Feb 25, 2022

Read Time 9 min

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


Startups in today’s environment have the challenge of meeting rising customer expectations while trying to determine product-market fit and a path for growth and probability. By investing in Customer Success from the start, startups can build loyal and engaged customers who ultimately become brand advocates.

Jennifer Chiang author of “The Startup’s Guide to Customer Success,” joined us to share how Customer Success can help you as you scale your startup. During the webinar, we covered:

  • What Customer Success at a startup looks like and the common mistakes to avoid
  • Why shifts in customer trends and technology make it imperative that startup’s implement a Customer Success strategy early
  • How to plan for scaling and the role free technologies can play for early-stage startups

If you missed the webinar, you can watch it on-demand.

Q&A recap

Speaker: Jennifer Chiang, Head of Customer Success, Seso

At the start of the webinar, we polled our audience to find out what the top Customer Success challenges are working in a startup environment. More than half (63%) said they struggle with time management – a common startup challenge. This was followed by 44% of respondents who cited onboarding obstacles and 40% who face issues with building a Customer Success function.

Q: Where should you start when building out Customer Success playbooks?

A: Focus. What are you trying to achieve with the playbook? Understand where you currently stand. What is your playbook right now? Even if it’s all in your mind, write that down. Use that as a version to start editing and understanding what works and what doesn’t work for the customer. For example, if my playbook in my mind is three steps, I write those three steps down and see that actually step two doesn’t even resonate with the customer. Half the time they’re just dozing off or checking their emails when I review step two. So, then I need to figure out what to do next.

What’s fun about Customer Success is that even though there are key principles that we all share, every single company is different and that’s why we have the product complexity and the user complexity frameworks to help us learn how to focus and better understand our customers. There’s no right answer, but I really recommend reviewing what you’re doing now. What isn’t working? What is working? Start iterating from there.

Q: How do you assess if you have an effective onboarding journey?

A: If you’re asking yourself those five questions that I shared earlier, that’ll give you a pretty good sense of whether you have a healthy onboarding journey. Of course, there are also metrics that you can look at when it comes to whether people are adopting your service. Are they dropping off after a week? Are they reaching out to your support channel very often? Little things like that can help give you signals.

A quick side note on metrics: add focus into your metrics. We can easily get bogged down with hundreds of metrics if we wanted. We want to make sure we’re focusing our efforts on three metrics when we’re starting off. Eventually, as our team grows bigger and our Customer Success organization matures, ramp that up to five focus metrics, and then 10 focus metrics, and then so on and so forth.

Q: What does a great sales-to-Customer Success handoff look like?

A: When it comes to the sales-handoff process, you want to make sure that everyone’s sharing that customer-centric mindset. We’re not two separate teams. We’re all wearing the same jersey. With that in mind, the best sales-handoff process understands everyone’s goals including our company and customer’s goals. What does Customer Success need to know from sales to make onboarding as smooth as possible? Sometimes you don’t need to know everything. Sometimes you only really need to know 20% of the things. Help focus exactly what you need and let sales know that.

Of course, it’s helpful for CSMs to also have access to all the sales data if they want to do extra research. Because sometimes with more complex customers, you want to dive a little bit deeper. But to keep it easy, what information do you need to make sure onboarding goes well? What are the three things? Make sure sales knows to focus on those three things. It makes the handoff much simpler. I’ve seen people do meetings for handoffs. I recommend those for much more complex customers, but I’ve seen Slack messages working just fine. It depends on what you need and what your customers need.

Q: What’s your experience with combining Customer Success and support?

A: Customer support is such an important team. They have so much value and so much knowledge. We need to make sure we’re working in lockstep with them. At my last company, I was in charge of both success and support teams. What made it great is that I could be that conduit to make sure that a CSM knew “We just got 10 tickets in the last hour from this one customer that you have, what’s going on?” and make sure that those communication channels are open and easy to understand and use. I do think there’s so much synergy between the two. I actually really enjoyed having both of them under one umbrella to make sure that the customer experience, especially post-sale, is smooth.

But it really does depend on your post-sale structure. For example, at my last company, I was in charge of everything post-sale because it was just Customer Success and support. But at my new company, we actually have five post-sale teams which is very exciting. We have the Customer Success team, but we also share support and we make sure that we are all aligned with how we think about support and what support actually means. We want to make sure that we’re empowering our support teams as well.

I’ve talked to a lot of senior Customer Success leaders at much, much bigger companies – series D, IPO’d, things like that – and they say their CSMs are still handling some support requests, and it just doesn’t go away sometimes. So don’t feel like you need to have this red line in the sand that this is support and this is success. It’s always going to be a little bit blurry even when you get bigger.

Q: What advice would you offer someone who is the very first Customer Success hire at a startup?

