From $1M to $2M ARR — How I assembled a team and crafted a vision

Benjamin Cahen
Published in
10 min readMar 30, 2021



Hi, it’s Ben again! Last time I had a chance to share my journey with you, I had just passed $1M annual revenue. Today, I get back to you as I just crossed the $2M mark! If you haven’t read about the first part of my journey: I’m Ben, CEO and founder of Wisepops, the SaaS for popups.

It took me 5 years to go from $0 to $1M ARR, with no funding, no office, and no team. It took me half that time to get from $1M to 2M.

It’s hard to believe it’s only been 2.5 years since I last wrote about how I bootstrapped my business. Since then, we brought in many teammates, launched a new product, powered through the pandemic, and much more. Let me tell you everything that happened, how it happened, no BS.

It looks like a calm and easy growth. It was not!

1/ What you do after you reach $1M ARR?

Crossing the $1M mark was super exciting. However, this feeling did not last long. For some reason, each time you get to the next level, you keep aiming higher. When you have 10 customers, you dream of having 100. When you eventually get 100 customers, you look up to companies with thousands, and it goes on and on. I quickly wanted more…

Wisepops was on cruise control. I had handed over a 9-month long roadmap to the development agency and the marketing strategy was set for the upcoming quarters. I had time to spare and cash to invest.

I took a step back and started to think about the future. Would companies still rely heavily on popups to communicate with their audience? What would be a great alternative to popups? While Wisepops was on cruise control, was there anything that could rock — or even sink — our ship? I had to guess “what the music might do a week, a month, a year from now”.

That’s how Wisp came about. The idea was for websites to communicate with their customers with native notifications instead of popups. I thought that could be a great tool for brands and also a serious competitor to Wisepops. If someone had to build it, I’d rather it be me! I took the decision to launch this new product as fast as I could.

After taking Wisepops from $0 to $1M, you would expect that it’d be easy. I thought so too, but it turned out differently.

2/ Building Wisp: from $0 to $0 in one year

Once the idea of Wisp shaped up, I turned to familiar faces to build it. I had been contracting with a developer agency to create Wisepops and naturally thought they’d be the best team to help me once again. Big mistake. Although the developers were largely skilled to do the job, the agency would not be a good fit.

We could not find an efficient way to work with them, it was super expensive, taking longer than expected, and we were getting no added value from them. As time passed by, my frustration built up… It went on until Greg (Head of Growth, employee #1) told me “we have to stop this ASAP”. One hour later, we were on the phone with the agency: “It’s over”.

What was the outcome? Well, I successfully burned $250K over 10 months in a prototype that eventually went to trash. Well done Ben! ✌️

3/ The decision that changed EVERYTHING

Greg made his point clear. “We need to have our own tech team to build the product in-house. It feels like we’re not even a startup.” He was 100% right. Although working with an agency was a great strategy when I started Wisepops, it was no longer the right solution moving forward.

So we decided to search for our first developer: the future CTO of Wisp 🚀. This was super exciting, and terribly draining. Finding a CTO is incredibly hard! We were 3 months in when we finally found that person: Clement. The company changed completely the day he joined. Having someone build Wisp in-house propelled us to new heights. We built on that momentum and searched for more talents to join our team.

Only a few months later, Boris, our project leader at the agency reached out. He wanted to join us full time. It felt too good to be true! Boris had been our lead developer almost since day one and having him as CTO for Wisepops had been a dream for years! In August 2019, Boris became our third employee.

Then Vincent, our designer who had been working as a freelancer for a couple of years decided to join full time as well. In 6 months, we shifted from a successful side hustle with a single employee to an actual startup building our code in-house. This was a revolution.

March 2019 — a team is born (missing Vince, he was in Thailand)

4/ Growing the team — not as easy as it sounds

We were now a team of 5 but we couldn’t keep up with everything we had to do. Maintaining Wisepops, improving it to stay ahead of the competition, supporting our existing customers, and launching Wisp. We needed help.

Wisepops was profitable so I decided to use our cash to grow our team. We quickly interviewed candidates for software development, sales, customer success, and more.

March 2020. Bigger team, meeting in Paris!

That’s when the road got bumpy.

We did find great talents such as Ernestas, our lead backend developer. He’s been instrumental in leveling up our product and I feel lucky he joined us. However not many people as talented as him applied. We made many wrong hiring decisions. In total, we hired 6 people and eventually let go 4 of them.. That’s a LOT of bad decisions and it is incredibly expensive when you’re a small team.

Just consider the cost of:

  • leading interviews
  • debriefing
  • making an offer / contract
  • onboarding the new hire
  • waiting a few months to see how it goes
  • assessing the new hire’s contribution
  • giving feedback
  • measuring progress
  • debriefing once again
  • making a painful decision and sharing it
  • managing the exit
  • resuming the whole process all over again…

We had built a solid recruitment process but our pool of candidates was not nearly as good as the one I was used to when working at Amazon.

I get it. A small bootstrapped company doing popups won’t attract as many talents as a $1 Trillion tech company does. 🤷🏻‍♂️

We learned from these mistakes, changed our approach, and it worked.

5/ The HUNT for experts 🥇

What did we do differently? We adopted a very proactive approach to find talents who may not have applied to Wisepops otherwise. We spent days and days on LinkedIn, sent personalized emails to the very best people we could find, and took the time to explain what we were building.

Then, I invited each potential candidate to have calls with the team. I think it was key to help them assess the opportunity, the team, and the culture we were building at Wisepops. None of our last hires would have joined if they had not been on these calls.

The last hiring decisions we made have been a total success! Building a top notch team is undoubtedly THE main achievement on this path from $1M to $2M.

A perfect example for that is Aleksander, aka Olek. Our former designer Vincent had just left to start a new venture. I spent a ridiculous amount of time browsing LinkedIn searching for superstar designers, until I ran into Olek’s profile. He was UX designer at Revolut. I immediately connected with him. This is one of the best decisions I have ever made. He has literally transformed the way we build our products.

One good outreach can transform your company.


And then Covid hit. As Wisepops was built on a fully remote model since day 1, it was pretty easy for us to adapt. However, it was such a weird and anxious period. No need to write a lot about it. Businesswise, the main impact was that during the first 3 to 4 months (June to Sept. 2020) we experienced absolutely no growth. This was a stressful time. I wasn’t sure whether Covid was driving the slowdown or whether it was something else. I remember seeing other SaaS companies bragging about their growth rates going through the roof. We were growing 30% YoY, which can sound very high or very low depending on your ambition. So we started questioning our strategy and realized we didn’t really have one.

3 months + no growth = 90 days of worry 😱

7/ Building the vision for Wisp & Wisepops

The first questions we asked ourselves were: “What’s our competitive advantage? What’s the unique value we’re bringing to our customers? And how does Wisp fit into it?” Believe me, when you struggle to answer these questions, you don’t feel great. Especially when you’re the CEO. The gloomy environment around us did not help cheer us up.

We knew Wisepops was a great product that people liked, we had passed $1M ARR, had a great team, and Wisp was now in beta. We just couldn’t articulate a clear vision and strategy.

And then, I ran into this video by April Dunford who perfectly described the situation we were in.

That video really inspired me. So I went back to the drawing board, brainstormed with our team, and called everyone one I knew to get outsiders’ perspectives. One person that tremendously helped me to structure my thoughts was a former Amazon colleague (also named Ben). Together, we unpacked everything the team had accomplished as well as our customers’ feedback, and talked through it for weeks. I later added Ben as an advisor to our company.

After a month or so, we laid out our vision for 2021 and beyond. Having a vision in which we believed generated a big flow of energy in the team. We finally had a clear direction that would guide our decisions and inspire both our customers and future hires.

Want to see the result? Look at our job postings. We went from this…

Wisepops is a SaaS popup solution that helps marketers design and publish eye-catching modals. It is used by 1,300 organizations around the world, including Mixpanel, Greenpeace, Ocado, and Postmates.

to this…

Wisepops’ mission is to help brands connect with their audience better. We’re building tools that serve a more vibrant, engaging, and personalized commerce experience for everyone.

8/ Getting ready for the next chapter

Once I got the vision straight, I knew what to prioritize, where to invest, and whom to hire. It kickstarted a virtuous circle in the company. When you have a vision, you can attract the best people. They become your ambassadors and attract other people as talented as they are.

Here’s how it happened:

We found a leader for Wisp 👨‍🎤

Running two products within one company is not an easy task. As we already had so much to do on Wisepops, we needed to have someone to lead the go-to-market strategy for Wisp. That’s how Jordan, ex Shopify, joined. A love story quickly started between him, Wisp, our team, and me.

We hired a Head of Data 🤖

With our vision set and this new energy flowing in, I felt confident in hiring for a senior strategic role in our team. I was on the lookout for a Head of Data. I knew exactly who the best person for the job was: Romain. He’s a brilliant engineer I met at Amazon who then joined Facebook. Having him on board was a long time dream. The timing was right for him, so we made it a reality.

Greg — our employee #1 — left 😥

Greg, who had played such a critical role in building Wisepops and whom I loved working with, decided that it was time for him to go for something new.

He was leading Customer Success, Growth, and Product at Wisepops. That organization was no longer manageable for him, nor the right one for growing Wisepops.

It was hard news to digest, but I knew it was the best decision for him. Talents come and go, and I’m proud I had him on our team for so long 😍.

We stepped up our game 3X 🚀

Greg leaving was a signal that I needed to staff up our team to match our ambitions. After talking with everyone in the team, I decided to bring in THREE new people to replace him and take his work to the next level.

Within 2 months, we recruited three senior profiles with an outstanding track record:

  • Pawel to drive our Growth — he was Head of Growth at Tidio, a major Shopify app
  • Lisa to take over our Customer Success — she was Head of Growth at Snapshift, a successful french startup
  • Anthony to become our Head of Product Management — he was Senior PM at Amazon for Alexa

Upwards and onwards

As I write this post, the team is just getting started. Great things are coming! Now you know where we stand while crossing this $2M mark. It was definitely not an easy road. Actually it was nothing like I imagined. It was painful, humbling, hard, and it was so worth it.

Now that we’re ready to scale, let’s see what goes into the next From $2M to $??M post! 📈🚀😘🤞



Benjamin Cahen

Founder, @WisePops (Smart Popups Saas — working with 1,000+ companies). Investor. Ex Amazon. $BTC.