As a technology leader guiding teams through the complexities of scaling and hardening systems, you face a unique set of challenges—especially during periods of rapid growth. In a recent Breaking Changes episode, Albert Strasheim sat down with Jean Yang, Head of Product - Observability at Postman to talk about some of these difficulties. Strasheim’s journey, from his days at Cloudflare and Segment to his current role at Rippling, is filled with insights into leading engineering teams through this phase. Let’s walk through some of the takeaways of their conversation for senior tech leaders looking to build resilient systems and teams capable of thriving amid hypergrowth.
Scaling through inflection points
A pivotal phase in a company’s development occurs when the initial systems, which were rapidly constructed to launch a product, begin to fail under the strain of growth. For leaders who join a company around the late Series B to early Series C stage, it’s not uncommon to encounter systems that can no longer support the organization due to the pace of expansion.
“What inevitably happens… is that all of the early systems spectacularly break down almost instantly because there’s so much growth. They were built quickly, they were built early on, and these version one systems reach the end of their design life in rather spectacular fashion.”
—Albert Strasheim
Advice for leadership: As your company grows, expect that the initial systems built to launch quickly will no longer support the increasing demands of scaling. Use this as an opportunity to lead through change by proactively identifying and addressing the need for infrastructure upgrades. Foster a culture of continuous improvement, encouraging teams to spot and resolve scaling challenges before they become critical. Guide your engineers to focus on “upgrading and fixing in place,” ensuring that key systems stay operational while being improved to handle future growth.
Cultivating a first-principles mindset
Strasheim’s early experiences, such as building systems from scratch in South Africa, allowed him to develop a deep, first-principles understanding of computing; breaking down complex issues into their most basic, fundamental elements and building solutions from these foundational truths. This hands-on approach laid the foundation for his ability to tackle complex data-intensive challenges later on.
“I had the opportunity as a young engineer to build that system from first principles. We spent a lot of time in the early days asking questions like, ‘How many bytes per second can we write through this hard disk? And how many bytes per second can we process through this core of the CPU?’”
Advice for leadership: Encourage a first-principles mindset within your teams by creating opportunities for engineers to break down complex challenges into their most basic components. Assign projects that require deep technical problem-solving, particularly to less experienced engineers, to help them develop a solid understanding of system fundamentals. This approach will foster stronger technical expertise, enabling your team to tackle more complex scaling issues as they grow in their roles.
Building high-performing teams
Scaling systems requires assembling diverse, multidisciplinary teams capable of approaching problems from different angles. Strasheim emphasizes the importance of blending experience levels, combining senior engineers with deep domain expertise alongside early-career engineers who bring fresh perspectives and unbounded energy.
“For some of these more complex systems, it’s really about assembling a pretty diverse team of generalists, and diverse along approximately every dimension. You sometimes need engineers early in their career that will run through walls and question assumptions just because they haven’t seen this before… Thinking about the team at Rippling, especially over the last 18 months or so, we have increased the number of more senior engineers on the team. There is something to be said for having built something once or twice before that at least looks like or rhymes with the next challenge. And then ultimately, I think you want to combine those groups together.”
—Albert Strasheim
Balanced teams composed of both seasoned experts and inquisitive newcomers foster an environment where assumptions are challenged, and innovative solutions are discovered. Studies show that teams lacking diversity tend to have a limited view of customer needs. This results in products that cater primarily to those with similar backgrounds, often failing to meet the broader requirements of their full user base (Hatch, 2022).
Advice for leadership: Develop a structured yet flexible team composition strategy. For example, create “pods” of 5-7 engineers, mixing early-career individuals with more experienced mentors. This structure provides mentorship opportunities while also ensuring a steady flow of new ideas and approaches to problem-solving.
Recruiting with an anti-sell approach
One of Strasheim’s key strengths lies in his ability to recruit top engineering talent for hard problems. He emphasizes the importance of storytelling in attracting candidates—clearly articulating the company’s vision, the technical challenges at hand, and the growth opportunities available. Interestingly, he also employs the “anti-sell,” where he openly discusses the potential challenges and chaos candidates might face.
