Scaling a Startup Team

I’m the CEO and co-founder of Preply, a global marketplace for online tutoring. I’m lucky to have awesome co-founders, Dmytro (CTO) and Serge (Product). Together we started Preply in 2013 and had been bootstrapping until we joined the Techstars family in 2015. We then started growing our team.

Here are some helpful takeaways from our journey as you start to grow your startup team.   

Changing Roles of Co-Founders

Your role as a co-founder of the company is not static and will change over time. Here are a few stages you may experience:

  • Operator. You are doing things yourself, whether it is email marketing, coding, designing or supporting customers.
  • Early manager. You have your first people on board. While still doing a lot of things on your own, you start learning how to be a good manager.
  • Manager. You stopped doing most of the things and focus on being a good manager.
  • Executive. You manage other managers across your company. From this point, you don’t have control over execution; you have to rely on your managers.

Three observations:

  • The essential skill of being an entrepreneur is fast learning. It’s difficult to overestimate it.
  • When you stop managing operators, it’s the right time to start thinking about building the right culture. It will be one of the few ways to impact your company. Someone said: “Culture is management on a scale”. I cannot agree more on that.
  • Start preparing yourself and co-founders for management and executive roles earlier. In the end, it’s a difficult transition with entirely different skill sets. You have to learn how to hire, delegate, teach, develop, and build the right culture.

Hire Finance and HR Earlier

We hired Finance and HR functions early, and it helped us a lot. First of all, I freed myself up and spent much more time on building the right product and marketing. Thanks, Jens Lapinski (MD, Techstars Berlin 2015) for that advice.

Secondly, people I hired were much better than me in building the right finance, HR and hiring processes. That helped to make fewer mistakes and grow faster. Here’s a good piece of content by Christoph from Point Nine Capital about the right timing and importance of hiring HR.

Hire the Best

You can read about hiring the best people in a lot of books and blogs, and it’s imperative. One wrong hire can significantly lower your chances to be successful. At the same time, I believe that old school rule “hire slow, fire fast” no longer works.

That was a safe option, but in our competitive world, the ability to hire fast is crucial. So, you better learn how to do that properly.

Here are a couple of resources that helped me in my journey:

  • Hire for strength rather than lack of weakness: Hard thing about hard things.
  • It’s worth spending time understanding what the key questions are that you want to ask a person for them to make an immediate choice. Here’s a legendary blog post with a good list of questions for hiring a product manager by Ken Norton, a partner of Google Ventures.
  • Paramount book about hiring: Who: The A Method for Hiring.

Another moment worth mentioning is that you have to build the right expectations for your leaders and co-founders about future hirings. It should be apparent for everyone that the company will hire new experts, managers and executives as it grows.

People that can lead the company today are not the same people that can drive it tomorrow.

Also, your ability to hire the best is growing as your startup grows. The most important thing here is to make sure your current leaders will stay and learn from newcomers.

Additionally, I would encourage you to spend time meeting opinion leaders in different areas. They may help you with advice and their network, but also one day you may hire them. At Preply, we did a good job hiring the best people, because we were in touch with them when they decided to change their life.

Cross-functional Teams

In 2016, we had marketing, development and design departments. As we raised our seed round, Mariusz Gralewski and Arthur Kosten introduced me to the cross-functional approach.

A bit later, my co-founder Dmytro learned more about that at a Paris CTO meetup by Point Nine Capital (his event review here). We decided to test it, and the results were outstanding. It completely changed the dynamics inside the company.

In a cross-functional organization, you are building squads around specific metrics, not functions. For example, a team that is focusing on conversion rates may include:

  • Product manager
  • Product designer
  • Front-end engineer
  • Two full-stack engineers
  • Email marketer
  • Customer success manager

Such an independent team will move much faster in reaching their KPIs. Spotify did an excellent job explaining how such an approach works in their engineering culture: Video 1, Video 2.