A: When it comes to being the very first Customer Success hire – and I was in your shoes not too long ago – it’s about having a listening ear to everything and everyone. I basically dedicated my first entire month to taking the time to listen. Oftentimes, especially if you’re not like the third person to be at the company, you’re going into a lot of processes that are already in place. So, you need to understand and respect them. Understand where they’re coming from and what their goals are. What are some of the gripes they have about the current process? What do they want to do? What do they not want to do? What do they feel empowered to do? You want to really understand and dig deep and ask why. Then, when you make your first playbook and stuff like that, you have a clear idea of how your policies or processes mesh with others.

Also, just have a good time. People always forget that. Building relationships is something that I love about the Customer Success organization, not only with customers, but within the entire team. Have a good time getting to know folks. Understand what makes them excited and happy and sad and angry and frustrated. Try to understand it all.

Q: What items or areas should Customer Success teams focus on standardizing and documenting first?

A: When it comes to documenting, the best advice I’ve seen is to just to start. Most people try to find out if Notion is better or if Google Docs is better or if internal wikis are better. Even if it’s a Slack message to yourself, start documenting things. Even if it’s the first time you’ve ever done a process, start documenting it now. Because it’s so much easier to edit than it is to write something from scratch. If it’s the very first time you’re hiring a new CSM, start documenting. What did they do for us? How did you create the JD? How did you post the JV? Then, when you’re ready to start the second hire, you already have something in place. You can edit. What worked well? What didn’t work well? It gets the momentum going and sets the example for everyone else. I will say as a Customer Success person who has worked at a bunch of startups, everyone loves it when you document things, especially product. And it’s always good to have a strong relationship with product.

Q: What key metrics should you track when building a Customer Success team from the ground up?

A: What’s so funny is that – and I talk about this in my book – when I first started in Customer Success, my very first metric was referrals. I do not recommend that to anyone. It was a rookie mistake. The Customer Success team was created to increase referrals. Of course, that’s all of our end goals. But when you’re first starting Customer Success, you shouldn’t think about optimizing step 25 when you have no idea what step one is. What I always recommend to folks, especially early on, is to not have a ton of metrics. You want to have three that you really focus on. And you want to make them earlier on in the process. Typically, what I like to see is an adoption metric. How do you make sure that folks are getting onto your platform? Secondly, I like to see an engagement metric. How do you know that folks are still using it time after time? Thirdly, how do you know that folks are coming back? What commitment are they making? Typically, you see this as renewals or something similar.

I will say, when you’re first starting out in Customer Success, having an eye on those first three metrics is good. But then I would put more focus on the earlier metrics. Because if people aren’t onboarding, they’re probably not renewing. I would put a lot more focus there. I’ll also add that you should feel free to “graduate” from metrics. For example, for my adoption metric, I can say that my very first version is having people sign into the platform. If only 20% of people are signing on right now, I want to make sure that gets up to 90% – or whatever that percentage is depending on your product – before I feel comfortable graduating. Graduation could be that after the customer signs in, they have to click two buttons. My next adoption metric after I graduated from people signing in could be the number of folks who click two buttons. Because I know that if they click two buttons, they’re set up for success.

To use a more concrete example – and I’m assuming a lot of people here use Slack – my first adoption metric could be a Slack login. Then, I might graduate to looking at the number of people who have sent their first message. Then, I might graduate to looking at the number of people who have joined at least three channels. You can graduate and make your metrics more and more useful as goals and as north-star metrics and to help you understand what’s going on in the business.

Q: How can you keep busy customers engaged with your product?

A: This goes back to that matrix of user complexity and product complexity. Sometimes, I don’t want 2,000 notifications from my tea kettle. That’s just not necessary, because I set it and forget it. It’s understanding what our place is. Of course, when it comes to engaging and getting those open rates up and those response rates up, it comes down to understanding your customer and how they communicate. For example, I was working with a company where they were sending emails that were really useful. They had decent open rates. But there wasn’t really a CTA, so they didn’t know how to make it better. They were just hoping that customers read it. But then once they added the CTA, they were able to understand if people took in the content. They also realized that their emails were three paragraphs long and no one had time to read those three paragraphs. So, they started bulleting, bolding, and highlighting the content. They started seeing response rates go through the roof because they were able to cater to the customer and what they need. There are times when customers want those paragraphs. I’m thinking about those legal scenarios where they want to make sure they dotted their I’s and crossed their T’s. But you just really want to understand what your customer needs. Maybe it’s not email. Maybe it’s text. That’s a huge trend I’m seeing as well. Understand what your customer is looking for and why to get your response rates.

At a startup, there’s never a shortage of work or tasks to be done. To learn Jennifer’s top three areas that new Customer Success teams should focus on first, watch the webinar now.


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