Podcast Episode 40 – Pipedrive’s CTO about exponential growth, mission teams, and his learnings at Skype, eBay & Microsoft

Sergei Anikin provides us deep insides, as he shares his experiences with Skype going through the hands of eBay and Microsoft. Also concerning Pipedrive’s development, he sheds light on the company’s exponential growth and how they maintain great product quality at the same time.

About the Podcast
Digitale Leute Insights is the podcast for passionate product people. We interview product developers from around the world and take a closer look at their tools and tactics.
Host: Oliver Thylmann

• In this episode, you will learn:
• about the early days of internet VoIP communication from the history of Skype going through eBay and Microsoft’s hands.
• how to maintain your organization healthy at a state of exponential growth.
• how to build an agile product development with high responsibility for every employee.
• how to develop a microservice architecture when every customer has its own database.

Besides providing a deep insight into how Pipedrive has been build and works today, in this episode, Sergei Anikin shares his very own story but also sheds light on parts of the development of the internet and its hurdles.
When Sergei studied at Tallinn University of Technology, the Estonian Republik had just renewed its independence towards the Soviet Union. In his studies, Sergei started developing for insurance companies but moved to banks soon, where he developed internet banking applications.

Estonian startups: 12 points

Meanwhile, in Estonia, four entrepreneurs founded a company that would go around the world and redefines how telephone conferences would work. When Sergei joined Skype, the company was already bought by eBay, integrating into eBay’s and Paypal’s services. At the same time, Skype started its transition to agile. As the structures had not been vertical but organized in products, Sergei commented that the transition proved to be difficult.

When Skype finally was sold to Microsoft, he saw it as an experience: “In Microsoft, I think it was kind of a relief. Microsoft internally is a very good organization.” One of his tasks was to develop a new application for Windows 8, which was partially not working at all, as the new OS was still in early development. As much as he enjoyed the organization and all the learnings he was able to make, Microsoft was about to pull him to Redmond, USA. He explains:

Before I get hooked too much into Microsoft of all the financial rewards, maybe I should join a smaller company with bigger missions.

He found this company also in Tallinn, where the CEO of Pipedrive asked him if he could make the three-year-old startup as big as Salesforce. Sergei saw enough ambition and answered: “Maybe not as big as Salesforce, but a quarter of Salesforce is good as well.”

How do you do exponential growth?

Sergei joined the company as the VP of Engineering when there were about 20 employees. Since then, the company was built to grow exponentially. The number of employees doubled every year, which made teaching and learning very important for the onboarding process when half of your employees are less than a year in your company, he explained. The exponential growth forced the company to open multiple offices “because if you have the ambition to grow, there is no way you can grow with just one location.” In this episode, he explains how they forced the company to create structures for such rapid growth.

Today, Pipedrive employs over 600 people, from which the half is working as developers. Asked how they were able to maintain that ratio, Sergei, now CTO, jokes: „We have a very good product.“ He further explains, that they are lucky as there is a high organic growth and demand for the product, which keeps the marketing department smaller than in other companies.

With great freedom comes great responsibility and the need for a great team structure

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Also, teams‘ size is remarkable: Between 20 and 45 developers build a team that is split again into maintenance and project teams. You are always part of a maintenance team but can pitch for a new project, chose a mission lead, and recruit the new team. If you are on a mission, you do nothing else but focus on the product. So much, that you are even asked not to take holidays when being on a mission.

At the end of this episode, Sergei also provides insights into the backend structure, which consists of a private cloud, where every customer gets its own separate MySQL database.

LinkedIn: Sergei Anikin

About the Host
Oliver Thylmann is a serial entrepreneur based in Cologne, Germany. He is the co-founder of Giant Swarm, a 60-person SaaS company providing managed microservice infrastructure to big enterprises.