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The art of scaling up while avoiding anarchy


How do you scale a high-growth startup? It’s a challenge to maintain the agility, energy and engagement of an early stage company while adding the processes and structure needed in a larger organization.


In my opinion, scaling is an art, not a science, with challenges unique to every company and every leader. It’s something that not just executive leadership, but everyone in the company should think about proactively every day.


I’ve developed a simple guiding visual, which I share in my all-hands meetings as CEO at Coupa. It’s as a seesaw balancing on the tip of a triangle, with a slippery slope on either side.

On one side, you're sliding towards an overly structured, CYA kind of culture. On the other side, you're sliding toward anarchy. There are signs all along the

way as you begin sliding down too far on either side. 



On the scaling side, you begin to see long, non-productive meetings and email strings. It takes longer to get things approved, and there’s less common sense in the process. Roles are overly defined and you start to hear people say things like, "That's not my job” and “Because that’s the way we’ve always done it.”


On the agility side, you have no meetings and multiple people are doing the same thing, stepping on each other's toes. There’s also less common sense but in a different way; it’s a free-for-all environment. In a software company, that might come out in coding, where the same bugs are being fixed in five different environments.


Slide to the bottom on either side and it’s hell on earth.


To scale effectively, there has to be a constant awareness of balance and what it looks like, and it has to happen in a climate of mutual respect and alignment with common goals.


I remember one situation we faced we were scaling SuccessFactors that perfectly demonstrates this balancing act. There were eight of us--four of whom started with the company at the beginning, and four new hires who had come from larger corporations--and we were meeting to discuss a marketing campaign.


A competitor offering a similar product was lowering their prices. Up until then, we hadn’t done much to create awareness around this particular part of our offering and a lot of our customers and prospects didn’t even know we had it. We needed to get the word out quickly while also differentiating ourselves in order to prevent our competitor from gaining ground.


The startup team would have pulled together an email campaign, sent a PowerPoint out to the sales team and then started calling customers and prospects. This would have taken us a week, maximum.

The new team members were talking about putting together a committee to refine the messaging, taking a week to figure out what resources to assign to the project, debating the right serial process for delivery, what targets to hit and so forth. It was beginning to feel really heavy.


The startup people felt these new people were going to bog everything down in Gantt charts and take a month and a half to do what we could in a week.


The new people felt that we were running a mile a minute but not putting together cohesive messaging or following replicable processes and best practices. They felt like six weeks to execute a campaign was pretty darn agile. To the old timers, it was a lifetime.


It was a tense meeting, with constituents from the company’s past and future coming together, starting to get to know each other and find that balance. I was aware in that moment of how the two sides were pulling at each other. I could tell that the new people were thinking, "These people are crazy." And the old guard was thinking, "Oh, my God, is that what we're like now? Is this the company we're going to become?" The meeting ended in frustration on all sides.


We slept on it, met the next day and negotiated a compromise: we would get the campaign done in three weeks.


The new people realized they were going to have to roll up their sleeves, work faster and apply the 80/20 rule. The old guard realized that perhaps their sense of urgency could be dialed back a little in order to deliver something of better quality, which we ultimately did.


The positioning was tighter than in the past because we took the time to hammer out the messaging. The email campaign was targeted at the right audience--it wasn't just our usual 'spam everybody' blast. The time taken to train the sales team to deliver the positioning paid off; we found that when customers and prospects called in they were much better qualified.


We achieved a better outcome by carefully balancing agility and scalability. It was a negotiation, and the key to success was that it was carried out in a spirit of mutual respect.


It was important for the startup people to respect the experience of the new hires and consider the best practices that were being proposed, and for the new hires to consider that a campaign like this actually could and had been executed by a small team within the space of a week.


Building that campaign, the team really came together. The campaign did well, but more importantly, we established a working relationship where these eight people now had a framework for balancing agility and scalability in other situations.


As an early person, I learned that I needed to slow down a little and put a bit more structure in the way I was doing things. The new people were trying to learn, "How does it work here?"


If the company is to have any hope of scaling properly, the answer has to be, “Well, you're now part of how it works here. We didn't hire you structured thinkers to come here so we could continue to work in the same way we’ve been working. We added you to the mix to change the color a little bit."


It’s the job each individual within the company to blend the old and the new while maintaining this balance. You can shift more in one direction for a little while and you won’t slide off, but when you start getting too far down, you have to pull yourself up. And you have to pull each other up.  That is the fun and the beauty that comes with scaling a high-growth startup.


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Rob Bernshteyn

Rob Bernshteyn , Chief Executive Officer, Coupa


Rob is the Chief Executive Officer of Coupa, and drives the company’s strategy and execution. Rob has over two decades experience in the business software industry. He came to Coupa from SuccessFactors, where he ran Global Product Marketing & Management, as a member of the executive management team, as the company scaled from an early start up to a successful public company. Prior to that, Rob directed Product Management at Siebel Systems, where he helped build Siebel ERM into one of the company’s fastest growing product lines. Rob also did a stint in management consulting at McKinsey & Company, and spent four years at Accenture, where he focused on global SAP systems implementations.


Rob is a guest lecturer at Harvard and Stanford business schools, and a frequent contributor to Forbes and Fortune magazines. He can often be heard providing commentary on major news channels including Bloomberg and NPR. Rob earned a BS in Information Systems from the State University of New York at Albany and an MBA from Harvard Business School.