The Make-or-Break Reality of Customer Onboarding: Insights from SaaS Leaders

Did you know that 90% of your customers decide whether they'll stick with your product within the first 30 days? In today's competitive SaaS landscape, effective onboarding isn't just a nice-to-have—it's a revenue driver and retention essential.

We recently hosted a panel discussion featuring customer success leaders who shared their insights on what makes customer onboarding truly effective. Our expert panel included:

• Neelu Sheikh: CS leader who has built global customer success teams for Coupa, Tipalti, Google, and ZoomInfo
• John Gleeson: Founder and managing partner at SuccessVP, previously led customer success at Motive from $1M to $300M in ARR
• Michael Salomon: Global support director at an ERP solution provider for heavy equipment dealerships

Moderated by Sakshi, founder of Hexus AI, a product storytelling platform for customer enablement, the discussion provided valuable perspectives on the challenges, strategies, and best practices for successful customer onboarding.

Key Challenges in SaaS Onboarding

Misalignment Between Teams

Michael highlighted the critical issue of misalignment between sales and customer success teams:

"One of the main issues I've seen in many companies is not having a clear understanding of what is the responsibility of sales versus customer success. That misalignment very often creates a lot of challenges in our customer journey."

Delayed Time to Value

Another significant challenge is delayed time to value:

"Anything that the customer cannot see the value in during the first 30-60 days is a major challenge. That's what's going to make it or break it," Michael explained.

One-Size-Fits-All Approach

Neelu pointed out how customer expectations have evolved:

"Customers are demanding a different relationship with businesses. Before, even with segmentation, we had onboarding tailored to SMB or mid-market. Now customers are asking for a unique relationship tailored specifically to them, regardless of their size."

Onboarding as a Growth Accelerator

John emphasized that great onboarding shouldn't be viewed merely as a defensive strategy but as an offensive one that accelerates growth:

"Great onboarding is an accelerant to growth. The faster we get this customer up and running, the more days we have to work with them on the other side of them finding value. On the other side of onboarding, you can sell them more, they become referenceable, and they start that flywheel for growth."

He added that well-onboarded customers typically place less burden on support teams:

"Companies who completed everything in a timely way and had driven a breadth and depth of feature use generally had fewer support tickets and fewer escalations."

Structuring Onboarding for Success

Neelu shared her approach to dividing onboarding into two key areas:

"I like to divide onboarding into two areas: customer enablement and product integration (implementation). The KPIs are different for each. Implementation is always going to be dependent on the data you need. Then the second part is enablement, where you can have more control about personalization and sending bite-sized information."

She highlighted the importance of identifying the most impactful adoption metrics:

"At ZoomInfo, we had about 20+ adoption metrics. We created an adoption committee with a cross-functional team to identify the six most important metrics for stickiness and retention. One of them was the Chrome extension. Customer interviews and data showed that having this led to a 30% adoption increase."

Aligning Customer Success with Business Outcomes

John emphasized the importance of connecting onboarding to the business outcomes promised during the sales process:

"When a customer buys from you, there's basically this promise: 'I have this pain point, you have this solution.' There's some sort of quantifiable metric in that mix. It's really important to go back into that sales process and capture what that quantifiable value-based outcome was."

He added:

"Generally, these things map to either more money made for the business or more money saved. Great onboarding should bridge into that sales process and ensure the customer journey is mapped to driving that business outcome."

Learning from Consumer Products

The panel discussed how B2B companies can learn from consumer product onboarding experiences:

John noted:

"In customer success, sometimes we're B2B software type people, and we forget that our customer is also living in the real world too. They have magical onboarding experiences in their consumer products, while B2B onboarding processes are often clunky and bad."

Neelu highlighted successful examples:

"Duolingo has one of the highest retention rates in the ed-tech space. The gamification of onboarding, giving customers clear progress and feedback loops, has been incredibly effective. Notion is another product that's done a great job with their onboarding process."

Keeping the Customer at the Center

Michael emphasized the importance of focusing on customer value rather than just metrics:

"Please remember the people we're working for. When we talk about defining successful customer onboarding, we need to make sure that we align our business outcomes to what brings value to our customers. Something that a lot of companies do today is focusing too much on metrics without taking into consideration if what we're trying to achieve is bringing value."

Evolution of Customer Success Team Structure

John provided insights on how customer success teams evolve as organizations grow:

"In the beginning, it's just the founders – someone technical and someone business-oriented. Then generally one person goes deep on selling but also supports those customers. Eventually, you hire a VP of Sales before a VP of Customer Success."

He explained the natural progression:

"First, you'll have one person doing everything – being proactive and reactive, handling onboarding and renewals. The first break that typically happens is separating reactive support from proactive work. Then onboarding will start to break out from the rest of the CS motion."

John explained why this separation makes sense:

"Onboarding is more like a throughput motion, more project-based work as opposed to account management. If you reach that time to value, customers pass out of this project-based beginning phase. It's an area where you can create real capacity and scale in your business as the velocity of new logos picks up."

The Future Differentiator

As the panel looked toward the future of customer success, Sakshi observed:

"As we start believing that AI and automation is going to get better, the differentiation won't be that you're doing automation. It's how well you really understand your customers. The human touch is going to matter even more – it already does, of course, but that's going to be a differentiator instead of the technology."

Michael concluded:

"One size is never going to fit all. Our ability to adjust our organizations and teams to our customers, depending on the segmentation and industry, is really what will make us successful long-term."

This article was based on a panel discussion featuring customer success leaders Neelu Sheikh, John Gleeson, and Michael Salomon, moderated by Sakshi. Read more here.

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