Customer Onboarding: The Start of Something Beautiful (Or... Not)

Let's set the scene. Your sales team just closed a shiny new deal. The gong goes off, everyone's high-fiving, and Slack is buzzing. Then... silence.

Now it's onboarding time. This is the pivotal moment when your customer decides whether they love you or regret everything. No pressure, right?

Onboarding is the part of the customer journey that many companies neglect. They then wonder why retention is plummeting. Here’s the secret: onboarding isn’t just a checkbox; it’s the beginning of a relationship. Like any good relationship, it sets the tone for everything that follows.

If you’re here because you’re trying to nail onboarding from the start, or fix the mess you’ve already made, you’re in the right place. Let’s discuss how to transform onboarding into the dream-building machine it should be.

Treat Onboarding Like a Product, Not a Process

It should feel intentional, not improvised over Zoom.

Most onboarding experiences are thrown together like IKEA furniture without instructions. A few calls, a dusty PDF, and maybe a checklist if someone is feeling fancy—that’s usually it.

If you want your customers to succeed, onboarding needs to be designed, tested, and improved just like your product is. Donna Weber, a customer success expert and author of Onboarding Matters, nails it:

"Structured onboarding is the key to retaining customers and driving adoption. Without it, you're just reacting."

To get started:

• Build a repeatable framework.

• Align your internal teams—including sales.

• Make it consistent while being flexible enough to adapt to different customer types.

  
  

You wouldn’t release a product without QA testing. Onboarding is no different.

Time to Value Is the Only Metric That Matters (At First)

Nobody buys software because it looks good. They want results.

Your customer has one goal: value. They don’t care about your vision or beautifully designed slides. They want to solve their problems, and they want results fast!

The quicker you can deliver that first win, the more likely they are to stay. This is known as Time to Value (TTV), and it can make or break your relationship.

Hopefully, David Skok won’t mind me borrowing one of his quotes:

"The first value delivered is the first step to long-term retention."

Ask yourself:

• What’s the minimum outcome a customer needs to feel it was worth it?

• How fast can you help them achieve this without overwhelming them with information?

  
  

That’s your TTV. Build everything around it.

Administer a Human Touch

Automate later. Be human first.

While scalable and automated processes are great, if you’re early-stage or selling something even slightly complex, forgo the automated messages. Instead, provide a real human contact.

Choose a Customer Success Manager (CSM), an onboarding manager, or even someone from your product team. Make sure this person has a pulse and a plan.

This isn’t just a hand-holding exercise. It’s about showing your customer that you care. They should feel that someone is actively watching over their journey, and they’re not just a logo on a slide.

Trust builds loyalty. Loyalty builds retention. Retention builds revenue. It’s not rocket science; it’s just customer success.

Bin the "One Size Fits All" Playbook

Because not all customers are created equal.

Here’s a fun fact: not everyone wants to spend six hours learning your product. Some prefer a quick call. Others want bite-sized videos, while some may wish to be left alone and just email you when they hit a wall. Yes, I mean face-to-face meetings!

Great onboarding adapts to your customer's learning style and goals. This means creating a modular approach that allows customers to choose their own path.

Segment your customers by:

• Size

• Use case

• Experience level

  
  

Then develop onboarding journeys that fit, rather than force. You’ll have happier customers and fewer complaints about misunderstandings or usability issues.

Set Expectations Like a Pro

Assumptions are the quickest way to ruin a good thing.

Do you know what customers dislike the most? Bad surprises.

Here’s a radical approach: communicate clearly. In onboarding, that means being upfront about:

• What the customer needs to do

• What your responsibilities are

• What “success” looks like and how you’ll measure it

  
  

Setting clear timelines and sharing roadmaps is essential. Document everything in black and white. Regular check-ins are also vital to ensure everything is on track.

Remember, don’t assume that silence equates to satisfaction. Sometimes silence just means there’s trouble brewing.

Bonus Tip: When in Doubt, Bring in Barre

Surely you saw that coming… right?

If reading this post made you realize your onboarding could use some work, you’re not alone. Many companies struggle in this area.

That’s why the team at Barre exists. We’ve helped numerous startups and scale-ups turn their onboarding horror stories into case study-level successes.

We are Barre far the best-secret weapon in your arsenal for making onboarding your biggest retention lever, instead of your biggest liability.

The Importance of Continuous Improvement

Onboarding is not a one-time event.

After initial onboarding, it’s essential to keep the momentum going. Check in regularly and gather feedback. Use it to identify areas for improvement.

Encourage customers to participate in surveys or give feedback sessions. Their insights are invaluable for refining your onboarding process further.

Investing in continuous improvement keeps your onboarding fresh and relevant. It shows your commitment to their success, fostering loyalty.

Final Thoughts

Onboarding isn't just the start of the customer journey; it's the bedrock of everything that follows. Get it wrong, and you'll spend your time putting out fires. Get it right, and you'll retain loyal, happy customers who not only remain but also grow alongside your company.

So go ahead. Build something exceptional. Or even better, let Barre lend a hand in making your onboarding process flawless. Your future customers will thank you for it!