Lessons learned over a career of saying yes with Jon Michaels
Jon Michaels began his career in the Marines, flying helicopters and learning early what responsibility actually feels like. The military provided structure, a clear chain of command, and the opportunity to operate under pressure. It also gave him something less visible: comfort operating in ambiguity and accountability.
From there, his path wasn’t linear. He tried, and ultimately stepped away from, a 100+ year-old family jewelry business, moved into energy, and eventually into tech. When he joined Volta Charging, it was a 25-person Series B startup with an ambitious mission and very few systems in place.
Over seven and a half years, Jon led supply chain, operations, network development, regional general management, and the people function. He saw the company through Series C and D, a SPAC at the height of the 2021 market, a near-bankruptcy moment, and ultimately an acquisition by Shell.
The throughline wasn’t a title. It was a willingness to say yes.
In this spotlight, Jon shares the lessons that shaped his approach to operating, and why the strongest operators think bigger than their function.
Lesson #1: Don’t shrink yourself to your job description
When Jon joined Volta, he came in as Head of Supply Chain. The company was small, infrastructure-heavy, and still figuring out how to operationalize a big vision.
Soon, the business needed tighter coordination between vendors, construction, and ongoing maintenance across markets. Within a couple of months, his scope expanded to include Operations.
Four years later, the challenge looked different. Capital expectations had increased. Go-to-market needed more rigor. Site selection had to become more data-driven. Sales, planning, and execution needed to sit closer together. So Jon helped build a new Network Development function, integrating those pieces under one umbrella.
Later, as expansion moved beyond the Bay Area mindset, he built a Regional General Manager structure to push decision-making closer to local markets.
Then in 2022, when executive turnover accelerated and the company lost seven C-level leaders in a matter of months, the need shifted again. Stability and continuity mattered. Jon stepped in to lead People and HR.
None of that was in the original job description.
Many operators unintentionally box themselves in. A title becomes an identity. Over time, that identity can start to feel like a boundary. Jon’s transitions were possible because he never let his function define the ceiling.
Saying yes didn’t mean agreeing to everything. It meant recognizing when the company had changed and choosing to expand alongside it.
Takeaways:
- Career paths don’t always show up on an org chart.
- Being company-focused unlocks invisible paths.
- Generalist skills compound over time.
Lesson #2: Say yes to the inflection point
Jon’s first lesson in saying yes didn’t come at a startup. It came in the Marines.
Early in his aviation career, his commanding officer nominated him to attend the Weapons and Tactics Instructor (WTI) course, the most prestigious aviation designation in the Marines.
He said no.
He didn’t think he was ready. Others seemed more qualified. That decision stayed with him.
Years later, Volta’s CEO asked him to step in as Chief People Officer—at a public company, during a crisis, with no formal HR background.
This time, he said yes.
What changed was a simple realization: if someone credible sees something in you, believe them.
You don’t say yes to every meeting or random task. But when an opportunity changes the trajectory of your career, you bet on yourself.
Takeaways:
- Readiness often follows responsibility.
- Inflection points rarely feel comfortable.
- When someone credible believes in you, pay attention.
Lesson #3: After thirty days, you own the sheets
When Jon stepped into the Chief People Officer role, he inherited systems he didn’t build, decisions he didn’t make, and challenges that were already in motion.
There was a short window to ask questions, assess, and learn.
After that, it was his.
He referenced a story from Colin Powell: when a new commander takes over a unit, they have thirty days to reconcile inventory. After that any missing equipment, from an important rifle to a seemingly insignificant pillow case, belongs to them.
“After thirty days, you own the sheets.”
That philosophy shaped how Jon approached every role he stepped into. No disclaimers. No pointing back at predecessors. No, “that wasn’t my call.”
Ownership builds trust. Especially in a crisis.
Takeaways:
- Leadership requires absorbing responsibility forward.
- Blame slows progress; ownership accelerates it.
- At some point, you stop learning the role and start owning it.
Lesson #4: Operate across stages, not just roles
When he joined, Volta was a 25-person Series B startup still operating with Series A maturity. The mission was ambitious, but the systems were scrappy. The first stage was about scaling the base business. It was messy, physical, logistical work that required hustle.
With time, the company evolved.
Stage two was about professionalizing.
