like making other people happy, so putting our customers’ happiness first for every team and every employee keeps people focused on why we exist. When you get it right for your customers and right for your employees, my experience has been the rest (investors, financials, shareholder returns) falls into place. So we are maniacal about making sure our customers are happy. And as a result, we have a special relationship with our customers. PagerDuty is a love story! As I mentioned, innovation is a key indicator to both our success and happiness. We’re providing our users with a technology to literally make their lives better. We can tell what resonates with users and what doesn’t as we work closely on product innovation with our key customers. It’s motivating everyone to put their complete self into this because we share that common goal.

Finally, I believe in leading by example — my role as CEO necessitates that I integrate my life as a business executive and my relationship with my family and personal interests. I view this as a unified approach where you don’t need to sacrifice one for the other. It’s not just about working smarter or putting in more hours; it’s what gets accomplished when you do put in the time an effort. It’s about how we feel at work and how our families feel about work. If it’s not fun, why bother? So I go to great lengths to make work fun for people — to laugh at myself and laugh with them, to not get caught up in taking ourselves too seriously all the time and making sure that our team feels like they have permission to live their lives. When it comes to employee health and well-being, I ask of them what I can only expect from myself. So I set a clear list of top priorities from the get-go in order of priority: 1. My family (my husband and daughter) 2. My health and 3. My customers and employees (tie). Other priorities like a quick weekend trip or a phone catch up with an old friend, I can reschedule these if life gets too hectic. I can’t reschedule motherhood or good health. If I don’t take care of my family, none of this is worth it. We are a family and if there is something they are not happy about, my door is always open to my employees.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

There are more than 5 things I can suggest for managers to improve their work culture but here are the ones that are top of mind:

  1. Create an inclusive culture you can measure. That means setting targets, and hiring and developing teams with diverse backgrounds and perspectives. How can you expect to disrupt your culture, your product and the market if everyone thinks like you do?
  2. Bring your self. I don’t mean just to physically bring yourself to work. This is really about bringing and being your whole self when you come to work. There’s no reason and frankly, no time to put on airs or present myself in an artificial way I am “supposed to be.” Model authenticity, especially calling out your own failures, demonstrating both vulnerability and your willingness to learn FAST.
  3. Be transparent with your team, customers and partners. We are building trust with our customers through our platform for action that helps teams respond to incidents and improves their lives at the same time. With your teams, set clear expectations and hold them to high standards. A high standard is a sign of respect. Then make sure your teams have the tools and support to go do what they are good at. Leave them to their own devices to make the magic happen.
  4. Create an environment to let your team take risks and fail if necessary. The “fail fast” concept is something that I believe in. We work in such a fast-paced environment and enabling an employee to challenge themselves even with the prospect of failure will hopefully ensure their ability to handle adversity.
  5. MAKE IT FUN and MAKE IT BIGGER. Gamify what you can, create healthy competition, and make the mission bigger than just the work. We started PagerDuty.org to give employees an outlet to share their gifts and their time, to do good and to feel good.
  6. It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

I think the key thing is having CEOs communicate with their employees. While we can’t guarantee everything that employees want, I strongly believe we can meet in the middle. One thing I’ve started to notice a lot with companies is working from home. I’m a fan of a flexible workstyle, as long as you’re getting your work done. It’s an option that I think more employers should offer.

I also think time off is another thing we have to work on. I lived in Australia for many years where almost all workers are legally entitled to six or more weeks of paid holiday per year. And I love how Aussies get out and see the world! Here in the U.S., companies tend to offer 10–15 days of PTO. Vacations are important since it gives you time to recharge and not think about work. Having more vacation days can help you feel refreshed and ready to get back into the groove of things for work. Feeling safe to take a vacation, that you won’t fall behind or be perceived poorly is also important and it’s the job of managers to encourage and insist on time off to recharge.

How would you describe your leadership or management style? Can you give us a few examples?

My leadership style centers on building trust. I care deeply about the mission, the team, the culture and the milestones we are aiming for. I have a degree in organizational behavior and I love the art and science of composing and developing a killer team. For example, PagerDuty’s executive team is mix of leaders who were here before me, leaders I have have worked with for many years and leaders who are brand new to one another. Sixty-five percent of the team was born outside of the US and the team is gender-balanced. We go beyond delivering great results and invest in helping each other improve the entire teams’ effectiveness. I am very data-driven so we use measurement tools and experts to help us.

I am an extrovert and I live for the moment when one of my teams realizes they exceeded a milestone once thought crazy and impossible. I work pretty hard to make sure we are ambitious and aspirational in our vision and goals, but that the team is empowered and feels like they have support to get help, fail or challenge me or anyone else for that matter.

