The CEO who hired actors to train his team [Inside Scoop 🍨: 🎧 Ep. #1 ]
And why you should work for him too 👀 (Want an intro? Read on to the "Interested in joining Plain" section below ↓).
In these next few weeks, we’re introducing a new format to 🤝 Hiring Humans - The Inside Scoop 🍨 is where we bring you the insider stories—the hiring managers you’ll want to work for and the candidates sharing how they recently got hired.
Listen on 🎧
Welcome to The Inside Scoop 🍨, where we spotlight the human stories behind hiring.
In our debut episode, we sat down with Simon Rohrbach, CEO of Plain (a $15M Series-A startup rebuilding B2B support tools), who is hiring a founding Support Engineer (and other roles across GTM, engineering and design) to join his team in London or San Francisco.
Catch the highlights below ↓
From Designer to Support Evangelist
Simon cofounded Plain after watching support teams grow to nearly half the org at his last company, yet still operate with the worst tools and the quietest voice in the room.
“Support teams are your link to customers. Why are they the ones with the clunkiest tools?”
He and his co-founder, Matt Vagni, didn’t just want to build better software; they wanted to build it with empathy baked in.
If you're interested in a job at Plain, skip to the "Interested in joining Plain" section below ↓
The Fake Customers Were Real
Instead of shipping features and hoping for the best, Simon hired a support consultant and an actor to simulate real customer calls.
Then he put the whole team — engineers, ops, designers — through live ticket drills.
“You’re on the phone with an angry customer. The queue’s growing. You don’t know the answer. And by the end of the day? The backlog hasn’t moved.”
That feeling of doing everything right and still feeling behind is now built into every product decision.
Support Is the Culture
At Plain, support is at the centre of the company's operating system. Everyone does it, everyone learns from it, and it informs every product decision.
Now they’re hiring a founding Support Engineer to keep that loop strong — working closely with high-growth startups like Cursor, Granola, and Stitch.
Why it matters: Every feature gets filtered through the reality of being overwhelmed, understaffed, and expected to do the impossible.
What Simon Looks for in a Candidate
Simon didn’t start with skills or titles. He looks for:
Intellectual humility – curiosity > ego
Ambition – not for status, but for building something meaningful
Emotional intelligence – the ability to read a room and give feedback
“If you’ve used AI in your take-home assignment, great — just tell me how. Show me clear thinking and purpose.”
What It’s Like to Work at Plain
Simon was honest about the challenges:
Priorities shift daily based on customer needs
The team is split between London and SF (an 8-hour time zone gap)
They’re going up against incumbents with a 10-year head start
But the tradeoff? A clear sense of purpose, a tight team, and a product that’s actually shaped by the people who use it.
What This Actually Means
Most support tools are built by people who’ve never done support. Most companies say they care about customers, but they build for scale, not understanding.
Simon chose a different path:
He turned his team’s biggest weakness — lack of domain expertise — into their greatest strength.
Plain just raised $15M and is hiring. But more importantly, they’re building something that might actually make support professionals' days a little better.
In a world full of productivity theatre, that feels quietly revolutionary.
Interested In Joining Plain?
Plain is looking for a Support Engineer who's tired of bad tools and who not only wants to work on support, but also help shape their product roadmap.
What they need: Someone with support experience who can communicate clearly with non-technical and technical customers. You should be curious about how things work under the hood, even if you're not a developer.
What you'll get: £50-85k (London) or $100-140k (SF) plus equity, real product influence, and the chance to establish support standards at a fast-growing startup.
Think you’d be a good fit? Send us a note and get introduced to Simon.
The Inside Scoop 🍨 series will uncover more behind-the-scenes stories with founders and hiring managers who are approaching hiring differently
Thanks again for speaking with us, Simon! So great to learn more about what it’s like working at Plain — you got a great team!!