Mastering Onboarding to Drive Retention in 2025

As we head into 2025, there’s so much to be excited about! AI-powered SaaS has shifted from being just a buzzword to delivering tangible ROI. The IPO window seems to be cracking open, and Customer Success communities are thriving like never before. It’s a refreshing departure from the doom and gloom that dominated recent years.

For those who know me, my optimism is no surprise—I’m always searching for the silver lining. If there’s one positive lesson from the challenges of the past few years, it’s this: Customer Success metrics have taken center stage. High churn rates forced many promising startups to stumble, bringing the importance of retention into sharp focus. While growth remains king, churn is no longer an afterthought—it’s a top priority for boards and investors alike. As we step into 2025, I’m confident that retention and its related metrics will continue to dominate conversations. It’s an exciting time to be in Customer Success!

The Role of Onboarding in Retention

In my role as an investor, I engage with as many as 20 founders some weeks. With my background as a VP of Customer Success, the topic of churn inevitably comes up. Reflecting on my advice to founders in 2024, one root cause of churn consistently stands out: ineffective customer onboarding.

Onboarding is the linchpin of retention. If your onboarding process doesn’t immediately address your customers’ pain points and set them up for success, you’re laying the groundwork for churn before the ink on the contract dries.

For early-stage founders, this is a constant topic of discussion as they scale. During Series A fundraising—and even more so in later rounds—churn is the #1 issue after growth. Founders who ignore onboarding essentially leave retention up to chance. And let’s be clear: retention isn’t just a Customer Success issue; it’s a growth issue.

Without strong expansion and renewals, that provable hockey stick curve never happens!

Why Onboarding Matters for Growth

Onboarding is critical for finding and solidifying product-market fit (PMF). If customers can’t quickly experience the “this is why I bought this product” moment, you may not truly have PMF—or at the very least, you still have work to do to get them there.

Next, assuming you’ve found product-market fit (PMF), here’s what happens as startups grow: onboarding is often the first process to break. Imagine you’ve achieved PMF, raised funds, and hired a larger sales team. As soon as those reps ramp up, the influx of new customers puts immense pressure on your onboarding system. And like any overloaded process, it’s bound to crack under the strain. I’ve seen this happen repeatedly with startups scaling quickly.

With a strong retention rate, revenue from existing customers begins to surpass new logo revenue earlier in the growth journey than many realize.

I learned this the hard way. During my time leading Customer Success at Motive, we scaled from $1M to $50M in ARR in just six months. It was a whirlwind, and we had to become exceptionally good at onboarding—fast.

The Competitive Edge of Great Onboarding

Investing time upfront to deeply understand your customers is a game-changer. The speed at which you identify their needs, pain points, and problems becomes your competitive advantage. While products are being developed and iterated faster than ever, the ability to translate customer insights into early value is what separates the winners from the rest.

Companies that truly understand their customers’ challenges and deliver value early in the journey build trust and loyalty. And that trust isn’t just a foundation for retention—it’s the fuel for sustainable growth.

The Impact of Onboarding on Loyalty and Advocacy

Good onboarding doesn’t just reduce churn; it creates loyal customers and brand advocates. On the flip side, poor onboarding can undermine even the best products or most advanced AI. Customers don’t care about your features—they care about solving their problems. Onboarding is the bridge where customer understanding translates into actionable outcomes.

Building trust early isn’t just nice to have; it’s essential for long-term success. By setting the tone from day one, effective onboarding ensures every interaction that follows strengthens the customer relationship.

Turning Onboarding into a Growth Engine

If you want to keep churn low and showcase strong Net Revenue Retention (NRR) and Gross Revenue Retention (GRR), start by fixing your onboarding process. Platforms like OnRamp—which helped me host some amazing Customer Success leadership dinners last year—are designed to simplify and personalize onboarding, giving companies a significant advantage in building customer trust and loyalty from day one.

When onboarding works, it transforms customers into advocates, turning retention into your most powerful growth engine. Don’t just measure success by how many customers walk through your door—measure it by how quickly and effectively you deliver value and keep them coming back.

2025 is the year to double down on Customer Success, starting with onboarding. The companies that prioritize this critical phase of the customer journey will be the ones that thrive in the years to come.