If you are adopting such an approach, I would try to make sure that you have T-shaped PMs to lead squads. They would need to build excellent communication within the team, so everyone understands what, when and why.

The beautiful part here is that a cross-functional approach makes your life easier when it comes to scaling a team. Growing from five developers to twelve in a functional structure will give the CTO a hard time reorganizing everything and continue to distribute tasks from the product, marketing and sales teams.

With the cross-functional approach, PMs are responsible for managing. The CTO needs to be an excellent tech mentor and build the right tech culture.

I would compare the cross-functional approach with building a business accelerator. Every squad is an independent mini-startup, and your VP level people are mentors. As mentors, they will provide with the right focus, metrics and their expertise when it’s needed. The squads will then execute it independently.








Hiring, Culture & Recruiting: Tips for Growing Your Startup

At Techstars, we often hear from startup founders that hiring is one of the most challenging things to do right. We recently held an AMA on this topic (Ask Techstars: Hiring & Culture – Scaling Your Startup) with Sabrina McGrail, VP of People at Techstars; Emma Straight, Sr. Recruiter at Techstars; and Natalie Baumgartner, Founder & Chief Psychologist of RoundPegg, a company culture and engagement tool.

This post is the first in a series of three with Q&A excerpts from this AMA. Check it out!

How can you keep a culture fun yet still ensure that teams get a lot of work done?

Natalie: I will say that the more you understand what is important to your people as an individual and as a collective, you can make sure you are giving them what they need to have fun and enjoy what they are doing. It makes them far more productive and engaged in their work. Food for thought around understanding what people value.

Sabrina: Fun is subjective. Understand what they want and the type of environment that is ideal for them. Do engagement surveys to see what people are looking for out of the next quarter and the next year, and take general surveys to find out what your employees think. Take the time to understand what the culture is and set expectations around that at the beginning of the hiring process.

Emma: There is this sense of camaraderie and doing fun things, happy hours, team building events and all that fun stuff and the line is crossed very easily to things that may be inappropriate. It is up to the executive staff to always set a really good example of what is appropriate and what is not, especially when you’re not in the office setting. If something goes too far, deal with the situation quickly and directly so that it sets the tone and an example of what is okay. For example, “That was great and really fun, but maybe that behavior was crossing the line.” Handling this directly is key so that the behavior does not continue.

When is a CTO a must-have as a founding member of a startup?

Sabrina: This is a challenging question. I know that when we look at companies that we are selecting, having a CTO or a strong technical hire is obviously really important. I think it depends on what you’re building a lot of the time. It is great to have the right person in early on, but you also want to take the time to find the right CTO. The person to fill this role is so important; if you are rushing to get someone in the door that is not strong enough, it does not benefit you. The CTO is critical to building the company, so I would say take your time to find the right person and supplement in whatever way that you can versus giving someone (who maybe should not be a CTO yet) a CTO title. Otherwise, you end up having a lot of really hard challenges and conversations down the line when you may need to hire over that person or find someone who is a stronger leader.

Emma: Yeah, and on that I would say also that it is a critical recruiting aspect to have a really strong CTO or leadership presence on the engineering team when you are hiring engineers. It is a great tool for us to be able to go to and say, “Hey, this person is really leading the charge and building a really great team around them.” But you have to be really careful that it’s the right person, otherwise it could really harm you much more so than not having anybody. It’s really an individual thing and depends on the company, the size of the company and what the product or service is.

