7 min read

I’m at a reflection point in my career. As I consider my next steps and explore new opportunities, executive recruiters often pause at one line on my resume.
Thirteen years at Parchment.
Sometimes the question is curious. Sometimes it is cautious.
“You were there for thirteen years. Why?”
I get it.
In tech, long tenure can be mistaken for comfort. But that single line compresses a decade of reinvention. If you want more detail on how my scope evolved over that time, I wrote a previous companion piece, “So, What Does a VP of Software Engineering Do?”1
I did not spend thirteen years doing the same job at the same company.
I spent thirteen years inside a company that kept changing its scale, constraints, expectations, and the operating model required to win.
When I joined, Parchment wasn’t yet the dominant product in its market. We had a strong mission and real traction, but we were still earning broad market awareness and trust. By the time we exited, Parchment had become the category leader. That arc alone is rare to live through, and even rarer to help shape.
Most of my work lived in the hard middle of transformation: modernizing while the business is still running, customers still depend on the platform, and the organization cannot stop shipping just because you are improving the system.
What changed
Over those years, the technology and practices changed dramatically.
We moved from an on-prem mindset to cloud architecture, modernized from a monolithic structure to a service-based architecture, and shifted delivery practices from waterfall to Agile and flow-based execution with stronger automation and quality discipline.
In the final chapter, we also began integrating AI into engineering, moving from ad hoc experimentation toward more responsible, secure usage patterns and learning loops.
One of my goals through that journey was to make Parchment’s transformation referenceable, especially in an industry where many leaders talk about transformation while also trading stories about Agile failure.
We had real challenges, but we were building something that worked: a modern delivery system that scaled without sacrificing reliability.
Over time, we went from two major releases a year to a high-velocity delivery engine measured in several daily deployments and thousands of production changes annually, enabled by automation and operational discipline.
Personally, it meant going from an early-stage business when I joined to a company doing roughly $ 100 M in revenue by the time of the Instructure acquisition. Instructure publicly stated that Parchment was expected to contribute roughly $115M in revenue in 2024, while the announced transaction value was approximately $835M.2
Why I stayed
And that is also one of the real reasons I stayed.
Very few leaders get the opportunity to live inside a hypergrowth company long enough to help build it from early-stage reality to a high-scale, high-valuation outcome. Even fewer get to do it while the company repeatedly reinvents its technology and operating model.
That kind of experience is worth far more than a salary. It is a form of leadership education you cannot fast-track, and many people simply do not get the chance to see it through.
In high-growth environments, many capable leaders do not make it to later chapters, not because they lack talent, but because the company changes faster than roles and expectations can keep pace.
One more point matters: none of this happens without elite talent. I had the privilege of working alongside some of the best technologists and leaders I have ever worked with, people who could think, innovate, and execute under pressure while keeping quality and customers at the center.
The leadership lessons
My own trajectory mirrored the company’s evolution. I joined as a director leading a small team, expanded to lead all of engineering, grew into a Senior Director role, and in 2019, I stepped into the Vice President of Engineering role.
The early years were more tactical and closer to the work. The later years were heavily strategic, with a broader operating system to build and sustain.
Early on, the critical lesson was how to modernize without breaking trust. I call it the Legacy Mirror. Legacy systems are not just old code. They represent customer trust, business rules, and constraints that fund the next chapter. So instead of betting the company on a rewrite, we modernized in safe slices while keeping the platform stable for customers.
Between roughly 2014 and 2019, we had to find our footing. The business was growing, but the technology division was changing underneath it. Leadership changed. Talent changed. Structures evolved.
A big part of the work was building a vision-forward leadership team, clarifying ownership, and stabilizing the operating model enough to compound later.
As the stakes rose, my role evolved from executing tactics to executive operating. Multi-year strategy. Translating engineering decisions into outcomes. Operating under pressure without letting urgency turn into chaos.
One moment that still sticks with me was the demand to measure individual engineer productivity, such as sales or support. I understood the intent, but I pushed back hard. Software engineering is knowledge work with unknown unknowns.
