Minami Rojas
PagerDuty's VP Sales Strategy & Analytics Michele Prashaw explores her global expansion journey, emphasizing the role flexible, adaptive, strategies play in PagerDuty’s sustained growth.
When it comes to SaaS, strategic planning isn't just something you do once a year and forget about. It's a constant cycle of adaptation.
This industry moves quickly—new competitors show up, customers' needs evolve, and the speed of innovation can sometimes feel like a blur. So, if you want to keep up, your plans have to move just as quickly; they need to pivot as the market demands. But with a landscape as volatile as SaaS, how can you plan just enough without planning too much?
Recently, two experts in this field – PagerDuty’s VP Sales Strategy & Analytics, Michele Prashaw, and Endgame’s Head of Growth, Minami Rojas – met to dive deep into this subject.
For almost seven years, Michele has been at the helm of PagerDuty's go-to-market strategy, a vital behind-the-scenes role that has played a significant part in their growth. But even before joining PagerDuty, Michele forged an impressive career path, marked by her natural gravitation toward data, analytics, and systems.
She began her career in the oil and gas industry, transitioning to on-premise software with JD Edwards. She then spent time at IHS and Ventyx before moving into SaaS with Dynatrace (formerly Keynote Systems).
In their one-on-one chat, Minami and Michele discussed how PagerDuty optimized its sales organization to reframe its product-led mentality using a simple (but adaptable) strategy.
Evolving from product-led to a joint product-led and sales-driven GTM is a little like navigating a maze. You've got a goal in mind, but as you make your way through, new turns and corners spring up, keeping you on your toes.
And Michele experienced exactly that when joining PagerDuty. When Michele stepped into the PagerDuty arena during its Series C funding round, its main strength lay in its product. Customers were flocking in, enticed by the innovative offerings, but PagerDuty was only just starting to dip its toes into the world of sales-assisted models.
So, naturally, like any company in hypergrowth, there came a point when PagerDuty had to switch gears and cultivate a robust sales-assisted organization, complete with a supportive cast around the sales representatives.
It was already a heavyweight contender in the mid-market space, also flexing its muscles in the billion-dollar customer ring (especially among the high-tech companies on the West Coast). But to further this success, Michele understood the need to push the boundaries of comfort – to adapt and evolve PagerDuty’s sales approach.
She needed to further evaluate the expansion of PagerDuty’s sales motion and most importantly identify where to invest resources for sustainable growth. “There were two big pieces to that,” Michele explained. “How do we meet the customers where they are, and how do we build a sales organization that would support that?”
Finding a viable solution only got more difficult the deeper she dug, so she broke it down into smaller chunks and got back to the basics. “We had to look at the overall strategic plan,” Michele said. “In our case, we had to ask, ‘How big is the market? How many developers are in that market? Which countries operated really well with SaaS-based companies in the United States?’”
The result of asking these questions? A bold and audacious expansion into Europe and Asia about a year and a half into their sales-driven journey. It was both exciting and challenging, requiring meticulous planning, assessing market sizes, and understanding the potential of these new markets. But this strategic groundwork ultimately laid the foundation for their operational plan: shaping hiring strategies and the distribution of sales territories.
“How do we meet the customers where they are, and how do we build a sales organization that would support that?”
With any global expansion comes the need for organized optimization. At PagerDuty, this meant structuring the sales organization into three pivotal tiers, designed to cater to three distinct market segments:
This structure, although maybe a bit more complex than the traditional sales-led organization, allowed PagerDuty to allocate resources more effectively and play to its strengths in each market. As a result, PagerDuty has more advanced customer segmentation, dividing their billion-dollar accounts among several field-facing reps.
These reps focus on expanding the "PagerDuty Operations Cloud Platform," a comprehensive suite of products, into its existing customers. The team utilizes the suite of products to drive engagement across teams, fostering cross-functional adoption, while simultaneously capturing new customers, primarily through their incident response and automation products.
With this not-so-secret weapon at their disposal, PagerDuty evolved from a single-product incident management firm to a multi-product platform, offering additional functionalities including Automation, AIOperations, and Customer Services Operations. And by expanding their target audience with the introduction of the Operations Cloud, PagerDuty actually maximizes their customers' performance across all digital platforms.
But it was that performance maximization that led Michele to ask two key questions:
The truth is: as product offerings grow more and more diverse, you can’t treat your customer base as a monolith. Here's where PagerDuty’s strategic pivot came into play.
With a diversifying platform and an ever-widening customer base, Michele highlighted PagerDuty’s strategic shift to distinctly approach developer engineers and IT engineers. “There are lots of tools in the market that help you enrich data and better understand what customers look like,” Michele explained. “But we've really fine-tuned our focus around DevOps, ITOps, and Customer Success.”
