Ian Russell is a Customer Success leader who founded and built the CS team at Loom, scaling it from pre-revenue through Series C and exit. More recently, he led Customer Success at Accord, guiding its growth and strategic customer journey. Today, Ian leads a consulting firm, where he partners with early-stage teams looking to build their first CS motion or mature it into a world class revenue engine.

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In startups, the focus often goes into acquiring your first customers. There’s excitement, momentum, and a sense of urgency to get that initial traction. But once you have those first few customers, the question becomes: What now? 

The most successful companies are those that see Customer Success and retention as integral parts of their growth strategy.

The secret sauce of exponential growth lies in what we call net revenue retention — not just acquiring customers but growing them over time. When you don’t prioritize this early on, you end up on your heels, scrambling to figure out renewals at the last minute. 

That’s not a sustainable approach, and it overlooks the value that early customers can bring if you’re investing in their success from day one. When you forgo actively planning how you're going to make your customers successful, you're leaving money on the table, missing out on the power of compound growth for the business in the long run.

From Day One: Building a Mindset That Prioritizes Retention

For any Customer Success team, the goal isn’t just to sign up customers but to keep them. And that journey begins the moment you close the first deal.

Too many teams treat renewals like an event, but in reality, renewals should be a process that starts on day one of onboarding. Next year’s sale begins as soon as you sign the initial contract. Every engagement lays the groundwork for the future. Work backwards from the contract outcome you want and towards the customer outcome they’re after. You’ll be able to plan more thoughtfully with these end-states.

Early CS teams should work with a long-term vision. Instead of focusing solely on the front-end go-to-market motions, they need to recognize the value of cultivating and growing these initial relationships.

When you view renewals as something that happens at the end of the contract, you’re already too late. A successful renewal starts on day one, with a mindset that focuses on what success will look like months or years down the line. When the renewal feels like a paper process and not a mountain to climb, you’ve hit your mark. 

How many of your customers are willing to lock in an early renewal? A good pressure test here is knowing the outcome from a hypothetical question: “If this customer’s renewal was tomorrow, would they sign?” The answer to that reveals what work you have left to do.

The Pitfall of Moving Too Fast: Acquisition Without Retention

In my experience, one of the most common startup mistakes is the tendency to keep pushing for the next new customer at the expense of time spent driving existing customer growth. I’ve seen too many teams with this split focus — where the effort shifts to chasing the next sale without ever ensuring that existing customers are seeing success. This isn’t just risky; it’s a missed opportunity to build stability into your revenue model.

A lot of early contracts, especially with startups, aren’t truly “recurring” in the way we’d like to think. How many of your customers are on multi-year agreements? This is the standard by which we should consider something ”recurring.” Many of these contracts have exit clauses or flexible terms, meaning they’re essentially one-year agreements, sometimes even month-to-month. And that means we have to re-sell our product every year. But if we wait until renewal time to focus on the customer’s satisfaction, we’re doing double the work — and risking churn.

To turn first-time customers into recurring revenue, we need to treat them like multi-year partners from day one. This means engaging with them in ways that consistently drive value, so we’re not left scrambling to re-sell the relationship each time renewal comes around.

Advice for Building a CS Playbook That Drives Retention

One of the biggest challenges for early CS teams is creating processes without becoming robotic or losing the personal touch. Especially in the early days, teams may not have full-blown systems in place — maybe you don’t yet have a CSP or even a well-defined onboarding process. 

And that’s fine; the key is to treat each customer experience as a learning opportunity, refining your approach with every interaction. Here are three elements of an effective customer retention process:

1. Start With Relationships

The best thing you can do early on is to build genuine relationships. Processes are critical, but if you focus solely on checking boxes, you’re missing out on the human side of Customer Success.

Even if your onboarding process isn’t perfectly smooth yet, a strong relationship can make all the difference. I’ve seen it save accounts and prevent churn, all because a customer felt that we had their back.

Relationships are the one constant in CS. If your team can focus on trust and rapport, they’ll be able to navigate even the messiest of implementations and retain customer loyalty. Small gestures, like sending an UberEats gift card to a customer who’s working overtime, create meaningful touchpoints that go beyond product features or KPIs. Be thoughtful and genuine about connecting with them.

In some cases gift cards are overdone, and that’s okay. I can remember one time we found out a customer was moving and we paid for their moving van to help make the chaos of that day a little easier. Genuinely seek to connect with others and you’ll find ways to delight them that go beyond a vendor partnership.Visit your customers in person. If there is one hill I’ll die on, it’s that visiting your top accounts in person will make relationship building 100x easier. I’m finding fewer and fewer teams are investing here and it's a massively missed opportunity. If you care it shows in spades and your customer will notice and reciprocate. Do this for your top accounts and the ROI will be delivered. If there is one thing you take from this article it should be this: Get on the plane and visit them.

