Chapter 9

When and how to scale your customer success efforts

This is a chapter from The Startup CEO’s Guide to Customer Success and Onboarding.

Common misconceptions:


🚫 Now that my first customer success hire is up and running, I'm set on the customer success front for a while.

🚫 Scaling customer success is a huge undertaking that requires a lot of time and money.

🚫 Automating parts of customer success results in a poor customer experience.


If you've made it this far in this guide, we are hopeful you've seen the value of investing in customer success. If you see the value, odds are that your customers do too, whether it's getting them set up during onboarding or supporting their needs beyond those early moments.

If your customer success strategy is "working", you are helping customers achieve their desired goals and keeping them around longer. Through customer feedback, you are learning what's working well. You're also learning what needs to be improved in your process, in your resources, and in your product. You're collaborating with your sales, marketing, and product teams to improve the overall customer experience. Said differently, you're improving your overall business and approach for your current customers, opening up the doors for new ones to show up!

Your customer success person has championed their efforts and illustrated their needs, and you supporting them has evangelized these efforts throughout your organization.

Customers are happier because they understand the value you provide, keeping them around even longer.

This is WONDERFUL, congrats.

This also brings forth the realization that as more new customers come to you for help and current ones stick around longer, there will be more onboardings to complete, more questions to answer, and more check-ins to facilitate.

As great as your first customer success hire is, they feel the impacts of this workload and eventually burn out. This is NOT SO WONDERFUL.


Customer success, just like onboarding, should never end. The sooner you begin to scale these efforts, the more impactful the results for your business.

Although you've been able to deem your customer success strategy as a "profit" versus a "cost" center, simply adding headcount to your customer success team is only part of the solution for scaling your efforts.

Obviously, adding more people gives you more "time" to interact with more customers, but adding more people after you add more content, processes, and technology is how you'll really see your efforts pay off for your customers and your business.

Scaling your content

The more you interact with customers, the more of their needs and questions you uncover. If you document explanations that clarify their needs and answer their questions, you are building scalable content!

This is something your might team of one can (and should) start today!


A great rule of thumb is that if you have to explain an answer, a process, or a feature more than one time, it should likely be a piece of content that you can use for future customers.

Whether you use simple word documents, a wiki page, or establish a robust help-center, there are 3 categories of content worth focusing on…

  • training tutorials - as you continue to onboard customers, take note of the questions that keep coming up. From there, create written guides or video tutorials (2-3 minutes) that capture your answers.
  • These will prove especially valuable when your new customer volumes increase and you don't have the human bandwidth (yet) to reach everyone right away.
  • best-practice posts - each customer is unique and came to you for help solving THEIR particular needs. That said, there are best practices for using your product or service that you are the expert on. These are behaviors that you see working well for other customers and are worth sharing.
  • Creating blogs or short write-ups to capture these tips gives you a chance to help customers continue to see the value you provide beyond those early onboarding moments.
  • help-center articles - regardless of where customers are in their lifecycle, they'll eventually need some product or technical support.
  • Pay attention to where some of your earliest customers keep getting stuck. They are likely sending in support tickets or questions about said moments. It's those questions or tickets that can help you prioritize where to start.
  • Having clear and concise help-center articles to help customers through these frustrating moments can prevent their frustrations from festering and turning into churn.

To go a bit further, you can look at these 3 categories from the lens of 2 themes:

  • "how-to" content - customers need to know how to do things, ideally sooner than later. They need to know how to log into your product, how to set up their account, or how to leverage your service.
  • Check-lists, step-by-step instructions, and tutorials are a great way to capture "how-to" content so you set customers up for success
  • "why-to" content - once customers know how to do something, you'll want to continuously teach them "why-to" keep doing it. Why should a customer log into your product daily? Why should they use feature A over feature B today? Why should they avoid a certain behavior or action?
  • Best-practice blogs, case studies, or strategic webinars are a great way to capture "why-to" content so your customers put into practice what your "how-to" content teaches them. Learn more about when to use "how-to" and "why-to" content here.

