Keep Your Feet on the Ground
Growing Without Getting Ahead of Yourself
Steve Heuring
There’s a critical moment in the life of a startup when the task list outgrows the core team.
You’ve onboarded customers. Revenue is coming in. Product adoption is increasing. Maybe you’ve raised a round and suddenly have enough money to hire people you couldn’t have imagined affording a year ago.
It took a heroic effort to get here. Now everyone has more work than they can handle, and the inevitable hiring sprint has begun.
That can lead you down the wrong path surprisingly quickly.
At this stage, it’s easy to think that you just need to scale what you’re already doing. But it’s also likely you don’t really have a scalable execution model. You’re still developing your understanding of who the ideal customer is, what their buying motivation is, what they find most valuable about your product, and how all of that turns into ongoing revenue.
On some level, you know that the motion you need to take you forward is different from the one that got you here. Inside knowledge, informal communication, and constantly figuring things out on the fly eventually have to give way to more repeatable ways of working.
You need to grow. The challenge is adding the right capabilities now without building too far ahead.
Don’t Jump the Gun
Your team is all asking for help:
“We need marketing.”
“We need someone to run sales.”
“We need an operations person.”
Maybe you do. But it’s worth backing up before giving the request a job title.
Suppose the team says it needs a VP of Marketing. What are you actually trying to accomplish? Maybe the positioning is unclear, the website doesn’t explain the product well, sales needs better materials, or there aren’t enough leads.
Those problems require different capabilities, and none of them necessarily require someone whose primary strength is running a marketing organization.
A startup in this phase often needs someone who can build and deliver the function before it needs an executive whose primary job is leading it at a much larger scale. Sometimes the right person can do both. The important thing is being clear about what is mission critical and what can wait.
And an executive hire rarely costs only the executive. Hire a VP of Marketing, and there is a reasonable chance the next conversation will be about the resources that VP needs to build the function properly. That may be exactly the right move. Or you may have committed to building a department before you were clear about the problem you needed it to solve.
A good test is asking yourself and your team, “What are our organizational goals in the next 12 to 18 months, and what is keeping us from getting there?”
Starting with the constraint tends to make the next decision a lot easier. The answer may be a full-time hire, outside expertise, a better process, or better use of the team you already have. Having this conversation as a group helps your crew think about priorities and get on the same page.
Stay in the Mix
At this point, everyone is wearing multiple hats, so there’s an understandable urge to hand things off. Some of that work absolutely should move to other people. Some of it is still informing how your business should operate.
Direct selling helps you understand who the decision makers are and why deals are won or lost. Customer support shows you where implementation gets stuck, how customers are adopting the product, and which features are having the most impact.
As you add headcount, those activities naturally start moving into dedicated roles. The risk is creating too much distance between the core team and the learning those activities generate.
The principle here is: Stay close to the initiatives that are still teaching you about the evolving needs of the business.
Of course, holding onto everything creates its own problems as well, and eventually becomes its own growth constraint. The key is finding ways to distribute the work while keeping the people making the fundamental decisions about the business directly engaged.
Check Yourself
As you build out the team, there’s a balancing act between hiring for what the endeavor needs today and thinking ahead to what’s coming next.
A senior candidate may show up who looks hard to pass up. There’s an obvious appeal in hiring someone who has led the function before, managed a large team, and worked at a company several stages ahead of yours. They may bring tremendous expertise, but they may also be a better fit for a business you won’t have for years.
What you may need instead is someone who can build the function while doing much of the work themselves. They can think strategically while still setting up the systems and building the initial processes.
This doesn’t mean every function should be built from the bottom up before you hire an executive. Some early companies need experienced senior leaders, and there are executives who are excellent builders. What you need to determine is whether the person fits the job and the organization you have now, along with the challenges you can reasonably see coming over the next year or so.
As the function matures, more specialization and executive leadership will make sense. The timing should follow the business, rather than the org chart you are projecting for the future.
Build for Today With an Eye on Tomorrow
This is a tricky point in a startup’s growth. The company is getting too large to run on informal communication and individual contributors simply doing whatever it takes.
At the same time, you’re still figuring out how much structure the business needs for the next phase. You want enough to keep growing without losing the knowledge, flexibility, and speed that got you this far.
That means making sure each new role or layer is solving a mission-critical business problem, rather than building around needs you expect a more mature company to have someday.
Keep your feet on the ground, and your head in the sky, but watch your step as well.