5 Years, 100 People and Lessons Learned

pipedrive 100 cake

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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Timo Rein

CEO and Co-Founder of Pipedrive

  • Very good article. I wish you luck and hope you continue imrpoving this awesome tool.

  • Raman Chadha

    Thanks for sharing your experiences, Timo. I’m going to share this with our companies, all of whom are dedicated to hiring right and building strong cultures.

    One thing to add, and possibly in a different context than you presented it. I believe that culture is what people do AND what they say…in the context of the workplace. I like to say that culture = language + behavior.

    If I walked around your offices, I’d probably hear people using certain words, phrases, etc. that reflect the culture. Do they mention the company’s values? Do they swear? Do they talk about customers? Do they gossip? Are they professional and businesslike or informal and street-like?

    That’s what I mean by language and why IMHO, culture includes what people say.

    • Thank you, Raman! I like the way you elaborate – even a culture in which people say one thing and do another is still a culture, right? 🙂 I’ve found myself to be attracted to the “wordless energy” that makes people do what they do (while saying whatever they say), but you have a fair point that culture contains both language and behavior. Let me take a step further – it also includes what people sing :).

  • Congrats on hitting a new milestone — and thanks for sharing the stories of the startup struggle. Cheers.

  • Jared Hansen

    Timo, that’s just awesome – congrats. I knew you guys were growing fast but had no idea you’d grown this quickly already. I remember signing up in 2011 and thinking it was magic – great work and very happy for you and the team.

  • Marc van Agteren

    Congrats on this great milestone Timo and team. We (at Usabilla) are big fans of Pipedrive, so we are looking forward to all that is yet to come.

    • Thanks, Marc! Looking forward to it, too :).

  • Great list of lessons learned, I can second the part about hiring into a not fully defined role. Founders sometimes expect the new hire will help them crystallize the role itself, and the new hire may even accept the challenge, but that road may as well frustrate both parties and lead to a break-up.


    • Yep, Ivan, I’m with you. Thanks!

  • Valters Grazulis

    Timo, I am proud that I know you and years ago I had the opportunity to work together, you are still my teacher !

  • Al Longtin

    Congratulations on hitting your milestone. We were believers and users when you were small then let a consultant talk us into switching to his favorite CRM. We lasted about a year with them and came back to our Pipedrive home where we should’ve stayed in the first place. Keep up the great work and don’t let growth get in front of your demand for quality user and employee experience. Be well and serve on my friend. Al Longtin , CEO of Longtin Family Companies

  • Boaz Maurits

    Congrats Timo, to you and your team! We at Buckaroo value Pipedrive every day. Keep up the great work!

  • Tom Scholet

    From all the comments, it looks like you have a bunch of very happy customers! This is better than customer reviews! And a great story too! What is not to like?