Jumped the Shark - Customer Success Manager Wayground Employee Review

2.0
Jul 4, 2026
Recommend
CEO approval
Business outlook

Pros

The first few "seasons" were genuinely enjoyable. The people were the best part of working here—I met some incredibly talented colleagues and made lifelong friends. Despite the usual startup growing pains, there was a collaborative culture, decent perks, and frequent U.S. onsites that made it easy to build real relationships across teams. The product was solid, and it felt like everyone was working toward something exciting.

Cons

Like a TV show that loses its magic after a few great seasons, everything changed when leadership was overhauled last year. The company seemed to swap out the "cast" instead of fixing the script. A wave of talented employees was laid off, not because the company needed to reduce headcount, but because new leadership appeared to want their own team in place. The result was a culture that felt completely different from the one that made people want to work here. Even before that, people would occasionally disappear with little or no communication, creating unnecessary uncertainty. Over the past year, restructures became the norm, goals became increasingly unrealistic, and employees were left wondering if they'd still be around for the next episode. From what I've heard, another major round of layoffs followed, suggesting the constant rewrites haven't solved the underlying problems. What started as a show I'd recommend to everyone became one I couldn't wait to stop watching.

Explore other reviews about Wayground

5.0
Feb 18, 2026
Recommend
CEO approval
Business outlook

Pros

Wayground is at a stage where you can have real ownership and make a tangible impact. People are trusted to take initiative, improve processes, and help shape how the company scales.

Cons

As with any fast-growing company, some processes and structure are still evolving. This can require flexibility and comfort with ambiguity, but it also creates opportunities to step up, lead initiatives, and directly influence how things are built.

1
2.0
Apr 11, 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

For an Ed-tech company, the base pay is better than most. Product is amazing, and product team is very responsive to customer needs. Product team is the best thing about this place. Fully remote, with quarterly(ish) in-person meetings. The company has always been scrappy and that was ok, because systems were always being built and employees had autonomy to build those systems and structures (this has since changed, and those structures that were built have now fallen by the wayside. It all started with the rebrand and when they brought in the new CRO and let go of SO MANY AMAZING PEOPLE.)

Cons

Like I said above, things were always a bit scrappy here and it still felt like a startup, but people truly cared about education, the product, and slowly making the structures better. That COMPLETELY CHANGED when they brought in a new CRO and fired half of the US team, including leaders who were instrumental in making these internal processes better. After they laid people off, the CEO met with the rest of the company in a Zoom and it was the most heartless “speech” I’ve ever heard regarding laying off so many people. Just talking about how excited he was for this change. They brought in tons of sales people and BDRs, and honestly, the heart has just completely left this company. It’s gone. I hope they can find it again. (That actually probably started when Deepak, the co-founder, left a little over a year ago. He was likely the heart of the company). Everything is reactive. Honestly, it has always been this way a bit, but now with the CRO it has gotten 200x worse. No forethought into anything. Even the quarterly in-person meetings are planned with 3-4 weeks' notice. So you end up having to reschedule your life and important meetings to be there. Things are promised and not followed up on. People are numbers. They have raised prices a ton just in the last year, with schools and districts in deficits and struggling to keep their own teams. They couldn't care less, completely greedy. The CEO wants one thing only, and that’s $$. I’d say, get out of the education world if that’s your goal. My advice is, if you’re looking to come to this company any time around the date of this post, run. Unless you’re completely desperate and just need a job, and this is all you can find… RUN.

5
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