Sentry is one of those companies that doesn’t just talk about being developer-centric—it lives and breathes it. In a recent Breaking Changes episode, David Cramer, co-founder of Sentry, reveals how their unwavering belief in building “for developers, by developers” shaped their trajectory. Let’s take a deeper look into the principles that drove Sentry’s evolution, the tough decisions they made, the lessons learned, and why clarity of vision is crucial when scaling.
1. The developer-centric approach in action
From a simple insight to a driving force
Cramer describes Sentry’s foundational thesis as “for developers, by developers.” This seemingly straightforward idea became Sentry’s competitive edge. Unlike many monitoring tools tailored for ops, Sentry focuses on putting actionable insights directly into the hands of developers, who are the ones responsible for introducing and fixing errors in the software they create.
This approach builds on the idea that the people closest to the problem are often the best positioned to solve it. By building tools that empower developers directly, Sentry ensured their solution felt intuitive and necessary. This cemented its place as an essential tool for developers.
Advice for leadership: Focus on creating products that resonate deeply with the primary users by empowering those closest to the problem to solve it. Avoid diluting your product’s value by trying to cater to too many stakeholders—this approach will result in a more compelling and user-centric experience, ultimately strengthening your product’s market position.
Right place, right time, but also intentionality
Sentry’s early investment in JavaScript was partially by design and partially by luck. While the rise of React made their decision look brilliant, Cramer points out that the real triumph was in doubling down on what was working, even if it wasn’t the original intention.
This adaptability turned an unexpected opportunity into a core strength. Luck often favors those who are prepared to recognize and act on it. Sentry’s ability to lean into what was working, rather than rigidly adhering to their initial roadmap, became a pivotal driver of their growth.
Advice for leadership: Embrace flexibility and responsiveness alongside intentional planning. Be prepared to recognize and act on what is working, even if it wasn’t part of the original plan. Sometimes, the most impactful growth comes from the willingness to adapt when circumstances reveal a new direction.
2. Handling breaking changes and mistakes
When things go wrong
Cramer is candid about the biggest challenges being people-related. From early hires that weren’t a good fit to misjudgments about scaling teams, the toughest lessons often came from trying to force things that weren’t aligned with Sentry’s stage or values. One of his biggest regrets was trying to diversify too early by bringing in junior hires without the infrastructure to support them, ultimately setting them up for failure.
For startups in their early stages, it’s essential to find individuals who not only possess the right skills but can also adapt to the unstructured and fast-paced environment. The right hire can navigate the inherent chaos, while the wrong one can slow down progress.
As Cramer puts it, “Recognize when something’s not working and do something about it.” If you notice recurring challenges with hiring or retention, it’s time to revisit your processes, expectations, and the support structures you have in place.
Advice for leadership: Prioritize hiring individuals who not only have the right skills but can thrive in the chaotic environment of a startup. Avoid the temptation to diversify too early if you lack the infrastructure to support more junior hires.
Making hard decisions
Sentry’s core values went beyond the surface-level idea of being “nice humans.” They were crafted around the central belief that everything they do should serve the developer. This conviction allowed Cramer to make tough calls, such as refusing to pivot to enterprise sales or resisting pressure to offer self-hosted solutions. These decisions weren’t always easy, but they kept the company aligned with its mission.
Strong values provide clarity when navigating tough decisions, serving as a steady guide in moments of uncertainty. Being willing to say “no” to opportunities that don’t align with your core beliefs preserves the integrity of your product and brand.
Advice for leadership: Ensure that your company’s core values genuinely guide your decision-making, especially when facing tough choices. As a leader, be prepared to make difficult decisions that uphold these values, ensuring they are more than just feel-good statements but integral to your company’s strategy and culture.
3. The founder’s journey
Stepping down as CEO
A pivotal moment in Sentry’s history was Cramer’s decision to step down as CEO and bring in a more experienced leader. He recognized that the CEO’s role required a different skill set—fundraising, scaling an executive team, and growing the business—that didn’t align with what he enjoyed or was best at. This choice was ultimately about stepping aside to ensure the company had the leadership it needed for its next phase.
Advice for leadership: True leadership often involves knowing when to make space for others. Be willing to assess your strengths and the company’s needs, and make space for others when necessary to ensure the organization has the right leadership for its next phase of growth.
Finding the right CEO fit
Hiring an external CEO isn’t easy, and timing is everything. Cramer emphasizes that it’s critical to have enough business stability before making this change. For Sentry, waiting until they were in a growth mode meant they could bring in someone capable of taking them to the next level.
Bringing in an external leader requires maturity from the organization and the founder. It’s about finding the right person who complements your strengths and can take the company further. For founders contemplating this step, the key question becomes whether you’re truly ready to entrust someone else with your vision and allow them to guide the company forward. It’s a decision that requires confidence in the new leader as well as in your ability to step back and support them.
4. Building and maintaining a high-performing team
Hiring for impact
One of Cramer’s non-negotiables in hiring is finding people who can “drive” rather than just be “passengers.” In an early-stage startup, every team member must be capable of taking initiative, creating their own roadmaps, and pushing projects forward without micromanagement. This kind of autonomy and proactiveness ensures that the team is actively propelling the company forward rather than simply executing tasks.
Advice for leadership: In a fast-growing company, you don’t have the luxury of hiring people who need constant direction. Prioritize hiring individuals who are proactive, independent, and capable of driving progress without close oversight. Look for candidates who can identify challenges, devise solutions, and contribute unique perspectives beyond the basic job requirements.
Nurturing early employees and recognizing limitations
It’s noteworthy that half of Sentry’s founding team remains with the company, a rarity in the startup world. This success comes from allowing people to grow into roles while also being honest about when they’ve outgrown certain positions. Cramer emphasizes the importance of being transparent about these transitions, ensuring that team members have the chance to evolve or find new paths when their position demands different strengths.
Advice for leadership: Invest in the growth of your early employees while maintaining transparency about role transitions as the company evolves. Regularly evaluate whether team members are still in roles that align with their strengths and the company’s needs. True leadership is about ensuring that each person is positioned where they can make the most meaningful impact.
The art of intentionality in tech leadership
Sentry’s journey underscores a powerful truth for tech leaders: success isn’t about being perfect or having a flawless plan. It’s about having the conviction to stay true to your vision, the courage to make tough decisions, and the humility to recognize when you need help.
For senior leadership, this journey prompts some key questions:
- Do your company values have the strength to steer you through the most challenging decisions?
- Are you prepared to embrace change, even if it requires stepping back or admitting when you’ve made a mistake?
- Are you surrounding yourself with a team of self-starters who not only align with your vision but are capable of driving it forward?
Sentry’s story isn’t a template, but it acts as an invitation to adopt a mindset rooted in intentionality, resilience, and unwavering focus on what matters most. By staying true to its thesis and values, Sentry has become both a developer tool and a developer-centric movement, offering valuable insights for any tech leader aspiring to create lasting impact.
For more of David Cramer’s insights, be sure to check out the full episode, “Most Founders Make the Same Mistakes: Brutally Honest Truths from Sentry’s David Cramer.” Learn more wisdom from industry experts by subscribing to Breaking Changes on Apple, Spotify, and YouTube.