The more of this content you create, the faster you can support future customers towards achieving their desired outcomes.

Scaling your process

Once you have your content, documenting and centralizing your internal processes is critical to creating a repeatable, positive experience for your customers.

As you engage with more of your customers, you'll learn what drives them towards success and what doesn't. The things that do work should trickle down to future customers. Ensuring this consistency allows your future customers to also achieve success.

We are not suggesting that every single customer will have the same exact needs at the same exact time. We are, however, suggesting that everyone at your company (especially your CS team) should be aware of what to do, how to do it, and when to do it. As your organization grows, you'll also want to clarify who is doing it.

The goal is to create a seamless experience for your customers. When everyone on your team knows their role and part in the customer journey, that seamless experience becomes a reality.

Your process for engaging with customers will change over time, don't let that stop you from documenting steps today. In fact, let that motivate you to get started sooner than later. Optimizing the process and documenting it as you go will be a much lighter lift than trying to document it down the road.

Here are some best practices…

  • create a customer journey map - it should be clear by now that customer success is a company-wide effort. Giving all departments visibility into the process is the first step to making sure your customers have a wonderful overall experience.
  • A customer journey map helps visualize where your customers are in the journey and who is responsible for their success. This guide covers how to go about creating your own!
  • create internal playbooks - a "playbook" is simply a document that captures the steps you want your internal teams to follow when engaging with customers. As you map out your customer journey, start creating playbooks for each phase.
  • An onboarding playbook is a great starting place for your success team. This should include how you define onboarding, when your CS team should reach out, talk-tracks for phone calls, email templates, links to those great pieces of content you centralized, and so on.
  • Do the same for the phases beyond onboarding to help customers stick around and grow their business with you too.

As your processes expand or change, be sure to update your journey maps and playbooks. These should be the source of truth for your teams. They also make it far easier for you to set your future CS hires up for success, giving them the knowledge and steps you'd like them to take to keep that positive customer experience intact.

You might quickly find yourself in a world where you have 6 or 7 different people engaging with your customers during their first year (sales, onboarding, support, customer success, billing, etc.). That's OKAY as long as everyone knows their roles and responsibilities; sharing and following your documented processes helps you avoid disrupting that positive experience you promised. Remember, customers are people not just KPIs to hit. Be sure to treat them as such.

Scaling with technology

Now that you have your initial content and processes figured out, automation can help you really scale your efforts.

The word "automation" tends to scare people. Don't let it scare you.

If done well, automating parts of your process does not necessarily result in a robotic, human-less experience for your customers. It can actually make your teams more efficient.

By no means does this mean take every step you documented above and try to automate it. The goal is NOT to eliminate humans from your customer success flow. Instead, think about where your CS team is spending a lot of time manually doing tasks and figure out what tools can help reduce those manual components (sending onboarding project plans, typing out answers to questions, going back and forth on scheduling calls, etc.)


If you are still rocking and rolling with your CS team of one, automation allows you to reach more customers. This becomes especially important if your business model allows for free or low-spend access; you don't want to completely ignore those customers just because your team of one doesn't have the bandwidth.

There are plenty of great tools out there to help you with these efforts. Here are a few of our favorites.

In conclusion…

Building a great customer success organization requires people, processes, and technology.

The stage of your business should help you prioritize which phase of the customer success journey to tackle first. If you're focused on bringing new customers through the door, onboarding should be your first focus. If you are trying to retain existing customers, focus on materials and processes to help them adopt your product or service. If you're trying to grow your existing accounts, think through what actions drive success in those later lifecycle moments.

Regardless of your stage, creating content, outlining steps, and leveraging the tools available will ensure your customers get the experience they are paying you for. In turn, they will keep paying you, ideally more and more, as the partnership extends over time.

Download the entire CEO's Guide to Customer Success

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