Mar 17, 2022

Read Time 9 min

Q&A Part 2: the startup’s guide to Customer Success


As a follow-up to our well-attended webinar on “The startup’s guide to Customer Success” with Jennifer Chiang (the author of the book by the same name), we wanted to get more of our audience’s questions answered.

Since we didn’t have the time to get to all the questions that came in during the live webinar, Jennifer took the time to go through and provide her responses to the unanswered questions, so we could share them with you here.

We hope this answers all of your questions on how Customer Success can help you as your scale your startup.

You can find the initial Q&A recap from the webinar here.

The startup’s guide to CS – Q&A part 2

Speaker: Jennifer Chiang, Head of Customer Success, Seso

1.) We are in a more mature phase with a wide range of customers (low to high touch). Would you advise to use the quadrant you showed per type of customer?


Great question – a quick primer for those that didn’t attend the webinar or read my book – when you are thinking about how to best focus your energies, think about how your customers view your product (user complexity) and how complex your product is (product complexity). Upon that reflection, you can then plot where you should focus based on the two-by-two matrix that I showcase in my book. You can see the matrix and learn more each quadrant here.

Going back to the question, you can use a quadrant that is specialized towards a certain type of customer if your low-touch customers have a different view of your product or approach your product differently than your high-touch customers. For example, if your low touch customers just view your product as a “set it and forget it” whereas your high touch customers view you as something that they think about every waking second, then you would want to focus your efforts differently.

However, on the whole, I would recommend having a cohesive “focus” for your company so that you can better present and weave the customer journeys of all of your customers and tell a better overarching customer story.


2.) Do you have some tips on getting started on customer health measurements/ starting a customer health score?

For startups, I highly recommend that you stay focused and not try to build a perfect customer health score at once (and be okay with a simpler-than-expected customer health score!). In fact, one of my earliest mistakes was building a customer health score that was too complex to the point where I was spending more time tracking and calibrating the score rather than pushing the customer success objectives forward.

When it comes to what should go into your customer health metric, keep it simple with three main things – an adoption metric (how is onboarding going?), an engagement metric (are customers using your product/service after onboarding?), and a retention metric (are customers showing commitment to use you again?). By keeping it to these three things, you can have a quick sense of how your customers are doing without being bogged down in the numbers. As your team and product matures (and you “graduate” to more granular metrics – like from % sign-ins to % first session creation), you will naturally add more metrics to fine tune your customer health score.


3.) How do you figure out the Time to First Value?  Do you survey customers to determine?

If you don’t know what your time-to-first value is, definitely survey your customers (and ideally, interview and talk to your customers more!). Understanding customer goals – and its nuances, like when do they feel they are starting to see a return from using your service – is key.

Another common mistake that I see here is when folks feel like they figured out what the “Time to First Value” is after a few customer conversations and then they don’t revisit it (with the same customers and with different ones) to make sure that it is still the case. Remember, customer needs can and will evolve and it is customer success’ role to stay on top of what customers are looking to achieve.


4.) How do you distinguish between Customer Experience and Customer Success?

Customer success and customer experience are definitely intertwined, especially at a small startup! Typically, “customer success” focuses more on customer interactions – diving deep into what are customers’ goals, how are they using your product effectively and how can we bring even more value to them as their trusted advisor. Customer experience is more product facing; so, while, yes there are a lot of customer interviews, you would be typically working with much larger segments (tech-touch) and solutions that would solve a larger group’s pain points instead of diving deep with every single customer. But again, very intertwined, and oftentimes shared amongst multiple customer-facing team members or even across departments (ex. Product and customer success own “customer experience”).


5.) How do I get leadership to buy into new CSM tech when you aren’t a key decision maker?

First, I’d have to ask – why isn’t a customer success person not a key decision maker? This could be indicative of a lack of executive buy-in for the customer success team (a red flag that should be addressed first!). I will note that this isn’t uncommon; customer success functions can be seen as only cost centers at first, and it can take a while (especially if there is leadership turnover) to build that trust and help folks understand the multiplier effect of a customer success team.

However, say you do have leadership buy-in for customer success, but not necessarily for customer success tech just yet. Like when we are working with customers, I’d challenge you to dive deeper – what is the cause of leadership’s hesitation (which is probably very valid!) and how can you address those concerns upfront. For example, if your leadership team didn’t realize that your CSM team is doubling in size from 5 to 10 in the next few months, perhaps knowing that would change leadership’s calculus of how they view this new tech.


6.) We’re a small company, not a start-up anymore, just small. We’re focusing more on Success now, but can’t stand up a full CS department, so we’re hybrid(izing) it with our Support folks, so not true CS. Any tips for that or pitfalls to watch out for?

Support is such an important function and Success and Support need to be in lock step with each other! In my experience managing both success and support teams, my best tip in this case is actually a management tip: understand how each of your team members (on both the success or support sides) wants to grow and support them in that journey. For example, I’ve worked with support folks that wanted to grow into success, and success folks that wanted to grow into support. When you have those conversations upfront, not only can you better guide your Support + Success ship, but you will have better customer outcomes because your employees will be more motivated.


7.) Do you have an example of how a customer success team has “delighted” customers when they have a low tech but a highly emotional product?

