Building an onboarding program from scratch...

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Hey CS Pro,

What happens when you’re told to build customer onboarding… but there’s no structure, no tooling, and no one to hand it off to? Cara Benecke lived it. And in this episode, she shares exactly how she made it work.

She didn’t just launch onboarding. She turned it into a revenue lever from day one.

Let’s break it down…

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Starting from a Blank Slate

When Cara joined Workflex, she wore every hat…sales, CS, onboarding, renewals. She was juggling 70 sales deals and 100 active customers. No joke.

But instead of building onboarding for onboarding’s sake, Cara started by asking one key question:

From day one, she prioritized giving customers fast access to a demo environment: no delays, no friction. That early value signal helped boost adoption and build trust before a kickoff call ever happened.

Even better? She wasn’t guessing what customers wanted. She interviewed users who had been through onboarding to find out:

• What actually helped?

• What fell flat?

• What was missing entirely?

Then she used those insights to build onboarding around outcomes, not features.

Why Onboarding Became Her Top Priority

As a CS leaders we tend to forget this one thing - onboarding is your customer’s first impression. And Cara saw fast that strong onboarding = long-term retention.

Since she’d worked in sales before moving into CS, Cara understood exactly how the customer journey began. That gave her a major advantage; she could design onboarding to feel like a seamless continuation of the sales process, not a handoff.

She even used the same tool salespeople were using to create shared digital spaces where customers could see onboarding steps, complete tasks, and track progress.

This wasn’t about fancy tech. It was about removing friction.

And when she got pushback from co-founders on hiring or tooling? She built a business case using hard numbers. Retention. Expansion potential. ARR impact. That’s how she earned her seat at the table.

The Messy Middle of Building a Process

Building from scratch isn’t glamorous. Cara had to make tough calls:

• Which customers got human-led onboarding?

• Which ones needed to be pushed into a digital journey?

• What feedback mattered most?

Her strategy? Link every decision to ARR.

If a 6K ARR customer hated digital onboarding, that was tough, but it wasn’t always the top priority when 100K ARR clients needed attention. It’s not about ignoring small accounts, but making data-backed trade-offs.

That said, Cara didn’t set and forget onboarding. She constantly refined it, often handing ownership of the process to her team.

She made it clear: feedback wasn’t optional.

The result? A living, breathing onboarding experience that adapts to segments, scales with growth, and puts customer outcomes first.

Weekly Challenge: Find Your Customer’s WOW Moment

Here’s your challenge this week:

Ask 3 customers one question: what made you say “yes, this was worth it” during onboarding?

Then take that insight and refine your own onboarding flow. Whether it’s a sandbox environment, faster access, or a quick win use case…make sure your onboarding delivers value before the first call.

Customers don’t stick around for long, but they do remember their first impression. Make it count.

That’s it for this week! This episode is a must-listen for CSMs, CS leaders, and anyone rethinking how to design onboarding that actually drives results.

Have a listen to the latest podcast:

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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