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5 Years, 100 People and Lessons Learned

This year Pipedrive turned 5 years old, and today we crossed the symbolic line of 100 employees. I am incredibly happy to see the idea for Pipedrive coalesce into a group of fantastic individuals who have come together to make our product and service world class. While it’s taken some time to get here, in the grand scheme of things, this is just the beginning of our journey.

So here’s a cheer to all of our 100 employees (and their dogs), to all of our customers and to everyone who has helped us get this far – thank you!

In reaching this milestone, everyone at Pipedrive has had to learn, adapt, rinse and repeat. With that said, it’s a good time for me to reflect and share a few things that we’ve learned over the last five years.

Getting to 100 hasn’t been easy

I’m sure that any founder whose company’s headcount has grown beyond this number can attest that getting to 100 people isn’t easy. Mainly because it’s never simply about finding 100 people to hire. The difficulty lies in finding 100 talented people who fit with the culture and the team, can continue to add value, and welcome more challenges ahead.

Talented people don’t have dull personalities, let’s put it that way. While we can have weirdoes and freaks in our company — many are, I should proudly say, starting with yours truly — we cannot have a-holes. We want people who are good companions and who we can regard as friends.

And then there is another set of challenges that come with serving a global customer base. We make our best effort to serve our customers in their respective languages, which means finding employees with excellent language skills — both acquired or native — to help us achieve that. Finding the international talent in Tallinn, Estonia, or New York has been tough — we left no stone unturned and even relocated people across countries and continents.

At times it’s been hard for our leadership team to step back and let others do what they do best. Early on, we founders did everything. But there comes a time when we need to relinquish control over many functions because the people we’ve hired are better than us at their jobs. You just won’t grow a company successfully without doing this.

And at times, we simply haven’t had the money to fill all the positions we’ve wanted to, in which case we’ve learned to deal with it.

Things we’ve gotten right in growing the team

We’ve been relentless about keeping our company culture, and only hiring the people who fit. Mistakes made in recruiting are tough to fix later. That is why we have rigorous interviewing processes in place where most candidates go through more than five interviews.

The principle we’ve followed with hiring leaders is that culture is what people do, not what they say. So our goal has always been to find managers behind whom others would want to align because of what these managers do. I believe we’ve done that rather well.

We’ve also maintained a high-touch relationship between employees and their managers. Even when it sometimes feels draining and time-consuming, we’ve kept on having regular one-on-one meetings. Regardless of how big, there has to be a feeling of a smaller company where people can continue to express their ideas, concerns, plans and ambitions to their manager, and find a solution together. There’s no way for it to be that way unless we keep on doing what we’ve done so far.

I’d like to think we’ve also kept things simple, sincere and real. I admire that quality in all of the people we’ve hired. There have been fights, and we’ve made a mess at times, but we’ve always strived toward keeping things simple and talking honestly and straightforwardly, even when it’s difficult.

We’ve also made some mistakes: ‘hire when it hurts’ doesn’t always work

Experts often advise startups like ours to “hire when it hurts.” Of course, you can never get everything right. Looking back, some of our best hires happened six to 12 months after they should have. By doing it this way, I’m sure we’ve lost time — a chance to build a stronger organization quicker and put a better product in our customers’ hands faster. Maybe we should have tolerated less pain.

But hiring a person to fill a role that has yet to be defined is a huge gamble that has also led to less-than-stellar results.

First of all, without a clearly described role, expectations are much harder to manage. Both the company and the person hired tend to have too much faith it’ll work out and hope for the ideal tomorrow that may never come.

Secondly, it requires both parties to justify the role’s existence, and that takes the focus away from where it should be. We’ve learned to become clear about the role we want to hire for and its place in the whole structure and dynamics of the organization.

Finally, I’d like to to think I can read people well. But, boy! I’ve misread both the motivation of some people and their values. Our lesson? Continue the tough learning process of how to hire for both professional and cultural fit.

What’s next for Pipedrive (and for you)?

We’ve reached a milestone, not the finish line. We’re more motivated than ever, and we hope to grow the same way (or even faster) in the future, using the lessons from our past five years.

If you want to have an impact on how millions of people sell around the world or our lessons in growing the team sound interesting to you, check out open positions on our jobs page.

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