“The anti-sell is just key. It can be quite intimidating initially, especially as you step into a new company. You’re like, ‘Hey, I desperately need to hire people.’ I’m probably going to paint them a rosy picture that always ends in tears. And then you embrace the anti-sell, which is basically to almost push the candidates away. And then the ones that fight to join you are actually the ones that are probably going to succeed because they really want to be there.”
—Albert Strasheim
Transparency around the potential difficulties of working at the company, balanced alongside a compelling narrative that includes the company’s mission and growth trajectory, helps attract candidates who are genuinely excited about overcoming these obstacles.
Advice for leadership: Develop a recruiting “sales deck” that outlines not just the company’s successes but also the tough problems your team is tackling. Use this as a conversation starter to engage potential hires in a dialogue about how they can contribute to solving these challenges. Authenticity in recruiting builds trust and attracts individuals who thrive in high-growth, dynamic environments.
Embracing change and pain as part of growth
In a hypergrowth environment, pain is inevitable. Systems, processes, and even team structures constantly evolve, often requiring individuals to adapt rapidly. Strasheim mentions that “every year or so, the company you joined a year ago is basically dead,” emphasizing the importance of embracing change.
Successful teams are those that embrace change and recognize pain as a natural part of growth. The individuals who excel in these environments are usually those who are comfortable with chaos and uncertainty. Research compiled by McKinsey backs this up—studies have shown that building an “adaptability muscle” leads to better performance, confidence, and creative output at work, along with physical wellbeing and overall life satisfaction.
Advice for leadership: Encourage resilience within your team by promoting a mindset of flexibility and adaptability. Provide opportunities for engineers to take on roles or projects outside of their comfort zones. This exposure helps them become more adept at handling the unexpected challenges that come with scaling.
Maintaining speed and execution as you scale
One of Rippling’s most remarkable achievements has been maintaining its speed of execution despite its rapid growth. Strasheim credits this to the company’s “founder DNA” and an intentional investment in tooling and processes that enhance productivity rather than slow it down.
Speed doesn’t have to be sacrificed as your organization grows. With intentional investments in tooling, automation, and process optimization, you can maintain—or even increase—your team’s velocity. A series of articles by Boston Consulting Group draws similar conclusions, noting that fast execution is inherently linked to a fast, adaptable strategy, which helps maintain alignment while granting autonomy to those directly involved with the work and the customers.
Advice for leadership: Conduct regular assessments of your team’s workflows to identify bottlenecks. Invest in automation and internal tools that reduce administrative overhead, enabling your engineers to focus on high-impact tasks. Encourage a culture where engineers continuously seek ways to work smarter and faster.
Structured mentorship and growth
Assembling a team capable of scaling systems is just the beginning. Strasheim emphasizes the importance of setting up high-potential engineers with the right mentorship and support structures to help them grow alongside the company.
“We actually were able to unlock a lot of productivity by just layering in some kind of mentorship bandwidth. Some folks with more experience in design and architecture, and then to some extent, having just a few of those people can suddenly unlock entire teams to produce really amazing work.”
—Albert Strasheim
Creating intentional mentorship structures accelerates the development of your engineers and prepares them to take on greater responsibilities as the company grows. Additionally, a 2022 report from MentorcliQ states that Fortune 500 companies with mentoring programs in place generate, on average, twice the profit compared to those that do not have such programs.
Advice for leadership: Implement mentorship programs where senior engineers actively guide less experienced team members. Establish peer groups, design review sessions, and regular knowledge-sharing forums to ensure continuous learning and growth.
Leading through hypergrowth with confidence
The path to scaling and hardening systems in a rapidly growing organization is fraught with challenges. As a technology leader, your role is to navigate this complexity, build resilient teams, and maintain the speed and agility needed to keep pace with your company’s growth. By fostering a culture of first-principles thinking, embracing diversity in your teams, and investing in mentorship and tooling, you can lead your organization through hypergrowth with confidence and success.
For more of Albert Strasheim’s insights, be sure to check out the full episode, “Surviving the Chaos: Leading Engineering Teams Through Turbulent Times.” Learn more wisdom from industry experts by subscribing to Breaking Changes on Apple, Spotify, and YouTube.