Talent That Scales: Make Yours An Organization Of Entrepreneurs

Advice for startups looking to staff up–fast.

Talent That Scales: Make Yours An Organization Of Entrepreneurs


Startups expect a lot of their people. They need to be able to work within the confines of a small company–be creative with tight budgets, willing to wear multiple hats, and eager to put in long hours. But they also need to be suited to big organizations; after all, most startups are designed to grow into big companies.

As the founder and CEO of one such aspirational startup,, I’m often asked how I balance rapid growth of company and team with getting the mix of people right. The beauty of creating a business that does things differently is that innovation doesn’t stop with the product. We, as leaders of these companies, have the rare opportunity to reinvent the hiring process. A trailblazing startup bucks convention, and building a team is no exception. 

At Betterment, we don’t seek to fill static roles. We look for people with complementary skill sets; people who can slot right into the team and fulfill multiple responsibilities. Ultimately, we just want people who can execute on our vision and bring their own critical thinking to the table. 

Complete the Talent Puzzle

Lots of startups begin with an original team of 2-4 people. In our case, a developer, a product lead, a lawyer and me, a banking and finance consultant. We launched at TechCrunch Disrupt in 2010 and immediately gained 1,000 new customers. It was clear we needed to staff up, and fast.

Luckily, we knew what we didn’t know and quickly identified the gaps–a shrewd marketing head and a whole team of developers who could bring our vision to life. Soon after we needed more bodies on customer service, product development, and to create a stronger brand and voice. 


We liken the hiring process to completing a talent puzzle. First and foremost, we look for absurdly talented people. Then we figure out where they fit into the team. It goes something like this:

1. Hire entrepreneurs: Entrepreneurs already possess the values, determination, and critical thinking to build successful businesses. They’re motivated, fast on their feet, and have original ideas. Entrepreneurs are smart people, but their drive is their biggest asset. Make them an integral part of your team and they’ll care about your business as much as you do.

2. Hire people better than you: Heading up a fast-growing company doesn’t allow you time to learn each and every facet in detail. You need to be able to trust the judgment and decisions of those you hire, and this only gets more important as you get bigger.

3. Look for flexibility: Our people have come from all over–banks, consultancies, and companies big and small. But they all possess the ability to respond to change and mobilize the necessary forces. Seek out people who welcome change and adapt easily. This is where you complete the puzzle: Harness their many talents to create new roles to fulfill your needs.

Holding on to Talent

Finding and hiring the right people is the first challenge, holding on to them the second. They’ve come to you because they see opportunity and inspiration in your company. Tap into those emotions to keep them motivated. I’ve found that entrepreneurs thrive under these conditions:

  • Communication: Align the interests of everyone in your company. It’s important for entrepreneurs to understand where their talents are most needed. Communicate your short- and long-term vision for the company so they can focus their efforts in the right place. 
  • Control: It’s important they feel important. People choose startups because they want to have an impact. Encourage individualism. Let people decide the best way to get your company to where it needs or wants to be.  You’ll find that not only do they give you their best work, they’ll also self-select, opting out of tasks they’re not right for and picking up positions where they can shine. It makes everyone accountable for their mistakes and success, and they’ll know they’re a part of something great.
  • Culture: In a nutshell: How do people feel when they are at work? Is their hard work rewarded and are their mistakes supported? Do they like their coworkers? Is it fun? Do they enjoy being at work? The answer needs to be yes.

Make It Scale

Create the framework and culture for a productive and positive business, and watch it flourish. Get these things right from the start. You’ll troubleshoot problems you’ll never know existed and you’ll have an army of evangelists on your side.

Navigate the talent puzzle and the last pieces will simply fall into place: a humming business and a happy team.

Jon Stein is the founder and CEO of Betterment. Passionate about helping people make smart decisions with their money, he founded the online brokerage in 2008. He is a graduate of Harvard University and Columbia Business School. 

[Image: Flickr user Steve Jurvetson]