I also attempt to personally connect with every person on my team and by that I mean, do the work to understand what makes them tick, what are their dreams, and what stresses them out or drives them nuts. I feel like when you understand where someone’s coming from and where they want to go, it’s easier to get aligned around a mission and dig into it together. I believe in kindness as the best SOP. It may be my midwestern upbringing, but I find being unkind is exhausting.

I’m on a constant mission to improve myself and my leadership skills. Most of the great CEOs in the valley and beyond have received calls or emails from me asking for help with a problem or educating me on something I’m trying to learn. I’m not the best active listener but I’m working on it. I’m a terrible meeting runner and easily distracted by interesting numbers and problems, and I can be an intense, impatient, hard driver (in a nice way) who moves at a fast pace. There are times when I notice the pace isn’t good for everyone.

I hope one day when our team looks back on our experience together, they will each feel like they experienced something truly special in not only what we achieved in out-performing our peers and creating value for our customers but in the way we went about it. We did it through creating access and equality, having social impact, and creating a place where everyone belongs. I hope they smile and tell funny stories about all the crazy things we tried, failed and achieved. I also hope they feel like they learned more personally than anywhere else they ever worked. And if I am honest, I hope I inspire at least some of them to be CEO’s, because the world needs more truly great CEOs who care more about their people.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My father, Paul Tejada, taught me anything is possible if you have a vision, surround yourself with great people, work hard and persevere through obstacles. Without his guidance and support, I probably wouldn’t be where I am today.

Over the course of my childhood, he worked very hard, working his way up to being a hospital CEO. His superpower was engaging others in a vision. He made it his life’s mission to bring better healthcare to the middle and lower class communities we lived in and on the side served in leadership positions or fundraised for the United Way, the American Heart Association to name a few.

Despite being a busy leader, he made time for my mom and siblings- attending our sporting and music events, taking us camping and on road trips and recruiting us for every fundraising event under the sun. He instilled a deep work ethic and sense of civic responsibility in all of us. When we complained he said, “life’s not fair, get on with it.” When we stumbled, “Get back up and try again.” He taught us to stand up for ourselves and each other, especially for others who couldn’t stand up for themselves. He expected us to “carry our own load”, and to contribute to the community around us with whatever we had.

I was especially inspired by my Dad’s drive and ambition to improve the lives of others. Whether it was through reducing infant mortality rates through access to prenatal care or bringing modern oncology treatments to towns outside of urban centers so patients didn’t have to drive hours from their homes for treatments. Even with little things like making pancakes for the night shift at the hospital, he found a way to make everyone feel important and to improve the environment around him. I was also inspired by his tenacity. Giving up on something was unacceptable. Expecting something to come easy, waiting or hoping for something to happen was ridiculous. Quitting was never, ever an option.

How have you used your success to bring goodness to the world?

I feel a responsibility to women and underrepresented people to prove we belong in the executive ranks, in the boardroom and in leadership in general. If just a few younger women see me and say, “I can do that too”, then I am making a difference. By demonstrating you can operationalize diversity, inclusion and equality in a business and deliver better performance, we not only provide an example for others, we decimate the excuses… “there’s no pipeline”, “it takes a long time”, etc.

Leading a high growth technology company that truly makes an impact in the lives of DevOps and IT practitioners across all industries is already something that we’re proud of achieving. But I also knew there was more we could do to bring this technology to other organizations like non-profits and groups that are focused on making an impact socially. In my second year as CEO, I proposed to the board that the company join Pledge 1% (committing 1% of our equity, product and employee time) and launch PagerDuty.org to enable these organizations with the same opportunities as our larger enterprise customers. The board was very supportive of this initiative and empowered me to make it a reality. PagerDuty is fortunate to have a board of directors that share our corporate values and the desire to make an impact for underrepresented groups as well as companies who also trying to make a difference in the world.

I truly believe PagerDuty is for people. It’s technology that real people use to make their lives and hopefully other lives better.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I worked with an entrepreneur who once said, “you won’t see the skid marks when we go off the cliff.” It was the late 90s in the dot com boom and I had fallen madly in love with the culture of innovation and fast pace of tech. Fast forward 20 years later and my husband, Michael, likes to say “predictable is manageable.” As a high growth CEO, I have to balance the dichotomy of both these concepts — moving, failing, learning and growing fast, and delivering on my commitments in a reliable, trustworthy way for all of our stakeholders. I find joy in the challenge of this chaos.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Magic happens when you unify people around a mission. Giving more, different kinds of people access to the kinds of career opportunities I have enjoyed is a movement I want to scale. First by building products that empower people to do their best, most purposeful work, and second by driving change in the industry through bringing people together rather than being divisive. Everyone wins when opportunity is equitable and accessible.

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