As capital requirements grew and expectations shifted, the business needed a more data-driven model for expansion. Jon helped stand up the Network Development function, bringing together sales, planning, and strategy.
He also built the Regional General Manager structure, pushing leadership into local markets like Boston, Dallas, Chicago, and Los Angeles. Success in San Francisco didn’t automatically translate elsewhere.
Scaling was no longer about speed alone. It required discipline.
Then came stage three.
In 2021, Volta went public through a SPAC at the peak of the market. For a few months everything looked strong. Then macro conditions shifted. Inflation rose. Capital tightened. The war in Ukraine disrupted markets. Growth became harder to finance.
In the second half of 2022, the company lost its CEO and President, followed by the General Counsel, CFO, CMO, CTO, and Chief People Officer. Seven C-level executives exited in roughly seven months.
Layoffs followed. Contingency planning began. Bankruptcy was a real possibility before the company was ultimately acquired by Shell.
That stage required something entirely different.
The leader who thrives in a 25-person startup sprint isn’t automatically the one who can guide a public company through executive churn and capital constraints. Jon believes great operators move across those stages, not just across functions. Different stages surface different weaknesses. They also reveal different strengths.
The operators who last aren’t the ones optimized for a single chapter. They’re the ones who can read context, adjust posture, and evolve as the business evolves.
Takeaways:
- Company stage fundamentally shapes leadership posture.
- Speed builds early momentum; systems sustain growth; steadiness carries crisis.
- Adaptability across stages is a defining trait of durable operators.
Lesson #5: The future belongs to expansive operators
Jon’s career has already required him to evolve across roles, functions, and company stages. The next shift he’s thinking about is different. It’s structural.
Technology is changing the shape of operating work.
Many tasks that once consumed hours are becoming dramatically faster. AI tools can generate analyses, summarize meetings, and surface insights in seconds.
Operators are still needed. But the leverage is shifting.
If someone defines themselves by a narrow band of execution, that identity becomes fragile as tools improve. Those tasks may still matter, but they won’t be the differentiator.
What remains difficult to automate are judgment and integration.
- Seeing how decisions in one function ripple across the business.
- Stepping into ambiguity when roles aren’t clearly defined.
- Helping teams navigate uncertainty.
- Making tradeoffs when information is incomplete.
- Carrying responsibility in moments that don’t fit neatly into a job description.
That kind of operating depends on judgment.
Jon’s trajectory reflects this. His value wasn’t tied to a single domain. It came from moving between supply chain, network development, regional leadership, and people leadership across different company contexts.
As operating work becomes more tool-assisted, that connective ability becomes more important.
Range creates resilience.
The operators who remain relevant will be those who can integrate across systems, synthesize complexity, and step into unfamiliar terrain as the business evolves.
Takeaways:
- Advances in technology will reshape execution, but not eliminate the need for leadership judgment.
- Operators who build experience across domains increase their long-term resilience.
- The ability to integrate, adapt, and take responsibility across contexts becomes more valuable over time.
Know your stuff, take care of your people, do the right thing
Jon’s leadership philosophy hasn’t changed across roles or stages. He wrote it down years ago:
Know your stuff.
Take care of your people.
Do the right thing.
Knowing your stuff means doing the work and understanding details deeply enough to make sound decisions. It also means seeing the broader system and anticipating second- and third-order effects.
Taking care of your people means remembering organizations are built through humans, not org charts. It requires patience, context, and sometimes restraint. Long-term trust often matters more than short-term wins.
Doing the right thing sounds simple, but it becomes clearest during difficult moments. It means making decisions you can explain—and live with—later.
Everything else sits on top of that foundation.
Refusing to be defined by one function ultimately rests on something steadier than ambition. It rests on competence, care, and integrity applied consistently, regardless of title.
Want to learn alongside operators like Jon?
Jon joined OG back when it was still Bay Area Operators and just a few hundred members comparing notes. He’s watched it scale while staying true to its core: operators helping operators.
His career mirrors that ethos.
Operators aren’t defined by one lane. They’re defined by how much responsibility they’re willing to carry. If you’re thinking about making yourself invaluable in your career, especially in a world that’s changing quickly, we’d love to have you join us.
If you want access to peers like this through chapters, events, and conversations that go beyond surface-level advice, apply to join Operators Guild.