What I Learned By Scaling a Customer Success Org 10X in One Year

John Henwood is the VP of Customer Success at Writer and a member of Vitally's Success Network.


When you’re building out the CS function at an early-stage startup, you’re up against limited resources, a barely-there team structure, and a constantly evolving business. It can feel like you’re going down a hill quickly in a car without brakes. 

I joined Writer when there were just four people on the CS team and scaled it into the robust, 40-person CS function we have today. I made many mistakes, learned hard lessons firsthand, and discovered strategies for building a valuable CS team for the business and our customers. 

I’ll share my most important learnings with you in this article.

1. Define Your Mission and Scorecard 

When I joined Writer, we had a very small and generalist CS function, like any other early-stage startup. 

There were only four CSMs responsible for everything post-sale — from onboarding to renewals and account expansions. We managed most of these processes out of spreadsheets and didn't have any tooling for revenue forecasting or customer lifecycle tracking

We got work done but didn’t really have an overall direction. So, my immediate priority was creating some structure for the team to improve efficiency.

First, I developed the team’s mission statement and core KPIs so each functional role was clear on what we wanted to achieve. Next, I created a scoreboard for core CS metrics like renewals and a simple reporting system to track them accurately. From there, we built out a forecasting system to generate more visibility and predictability across the entire book of business.

Once we had these fundamental processes in place, I turned my attention to fine-tuning the customer experience. We implemented basic customer segmentation to help us deliver the right experiences to the right customers. This involved creating different tiers of experience and mapping out separate customer journeys for each tier.

Learn more: How to Build Your First Customer Success Team

2. Build for Scale From Day One

Your startup might grow much faster than you expect. In our case, the business was experiencing 400% or 500% growth year over year. We couldn’t afford to play catchup. That’s why it’s so important to anticipate your business’s growth and build the systems, processes, and people to scale.

But scaling isn’t linear. Like other CS leaders, I had an ARR per CSM capacity goal in mind. I also knew I wanted to specialize the team beyond the CSM role to deliver more value internally, and to our customers. 

So, my first hire was someone who could own and scale our customer education and adoption initiatives across the whole user base. We built the team from there to include other more 1:1 high touch engagement roles like technical account managers, implementation and to support the CSMs and Support functions in place. 

Now, we are a 40-person team comprising scaled CS, enterprise, strategic CSM functions, implementation managers, technical account managers, and education and support functions. 

We also started our solutions architects team, baked into the pre-sales process. I wanted CS to have ownership and participation in that presale journey so that we can really stay close to what's being scoped pre-sale and what we could deliver repeatably.

Related: Building the Foundation of Scaled CS

3. Invest in a Reliable Tech Stack

An important aspect of scaled Customer Success is having the right tech stack. Investing in software that speeds up time-consuming tasks is crucial, yes. However, you also need software that provides 360-degree visibility on your book of business for data-driven decision-making. 

Vitally does the latter for us. We use it to set and track customer journey milestones, monitor health scores for different customer segments, and create playbooks to deliver consistent experiences at scale.

To save time on day-to-day tasks, we use our generative AI tool, Writer, for personalized customer messaging and Matik to automate deck creation. 

Learn more: How to Use AI for Customer Success

4. Don’t Compromise on Talent Quality

When the business is growing quickly, you're often underwater with resources and desperate for people that it’s easy to lower the bar for who you hire. But this is the most destructive thing you can do. 

Hiring someone just because they’re “good enough” or look like they can reasonably do the job can, frankly, be a team killer. Early team members have leveraged impact on the culture, standards, and outcomes your team will create. A handful of “good enough” hires can dilute your team from World Class to mediocre. We started by hiring a team of high velocity “builders” with experience wearing multiple hats; tested their ability to deal with ambiguity, change, and ownership of their business.

Write down the specific things you’re looking for in a role (and the deal breakers) before the hiring kickoff. Then, work with your talent sourcing team to qualify applications early — so you’re not stringing the wrong candidates along. The hiring team will keep you accountable, ensuring that the candidate selection process is rooted in the defined expectations and requirements of the role.

Great people know great people — we were incredibly successful in using our first few hires to refer other top peers they worked with. We asked each new team member “who’s the best CSM you’ve ever worked with?” and created a shortlist to assess from there.

Learn more: The First Five CS Hires at 15 B2B SaaS Companies

5. Set Up Performance Incentives Early

While we had a clear scorecard across the team, and by role, a fundamental mistake I made was not putting the right incentives in place for the CS team from the start. 

When I joined Writer, our CSM compensation structure didn’t include any variable components like renewals. So, we couldn’t properly reward CSMs for their outstanding performance. I didn’t change that quickly enough, and it set a pretty bad precedent for the team. And as time passed and we hired more CSMs, it became much harder to correct this mistake. 

My advice for CS leaders in early-stage startups is to work out an objective compensation system that goes beyond salaries and motivates the CS team to exceed their KPIs and deliver impressive results. This Vitally article shows you exactly how to go about this: Decoding Commission Structures for Customer Success Managers

6. Avoid the Data Trap

Data is really important to everything we do in Customer Success, but it’s not absolute. 

As customer behavior changes (and it will) and the business scales exponentially, you’ll discover that you can’t use history to predict the future in the same way. In other words, you can’t rely solely on historical data to set reasonable targets for CSMs, assess relative performance or forecast revenue. 

When that happens, you need to be more hypothesis and scenario driven. Sometimes, being a CS leader at a startup means making an educated guess, testing it out, and learning from the results.  We also had a base and best case scenario in place, with options to change strategy depending on how results were trending. All of this is only possible if you have real time reporting signals in place.

7. Become the Source of Truth for Everything “Customer” 

Your CS team needs to be a river of information, educating the entire business about your best customers and where to find them. 

At Writer, our Go-To-Market team constantly comes to us with questions like: Who are our best customers? What are they using us for? What are they getting value for? We always have the right answers for them because we’ve built the CS team to serve as the Voice of Customer internally. 

One thing that worked really well for us was creating a public Slack channel where we share customer wins and interesting product use cases — that is, what they’re getting the most value from. We also have a customer delight channel where the team quantifies the dollar-based impact of our CS operations for each of our customers. This has created a library any colleague can search to find potential advocates and stories to socialize. 

On top of that, we host weekly internal lunch-and-learn events where we discuss customer stories and share ideas so everyone has access to the same information. 

Learn more: Why Storytelling Is Crucial in Customer Success

Wrapping Up: Know the Fires You Need to Let Burn

Scaling your CS team when in hyper-growth mode means letting some fires burn because you can't handle everything simultaneously. You must distinguish between the fires that need to be put out today (lest they become craters) versus the ones that can be left to burn for a little longer without impacting the business negatively. 

You have to find a way to focus the team, reduce the cognitive load, and avoid whiplashing them across initiatives. We did so by looking back to our CS scorecard KPIs and prioritizing the most urgent/important workstreams to move those metrics, and nothing else.

That way, you can focus on what truly matters: Delivering value to your customers and driving business growth at every stage. 

If you enjoyed reading this, check out Vitally’s Success Network blog for more tips on leading a high-performing Customer Success team.  

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