Individual metrics like lines of code, commits, or tickets closed are misleading and create dysfunction. People optimize their personal scoreboard instead of helping the team, collaboration drops, and throughput often goes down.
Teams deliver software, not individuals. So I reframed the conversation around team flow, quality, and outcomes.
You know the cost of a team. Team and flow metrics tell you whether the investment is delivering predictably, stability, and customer value. Individual issues belong in coaching and accountability at the manager level, not system-wide individual scorekeeping.
As expectations grew, I also learned how to speak the language of valuation without losing the plot.
In many environments, EBITDA becomes a scorecard because it forces explicit tradeoffs and a cadence that reduces surprises. That changes how roadmaps get justified. Work needs to map to growth, retention protection, risk reduction, and margin improvement through lower cost-to-serve.
Depending on the stage of the investment and the time box for outcomes, the ratios and targets shift, and the tension between capital for growth and operational spend tightens or loosens. That directly impacts what gets funded, what gets deferred, and how quickly technical debt accumulates.
In that environment, technical hygiene becomes one of the hardest leadership decisions. It is easy to fund features. It is harder to fund refactoring, dependency upgrades, test reliability, and platform maintenance when EBITDA is tight. But ignoring hygiene creates compounding drag: slower delivery, higher incident load, and more effort spent keeping the system upright.
The only way to protect it in a time-boxed, target-driven environment is to translate hygiene into a business case: reduced cost-to-serve, fewer incidents, faster delivery, and avoided risk that would otherwise show up as churn, support cost, or missed commitments.
At the same time, you still have to keep the human system healthy. Meeting efficiency demands while sustaining engagement is not optional.
In the later years, a meaningful part of the strategy was building the people system: career paths, performance reviews, coaching expectations, and clearer growth signals that made it easier to attract and keep top talent.
We did not always pay the highest in the industry, but we maintained strong retention of top performers, and our division consistently carried some of the highest eNPS scores in the organization.
But none of it matters if customers are not winning.
Putting the customer first is not a slogan. Transformation only counts if customers benefit while you are changing the organization. If quality drops, satisfaction drops. If you start losing customers, you cannot fund the next wave of improvement. The hard middle is learning how to change without breaking trust.
Another major part of the experience was M&A. I participated in technical diligence across multiple acquisitions and then helped integrate the teams and technologies afterward. Integration is where operating models get tested. Can you absorb change without breaking delivery, quality, or culture?
What I carry forward
The last point is this: digital transformation takes time, and it is never done. Modernizing architecture, delivery practices, team design, and culture is not a one-year project. It is reinforcement, iteration, and rebuilding what breaks at the next scale.
The work will continue after my departure.
We built an operating system designed to survive leadership transitions, as long as the culture and talent remain strong. The next chapter is theirs to write, and they have the ingredients that matter: strong managers, durable practices, and a well-performing delivery structure. With that foundation in place, they can keep improving visibility into flow and outcomes and keep integrating AI in responsible, practical ways.
So the real reason I stayed is simple: it was compounding.
I contributed to shaping the strategy through major growth, shifting market demands, and changing stakeholder pressures, then live with the consequences and lead through the hard middle. That combination is rare, demanding, and deeply rewarding.
And my core belief coming out of it is simple: the hardest thing to build is not software. It is a system and culture that can absorb change and still deliver at today’s pace.
Author’s Note: The experiences referenced in this article reflect lessons learned across multiple organizations. Certain identifying details have been generalized to preserve confidentiality.
Poking Holes
I invite your perspective on my posts. What are your thoughts?.
Let’s talk: phil.clark@rethinkyourunderstanding.com
References
- Phil Clark, “So, What Does a VP of Software Engineering Do?” Rethink Your Understanding, August 21, 2025, https://rethinkyourunderstanding.com/2025/08/so-what-does-a-vp-of-engineering-do/
- Instructure Holdings, Inc., “Instructure Signs Definitive Agreement to Acquire Parchment, the World’s Largest Academic Credential Management Platform and Network,” press release, October 30, 2023, accessed February 28, 2026, https://www.instructure.com/press-release/instructure-signs-definitive-agreement-acquire-parchment-worlds-largest-academic






