Alex Solomon and the art of handing over the pager

The pager had already interrupted Alex Solomon’s life once. Years later, a venture capitalist found a more agreeable use for it. In 2014, Bessemer’s Ethan Kurzweil handed the PagerDuty founder a Motorola Advisor II, then sent a message saying the firm wanted to fund his company. A term sheet followed. For once, the little machine was reporting something that required a celebration rather than a repair.

It was an apt joke. Solomon had helped turn a piece of engineering housekeeping into a business. He understood what happened after a system announced that something had gone wrong: a person needed to answer. His company would grow around making that responsibility clear. Eventually, he would face a version of the same question in the CEO’s office.

A job you could wear on your belt

Solomon’s route into software began well before the pager. His parents taught him QBasic. Games supplied another reason to keep programming: he wanted to make his own. At the University of Waterloo, he studied software engineering, mixing coursework with practical experience through the co-op program. His final two placements were at Amazon, which became his employer after graduation in 2006.

At Amazon, writing software came with an ongoing obligation to operate it. Engineers tested their work, deployed it, and answered for what happened in production. An alert could arrive through an actual pager attached to a belt. Solomon remembered incidents that ran for six or eight hours. The code had acquired a remarkable ability to rearrange its author’s evening.

That arrangement taught a precise lesson about ownership. A monitoring system can identify trouble without resolving the human questions surrounding it. Who is available? Who understands this service? Who gets called if the first person fails to answer? Each question sounds small until it remains unanswered during an outage.

Three engineers, one familiar nuisance

Solomon founded PagerDuty in Toronto in 2009 with Andrew Miklas and Baskar Puvanathasan. The three had worked at Amazon; Solomon and Miklas had also been classmates at Waterloo. Their shared experience gave them a problem they could examine at close range. Other organizations needed the kind of on-call tooling that large technology companies had built internally.

The initial opportunity was to connect monitoring tools to a dependable process for reaching people. PagerDuty could sit across a company’s existing systems rather than demand that everything be replaced. The appeal lay in the handoff: a technical signal becoming a task with an owner.

There was also the pleasant discovery that the domain was available. Solomon later joked, “If it hadn’t been available. Who knows where I’d be today.” Even software companies with serious responsibilities sometimes owe a small debt to an unclaimed web address.

The company joined Y Combinator’s Summer 2010 batch. By then, it had a product and paying customers. The next education concerned investors, fundraising, and how a narrowly useful service might support a larger business. Three engineers had to learn to explain the future in terms other people could finance.

The customers had questions

A software engineer is an excellent first customer and a hazardous stand-in for every customer. PagerDuty’s early approach allowed people to try the product and pay online. Its founders understood that route. Other buyers arrived with questions, purchasing procedures, and a preference for talking through what they were about to depend on.

The company developed a sales operation alongside self-service adoption. In his later discussions of the business, Solomon emphasized the usefulness of salespeople who understood technical work. An engineer considering an incident-response tool has questions about the tool’s behavior. A conversation becomes useful when the person answering understands why those questions matter.

The broader strategy was similarly practical. PagerDuty could work with monitoring vendors instead of trying to replace all of them. Solomon described the company’s position as the “Switzerland of monitoring.” An independent layer could be useful to organizations running a mixture of services and infrastructure. The diversity of the customer’s tools was part of the opportunity.

By June 2014, PagerDuty had reached $12.6 million in annual recurring revenue. Bessemer’s investment memo recorded a business whose customers were expanding their use over time, as well as a management team developing its sales, marketing, and financial processes. The original engineering problem was supporting an organization with responsibilities of its own.

The memo offers a quieter detail about Solomon. He had asked how the investors would think about a coach to help him grow. Alongside the revenue figures sits a founder considering whether he needed help. It is a useful detail to keep in mind when looking at the decision that followed.

Finding someone for the founder’s chair

By 2016, PagerDuty had more than $50 million in annual recurring revenue and about 200 employees. Solomon’s working days were increasingly occupied by hiring and management. He wanted more time for customers and product. After considering the problem and speaking with other founders, he decided to recruit a new chief executive.

The search required more than finding a plausible résumé. He spent over 40 hours getting to know Jennifer Tejada through interviews and meals. The time matters: a founder was choosing someone who would make decisions about a company he had spent years building. Personal compatibility and professional capability would have to survive actual work together.

Tejada brought experience in strategy, operations, and bringing products to market, including leadership at Keynote Systems. PagerDuty announced her appointment on July 21, 2016. Solomon became CTO, retaining a place on the board and responsibility for product strategy. The announcement laid out a complementary division of work between the incoming chief executive and the founding engineer.

A change on an organization chart can be completed with very little effort. A working transfer of authority takes longer. Tejada later described Solomon giving her the autonomy to lead. That makes the decision more interesting than a simple title change. Choosing a successor also meant accepting that she would run the company.

“Alex and I have developed a true partnership anchored in humility and a desire to inspire each other”

Jennifer Tejada · 2018

In June 2018, the two received EY’s Entrepreneur Of The Year award for Infrastructure & Operations in Northern California. Tejada spoke about their partnership; Solomon described wanting a partner who could take the company into its next stage while preserving its culture. The recognition belonged to both of them, an appropriate arrangement for a decision that depended on both people making it work.

PagerDuty went public on the New York Stock Exchange in April 2019. Solomon called the experience surreal. A decade after the company began, the engineer who had carried the pager was watching the business enter public markets. The milestone also followed several years in which he had contributed from a different chair.

The problem of remembering everybody

There is another way to trace Solomon’s approach to growth, and it involves fewer ceremonies. When PagerDuty reached roughly 30 or 40 people, he found he could no longer remember everyone’s name. During a Hack Day, he teamed up with another engineer to build a Rails application for the employee directory.

The tool made colleagues and reporting relationships easier to look up. It was the kind of useful internal system he had encountered at Amazon, now adapted to a company he was helping run. A familiar instinct had reappeared: find a repeated inconvenience, then give people a clearer way through it.

His accounts of that period also emphasize documentation and access to company information. Teams recorded their work, and business dashboards were available internally. The phrase he used was “open by default.” A growing staff could learn how the company operated without relying entirely on whoever happened to be nearby.

These details explain something that revenue milestones leave out. An organization grows in headcount, but each new colleague also changes the number of relationships and handoffs inside it. A directory or a well-kept document can seem mundane. Being unable to find the person or the answer is considerably more distracting.

Knowing when to pass it on

Solomon moved from CTO to General Manager of Flexible Platform in January 2021. His employment at PagerDuty ended on July 2, 2024, and he retired from the board on December 30, 2025. The company said the board departure did not arise from a disagreement over its operations, policies, or practices.

His history at the company contains several different assignments: recognize a useful problem, build a service around it, learn how to sell it, recruit leadership, and develop the platform. Keeping all those jobs attached to one title would obscure what changed. The work kept moving, and his role moved with it.

At the beginning, his ambitions had included a comfortable bootstrapped business and drinks served in coconut shells. Public markets and years of management were a fairly elaborate detour from the beach. The account is funnier because Solomon has been willing to tell it himself.

The pager provides a more durable image. It gives responsibility a location, and it allows that responsibility to move. Solomon’s career at PagerDuty shows how much can follow from taking a call seriously, including the moment when someone else should answer it.