How to Scale a Customer Success Team Without Losing Customer Value

When scaling customer success, one of the biggest challenges CS leaders face is delivering personalized customer value at scale. In this episode of The Customer Success Pro Podcast, I sat down with Saahil Karkera, VP of Customer Success at Oaky and Founder of CS Connect, to dive into exactly how his team navigated scaling their CS operations—while still ensuring each customer received meaningful value at every stage of the journey.

In this blog post, we’ll explore some of Saahil’s top strategies, lessons learned, and practical tips for any CS professional looking to scale successfully without losing the human touch.

Meet Saahil Karkera: From Sales to CS Leader to Community Builder 

Saahil’s career in Customer Success started with an important realization. As a former enterprise sales executive, he quickly saw that closing a deal was only the first step—keeping customers successful (and renewing) was just as critical. That led him into CS, where he’s spent the past nine years building and scaling teams at early-stage startups. Today, Saahil leads the Customer Success team at Oaky, where they serve over 2,500 customers globally.

But Saahil’s impact doesn’t stop there. He’s also the founder of CS Connect, a thriving community for European CS leaders, focused on practical, no-fluff frameworks to level up their careers and teams. For Saahil, giving back to the community is just as important as driving success for his customers.

Scaling Customer Success at Oaky: From 200 to 2,500 Customers 

When Saahil first joined Oaky, the company had around 250 customers, primarily in the Benelux market. Fast forward to today, and Oaky has grown to over 2,500 customers across the globe, serving a mix of independent hotels and luxury hotel chains.

This rapid growth came with new challenges—especially as the business moved upmarket to serve larger, enterprise accounts. With that shift, the CS team had to rethink their approach to customer value, moving from a one-size-fits-all approach to a more nuanced, multi-stakeholder strategy.

What Does Customer Value Mean—And How Do You Define It at Scale? 

For Saahil, delivering value starts with asking a simple but powerful question:

“What’s in it for me, from the customer’s perspective?” 

But it’s not just about understanding the product value. Different stakeholders define value in different ways:

 • Economic Buyers might focus on ROI, cost savings, or revenue impact.

 • Champions might prioritize ease of use and quick wins.

 • Technical Users might care more about product stability or integration capabilities.

This layered view of value is critical when scaling. As your customer base evolves and your Ideal Customer Profile (ICP) shifts, you need to continuously revisit and redefine what value looks like—for every type of customer and every key persona.

The Biggest Mistake Companies Make When Scaling CS 

According to Saahil, one of the most common (and costly) mistakes is failing to revisit your ICP and value proposition as your business matures.

“Your product evolves, your market evolves—so why would you assume the same value message applies to every customer forever?” 

This is especially true when moving from SMB customers to enterprise accounts. What works for a small, independent hotel won’t resonate with a luxury hotel chain. Yet too many CS teams rely on outdated assumptions about what value means to their customers.

How Oaky Delivers Personalized Value at Scale 

1. Map Value for Every Stakeholder 

Oaky’s CS team regularly holds in-depth conversations with both their largest and smallest customers. They map out the specific value drivers for every key persona, from the executive sponsor to the end user.

2. Segment and Prioritize Accounts 

Not all customers need the same level of touch. Oaky segments their customers into tiers and adjusts the engagement model accordingly. High-touch accounts receive tailored, 1:1 strategies, while smaller accounts receive automated, data-driven value updates.

3. Operationalize with a Customer Success Platform 

To scale personalized engagement, Oaky leverages a Customer Success Platform (CSP) to track milestones, usage trends, and value delivery across every customer. This helps the team trigger proactive, personalized communications—without adding manual work for CSMs.

4. Celebrate Milestones and Showcase Value in Real-Time 

One example Saahil loves? Canva’s real-time ROI notifications, which show how much money you’ve saved with each download. Oaky is building similar automated touchpoints, where customers are notified every time they hit a key milestone using the product.

Personal Value Matters Too—Not Just Business Value 

One of Saahil’s favorite questions to ask customers is:

“What would we have to do to help you get a promotion because of our product?” 

This personal angle reframes the conversation and helps Oaky align their value delivery not just to business outcomes, but to individual career goals. It’s a simple but powerful way to build champions who will advocate for your product—inside their company and beyond.

Scaling Smart: When to Hire vs. When to Optimize 

As Oaky grew, Saahil’s team didn’t immediately hire more CSMs. Instead, they followed a systematic approach to balancing headcount with efficiency:

 • Audit Existing Processes: What non-value-add tasks can be automated or outsourced?

 • Leverage Technology: Maximize the existing tech stack before adding headcount.

 • Prioritize High-Value Accounts: Focus CSM attention where it matters most—on customers with the biggest expansion potential.

 • Work Cross-Functionally: Partner with Product and Engineering to embed value messaging directly into the product itself.

The Biggest Lesson? Don’t Scale Alone. 

One of Saahil’s most important takeaways is that scaling CS is not just a CS problem. It’s a company-wide effort.

From Product embedding value into the user experience, to Sales setting clear value expectations during the sales process, to Marketing reinforcing value in ongoing communications—it’s all connected.

And internally, investing in your own team’s growth is just as important as delivering value to customers. As Saahil puts it:

“If your CSMs aren’t constantly leveling up their skills, no amount of technology will save you.”

What’s Next? Hyper-Personalization Powered by AI 

Looking ahead, Saahil predicts the future of customer success will be all about hyper-personalization—understanding every customer, every user, and every touchpoint in granular detail.

AI will play a key role, but it’s not a silver bullet. It takes human insight plus smart technology to truly deliver value at scale

Final Thoughts 

Whether you’re a CS leader at a fast-growing startup or a seasoned exec scaling an enterprise team, Saahil’s story is a powerful reminder that delivering value at scale requires both art and science. By combining deep customer understanding with smart processes, technology, and cross-functional collaboration, you can grow your business and keep your customers happy.

Listen Now & Build Value at Scale

This episode with Saahil Karkera is a must-listen for CSMs, CS leaders, and anyone looking to master proactive churn prevention and data-driven engagement.

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Want to take your CS career to the next level? 

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Connect with Us 

📌 Follow Saahil Karkera on LinkedIn

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