Pipedrive’s Timo Rein on How to Stay True to Yourself and Find Success as an Entrepreneur

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Timo Rein keeps a note to himself on his desk that greets him every morning. It reads: “Let it be easy.”

In spite of these words of wisdom facing him daily, he admits that it can be tough to follow his own advice. After all, working 12 hours a day isn’t easy. Juggling fatherhood into his schedule certainly isn’t easy. And building a startup from scratch is anything but easy.

But no matter how busy things have gotten, Rein’s path toward entrepreneurship has always seemed inevitable. A psychology major in college, he started his career as a consultant, expecting to be helping clients build better things for their businesses. Instead, he found himself selling sales CRMs (customer relationship management systems) to clients, which he did for 18 years. A salesman that sold sales tools—pretty meta.

But the itch to build something new never left him.

After working in sales for so long, Rein realized that there was a huge gap in the industry: an easy and usable CRM. Rein decided that he was done with simply counseling people on the products to buy—he was ready to build something entirely new and better.

That’s when Rein was jolted out of his steady sales career in Estonia, and into the high-powered tech startup world of Silicon Valley, with the creation of Pipedrive.

Pipedrive has since grown to more than 50,000 customers with over $1 million in recurring monthly revenue. How does he do it? Rein thinks it’s pretty simple: He and his team have a rare combination of resilience and determination.

That’s definitely part of it, but it’s only where the Pipedrive story begins. Rein has learned some major lessons in his long career in both sales and as a CEO that have made his journey easy. Sometimes.

From Idea to Reality

As sales industry specialists, it was the tools their customers used every day that gave Rein and his co-founder the initial idea for Pipedrive. They’d seen what was working, what wasn’t, and what customer need was left unaddressed. They were ready to build the perfect CRM.

By 2010, the group relocated to the United States, and today Pipedrive has offices in San Francisco, New York, and Estonia, serving businesses around the world.

In 2016, their database grew to include 50,000 customers worldwide.

Referring to his team of 200+ Pipedrive employees, Rein says their impressive growth is because of “this amazing organization of people, without whom I don’t think we would have ever been able to scale to this point. Together, we’ve been able to continue building towards the vision that we have.”

Rein says that developing himself as a leader is one area of business that presents a continuous challenge.

“How can I help these people by serving them, in order for them to be really good at what they do?” Rein continually asks himself. “The more we’ve developed a company, the more I’ve understood that I’m really there to serve all the team leaders that we’ve brought into the company in the best possible way.”

Lessons From a Veteran Salesperson

Timo Rein’s sales experience actually became even more relevant once he became a CEO.

Salespeople need thick skin. Sometimes they even need to develop an alternate persona, and sometimes they can take that too far. As a result, the attitude and confidence that sales reps sometimes see as necessary to make deals can actually distance themselves from customers.

During his time in sales, Rein learned that when you lose that real connection, trust is lost, and that hurts your results. It’s a lesson that’s translated well in his life as a founder and CEO.

It is truly amazing how people will react and respond to genuineness and sincerity, Rein says. When you learn to be yourself in customer conversations, you gain a certain level of trust and understanding with your prospect, even though you both know that you’re there to sell them something. Openness and trustworthiness can take you a long way.

What’s the best piece of concrete advice Rein would give, both in sales and entrepreneurship?

“Ask new questions as you go along.”

He says that entrepreneurs should get into a routine of asking the tough questions that will move their businesses forward.

“When you’re not getting the results that you want, you just have to raise the game in terms of questions you ask,” he says, noting that the desire to keep asking is just as important as the questions themselves.

In the early days of Pipedrive, the team was pulling in around 15 to 20 customers a month, until one of them asked, “What would we need to do to get 100 new customers a month?”

Rein was a little shocked, mostly because he’d never asked that question himself. He found himself wondering: How do we reach that level?

“I realized I was both intimidated by this question, and also inspired. Ever since then, we’ve always asked ourselves: How do we get 1,000?”

Rein encourages entrepreneurs to ask the uncomfortable questions and tackle the seemingly out-of-reach goals, because the risk is worth the reward. When you don’t get the feedback you expected, it simply means that your reality isn’t quite there yet. “But if you answer that successfully,” Rein says, “you will raise the whole game, and get the results you want.”

Rein’s rules for serving as a leader, and leading as a servant:

1. Find the best people possible.

Strong teams aren’t just built by hiring talent, but by growing key figures within your company. Consider whether you can elevate a teammate into a leadership role before looking outside for new people. Place value in the players who came first, and let them know you appreciate their loyalty.

2. Put them in a good place.

Getting all of your talent to work together toward the same goals is a fascinating and challenging objective. Their individual ambitions may shine clearly, but aligning your team to work as one is crucial to your overall success. A leader’s job is to ensure departmental teams and structures can function in a productive manner and to an effective degree.

3. Get out of the way.

Coworkers need to be able to show each other respect, and that often means leaving each other alone to let them do what they do best. When you give them space, your team is more likely to be building something together rather than fighting over the process.

4. Serve them to reach your collective goals.

Teach your talent to carry their own loads, and hold themselves accountable for their contributions, while you all move toward your shared future together. Separate you may struggle, but together you will succeed.

Finally, when working with sales professionals, Rein’s #1 tip is:

“Figure out how you can be the real you—while doing your job.”

Crack that code of how to stay true to yourself within your work environment, and the rest is, well, easy.

AUTHOR = Rachel Davidson is a copywriter and mountain climber located in Seattle. When she’s not on the trail or writing about her adventures, she’s eating Mexican food, attending live shows, and disappointing her team at trivia night. Learn more about Rachel by connecting with her on LinkedIn.


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