4 game-changing lessons I learned leading Customer Success for a young startup

Tami Titheridge
Oct 22, 2018 · 5 min read

Howdy folks,

Tami here, your trusty CX Geek from Down Under! 👋

After recently wrapping up what was a pretty epic journey leading Customer Success (CS) for a young tech startup, I’ve been spending some time getting to know the leaders of some really exciting startups in Australia as I begin to map out the next chapter in my career.

One of the most common questions I’m being asked by founders is “What are some of the key lessons I’ve learned so far?” which is what has ultimately inspired today’s ramble (err, I mean, post).

So, with this mind, here are 4 game-changing lessons I learned while leading Customer Success for a young startup!


#1: Don’t underestimate the value of your existing customers.

While it’s exciting to experience high-velocity growth and customer acquisition, if you don’t have a plan in place to proactively support and grow your existing customers as well, you can actually end up hurting your revenue in the long run (which, I unfortunately, had to learn the hard way!).

The last thing you want is to be caught off guard when the customers you’ve been working so hard to obtain begin to churn because they aren’t receiving the proactive support and guidance they need in order to achieve their (the main reason they signed up for your product/service).

Beyond preventing unnecessary churn, there is also loads of value that comes with developing strong, proactive relationships with your customers.

Here are a few examples which are based on my personal experiences:

  1. It’s easier to retain and sell to existing customers than it is to find and sell to brand new ones, but only if you understand and have a great relationship with them first
  2. You will learn A LOT from them, such as how and why they’re using your product, what they’re finding the most value in as well as where the biggest gaps are, which empowers you to make more informed and subsequently more meaningful business decisions
  3. Investing in the happiness and success of your customers not only reduces churn and improves expansion opportunities, but it’s also the best way to inspire your customers to become powerful ambassadors of your brand, which can also result in increased revenue through word of marketing!

#2: Churn hurts, so make it count.

There’s no doubt about it, churn hurts (especially early on), but it’s also inevitable. With this in mind, instead of fearing it or letting it catch you off guard, embrace the opportunity to learn why it happened so that you can prevent it from happening again for the same reasons.

The good news is that you don’t need to build a complex strategy in order to turn customer breakups into meaningful learning experiences for your company. In fact, all you really need is a few simple questions, a spreadsheet to track your learnings and a commitment to speak to every customer who requests to churn!

I recommend picking the same 3–5 questions to ask every customer as this can make it easier for you to spot trends and should also help with your engagement rates if you’re sending out your questions digitally, such as via an email or survey.

Here are some of my go-to questions:

  1. What problem were you hoping to solve by using our product/service
  2. [Follow up to #1] What could we have done better to help you with this?
  3. Can you tell me about your experience?
  4. Why did you decide to leave/not to renew?
  5. What was it like doing business with us?
  6. Is there anything you’d like us to know?

Need a hand getting a basic churn system up and running?
Flick me an email via or drop me a line and I’d be happy to offer you some suggestions/guidance (free, of course!)


#3: Be aware of the expectations you’re setting, before you set them.

For those of us who care deeply about our customers and their experiences, it’s easy to get into the habit of doing things for them, even when it’s something they’re capable of doing themselves (usually because we want them to feel loved and special!).

Although this comes from a place of good intent, if you aren’t careful, it can result in setting unrealistic expectations that can’t scale, which is a valuable lesson I learned while onboarding my first enterprise customer who needed to add 250 users to their online dashboard.

You see, our product hadn’t been designed for a customer of this size which meant that each user had to be manually added one at a time (a very long and tedious process). So, to protect my customer from what I proactively decided would be a pretty crappy experience, I managed the process on their behalf.

What I didn’t realise, though, was that I’d unintentionally set the expectation that I would manage their users on an ongoing basis, which resulted in a fairly significant overhead on my side and eventually lead to them having a crappy experience anyway because as our company grew, so did my workload, which meant that what would take the customer minutes to do on their side, was sometimes taking me days.

Pretty ironic, huh?

In hindsight, what I should have done was use the time it took me to add their users to instead create a thoughtful video with some tips around how to make the process more effective and a bit less painful.

Not only would this have helped my customer while preventing them from having a crappy experience long term but it also would have helped all future customers as well!


#4: Using open-ended questions when interviewing customers will often provide you with more meaningful (and more accurate) insights.

One of the most powerful lessons I’ve learned thus far is how dangerous it can be to make decisions based on assumptions and opinions before validating them with customer-driven insights and feedback.

I learned this lesson while conducting a customer research project designed to help us determine which product features we should be prioritising in order to pack the most meaningful punches for our customers.

Sadly the project failed before it even had a chance to take off because we’d unintentionally biased the data by asking multi choice questions with set answers instead of asking open-ended questions that would give customers the freedom to tell us in their own words what they really wanted.

Because of this mistake, we ended up building a (very expensive) feature that suffered extremely low usage and adoption rates because although the data told us that “50% of customers said that Feature C would be of most value to them”, what it didn’t tell us was how many of those customers would still have chosen Feature C if they weren’t bound by a specific list of options.


So there you have it, 4 game-changing lessons I learned while leading CS for a tech startup!

Which one resonates with you the most? 😊

Tami Titheridge

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I love working with early stage startups, helping them to grow by designing and executing awesome customer experiences and customer success strategies.