Building a company for $0-$1M in revenue differs wildly from $1-10M ARR. And scaling from $10M to $100M is wildly different still. 

Sameer Dholakia, Partner at Bessemer Venture Partners with decades of operational experience, shares what you need to change as you scale from $10M to $100M ARR. 

The short answer is almost everything. 

Keep an open mind as you move into the next chapter of your company. 

“Everything that got you to where you are isn’t going to get you where you want to be,” says Dholakia. 

You Won’t Know The Names Of All Your Employees

Almost everything changes once you reach that scale of ten or tens of millions of revenue, including your leadership model. 

When you’re growing from $0-$1M, or even $1M-$10M ARR, the percentage of employees you’ll directly influence and interact with is really high. 

But as you push beyond $10M, you won’t know the names of all your employees, and that might feel a little weird. 

Once you get to $100M, you probably only interact with a single-digit percentage of the people in your company on any given week. 

Your leadership style has to evolve to match that. 

Leading by example in a room on a whiteboard or over a meal might happen at $1M-$10M, but from then on, you need to figure out how to scale your leadership. 

How do you scale leadership? 

Through ideas, stories, and anecdotes. As CEO, you’ll have to empower and enable the people in your organization to act according to your values without you being in the room with them. 

Teach them how to make the right calls, and guide them through your ideas. 

You Have To Think In Years, Not Weeks, Months, or Quarters

As a super early-stage startup, you’re thinking about what needs to get done this week and month to move the ball forward. From $1M-$10M, the aperture shifts from weeks to quarters and one year. 

But once you reach the $10M-$100M stages, you must stretch that way out and begin thinking about multiple years ahead. 

If you don’t, you’ll hit a massive growth wall. Nobody wants that. 

Ask yourself what you would need to add three years from now to hold a respectable growth rate.  

Do you want to know something wild? 

In your third year alone, you will add as much as your company has ever done in life to date. 

You will have to find a way to condense five years of work into 12 months in just a few years. 

So as you make decisions today — product and GTM investments, and everything else needed to scale —  you have to base it on new ARR years out. 

The Takeaway — You can no longer look at what will happen in weeks, months, or quarters. It has to be a multi-year view. 

The Rhythm Of Your Business Changes

Your operating model and communications architecture will change as you scale to tens of millions of revenue. 

From $1M-$10M, you probably started your annual planning cycle in November or December for January approval. 

At scale, the cycle moves further back in the year and needs to be robust. 

The way you communicate changes a lot too. 

One of the most complex parts of leadership at scale from $10M-$100M is figuring out how to orchestrate the individual behaviors of dozens or hundreds of humans so they all go in a straight line in the same direction. 

Without great leadership and clarity, everyone in the business is moving every which way because there isn’t alignment across every function. 

People Love Wearing Many Hats, And Now They Can’t

Managing people through big transitions is one of the more challenging parts of growing a company. As you scale, role specialization changes. 

People love startups because they’re fast, fun, and diverse. People enjoy wearing multiple hats. 

You need to move from athletes who are good at many things to a narrowing of the swim lanes as you scale. You want people who are deep experts, best in the world at what they do in one of those swim lanes, not all of them. 

You might notice some teammates struggle with this and that they’re better suited for an earlier stage company because wearing all those hats gives them the most joy. 

That’s ok. 

It’s a leader’s job to help people understand what a company needs at different stages in its life and help them find what fits their skills and interests best. 

A mistake many companies make between $10M and $100M is hiring for a role you need to be filled right now. 

Your company is growing so quickly that by the time you start the search, hire and onboard someone, and make them productive, six to twelve months have passed, and your business is different. 

Hire two to three years ahead of what you need now. Someone who has done the job at that scale has seen what great looks like, helps you look around corners, and brings the team along with them. 

Stay Nimble And Get Out Of Your Way

People leave as companies scale because they’re tired of slowness, the age-old cliche of a giant company that moves at the speed of a battleship vs. a startup speedboat. 

As you scale from $10M-$100M, your job is to maniacally focus on staying nimble and getting out of your own way. 

Your people need to be able to make quick decisions without you being in the room so they don’t get frustrated and you don’t become a bottleneck to growth. 

Dholakia likes the idea of one-way and two-way doors. One-way doors are hard to unwind, and two-way doors are easy to course-correct. Most decisions are two-way doors. 

Give your team the latitude to make decisions quickly. 

More Products, More Customers, More Complexity

When starting, companies usually have one product sold to one ICP in one segment. 

When you scale $10M-$100M, you have multiple value props, products, and segments. 

When you add more money, your business gets more complicated, and it’s harder for leadership to evolve. 

One question you should frequently ask yourself: Is my leadership team capable of managing, running, and growing this more complicated business? 

If they aren’t, that’s good to know. You can make the necessary adjustments to ensure a strong team to carry you toward your goals. 

The One Thing That Shouldn’t Change As You Scale

Let culture be the one that doesn’t change as you scale. Invest the time and energy behind scaling your culture because it will be one of your most competitive differentiators — if you do it right. 

Culture can get away from you quickly in a high-growth company going from $10M-$100M. 

You’ll be hiring dozens, if not hundreds, of people in the years ahead. What percentage of employees have been with you for over 12-24 months? That percentage will continue to shrink. Those around long enough are your culture carriers, and their number will get smaller and smaller. 

How do you scale culture? 

Say, for example, you have employees in a room, and they see a behavior that’s incongruous with your company’s values, and no one calls them out. Everyone around them will take that as approval that the behavior is ok. Culture starts to slide. 

Even if you have it written on the walls, people will pay attention to how people act every day as their truth of what is and isn’t ok. 

The only way culture scales is if leaders are driving it home for every single teammate that joins. 

Dholakia would go to every onboarding session and talk about culture, imploring employees to be a steward of the culture, celebrate the people living it, and call out deviations. 

It’s the quickest way to destroy a culture if they don’t. 

Why does culture matter? 

Because it helps you reach your goals more smoothly. Imagine you’re in a rowboat, and everyone’s oars hit the water at the same time. You’ll be gliding across the water. 

But if everyone’s oars hit at different times, you’ll spin in circles and go way off course. 

The Takeaway 

What you need to change at $10M to scale to $100M will differ for every company. But generally speaking, you can expect to encounter most of these changes: 

  • Leadership roles shift as your company grows. You’ll no longer know the names of everyone who works for you. 
  • You have to play the long game. Think in multiple years, not weeks, months, or quarters. 
  • Your operations and communications architecture change, so you’ll need to plan ahead and ensure everyone is moving in the same direction. 
  • Role specialization requires helping leaders and team members find their roles in this new growth. Gone are the early days of one person wearing multiple hats. 
  • Stay nimble and get out of your own way. Empower and enable your people to make decisions without you most of the time. 
  • Ensure you have a team who knows what great looks like and how to manage and grow your company in this new chapter. 
  • Prioritize scaling your company culture. It’ll make for a better experience all around and will be a competitive differentiator. 


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