What does it take to scale a team from 2 to more than 1,100 people in just a few short years? Hannah Seal, Partner at Index Ventures, chats with Job van der Voort, CEO and co-founder of Remote, about just that. Remote launched in 2020, just as the pandemic hit, and it continues to be the fastest-growing portfolio company in Index Venture’s history.

Remote started in 2019 with nothing: no money and not a very good idea. In 2020, they still didn’t have a finished product until May, when they onboarded their first customer. In 2021, they grew from 50 people to 650 people in one year, and now they have over 1,100 people in 170+ countries and tens of thousands of customers.

Let’s see what Job’s biggest learnings are during this wild ride of growth.

Founders Typically Evolve Over Time. Was That True For Remote?

It’s common for founders to evolve from the early days as people and leaders into who they are today. That hasn’t been the case for Job. “The role of the founder is always the same, of doing whatever you have to do to make sure your company grows,” he says.

He prioritizes and optimizes his day by focusing on the things that have the highest impact or are fun, and that never changes. Of course, the things that have a high impact are very different from the early days.

When you start your company, you ensure it survives at all costs. As it grows, it changes significantly, especially as you move from hiring people who can do everything to hiring more specialized roles.

Job Stopped Participating in Every Interview Early On

Many founders still interview everyone when their company is at 200 or 300 people. Job stopped when they were at 120 people, which is fairly controversial. What is the CEO’s role in hiring during different stages? A founder’s role in hiring depends on what you want to do as a founder and the impact you want to have as an organization. Job still does interviews for everyone, director and up, but not for the ICs and managers of ICs, for the most part.

When Remote had 120 people two weeks into 2021, they planned to scale to 600 that year. The VP of People at the time said, “I don’t think it’s doable for you to do 70 interviews a week.” And it was true. Many founders don’t have the capacity to evaluate how good a person would be in any particular specialist job when growing rapidly. At the same time, you want to give trust and power to people who recruit, and you do that by ensuring they understand what the culture is.

Your culture can’t be ephemeral, where only the CEO knows. The people doing the hiring need to be able to hire based on company values instead of the CEO bottlenecking the process because the culture is unclear.

Creating A Strong Culture When Everyone’s Remote

How do you create an incredible culture when everyone is remote? First, acknowledge that it’s different from working in an office together. You don’t want to recreate the office in a remote environment. No one wants to sit in real or virtual meeting rooms all day.

You have to be incredibly deliberate about the kind of company you want to build and the structure you need to give them to achieve it. Job and his co-founder first thought about what the scaffolding of a great culture is. In their case, they created a handbook with company values to guide the kind of people they wanted to hire and how they would treat each other. It’s also an important part of how they do performance evaluations.

The layers of cultural scaffolding include:

  1. Communication – Be transparent, direct, and clear. 
  2. Lower the barrier to connecting with each other with tools like Slack. 
  3. Give them money to meet up. 
  4. Treat people well. 

That’s really it. You want to try to create opportunities where people who are unlikely to seek them out can still connect outside of the context of work. You also want people having non-transactional conversations, where they’re talking just to talk rather than to get something completed.

If you treat people well and give them the tools to succeed, there’s not much in the way of developing a strong culture. Kindness is Remote’s first value “because I don’t want to work with assholes,” Job says. You establish that by firing people who aren’t treating others well. Then, building a welcoming culture becomes very easy.

The Difference Between Kind and Nice

Hannah asks how you balance a culture of hiring for kindness with the leadership team’s intensity for hard work, ambition, and getting things done. The answer is that kind is not the same as nice. You can be kind to someone by giving them very direct feedback.

You can be unkind to someone by being vague with the truth of things, and they’re left guessing or believing they’re doing a great job. You are kind by being clear about your expectations.

It’s important to establish that difference and reinforce that kindness is treating each other well. It means avoiding common communication methods of saying something harsh sandwiched between two nice things. You say what you need directly and honestly while being kind to the person.

How Can You Tell When You Have Product Market Fit?

As an early-stage founder, you’re usually finding a problem and building a solution to solve that problem. Over time, you establish product-market fit and determine how to sell at scale. At what point do you know you have product market fit?

When Job started but had no product yet, they would call prospects to ask what the problem was and then mostly sit and listen. Afterward, they framed the pitch to say how they were planning to solve that problem and what the prospect thought of it. This process showed the Remote founders that they would probably solve a real problem if they achieved what they were proposing.

Then the pandemic happened. Remote.com was a good domain to have then. There was overwhelming demand, and they only had a team of nine, including one support person and no salespeople. So that support person, Mafalda, started doing sales, too. She still works at Remote.

They ran out of Mafalda, who was working 20-hour days with everyone else, so hiring 50 more people like her was essential. Instead of fixing the pipeline so it was stable, they had to keep hiring people, which is why they grew so quickly.