Sure! So, an example is Rover, a pet sitting service app. It’s a relatively simple technology (again, I know it’s not simple, but compared to something like Salesforce, it’s easy to use and not too complex. If I were to show it to someone who’s never used it before, they would understand how it works pretty quickly). But despite the simplicity, the product is high in “user complexity” – meaning that if anything were to happen to a person’s pet, they would want to know as soon as possible!

An example of how they’ve delighted customers is by encouraging sitters to send photos and updates of how the pet is doing. For example, I was out with a friend the other day and she had used Rover to get a dog sitter while we went out to brunch. I can remember the moment my friend leaned over to show me a picture that her Rover sitter had sent her of her dog watching the football game. It truly “delighted” my friend (and me!).


8.) We have a reseller model.  Any suggestions for getting started when we are often one removed from the end customer?

The biggest thing here when you are one removed (or twice+ removed!) from the end customer is to understand each of the stakeholders’ goals throughout the customer journey – even interviewing end customers or people like your end customers so that you can make sure that all of the goals are aligned throughout the full experience. After all, if the middle company’s goals are counter to the end user’s goals, it will become difficult for you to make either the middle company or the end user successful.

Once you’ve better understood the goals of every stakeholder involved, understand how each of them would derive value from your product. Then build a good onboarding system to make sure that even those you aren’t directly interacting with can still get onboarded properly. At times, this may include “train the trainer” onboardings so that folks can evangelize on your behalf and help the end user become more successful.


9.) After the initial startup phase of the business, what is your approach to scaling?  Not necessarily with onboarding but more so the lifetime of the client thereafter?  What programs have you implemented that help stabilize?

When your onboarding is pretty solid, I would start to look at your metrics and see what the best opportunities are to increase value to the customer (ex. underutilized features, lack of more-advanced-success support). From there, you can strategize what the best next step is – sometimes that is technology, sometimes that is a hiring plan, and sometimes it’s both! Whatever it is, by being objective-based in scaling, it will help stabilize the later phases of your customer journey instead of just implementing another company’s scaling playbook.


10.) What are some of your favorite channels to establish to be sure CS informs very early product development?

The best channel is to develop a strong relationship with your head of product (and the entire product team)! To learn more about how to do this, check out this blog.

That is by far the easiest way to stay involved in product development! Remember to also continue to share the customer pulse with the product team (from the Head of Product to the Product Analyst that just started yesterday) because the more they realize that your input and feedback is valuable, then the more you’ll be involved in the upcoming features.


11.) When going in to build out a brand-new CS function at a small startup (15ish folks). What is the number one question I should ask leadership to help set me up for success?

This is very exciting! While it may not be a question that you explicitly ask leadership (you could though, of course), I would want you to get an answer to: “How does leadership think of customers?” Even if you do ask explicitly, I would also look at folks’ actions to tell the full tale.

This is important because as you get to know the team and the customers themselves, you want to check for consistencies (and inconsistencies) among the story that leadership is telling and the story that you are hearing from customers. As a CS leader at an early startup, you need to beat that customer drum loud and clear for the rest of leadership so that folks are making customer-centric decisions (and therefore smart business decisions) early and often. If they have a different perspective of the customer that doesn’t match what you are seeing, then it will be a tough time going forward.


12.) Can you give advice for Customer success business reviews (best practices on how often and agenda)?

The best advice I can give here is understanding why you are doing them in the first place! There’s an example that I share in my book, The Startup’s Guide to Customer Success, where a company realized after years of doing business reviews that 70% of their customers didn’t really care for them and it didn’t move the needle when it came to renewals and expansions. So they realized that they can save so much time from doing a simpler, meeting-less version for 70% of their customers and do a much better job for the 30% that do care about business reviews (and more).

If you feel like business reviews are the way to go still, I’d then recommend you think about your customer and their decision-making process. For example, when I was working in the education industry, I noticed that many budgeting decisions were made as early as March. So, I knew that my business reviews needed to happen before then so that we could be in the budget for the next year (perhaps as a bigger line time!). If I didn’t take that timing into consideration, then I may have been too late and missed a great opportunity to help a customer get even more value.


13.) How do you determine what amount of customer spend justifies a CSM managing their account vs only self-serve + Support?

This really depends on your business model, team maturity, and what your customer success (and larger business) objectives are. If your team doesn’t really understand what motivates or frustrates a customer, then you should probably have more CSMs managing accounts if bandwidth is truly an issue, but if you feel like you have a pretty good grasp and are ready to scale, then that is when you can start raising the bar re: spend for customers that would get a CSM.

Quick reminder here that even when you have a strong tech-touch segment that it is not a set it and forget it segment! Harking back to some of the previous questions on customer experience vs customer success and how to handle a hybrid customer success + customer support team, it is still important to have an ear on what is going on with those customers that only get self-serve + support.


14.) What are the “staples” of a complete customer experience?

Just like a good story, a complete customer experience has a great beginning, middle and end! Beginnings typically include some way to help folks get acquainted and comfortable with your product; a middle includes ways to keep customers engaged throughout; and an end to discuss best next steps on how to move forward (ex. Renewal or expansion). However, where the story metaphor doesn’t work as well is that you also need a good self-serve help function (or a CSM that is proactively looking out for an account!) so that folks that deviate from the experience can get back on the right path to success.


Customer Success around the web


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