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Evolving Enterprise: Scaling as an Enterprise CEO

April 5, 2022

What does it take to be a great enterprise CEO? One key to success is hiring functional leaders who will execute on strategy, but who can also see around corners and adapt to change. 

We recently chatted with two CEOs who have grown their companies from the earliest days into thriving businesses: 

Check out their tips on managing through hypergrowth and supporting leaders at every stage, or watch the replay:

What early hires should founders focus on?

  • Choose people who love a challenge and who will push through when the going gets tough. Tell them they may fail, and double-check that they’re okay with that outcome. Early team members share a big risk—and an opportunity—with the founders.
  • It sounds cliche, but find people who are builders. The right first 20 people you hire should 10X your business in a year.
  • Ensure that at least one person on the early founding team is a great storyteller. Having a great product won’t matter if you can’t articulate its value to the market in a visionary way. It might seem counterintuitive to put marketing first, but for enterprise companies (especially product-led ones), getting developers to believe in your story is what creates the market for your product.  

How should founding team roles be divided up? 

Assess each person’s skill set, and figure out where they can add the most value. Don’t worry too much about titles, but instead think more about roles and responsibilities.

Be intentional about who will be responsible for which decisions. For example: One person might make the decisions around which customers to target, another might own marketing decisions, and another product. 

Remember: A company is like an orchestra, and you need different people in different positions to make the music happen. Finance is no less important than marketing, product, or engineering. Accept that your company is made up of many intricately connected systems, and then find people to lead each system. 

How can functional leaders help drive growth?

Hire functional leaders in early days who are open to direction, because these people will be your arms and legs. You need to be very direct with these hires and not afraid to tell them “this is how it works.” That can be uncomfortable, but it’s important to ensure early leaders get your systems up and running.

Once growth is humming, then hire people who are self-directed doers in their disciplines. Ask them how they plan to approach something, assess metrics to their plan, and then let them do their thing.

Great functional leaders evolve with the company. CEOs should work with leaders to craft a framework for each function, which will change over time, and then support them to succeed.

What are the ideal traits of a senior hire? 

People who have been at a rapidly scaling SaaS company are invaluable. Maybe they worked at or Marketo, or they grew an enterprise startup from the ground up. Pick leaders who know the SaaS playbook.

Make sure the experienced leaders you hire are flexible. Sometimes, an executive will need to unlearn something they did one way at a previous company.

Pick people who move fast and execute quickly. Your best leaders should ask: “Why can’t we get this done today?”

Intellectual curiosity is the most important attribute of any leader. Make sure any key hire is genuinely curious about your sector and loves learning.

How can founders hire in a tight talent market?

When interacting with candidates, play your best hand. Don’t pretend to be a company that’s great at everything, but instead double-down on your strengths. For example, the early days of any developer-driven company should be centered around creating tons of educational content for the developer community. If you do that, developers who resonate with your vision will come to you.

Hire for each stage. You’ll want different people for the early market—these people are your risk-takers and visionaries—than you will want for the “messy middle.” That’s when you need folks who are doers and organizers. 

Do core values still matter while scaling?

You have to define a true north, and live it every day. Otherwise, how will you convince great people to leave their cushy jobs and take a chance on your startup? Here are three principles to lead by:

  • Your values should guide your company’s goals. Set team goals that everyone can work together toward achieving, and then celebrate together when you get there.
  • As a CEO, don’t become complacent. Survey your employees anonymously at least twice a year to ask for feedback on how you’re doing, especially whether they believe you’re living the values you espouse to. Then share that feedback transparently with everyone in the company so you can be held accountable to your vision.
  • Don’t stray too far from the founder mythology, even when you grow into a company of hundreds or thousands of employees. The founders’ vision is the core of the company, and anything else feels fake. 

Any tactical advice on how to be a great CEO?

Write yourself a job description each quarter. Ask your team for feedback on whether it’s accurate and what they would change. Think of yourself as being on a quarterly contract so that you’re always executing in the here and now.

Go spend time with customers. Then go do it again. There is no better way to truly understand where your company needs to go.

Set your functional leaders up for success, and then get out of the way. Always let them know you’re there as a sounding board to provide feedback.

Solve problems within 12 weeks, but think ahead 36 months to anticipate what might be coming. And ask your customers, partners, and the press what they see coming, so you can identify your blind spots. 

Get more actionable advice in our Evolving Enterprise series: