A year of learnings: Josh Crossick shares his 4 key takeaways as a CPO at Preply

We Are Preply
4 min readNov 8, 2021

Our Chief Product Officer recently celebrated his first year with us 🎉 and took some time to reflect on his journey building products at Preply and key learnings.

Josh Crossick, Chief Product Officer at Preply

I joined Preply almost exactly a year ago as Chief Product Officer. I’ve worked in Product for around 20 years (pretty much since it was invented!) in everything from tiny startups where I was the only Product Manager, to huge organisations where I led teams of over 100, and it’s been super exciting to be here at the bridge between all these different types of company. We’re small enough to be scrappy, we’re very much a startup, but we have the scale and reach to have a big impact.

My last 12 months at Preply have been a rollercoaster and it feels like my feet have barely touched the ground.

  • We’ve launched countless evolutions of our products — everything from tiny tweaks to our conversion funnel, to brand new products and business model changes.
  • We’ve doubled the size of the team from 200 to 400, including hiring our first Preplers in the US.
  • We’ve raised tens of millions of dollars in funding from some of the most well-respected VCs in the world.
  • And we’ve managed all this while swinging back-and-forth between hybrid office work and full remote work based on how Covid evolves in our different locations.

It hasn’t always been easy to manage building a great product and a culture, while scaling the team and company so fast. But it’s been a blast — and a huge learning experience.

Here’s some of my top learnings from the last 12 months at Preply:

Be interested in (and curious about) the Product you’re building
If there’s one thing I’ve taken away from 20 years building products is it’s WAY easier to build a great experience and stay motivated if you love what you’re building. I’ve found the product at Preply fascinating. We’re a marketplace, and retention-driven learning platform. We are a B2C product with a fast-growing B2B business. We have students and tutors in dozens of countries around the world. Plus we have a fast-growing core business but are comfortable experimenting with new and innovative products.

These product challenges are some of the most fascinating I’ve worked on, and the outcome (people learning stuff!) is hugely inspiring.

The first ever Preply Learner Townhall

Launch embarrassing products fast — and don’t forget to iterate
I’ve heard this so many times, but Preply is where I’ve put this into action more than anywhere else. I love building products that make me and the team proud, however there’s always a risk that this results in moving slowly to get the ‘right’ product out of the door.

Preply truly embraces the principle of getting a scrappy first iteration launched — and then iterating to make it a success based on what we learn. We’ve seen this most recently when we launched our new “Group Class” product. It’s a basic, far from perfect experience, but the first launch has allowed us to learn — and now we’re iterating super fast.

Preply’s new Group Class product

Talk directly to your customers — it builds empathy and helps keep you motivated
Preply’s customers love our product. One of the things I’ve personally enjoyed is spending time talking directly to our Learners and Tutors.

We have periodic ‘Town Halls’ where we invite students to come meet us (via Zoom) and do an open Q&A with them. They tell us their stories, and what they love and hate about Preply. It’s the first time I’ve done this and was frankly terrified the first time (always a good sign you’re out of your comfort zone…) but it’s been so much fun.

We have a world class customer research team at Preply who bring great customer stories and insights to the table, and there’s something special about connecting directly with your users as well.

Embrace the pace of startup life
I’ve worked in lots of different types of company, and I’ve learned something: there is no ‘right size’ of company. Some days in big companies the structure and bureaucracy is going to drive you crazy; some days in smaller companies the pace of change will leave you reeling.

The thing I’ve learned in Preply is how to embrace the speed and uncertainty, while finding new ways to make space to think and decompress. I’m never bored for sure!

Looking forward to what I learn in 2022!

We’re actively looking for talented candidates with a can-do attitude and a hunger for growth to join our ambitious journey at Preply. So if you’d like to work with Josh and other talented Preplers check out our open positions here.

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