That’s right; more isn't always better. Whether it be in market penetration or tool selection, a focused strategy aligned to agreed upon opportunity for improvement is the best path forward.
While early-stage companies might be tempted to throw tools at every problem, it’s more advantageous to take a good, long look at your operational maturity and carefully evaluate each tool’s ROI. And that’s not just about monitoring KPIs or traditional metrics. In reality, it's about actual usage and adoption. Everyday use by the team is the real test of a tool’s value.
Ultimately, it boils down to balancing your investment in tools with simplifying interfaces for the sales organization. “You could have the best-in-breed tool, but if the sales organization isn't using it, it doesn't matter,” Michele said.
As an operator, if you're questioning a tool's usage, try canceling it. The sudden absence of a valuable tool will spark an immediate response, providing a clear measure of its importance. Of course, this is a last resort, but it emphasizes the point that tools should be seamlessly integrated into the workflow and not just a flashy feature that goes unused.
After all, the internal operational management of numerous tools can be a huge burden, both on time and resources, particularly as the number of tools increases. This situation often creates unnecessary noise for the end users and, in Michele's own words, makes finding the "single version of the truth" a bit of a struggle.
In a diverse role that straddles planning, strategy, and operations, allocating your time can be, well, tough. Luckily, with the structure of the PagerDuty team, Michele spends the majority of her time on strategic tasks.
Specifically, she focuses on forecasts and the metrics that support them. And with all that scrutiny comes a boatload of wisdom, both of which assist in the transition to the ‘rolling thunder’ planning approach. Instead of an annual plan, she strives to focus on the next four to six quarters in her projections which, she finds, is much more adaptive than the typical annual planning cycle.
Of course, it’s not easy. “It's a beast in its own way because it covers hiring strategy, investment strategy, deployment of sales, quota roll up of targets, and defining of comp plans,” Michele explained. “But those are the kinds of things that always tend to fall my way, because of my operations and finance experience over the years.”
Operations serve as the glue that binds different functions. And an effective operations leader is one who can interpret and communicate problems and solutions between technical resources and business stakeholders. This ability to bridge gaps and integrate functions is crucial in a strategic role. Diverse experience, ranging from marketing ops to stints in business systems, equip you with a unique ability to 'speak the language' of various domains.
But how do you acquire this skill set? Well, Michele attributes her proficiency to actively engaging in the details of her role. In fact, she advises early career professionals to take on work that others might avoid and to embrace the opportunity to learn and grow, even if that means making mistakes along the way.
“It's all about getting your hands dirty, getting in and participating, making mistakes, acknowledging when you're failing fast, and pivoting quickly,” Michele emphasized. “There's no better teacher than failure.”
“It's all about getting your hands dirty, getting in and participating, making mistakes, acknowledging when you're failing fast, and pivoting quickly. There's no better teacher than failure.”
Part of this learning curve involves cultivating a deep understanding of compensation and its role in driving employee behavior. It goes deeper than just exchanging some money for services rendered; it's the very crux of incentivizing and shaping employee behavior toward achieving the company's goals.
According to Michele, this insight early on became a valuable tool throughout her journey, allowing her to strategically design compensation plans that align with the primary behaviors necessary for enhancing business performance. And that all came from direct conversations with executive and senior leadership teams. Open dialogue, especially in terms of compensation planning, can make or break your company’s future goals by identifying the most important tasks in the present.
But even with all that stakeholder input, remember to keep it simple. You can easily disrupt a compensation plan by trying to incorporate too many elements into it.
Open dialogue, especially in terms of compensation planning, can make or break your company’s future goals by identifying the most important tasks in the present. But even with all that stakeholder input, remember to keep it simple. You can easily disrupt a compensation plan by trying to incorporate too many elements into it.
That means that even if you face some resistance from executives who want to include every job role in the compensation plan, focus on employees' primary roles. A compensation plan should be centered on an employee's primary job function rather than the peripheral duties they perform in support of others.
So, in her experience, Michele has found that sticking to two or three key metrics is optimal for driving the right behavior. Adding more metrics only causes confusion and dilutes focus, leading to inefficiencies in business operations.
While sales representatives should be supportive of various motions within the company, their primary responsibility should be – you guessed it – selling. Let the management of churn, for example, be primarily handled by the Customer Success group.
With that, Michele closed out by highlighting the importance of transparency and communication when managing compensation plans. The livelihood of the employees is at stake, so you must have an empathetic understanding of their positions – you can’t work in operations without some degree of appreciation for salespeople.
After a short stint in Business Systems Administration “I came back to operations because I just really love all the things associated with seeing salespeople and their leadership teams be successful,” Michele noted.
Here’s to you, sales folks!