A few weeks ago, at the Stage 2 Capital Annual Summit, I had the privilege of sitting down with three leaders whose careers I had the opportunity to be part of and have been admiring from the stands for many years. Amit Singh, former CBO of Palo Alto Networks and President of Google Cloud; Erica Ruliffson Schultz, former President and CRO, now a board director; and Doug Robinson, former Co-President of Workday and long-time operator and investor.
Our conversation was designed to be candid and practical, less about glossy career arcs and more about the truth of what it takes to grow from a GTM leader into an executive who can operate at board-level altitude.
What emerged was a set of hard-won lessons that cut through the mythology of the C-suite and speak directly to what operators actually experience at the top.
One of the first misconceptions I raised to the group was a belief I see often among GTM leaders: If I just keep performing, the promotion will come.
Amit didn’t hesitate.
He said the most significant misunderstanding is thinking that effort alone is enough. Everyone at that level is already operating at maximum intensity. What differentiates an executive isn’t the grind. It's the ability to shift from functional execution to enterprise leadership.
That shift requires:
As Amit put it, “If you’ve only ever run your functional system or process, you haven’t yet built the muscles that the C-suite depends on.”
At Stage 2 Capital, we see this transition across our portfolio regularly. The leaders who thrive are those who look beyond their swim lane well before they’re invited into a new one.
Erica further punctuated the learnings of this topic: the identity shift that happens the moment you take a seat at the table.
“In the C-suite, you are a member of that team first, not the representative of your function,” she said.
This sounds simple. It isn’t.
For many high-growth operators, loyalty to their team is a point of pride. But at the executive level, the job becomes fundamentally different. You can’t show up with the goal of “defending” Sales, or Marketing, or Customer Success. You have to show up to solve problems for the company, even when those decisions create friction with your own org.
Erica shared a story about working with two different CFOs at Confluent. They built such a trusted partnership that, even during years of hypergrowth, they never once had to escalate to the CEO for arbitration. Every conversation — every one — started and ended with a mutual check-in:
“Are you getting what you need from me?”
What she was describing is the executive version of “team-first,” one that requires maturity, humility, and a deep respect for your peers.
I asked Erica a question I’ve wrestled with myself: “What’s the cost of getting to the top?”
She answered with honesty, which visibly resonated with the room.
“You’re all in,” she said. “The commitment level is extremely high, and the personal tradeoffs are real.”
She talked about security breach incidents that derailed long-planned vacations, emergency acquisitions that require all-hands communication, board meetings that consume weekends, and the shared reality that both executives and their families must accept the intensity.
Amit underscored this when he described missing only one product number at Palo Alto Networks, only to face an army of analysts and reporters asking variations of the same question in public forums. The scrutiny is relentless.
What struck me was not the hardship, which every executive accepts to some degree, but the emotional toll each of them described and the deliberate effort required to stay centered. Success at the top isn’t just professional stamina. It requires psychological resilience.
I asked Doug, who played a pivotal role during Workday’s rise, how they preserved culture during periods of explosive growth. His answer surprised me in its simplicity and rigor.
“When politics and big-company behavior crept in, we called every manager in the company together, globally, for two days,” he said. “And the only thing we talked about was how we wanted to treat people, treat customers, and how we wanted to lead.”
No forecast reviews. No product roadmap. No pipeline discussions.
Just values, expectations, and behavior.
Workday didn’t assume culture would scale passively. They codified what outstanding leadership looked like, trained against it, and reinforced it relentlessly.
Doug also made a subtle but profound observation: Workday employees weren’t molded by the company’s values. They chose Workday because of them. The culture succeeded because it attracted people who shared the same instincts and beliefs.
For founders in our network, that point is critical: culture isn’t taught; it’s chosen. Your job is to define it tightly enough that the right people know it’s where they belong.
I asked Doug, “What’s the fastest way to lose your team’s trust?” He answered instantly:
“Be a hypocrite.”
His point was sharp: every problem you ask your team to solve requires tradeoffs. If leaders demand depth, rigor, and transparency from their people but fail to model them themselves, credibility evaporates.
“To be human is to be a hypocrite,” he said. “The point is not to be a big one.”
At the executive level, nothing undermines a team faster than leaders who don’t model the expectations they set.
One of the founding principles of Stage 2 Capital is that founders and GTM leaders deserve more than capital. They also deserve the knowledge, playbooks, and lived experience of operators who have been in the arena.
Amit, Erica, and Doug aren’t theorists. They’ve run multibillion-dollar businesses, navigated public-company scrutiny, and led organizations through cultural and operational turning points. Their insights weren’t philosophical; they were earned.
If there’s one throughline from the conversation, it’s this:
The journey from GTM leader to the C-suite isn’t a promotion; it’s a transformation. It demands new skills, a new mindset, and a new understanding of what it means to lead.
I hope that every GTM operator in our community takes one lesson from this discussion and begins building those muscles today, long before they’re tested.
That, ultimately, is what the Stage 2 network is here for: to learn from those who’ve scaled before us, so that each generation of leaders can grow faster, smarter, and stronger.