Jennifer Tejada is not the typical head of a Californian software company. The corner of the tech world she inhabits — that of cloud-based companies that dominate the modern business software industry — is even more male-led than other parts of the sector.
But it isn’t just her gender that marks her out. The chief executive of PagerDuty, a software company that went public earlier this year, has an outsider’s mentality that stands out at a time when Silicon Valley is under pressure to change, from boosting gender and racial diversity to reinforcing its ethical underpinnings.
Ms Tejada doesn’t talk much about tech. A marketer by training who plotted a course through general management, she seems most animated when discussing businesses with a close connection to users — whatever the industry. “You can build fabulous technology but at the end of the day, in enterprise software, people still buy software from people,” she says.
Ms Tejada got her first exposure to tech at the peak of the dotcom bubble two decades ago, with i2 Technologies, a supply chain software company that was riding the new wave of e-business.
The lack of management discipline and structure in the middle of a boom was formative. Ms Tejada had started out at Procter & Gamble, a renowned training ground for management, which she says left her with an appreciation for colleagues with both a high degree of professional competence and a strong sense of their role in an organisation.
In the dotcom bubble, things could hardly have been more different. “I was the only person who knew how to do a performance review,” she says. “I was like, ‘how do we determine who’s winning here and who’s not?’”
Companies such as i2 were unable to deliver the online business-to-business marketplaces they promised. The company’s stock market value ballooned to more than $25bn before collapsing in the dotcom bust.
Twenty years later, in a different tech boom, the challenge is how to take a company, which has honed its service and is looking to scale up, to the next level. After working for companies at all stages of their life cycle, Ms Tejada says she is most excited by late-stage growth companies like this. “I like the creativity of building,” she says. “I like building teams, I like having resources, I’m comfortable driving scale.”
Her formula for supercharging companies rests on a mix of high-energy motivation (Ms Tejada talks fast), an analytical style that depends on devouring massive amounts of data and a close attention to people.
Winning over PagerDuty’s staff was an early challenge. She joined in 2016, replacing the founder, Alex Solomon — always a tough act in the founder-centric tech start-up world. She credits Mr Solomon, who is still a senior executive, with smoothing the way, but she had to resist playing the new broom. “When you come into a business it’s human nature to say, ‘Here are the things that are wrong, I’m running it as the fixer, here’s what I’m going to do to fix all the things you stupid people screwed up.’” Instead, she tried to “celebrate everything we do really well” — then focus on things that could be improved.
Ms Tejada admits to being very demanding. Her tool for challenging the organisation is marshalling the massive amounts of data thrown off by a cloud software business, which give insights into how the business is performing — provided you know where to look.
“SaaS [software as a service] to me is applied math,” she says. The passion for data also runs through her personal life — down to keeping track of the hours she sleeps and food she eats. “Big data’s been around for a while, but what people really want is a few actionable insights that are game-changers,” she says. “How do you shift an organisation from drowning in data to really being thoughtful about the four or five or ten insights that really matter?”
Ms Tejada’s answer is to try to home in on a few leading indicators. It took nine months to find the metric that gave the best indication of where the business was heading — a magic number she has yet to disclose.
She warns of two traps that managers who rely heavily on data tend to fall into. One is “analysis paralysis”: becoming overwhelmed and failing to find the right “north star” to focus on.
The other is not interrogating the data in enough detail. “When you’re staring at a lot of data, in order to simplify it people tend to aggregate it,” she says. “Aggregate data points are very dangerous, they can be very pernicious.” That makes it essential to unpick the number to get a true picture of the dynamics of the business.
Ms Tejada returned to Silicon Valley in 2013, after a stint in Australia. Faced with breaking into a male-dominated sector, she set out to build the relationships she would need to make it in the hyperconnected local tech world. She studied what she needed to do to become part of “the fabric of things”, then found sponsors who would promote her cause.
She believes the tech industry is open to change and eager to bring in the women and minorities who have been heavily under-represented. But change won’t come quickly. The men who control the purse strings haven’t worked out how to bring in people who aren’t like them, she says, since that would mean taking a leap into the unknown, bringing a higher degree of risk.
Ms Tejada calls it an “equity problem” and a “social justice problem” for the industry. “The way you change the mix of leadership is to go as far back into the supply chain as you possibly can and create equitable processes, equitable opportunities for people,” she says.
But she is not one to rock the boat. Rather, she says she doesn’t “align as well” with many of the people pushing for change in Silicon Valley, because she doesn’t “believe in being divisive in driving this change”.
“So much more gets done through being unified and working together, I worry that we over-rotate sometimes — whether it’s feminism, or equal rights, or the natural emotion of being angry and having feelings about being unfairly treated.”
Three questions for Jennifer Tejada
Who is your leadership hero?
My late father, Paul Tejada. He was a fierce competitor, yet warm and funny. He made every person in the room feel heard and important.
What was your first leadership lesson?
You do not need a title to lead. You need a vision, the ability to engage others and perseverance when they test your conviction.
What would you be doing if you were not a CEO?
I would sail with my family around the world, and then start a new career in healthcare, an industry I am passionate about.