Natalie: For me, my co-founder was a CTO previously so it was not something that we had to go out and look for, but I want to take this opportunity to have a public service address moment to piggyback on what Sabrina and Emma were saying in terms of fit. You can not underestimate the importance of culture fit in making a decision around filling a very fundamental position in an organization. In the early days of Roundpegg, we had someone who was functioning as our CTO, but we needed a lead engineer. During this time, we were actually in Techstars, so this is back in 2010 when we made our first hire. We hired a guy who was a wonderful engineer, a great developer and a great human being, but we used our own tool (Roundpegg) and he was a terrible culture fit. So, great person, great technical expertise, but not a good culture fit and we hired him anyway. Our rationale was that we were still in research and development and not sure if our product worked yet, but all of the culture fit pieces really ended up playing out and it was a challenge for all of us. It was not a great decision for him, not a great situation for us and it took us awhile to part ways because we really liked each other. Fit is important for any position and certainly for a position with that level of impact.

What are some ways you’ve seen companies making office/culture more welcoming to parents and families?

Emma: I will jump in since I’m a new mother. I have two young kids and it has been a transition in my personal life to wrap my head around what this looks like as a working parent. Where is the balance? How do I give my all to both work and personal life? It’s a daily struggle of mine, so I’m still learning as I’m going and I still would love any advice and suggestions from any parents. I think I got really lucky; Techstars hired me when I was 9 months pregnant, I worked one month and then I took off three months. I feel very fortunate and very lucky that I got that opportunity. I think giving leave and making sure people feel supported when they are not only out of the office but the transition to come back is really important, not only to feel welcomed but also to understand that it is something that they are probably trying to navigate around as well. They may not have all the answers, so just being supportive in the flexibility of hours or having a pumping room helps. There are a number of different things, and it has been more of a focus of conversations lately in the tech world, which I am really excited about. I’m a parent that does not want to be a stay at home parent, so it’s really nice to see that people are embracing the challenges that may be involved. We are very hardworking and time management is a necessity for parents, so we are able to work much more efficiently and produce better results than I think sometimes people who don’t have kids.

Natalie: It’s definitely a topic that I love and a topic that has been front and center for me as a co-founder. I have three children who are 7, 5 and 2 years old, and they were all born during the life of RoundPegg. We have photos of all of them sleeping under my desk or in boardroom meetings. When I think about the question, the first thing I’d say is that as founders or leaders of an organization, you have to understand what your values are and what the aspirational values are that you have for your company and how you want to drive your organization. For me, it would be critical to work for an organization that really values flexibility and incorporates the balance that is necessary for parents. That is not always going to be the case for every company and for every leadership team, so first you need to get clear on where your values sit on that kind of flexibility. I know plenty of organizations where that’s just not part of the core values and as long as you’re clear about that as an organization, people can then self select in or out. I wrote an article two years ago about being a founder and being a mom. I was encouraged by our PR firm to write this when we were in a PR meeting and I was nursing my baby. My main position is that to be welcoming, you have to be flexible and you have to be willing to get creative and get messy about how you structure your work day. My co-founders were incredibly supportive and I was really fortunate, even though they had to work with all the nuances of working around my schedule as a parent – they are wonderful and make that possible for me. But, it does require me to be creative. I have been at meetings where I have a newborn downstairs in the lobby with a nanny and I’m trying to run a meeting and then go down to feed her and go back up – my colleagues have helped with that too. My efficiency has really increased with being a mom.

Sabrina: Make it okay to be human at work – it is something that Techstars talks about a lot. Create a space as you’re building a company. Make sure, whether for you or your managers, that you’re having one on ones and you can really genuinely ask, how are you? Not just how are you doing at work, but how are you doing in life? We have some tools that we use at Techstars to make sure that we are having both sides of that conversation. Creating that space is really important because then you know where someone is coming from, we don’t leave ourselves when we walk through the office door, we are carrying everything that is going on outside of work with us. Create an environment that comes from having a discussion about your values and what kind of company that you want to build. Being able to say that you are having a really crazy day at home and I really need to work from home for the next two hours, is totally okay.   

Click here to listen a replay of this AMA.


Join us for our next Ask Me Anything session with David Cohen, Co-Founder and Managing Partner at Techstars – June 23rd at 10am PT! Ask anything about startups, fundraising, accelerators, and more! REGISTER.