How to scale as a startup CEO from seed to Series A (and beyond)
If you’re a founder of a startup transitioning from seed to Series A and beyond…
What got you to this point isn’t enough to ensure success at the next stage. Some tips on taking the leap:
📅 Schedule a weekly co-founder sync
The easiest way to start is by scheduling a regular meeting with your co-founders focused exclusively on discussing the state of the company and the team — not the pressing sales deal or product challenge. Accountability starts here.
🏗️ Build a “personal board of directors.”
This should include 2–3 people who can evaluate your performance and give you feedback on how to be a more effective CEO/CTO. I’d try to find people who can fill three roles:
🔬 A peer founder who can provide a regular sanity check
You need someone who you can text to ask about how to handle a problem employee, where to find a good bookkeeper or thoughts on how to resolve a dispute with your co-founder.
🔭 A founder who is ~2 funding stages beyond you
The most useful find is a person who can do things like run through your board deck in advance of a meeting and help you spot major gaps/weaknesses before your investors do. This kind of “player/coach” is invaluable.
🛰️ A mentor who can provide a longitudinal assessment
Are you prone to getting stuck in ruts? Are you really growing your skillset? Someone who has known you for years and is more removed can provide key insights into your long-term development.
📤 Make a delegation plan
Like asking children to eat their broccoli, this advice is frequently given and rarely followed. Map out a process so that in < 12 months, you no longer have e.g. any day-to-day deliverables beyond holding your team accountable.
🔗 Network like mad
Make a list of the challenges and opportunities that cause you the most stress. It’s your mission to meet with as many people as possible who might be able to help you. Think broadly:
- Big Co. execs
- Service providers
- Technical experts
- YPO-style orgs
I know there’s always more work than people to do it, but the hour you spend at lunch with an advisor will almost certainly have a better ROI than the marginal work hour on a given initiative. But you must have delegated responsibility first or this will never happen.
👂 Listen to your execs
Great startups may have the rare advantage of being able to recruit from GAFA+ co’s. Often, the founders don’t take advantage of this. They can chafe against new execs and the emphasis on process, scale, and management they bring.
This is a huge mistake. While it’s likely true the exec won’t be a “startup person” your goal is to now graduate from being a startup! i.e. begin trading flexibility for planning, intuition for data. A huge amount of your time should be asking questions of these new hires.
How did Amazon think about X?
What was Facebook’s approach to Y?
You don’t have to implement every suggestion, but internalize these perspectives and figure out how the lessons apply to your company. What got you from seed to Series A will not get you to an IPO.
🆘 Consider recruiting a COO
If you feel well beyond your comfort zone, consider recruiting a COO. Some of the best companies of the last generation did this to great effect.
In total, you should expect to spend at least a day a week, and likely more, pursuing these objectives.
It may seem like wasted time, but I promise that if you don’t, your startup will languish. This work cannot be delegated, and it’s likely been delayed too long already.
At most companies, it’s abnormal for a person in their 20s or 30s to be a CXO — and for good reason. Experience is valuable. Most corporate execs aren’t ossified relics — try to find some of those canny operators who navigated tech shifts and macro shocks for decades.
A startup founder can become a world-class executive of a big company, but it doesn’t happen just because you convince a VC to invest $20M. There needs to be a concerted effort to embrace the learning curve. You are simply playing in a bigger league now.
Success at seed is typically based on your unique insights into an emerging space, and a healthy dose of hustle. Success at Series A (& beyond) is a function of the founder’s ability to scale the learning curve and better execute both old and pedestrian business functions.
Ideally, the boardroom would be a classroom. The VCs invested in your company should be eager to help their founders scale up. But hallmarks of a great leader are tenacity and curiosity, so don’t wait for your investors — Start scaling yourself today.
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