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PagerDuty’s CEO Jennifer Tejada on Selling Software and Demanding Diversity

“People will test your conviction as a leader all the time. If you’re not consistently demanding and painting a vision for what you want this community to look like, you’re not going to get there.”

Jennifer Tejada has come a long way from selling Sunny Delight in the mid-1990s, but she’ll be the first to tell you that pitching ‘Sunny D’ was how she learned to sell software.

Today Tejada is leading the San Francisco-based PagerDuty, a global SaaS company that remedies IT headaches like server downtime and DDoS (denial of service) attacks.

She cut her teeth in the tech sector while working in marketing at Procter & Gamble. It was there she saw the internet take off with the dot-com boom and decided she didn’t want to miss out on the rapidly evolving and fast-growing field.

In the past two decades, Tejada has moved from heading global marketing at i2 Technologies to senior leadership at Mincom in Brisbane, Australia. Back in San Francisco, she took on the chief executive role at Keynote in 2013 before moving to PagerDuty in July 2016.

PagerDuty’s alarm aggregation and dispatching service notifies support teams of events that may impact customers and helps on-duty engineers manage business-impacting incidents in real-time. The high-growth startup boasts 10,000 customers like IBM, Lululemon, Groupon and Panasonic, and partners with dozens of companies like Slack and Cisco.

Named one of Deloitte’s fastest growing companies in North America, PagerDuty expanded into the U.K. and Australia this year after closing a $43.8 million Series C in April. Now the company is doubling down on Toronto—the city where three University of Waterloo graduates first founded PagerDuty in 2009—and is expanding the region’s 70-person engineering and sales team.

What inspired you to switch from a marketing career to software?

I have a low degree of fear when it comes to tackling the unknown.

I started my career sort of by accident at P&G in consumer marketing and sales. I learned a lot about how consumers make decisions: how they seek, research and acquire goods, services and products. At the dawn of the internet, I accepted a role in a P&G think tank that explored emerging technologies for global retailers and found new ways to increase traffic and customer loyalty.

It was then that I realized tech was my thing.

My first opportunity with technology was with i2 Technologies. I loved that you could see how the software was cutting costs and you could keep score — that reflects the athlete in me; I’m super competitive.

It was very complex software but someone needed to explain it to the executives that wrote cheques in simple terms. That was my job–I was the director of dumb it down.

I like the pace of innovation, the culture of failing fast, and I don’t like a ton of structure.

I love the creativity of being in an early-stage business where the market isn’t yet defined and you have to figure it out.

What lessons did you learn from selling consumer products that you apply to the enterprise technology space?

Selling Sunny Delight at P&G taught me everything that I needed to know about selling enterprise software. It starts with really getting to know the customer and understanding their biggest pain points: what’s keeping them from working at their best—from being their best self in their business—and identifying solutions that address those issues in a very palpable, quantifiable way.

More than that, it’s about having empathy and understanding what success looks like for them. That approach is exactly the same whether that customer is a stay at home mom or a busy engineer in a large Fortune 500 company or even a startup.

It doesn’t matter whether you’re selling peanut butter or AI: if it doesn’t solve important problems for a large number of people, then they aren’t going to buy it.

PagerDuty has attracted some huge clients. How does your platform streamline these business’s digital operations?

Every company now has software and hardware systems that send off signals, whether it’s an automation system on a manufacturing line or the way inbound web traffic is being monitored.

All of those signals are proliferating at a highly accelerated rate. The good news is we have those signals, we actually don’t have to send a human to watch a machine and figure out what it is doing, the machine tells us.

PagerDuty consumes those machine signals, interprets them, then identifies if it’s operating the way it is supposed to and connects that event to the right person. That means resources can be pulled in to address that issue and make sure that it doesn’t create a customer impact or an employee impact; that the issue doesn’t stop productivity or affect a consumer’s ability to engage with your brand.

That’s a real-time process—we call that modern incident lifecycle management.

What’s changing for us is that we’ve historically done this for the engineering community. What we’ve seen over time is our customers identified the opportunity to use PagerDuty in other parts of the business: in customer support, security, and even in places like marketing.

So we’ve expanded from on-call alerting and automation to becoming the platform for action across employees, across a business, where those employees’ jobs are automated across their tech stack.

How have evolving consumer expectations challenged PagerDuty’s business?

We live in a truly real-time world where consumers expect immediacy for the convenience, benefit and performance of the applications they’ve grown to rely on, from Uber to Spotify. So when the immediacy doesn’t happen for them, that’s an incident PagerDuty can recognize and address.

But there’s a consumer to IT gap that we’re seeing where a consumer will wait between 30 to 90 seconds to resolve something that’s not working for them, but the average incident takes six hours to respond to. Between 30 seconds and six hours, you’re letting your end customer down.

That’s where we have to shift away from the old version of products and solutions that were built for a hardware-centric data centre environment and more to a real-time world where you aren’t waiting for something in the queue to make a meaningful difference.

PagerDuty is experiencing global growth, so why expand in Toronto where the business started?

As we scale as a global company, there’s a huge business opportunity in Canada and to serve other regions in North America from Toronto.

It’s exciting to invest in an ecosystem that the local government, the provincial government and federal government are all supporting in terms of not only STEM and AI, but also diversity and inclusion. I love that the Toronto community is colorful and not so gender-centric as some of the other regions and communities we’ve seen in the past.

It has a strong cultural fit too. The humility, the frankness and the openness to learning—this learn-it-all mindset instead of a know-it-all mindset of Canadians is right in line with PagerDuty.

You’re one of few female CEOs in Silicon Valley. Did you ever perceive gender as a barrier?

My parents were great role models. My dad worked hard to consistently instill a sense of self-belief; that I had control over my own destiny, that if I was willing to work hard and align myself with the right mentors, that there were no limits to what I could be.

So I entered the workforce with very little fear and sense of limitation, that I was only limited by my own ability to imagine what I could be and what I could do, and my willingness to put in the work and dedication to get it done.

I lucked out on finding great sponsors. Early in my career at Procter & Gamble I had a manager who was super frank about how I could improve but would advertise my success to the world when I got it right.

I learned the difference between a mentor and a sponsor. He absolutely expected me to work really hard and make the team look good and deliver results, but when I did, he went out of his way to make sure people above him that could create career opportunities knew who I was.

It certainly never felt that there was a difference because I was a female or a male.

For the early and mid-part of my career, I didn’t spend time thinking about bias or the discriminatory things that can happen to you as a woman in the workplace.

I was almost always the only woman in the room or the only woman at the conference. But that was my normal. Someone gave me advice quite early on to think of that as strength, not a weakness and most certainly not a disadvantage.

Do I think that the world is fair and just? No. And I want to change that. Part of the reason I joined PagerDuty is because I see it as a platform to prove that diversity and inclusion can make a marketed difference in your outcomes.

Technology companies are acknowledging that diversity is a challenge, but meeting the challenge isn’t so simple. How are you addressing the diversity gap at PagerDuty?

I’m committed to proving through numbers that we can deliver an outsized result because we are committed to diversity of thought. To get that, you need diversity of age, gender, ethnic background and experience. Diversity was already part of PagerDuty’s culture when I joined but I’ve just amplified that message and demanded that we operationalize it from the top.

People will test your conviction as a leader all the time. If you’re not consistently demanding and painting a vision for what you want this community to look like, you’re not going to get there.

The way I’m approaching this now is the same way a great tech leader would approach any big, challenging problem. We’re going to hack. We’re going to apply a growth mindset to it, we’re going to look for best practices, and find people who are doing it right.

This interview was edited for length and clarity.

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