6 secrets of maintaining culture as your company scales, as told by a board member of JFrog and Rubrik

Yvonne Wassenaar, member of the board of tech companies including JFrog and Rubrik

It’s what you might call a champagne problem: A startup achieves product-market fit, their messaging is clearly resonating with customers, and sales is showing hockey-stick growth.

Suddenly, founders who shipped their first product out of a garage find themselves in charge of a company with dozens, hundreds, or even thousands of employees. Each phase of that growth presents a new challenge for a startup, as they try to retain the culture that helped them succeed in the first place, while also building up the process and discipline that will help them up their game and move to the next stage.

In a talk at Vertex Intersect ’24, our annual gathering of investors, founders, CEOs, and technologists, Yvonne Wassenaar laid out the ways that she thinks about how founders can meet the moment when it comes to growth. It’s something that Yvonne has seen many times over the course of her career — first as a top executive at companies including VMware, Puppet, and New Relic, and more recently as a board member at companies including JFrog, Rubrik, and Arista Networks.

Yvonne urges founders to think about company-building in the same way you do software development. When you only have two developers hacking away at a project, it makes sense to build a monolithic codebase without taking much time out for commenting the code or thinking about the architecture.

At a certain point, however, the team gets too big and the code gets too complex for that approach to be workable. Suddenly, it seems like a good idea to take a step back and break the app up into microservices so different teams can work on different things, or to invest more into documentation so onboarding and debugging get easier. Companies are the same way: When you hit certain levels of scale, the old way of doing things as an organization can increase the latency of decision-making and hamper performance.

Here’s some of Yvonne’s best advice for founders navigating those inflection points of scale:

• Don’t get ahead of yourself: When people join a startup from a big company, they often bring with them an idea of how things should be done. Founders may be tempted to adopt those ideas, but Yvonne warns against it. Just because something worked at Google or Microsoft doesn’t mean that it’ll work for your startup, in your market, at your scale. If you try to simply cut and paste the processes and procedures of much larger and more complex companies don’t expect success. You are more likely to only frustrate your employees and slow your progress. Yvonne urges founders to try to hire agile learners who can adjust to and tailor how the company is run to make the most of the flexibilities and constraints of startup life.
• If you have too many priorities, you have no priorities: As a startup grows, the founder loses their ability to oversee every single aspect of the business at all times. This is why it’s so crucial for leadership to clearly communicate a vision, values, and priorities: Getting this right helps employees to know what they should be doing with their time even when the CEO isn’t looking over their shoulder. Crucially, Yvonne says that companies should have no more than 2 or 3 super-clear priorities at any given time, alongside the leading and lagging metrics used to measure progress against them. Anything else, and it’s too general to be useful.
• Make the most of your budget: In the not-so-distant past, when investor money was cheap and plentiful, startups got used to throwing money at their problems. With cost discipline now more important than ever, Yvonne says that being thoughtful about how money gets spent can also be a powerful tool for maintaining company culture. Instead of overhiring or buying expensive new sales prospecting software, Yvonne says that founders should double down on high-performing people and processes, orienting around their own vision and priorities rather than opening their wallets and hoping for the best. You can’t spend your way out of hard problems.
• Be direct about ownership: Unless you’re careful, the size of any given meeting will scale alongside your headcount. Office politics play a role here, too, with stakeholders across multiple groups wanting their say on everything. Left unchecked, this dynamic can undermine the agility that is the greatest strength of a startup, as almost every decision ends up being made by committee. The antidote is for the CEO to be very clear about which parts of the organization have ownership of which decisions, disregarding any political considerations. The meetings get smaller, the decisions get faster, and overall clarity goes up.
• Run experiments: Yvonne says that startups are sometimes too quick to abandon the old way before trying something new. In much the same way as web developers run A/B tests to figure out how to maximize app engagement, Yvonne says that startups can apply that same methodology in fields like sales and marketing as well. If you want to test out a new sales playbook, for example, break off a chunk of your prospects into a test group and see how it performs there before rolling it out to the rest.
• Play to people’s strengths: In a startup’s early days, it tends to attract generalists — people who may be good at a lot of things, but exceptional at only one or two. As more people join up, there’s an opportunity to have each member of the team focus more firmly on their respective strengths, taking everything else off their plate. The hazard here is that it can feel like a demotion, particularly if you’re taking away some of a manager’s functional responsibilities. But Yvonne says that if leadership communicates clearly how leaders are trading off functional responsibilities for managerial empowerment over a discrete piece of the business, it can be a win-win for the manager and the company. The highest performers tend to rise to the occasion.

On a final note, Yvonne also talked up the benefits of executive coaching for business leaders. Yvonne says that books and videos on management are too general to be very helpful once you hit the C-Suite, but a coach can give you the personalized feedback you need to grow.

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