31 min read

Why Retention, Renewals, and Upsells Are the Real Growth Engine for Your Business with Stuart Balcombe

Let me ask you this: Are you spending all your time chasing new customers while quietly ignoring the ones you already have? If so, you’re not alone. Most companies get caught up in the thrill of the hunt, pouring money into new customer acquisition while leaving retention, renewals, and upsells to chance.

But here’s the reality. If you’re in a recurring revenue business, renewals and expansions aren’t optional. They’re the lifeblood of long-term success. That was the heart of my conversation with Stuart, Head of Growth at Arrows and creator of the popular “Steal This Workflow” series for the HubSpot community. Together, we dug into what it really takes to build customer retention into the DNA of your business.And Hub Heroes, let me tell you, this conversation might just change the way you think about growth forever.

Why Are Renewals and Retention More Important Than Acquisition?

Too many companies treat onboarding and renewals like an afterthought. They celebrate the big new deal, then simply hope the customer sticks around. That’s a dangerous gamble.

Think about it: customer acquisition costs are climbing higher every year. Your revenue model probably depends on customers sticking around for two, three, maybe even five years. If they leave early, you don’t just lose revenue. You lose the opportunity to expand that account and the referrals that come with a happy customer.

Retention isn’t just about saving money. It’s about unlocking long-term growth. If you don’t have a proactive renewal and upsell strategy, you’re already behind.

When Does Retention Really Start?

Here’s the mindset shift most businesses miss: retention doesn’t begin at renewal. It starts on day one.

Every interaction a customer has with your company sets the tone for their future. If your sales team oversells and sets expectations you can’t deliver, you’ve already lost. If onboarding is clunky or confusing, you’ve planted seeds of doubt.

The companies that flourish don’t wait for renewal dates to start thinking about retention. They make sure from the very first conversation that the customer’s expectations and outcomes are aligned. When you do that well, renewals stop being events you have to fight for. They become non-events, because customers already see the value and want more of it.

What Strategies Actually Drive Renewals and Upsells?

Stuart shared a few strategies that every business can apply:

  1. Set clear expectations before the sale. Don’t tell customers they’ll be up and running in five minutes if it actually takes 90 days. Honesty builds trust.

  2. Address blockers early. Every objection or question your customers ask should be answered upfront. Use those insights not just in sales but in your marketing content.

  3. Educate as you grow. Growth isn’t just about getting more deals. It’s about helping customers solve problems. If your role is tied to growth, your focus should also be tied to education.

The magic happens when sales, marketing, and customer success stop working in silos. The customer doesn’t care which department they’re talking to. They care about their experience and outcomes.

How Does Customer Experience Drive Retention?

Customers don’t think in terms of “sales” or “support.” They only think about their experience with your brand.

If you make it hard for them to find information, force them to repeat themselves, or deliver inconsistent experiences, they’ll see your company as frustrating. But if you make it simple, easy, and valuable, they’ll stay.

Remember, customers don’t actually care about your company or your product. They care about their own goals. Your job is to help them reach those goals as quickly and easily as possible.

What Metrics Should You Track?

Retention might feel abstract, but Stuart laid out clear metrics you can track to measure success:

  • Time to engagement. How quickly do new customers take their first meaningful step after signing? Those who engage within 10 days are 70% more likely to stick around four years later.

  • Pipeline quality. Don’t just measure marketing by leads collected. Track how much qualified pipeline is created and whether those customers renew.

  • Renewal patterns. Look at which types of customers stick around and which ones churn. Not all churn is bad. Sometimes it reveals customers who were never a good fit.

What Roadblocks Can Get in the Way?

The number one killer of retention is silos. When sales, marketing, and customer success don’t talk to each other, customers feel it. They either get inconsistent information or they’re forced to repeat their story over and over again.

This is why tools like HubSpot matter. HubSpot allows you to connect the entire customer journey into one system. When teams have visibility into the same data, they can hand off customers smoothly and build a unified experience.

What Role Does Personalization Play?

Personalization is often misunderstood. Many companies reduce it to demographics: company size, location, or job title. But that doesn’t tell you what outcome your customer is trying to achieve.

A more powerful approach is to apply the Jobs to Be Done framework. Ask: what job is this customer hiring our product or service to do? The answers will differ across personas within the same company. A customer success manager cares about efficiency. A RevOps leader cares about clean data. A VP cares about reporting and ROI.

True personalization means helping each person achieve the specific outcome that matters most to them.

What Are the Long-Term Benefits of Focusing on Retention?

Here’s where the magic really kicks in. When you prioritize renewals and upsells, you don’t just cover your acquisition costs faster. You build a growth engine powered by expansion and referrals.

Happy customers refer new ones. And nothing beats the cost-effectiveness of referrals. Over time, this focus makes your business more profitable, more sustainable, and more efficient.

What Tools Can Help You Build Retention into Your Process?

The best tool is the one your teams already use. For many of you, that’s HubSpot. Use Sales Hub to manage renewals and upsells. Use Service Hub to manage onboarding and customer success. Build pipelines that reflect each stage of the customer journey, and connect your data so nothing falls through the cracks.

If you want to take things further, tools like Arrows can enhance onboarding and activation, while integrations like Zaybra help sync billing data directly into HubSpot. But the golden rule is this: keep it all connected. The more fragmented your tools, the harder it is for your teams to collaborate.

The One Big Takeaway

If you remember one thing from this conversation, let it be this: retention starts on day one.

It’s not just about preventing churn when renewal comes around. It’s about aligning expectations in sales, delivering value in onboarding, supporting outcomes through customer success, and making it easy for customers to see your worth every step of the way.

Retention is not a department. It’s a full-team, full-journey effort.

So ask yourself: are you building a customer journey that makes renewal a no-brainer? Or are you leaving it to a wing and a prayer?

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