Journey of a Founder: Series A Is a Reckoning—Operator Imperatives for Getting to Series B
Hi there - I'm a startup fractional COO who works hip to hip with founders as their operating partner. I amplify founder contributions by serving as a thought partner and assuming critical and delegable growth and operations responsibilities, particularly for companies in the $1 to $10 million revenue range. Over 20+ years, I have worked on dozens of startups (Synervoz, Feldspar, Axiom, Spartan, IAN), helping build one industry-transforming business to exceed $100M in revenue and a second to (so far) nearly reach that very rare milestone.
Jimmy Malik and I hosted this second roundtable in our Journey of a Founder series in collaboration with the Operators Guild (OG), where we're both members. Our guest co-founders (and fellow OGers) were Alice Nawful, of Notabene, and Justin Etkin, of Tropic.
The roundtable video recording isn't available publicly; however, I have summarized some of the top insights for you here. I also recommend checking out the OG if you're a company founder, co-founder, or operator at a high-growth business looking for a like-minded community of peers.
We don't cover everything you need to know to run a business, but we cover a lot of ground. Enjoy.
Introduction
Scaling a startup from Series A to Series C is full of tough choices, shifting priorities, and relentless tests of leadership. What worked at Series A can fall apart at Series B, or later, in the face of increasing demands for growth, structure, and disciplined execution.
This post breaks down what it feels like, critical areas to focus on, and lessons every operator can apply. These insights aren't just for venture-backed companies either; they're relevant if you're the founder of a growing business that needs to evolve from scrappy, founder-led leadership to making major leaps in performance.
(This is Part 1. If you're looking for Part 2 on Series B → C, read it here.)What Series A to Series B Feels Like
You've shown notable progress with the business. However, it's not yet clear you're on a reliably upward trajectory. There's going to be a lot more fight before you can declare victory (or defeat). Founder-financed companies often find themselves in a similar spot after they've proven their business works when there's potential and the path forward isn't obvious.
I see this period as a reckoning.
The basics that got you here still matter: understanding customers, testing assumptions, making thoughtful decisions, hiring smartly. Capital in the bank doesn't change that; if anything, it raises the bar. What are you going to do with that money?
At the same time, the work itself shifts. The breadth of problems, the pace of decisions, and the complexity of the business all spike. One hour, you're deep in the weeds fixing a broken operational process; the next, you're selling a senior leader you want to hire on your vision. This context switching is relentless. And because the data you wish you had doesn't exist yet, you need to rely on gut feel over hard knowledge more than you like.
This stage also brings a psychological shift: Trust becomes an increasingly valuable currency. The only way you, the founder, can share the management burden with teammates is if you have trust in them and the way you work together. To reach this point, a high-performing company has likely tapped an operating partner to the CEO, allowing the CEO to promote the company vision and focus on strategy and top initiatives only they can lead. If this hasn't happened yet, and you want the business to continue to move forward in leaps and bounds, it's time.
Likely, you're gearing up to hire for other roles, too. In addition to filling staff roles to keep up with growth, you may be bringing on more experienced people who know more than you do in their area of expertise. That's the point. But it can still feel jarring when you're ready to make your first full-time finance hire, for instance, and you realize how much more they know than you do. It's humbling.
Meanwhile, your operational foundation gets stress-tested: finance, legal, HR, and other business ops. Building operations to date has been iterative, making trade-offs and putting together "good enough" processes to serve your current and near-term future needs. Systems or processes you justifiably deprioritized before might cost you time, money, and goodwill now. You may need to revamp what you had prioritized and put into place earlier, and quickly catch up on things you ignored or hacked together … or risk dragging down the business.
In this period, as well, unexpected and hairy challenges lurk. Every company has its version. The business is not entirely settled. You're confronting unknowns as well as potentially disruptive events in the external environment, like a shift in market demand. There's always something material still to figure out.
Was product‑market fit (PMF) real or a fleeting bump?
Is the market big enough to support your scale objectives, or you we about to hit a wall?
Are you ready for the larger customers and new segments you’re chasing?
One thing that's not unique to this period is the careful decision-making required around how to use your resources: Remember that cash in the bank? For a venture-backed concern, this is your latest round. For a high-growth business, it's your accumulated war chest. You'll need to make deliberate decisions between extending runway, investing in critical infrastructure, and accelerating growth.
Series A is about continuing to refine the business and building certainty while everything—your business model, your market, your product, your processes, your team, and you—is being stress‑tested. It's exciting. It's demanding. It's a trial that you need to survive to build and sustain a successful business that has a big impact on the world.
Read also: Journey of a Founder: A Startup Story
Top Imperatives
Remain customer-focused and dialed into the problem you solve for them. Stay curious. Treat PMF as a moving target. There may be a difference between the early signs of PMF (what gets you to a Series A) and the durable, scalable PMF you need to reach Series B and beyond.
Shift your time, as founder, from the early days, when you did it all. Ideally, you did that before now. Less time in the weeds, more big-picture leadership. You can't solve every problem.
As the founder, you need to reduce your information advantage by spreading what you know among the team. (It can feel scary.) The quality of your operational rhythm dictates how comfortable you may be staying out of the weeds. Bi-directional processes giving all parties the information they need will tell the founder where the team is headed. If that's the right direction, you'll be able to focus confidently on your uniue founder’s agenda. Low trust resulting from poor hires or operational deficiencies is often what leads to micromanagement. When this is all working perfectly, it can still feel stressful, since you aren't as close to the details of the business anymore.
Accept that your team is in a period of flux. You still need standout generalists, and you're also bringing on subject matter experts and possibly introducing different levels of seniority. It's going to get a bit messy. Don't let your ego get in the way of hiring people who outclass you. Be careful: It's tempting to over-title early hires or promote generalists too quickly.
The company may be transforming itself every six months. Don't let your leadership approach or the team fall behind. Pick a frequency (quarterly, for example) and conduct a holistic check-in on the current business needs and how you and your team is aligned.
What's working well?
What's not working?
What's missing?
Who can step in or step it up?
How do you fill the gaps?
Suppose someone isn’t scaling to match business needs. They may need additional support, or if the situation can’t be improved, you may need to n that case, acting sooner may feel uncomfortable than later, but it may be the right move.
Prioritize like your life depends on it. The team can't do everything that needs to be done either. Be explicit about what matters most right now. Consciously pick what you're going to knock out of the park, what's going to get midling attention, and what's less important. Be explicit about it. Decide how to sequence initiatives.
Keep ops lightweight but strong enough not to break. The startup debt that hurts the most isn't always engineering. It may be in finance, customer success, or another area. Stay alert. Invest in the key areas. Expect many of the ways you do things now will break, and you'll need to patch them up or replace them later.
Avoid this misstep: Growth is the ultimate imperative, but so is avoiding an existential crisis originating from the failure of the company's operations. Ask yourself: What do we need to be working on today that might not have an immediate impact but will be critical soon? Some improvements have long lead times. Plan the rebuild before events make change a crisis or impossible.
Read also: Defining our Terms: What is a Fractional Leader Anyway?
If you're in this stretch of business building (i.e., wrestling with growth, hiring, patchingor rewiting operations), I'm always up for a conversation.
Read Part 2: Series B to Series C—Scaling Challenges and Leadership Imperatives