That’s the long answer to knowing when you have product market fit. The short answer is that you know you have it when you get a paying customer and another before you even have a finished product.

How GTM Changes As You Scale

If you’re a technical founder or very involved with the product, it’s easy to underestimate how incredibly complex and detailed the workings of a GTM team can be in terms of marketing and sales (how you address the market, what channels you use, how you incentivize the sales team, what they do).

Initially, you have a small group of people who do everything. This phase is fun for many founders because they can be super involved. There’s very little technique and a lot of pure hustle.

As you grow, you hire specialists, GTM leadership, sales leadership, and others who have done this at a similar scale or in a similar market. There’s so much nuance to it, and you end up with an organization with many specialists and a very clear funnel where there are a million things you can do to make a meaningful difference in your business.

The biggest mistake Remote made in GTM was looking at what others were doing and trying to replicate it exactly. If someone else succeeds at some GTM strategy, you will, too, right? Not always. You have to think a lot about your own organization, how it is structured, and the best ways to incentivize people.

The When and What Order of Hiring Leaders

As your company grows, no matter what leadership you hire, your company will probably outgrow that leadership pretty quickly. Job always thought he’d hire a sales leader and be done with it forever. But his experience has been almost the opposite.

When your company grows quickly, it outgrows quickly. In the beginning, you hire for raw attitude and the ability to get stuff done. And then you start hiring more specialists.

The one trait you should always hire for, whether early-stage or mature, is the people who get stuff done. Someone can be a senior leader with really relevant experience, but they’re still get-stuff-done people.

The Most Transformative C-Level Hire for Remote

The CFO. If you hire a really good CFO, that person helps you figure out finances but also helps you deeply understand your business and drive significant change. Remote only hired their CFO a few months ago after a nine-month search.

Before the current CFO, they had someone who had the get-stuff-done mentality. Now that they’ve scaled, they needed someone with experience at a large scale, dealing with billions of dollars, so it’s crucial to hire for relevant experience at later stages.

Remote Doesn’t Have an Official Chief Product Officer

As the previous VP of Product at Gitlab, Job’s domain expertise is product. So, he is acting CPO. They used to have one, but it didn’t work out. His greatest learning from that experience is that, as a founder, if you care about something in your business, you should be super close to and on top of it.

It doesn’t matter if you have a lot of people on your team who are experts or have decades more experience than you because the moment those people build and ship something that doesn’t align with what you want, you will feel estranged from that part of your company.

All of Job’s deepest regrets about building Remote are centered around letting go of something he truly cared about and passing it off to someone more experienced or intelligent than he was. Don’t do it.

It’s your company. If you care about it, stay close to it.

How Much Time Founders Should Spend On Hiring

Founders typically spend about 50-70% of their time hiring in the early days. Hannah’s advice to portfolio companies is if you’re going to hire 25 people or more in a year, hire a recruiter. Founders tend to resist using agencies, but the ROI is pretty high.

In the beginning, Remote founders spent a lot of time on hiring, whatever was necessary, especially as your team grows quickly. Those first hires are so impactful, so you need to do everything.

Nowadays, it depends. If you’re at scale and hiring some executive who reports directly to you, you might spend 90% of your time. If it’s not that person, the time spent as a founder may be significantly less.

Biggest Mistakes Founders Make

The mistake founders make most often is not moving on from early employees once they reach the limit of where they can scale in the company. Loyalty is a great quality, but not to a fault. Those people may have been instrumental in helping launch the rocket, but they may not be a fit later.

The data shows that once you reach 1K employees, typically, only one of the first 10 is still in the organization. Remote has a different experience.

Seven of the first ten people they hired are still with the company. They may have been lucky with that. Some people became directors or high-level management; a few stayed ICs and did well.

With that said, out of the first 50, a much smaller percentage of people stayed, maybe 20. Getting rid of people who don’t fit anymore is stressful for both parties. But the more aggressive you are as a founder at keeping your team strong, the better you’ll be.

“Most founders don’t regret firing someone too early,” Job shares. “It’s harsh, but true.” A founder’s journey is non-stop failing, learning from mistakes, and continuing on.

Key Takeaways

  1. In the early days, it’s all about people. You’ll spend most of your time on it, so don’t short-change it. It’s worth it.
  2. As you scale, hire leaders and delegate to them. You want to spend less time hiring directly and more on leadership team alignment.
  3. As you evolve as a founder, don’t be afraid to iterate and grow as you go.

“As a founder, your sole job is to make something out of nothing, to create value where there wasn’t. The only way to do that is by not stopping. That’s your job. Get shit done forever, and at one point, you’ll make some money,” Job concludes.

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