2. Iterate on Your Processes Every Step of the Way

I always tell my team that building a playbook is an iterative process. Don’t follow them like a checklist, use it as a GPS and intentionally take wrong turns when you think it’ll lead to better outcomes. In the early stages, you’re building the plane while you fly it.

Every time you work with a customer, you’re learning something new. What worked? What didn’t? What could you systematize next time? As you gather these insights, you start to build out your MVP playbook, which will become more robust as you grow.

By drawing from these early experiences, you can identify the common levers that drive success and start to template them. This won’t just make your team’s job easier; it also creates a consistent and scalable approach to onboarding and retention. The consistency in the approach will allow you the gift of measuring what’s working and what’s not. Without that, iteration is done blindly and could lead you to spinning your wheels. You’ll find over time that there are typically only a few milestones that need to be hit to make a customer successful — find out what these are as fast as possible and iterate around them continuously.

3. Embed the Idea That Retention Is an Ongoing Sale

Too often, teams treat retention as a passive process, but renewal is a sale that never ends. You’ll have stakeholders leave, new budget prioritization, company goals that shift quarter over quarter…Change is constant for your customers and the only way that you stay ahead of these is by riding shotgun with your customer through it all. Start the retention process on day one, not 90 days before the contract ends. The more proactive you are, the more likely you are to identify growth opportunities and mitigate risks.

How to Handle Misalignment With First Customers

One unique challenge for startups is that your early customers may not always be the ones you scale with. Your product, market, and go-to-market motion will evolve, and your customer base will, too.

In these cases, it’s essential to understand that some early customers are meant to be transitional — they help shape your processes and provide valuable feedback, even if they don’t stick around forever.

Sometimes, your first customers just aren’t a great fit for the long haul, and that’s okay. The critical thing is to recognize the role they play in your company’s journey. They took a bet on you and were there through all the bugs, challenges, and built alongside you.  These customers may not bring the biggest contracts, but they’re invaluable in guiding your team as you refine your product and Customer Success strategies.

Related: Can Customer Churn Be Good for a B2B SaaS Business? Sometimes…

Lessons in Customer Fit and Feedback

Customer Success teams often end up working with less-than-ideal fits, especially in the early days as a company refines its ICP and offering. I encourage teams to use this as an opportunity to gather feedback and guide the company’s direction.

At Accord, we had go-to-market feedback sessions every two weeks, where we’d dive into what’s working, what’s not, and what our customers are really looking to achieve. This gives our product and engineering teams a close connection to our customers’ needs, even if they’re not ideal long-term fits.

At Loom, we went even further by involving engineers and designers in customer interviews. This direct exposure helped our teams build empathy and a clear understanding of what we needed to build. This built customer obsession into the culture that continued as we scaled the company. Everyone had a part in delivering outcomes because of this feedback loop. This was a massive lever for us in building a product that would go on to be loved by so many. 

Prioritizing Your Efforts: The 80/20 Rule in Customer Success

Not every customer will be a perfect fit, and that’s okay. In CS, you have to learn where to focus your energy. I’m a big advocate of the 80/20 rule — the idea that 20% of your effort will yield 80% of the results.

While I want to say that you need to spend time with all customers equally, that’s just not a reality for every team through every growth cycle of a business. When you start to mature your services offering, you can start to segment your approaches (tech touch, hybrid, high touch, etc.) but until then you need to be smart about resources you have available at any given moment. So what do you do instead? Spend your time with the customers who are likely to grow with you and bring long-term value. Recognize when it’s best to let go of a customer that isn’t aligned with your product, so you can devote your resources to those who are. 

This approach doesn’t just prevent burnout; it allows your team to prioritize effectively. Of course you need to be thoughtful about how this affects revenue numbers for the exec team/board. Approach this from an opportunity cost perspective. Calculate your addressable market that you have in your accounts that have potential for growth and weigh that against time spent with poor fit accounts and churn numbers. This analysis will help you both sell your approach to leadership but also get everyone aligned so churn doesn’t come as a surprise.

By setting clear expectations and learning when to let go, you can focus on creating meaningful, high-impact relationships that drive real value.

Recurring Revenue Begins with the First Customer

The path to recurring revenue doesn’t start at renewal — it starts the day you bring on your first customer. By building strong, trust-driven relationships and keeping retention front of mind from the beginning, you set the stage for sustainable growth.

Yes, systems, processes, and playbooks matter, but nothing replaces the power of genuine connection.

For early-stage CS teams, the most valuable advice I can give is this: Remember that Customer Success is as much about people as it is about processes.

Approach each customer with empathy, curiosity, and a commitment to their success, and you’ll lay the foundation for long-term, meaningful partnerships. And if you’re only two things, be infinitely curious and relentlessly helpful — it’ll open so many doors for you.