Journey of a Founder:Series B to Series C—Scaling Challenges and Leadership Imperatives
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.
In case you missed my first blog post on the messy middle between Series A and B, in this follow-up, we zoom in on what it takes to survive and scale between Series B and C, when expectations shift, systems strain, and leadership is under the microscope.
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.
I summarize the top insights for you here.
We don't cover everything, but we cover a lot. 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 2. If you missed Part 1 on Series A → B, read it here.)What Series B to Series C Feels Like
Series B is another test, a different kind of proving ground. The scrappiness that got your startup from zero to Series A, or your high-growth business to substantial annual revenue, is no longer enough.
You're not proving the business can work anymore; you're proving it can scale and operate reliably and efficiently without running off the rails. You need to do this with rigor without sacrificing speed. The stakes rise as customer numbers and expectations increase and the number of team members swells. If you have a Board of Directors or investors, they're demanding proof you're on top of things at a whole different level.
This isn't easy, in large part because the practices, habits, and ways of working that served the company so well through Series A may be becoming liabilities at Series B, which can feel disorienting. Being creative and scrappy isn't always enough anymore. Sustainable process-building feels different.
Leadership issues and people management are more stressful than ever. Delegating significant responsibilities to new leaders is an emotional test. Unnerving. Functional leaders are popping up and (hopefully) stepping up. Trusting and supporting new leaders while holding them to high standards is a delicate balance. Meanwhile, existing and new team members may be nursing bruised egos if they were passed over for a new senior role or managed, or they don’t get the exact title they were expecting.
For the first time, company operations take center stage, and ops is in the hot seat. Can they handle increasing complexity, rising expectations, and higher volume? Operational issues can snowball into an avalanche. Some teams are entering the Series B phase with weak systems that need upgrading. Others arrive with no real systems at all, having punted on operational investments after Series A. For the latter, it can be a brutal awakening.
Unexpected challenges arise at this stage, too. It could be growth concerns, team misalignment, or broken systems. Things that can create friction or stall progress. The issues may be different from Series A, but they are just as critical to overcome.
Finally, resource management is still in sharp focus. It's not just about growth. More parts of the business demand investment. So you need to decide what to invest in and when across the company to optimize revenue and keep the business humming. You can't succeed on the growth front if the rest of the system seizes.
Read also: Overlooked Traits of Successful Startup CEOs
Top Imperatives
Series B demands a shift: from chasing growth at all costs to building repeatable, sustainable growth that can scale without breaking the business. Companies can't simply continue doing what worked before; they must evolve their DNA to meet new demands. Embrace this reality.
Be deliberate about who belongs at the decision-making table with the CEO and COO. Your operational rhythm, how your team communicates, aligns (or not), and executes, will be tested hard. Scrutinize it for fractures. Line up the functions and teams behind this group.
Understand that you're building complete functions now. Structure and build a world-class team from the existing bench and new hires, believing in people, but not overbelieving, and drawing in newcomers who help, not hurt. You may need to correct Series A missteps. Some of your early stars may struggle in this new version of the company. They haven't failed, but needs have changed.
As founder and CEO, you've been out of the weeds for a while by now. Your COO has also begun to pivot in their role, and this will continue. They need to be more focused on prioritization, alignment, and accountability. They're no longer the single source of truth or the person closest to every operational detail.
Layers of leadership and cross-functional dependencies can create bottlenecks. You need to deliberately balance speed with alignment. Too much time spent on getting alignment, and decisions stall; too little, and the organization fails to make progress on what it’s decided.
Just as you were in the prior period, be honest about who fits in, and make the tough calls when they don't (with care and consideration). Putting the wrong people into the wrong roles may not cost you the business at this point, but it will come at a cost.
Read also: When Top Performance Becomes a Hiding Place
Triage broken processes and then revamp, rebuild, or build. Did you invest, soon enough, after your Series A, in critical systems you need now? Series B is when cracks stop being theoretical and start costing you real time and money. Avoid crashing out completely. Remember you're building for today and tomorrow.
Lean into data-informed decisions, but don't lose your agile instincts. The new systems and processes you're implementing are generating a vast amount of data. You need that to get your arms around what's happening with a business of this size, but don't let it drag you down; remember that you still need to be moving quickly.
Board expectations shift from a grand narrative delivered by the founder to hard metrics during this period. You can't just tell the story anymore. You have to show measurable, data-backed results. The Board will be looking more carefully than ever at those gorgeous financials prepared by your first, top-notch VP of Finance. Resource decisions are about growth and efficiency now. Can you show that you are scaling without overspending?
If you're strategizing your next phase of growth at your founder-led business, I'd love to discuss your plans.
Read Part 1: Series A Is a Reckoning: Operator Imperatives for Getting to Series B