Growing a startup from seed funding to Series D (and beyond) is a wild ride—and your executive team is at the heart of the journey. As your company scales, so must your leadership team. What works when you’re small and scrappy may not work when you’re expanding rapidly, bringing in bigger investors, and targeting new markets.
So, how do leadership roles evolve as your company moves from the early days of hustle to the later stages of strategic growth? Let’s break it down and explore what scaling a leadership team really looks like.
Seed Stage: Wearing Many Hats
In the early days, a startup often looks like an all-hands-on-deck operation. The CEO might also be the head of sales, the marketing director is figuring out product development, and everyone is pitching in wherever they can. You’re running on adrenaline, passion, and probably a lot of caffeine. At this stage, being flexible and taking on multiple roles is just part of the hustle.
Think of it as the Swiss Army knife phase. You need leaders who can do a bit of everything and are willing to jump into any challenge, but there’s a limit to how long this can last.
Challenges: The key here is survival and quick wins. The goal is to get through this phase by being resourceful and nimble. You need leaders who aren’t afraid to roll up their sleeves and take on whatever comes their way.
Growth Tip: Successful leaders at this stage have a growth mindset. As challenges pile up, they embrace them as opportunities to learn and adapt. Every task may feel like a stretch, but those who adopt this mentality are setting themselves—and the company—up for long-term success.
Series A & B: Finding Your Specialists
Once you’ve secured Series A or B funding, the game changes. Suddenly, you’ve got real capital to work with, and you need leaders who can own specific functions, whether it’s finance, marketing, or product development.
Here’s the tricky part: not all your early-stage leaders will be able to make the leap. Maybe your head of marketing was great at guerrilla campaigns in the early days, but now you need someone who can run a full-scale marketing operation. It’s a balancing act—do you bring in someone new or help your existing leaders scale with the company? As your executive team evolves from a group of generalists to functional experts, now is the time to start hiring specialists to fill in the gaps.
Challenges: The biggest challenge at this stage is ensuring your leaders can scale as the company does. Some may thrive, while others might struggle to keep up with the demands of a rapidly growing organization.
Growth Tip: It’s crucial to know when to hire senior leadership and when to help your current team level up. Understanding when to bring in new executive talent can make all the difference.
Series C & D: Leading Through Complexity
By the time you hit Series C & D, things are getting more complex. Your company is scaling rapidly, you have multiple teams working across different functions, and the executive team is taking on a more strategic focus. At this point, leadership is focused not only on managing daily operations within specific departments, but on building a network of cross-functional teams and executing long-term strategies. It’s all about steering the company toward its next big move, whether that’s preparing for an IPO, expanding into new markets, or making major strategic decisions.
Leaders here must transition from hands-on operators to strategic visionaries. They need to guide their departments toward sustainable growth while keeping the company’s long-term goals in sight.
Challenges: As teams grow, so does the complexity of managing them. Communication and collaboration between departments become critical, and it’s vital to have the right leaders in place to manage large teams and make strategic decisions.
Growth Tip: The ability to innovate and think long-term will define the success of your leadership team at this stage. Leaders who can balance strategy with communication and execution are essential for navigating the challenges of Series D and beyond.
Leadership Scaling is a Journey
Scaling a startup isn’t just about growing the business—it’s about growing your leadership team, too. From the all-hands-on-deck mentality of the Seed stage to the strategic, big-picture thinking required at Series D, leaders must evolve at every step of the journey.
Your company will only scale as far as your leadership team can take it, which is why you should invest in the growth of your leaders just as you invest in the growth of your business. If you’re looking for more insights, dive into Bolster’s Leadership at Scale report for a deeper exploration of this topic.
Unlock the Secrets to Building an Effective Executive Team
Are you looking to scale your business but unsure what leadership roles are critical at each stage of growth? Download our comprehensive Leadership at Scale report, where we explore the evolving needs of executive teams from Pre-Seed to Series D. Learn how to align your leadership strategy with your business goals and discover the CXO archetypes that will take your organization to the next level.
Download the report now and start building a leadership team that drives success.
