The Support Automation Show: Episode 25

by | May 5, 2022

In this episode of The Support Automation Show, a podcast by Capacity, Justin Schmidt is joined by Jennifer Chiang, Head of Customer Success at Seso and Author of The Startup’s Guide to Customer Success. They discuss how startups can adopt automation to engage with customers positively and gain a competitive advantage.

Listen now!

Justin Schmidt: Welcome to the Support Automation Show, a podcast by Capacity. Join us for conversations with leaders in customer or employee support who are using technology to answer questions, automate processes, and build innovative solutions to any business challenge. I’m your host, Justin Schmidt.

Good afternoon, Jennifer, welcome to the Support Automation Show. Where does this podcast find you?

Jennifer Chiang: I’m coming in from San Francisco, California.

Justin: I love San Francisco. Jennifer joins us as the author of The Startup’s Guide to Customer Success. She’s also the head of customer success at Seso, which does– It looks like you guys have a platform to manage the H-2A Process for companies, is that correct?

Jennifer: Yes. You can almost think of it as all of our lovely farmers, they need people to help work their lands, harvest the crops, and all that really good stuff, and oftentimes, they can’t necessarily find the workers right on their farm or right next door. They often have to get migrant laborers to come help out, especially for those busy seasons. We have that software to make sure that they can do everything all in one place legally, so just in case they get audited, everything looks good and with no hussle, no drama, all good. That’s what we do.

Justin: Awesome. You lead up the customer success team there?

Jennifer: I sure do.

Justin: You have an interesting background because not only are you leading the customer success team, you also wrote a book. Congratulations on that.

Jennifer: Thank you.

Justin: I’m sure that was a great process. How did you get into customer success? Maybe give us the sort of cliff notes version of your career path that led you to where you’re at now, but then also, I’d love it if you could talk about the impetus behind saying, “You know what, I’m going to write a book,” because that’s something a lot of people maybe think about or National Novel Writing Month, which I think is November comes around, and they get really excited about it. They get through half a paragraph and they’re just like, “No, this isn’t for me.” You actually did it, so I’d love to know how you get in customer success, and then, what was the spark that led to that book.

Jennifer: I was born and bred in the startup space. I started my career in the startup space. I was employee number 10. I think there were just 10 people and one dog. Dogs were very, very important. Very cute security, not very good security, but anyways, we all love him. [chuckles] Because I joined so early on, I did everything under the sun, data, product, marketing, operations, sales, customer success, of course. Through that experience and particularly through the sales experience, I remember going out and pitching to folks, and thankfully, doing a decent enough job where we were able to get customers in the door. I remember going to my supervisor and saying, “Hey, what’s the plan here?” He was like, “I don’t know.”

Me thinking, “I just worked so hard– The whole team worked so hard to bring this customer, and we have no plan of what to do next, and what onboarding looks like, and how do we get them started.” We were just like, “Maybe we send them an email, and hopefully, they’ll figure it out,” and I’m like, “This doesn’t feel right.” I started thinking about, “Hey, what if I help to create–” I didn’t know the term customer success back then, but like, “If I helped figure out what post-sale is?” I realized that there was a term out there called customer success, and I did what every person does now, go to Google, type in customer success, and start reading.

Justin: Great.

Jennifer: I was immediately overwhelmed. There’s so many articles out there, and this was five, six years ago, so there’s a little less– There’a a lot more now but I remember back then I would start reading and things just wouldn’t resonate with me. There would be something where it said, “Okay, you just buy this platform,” and I would say, “I don’t have a budget for a platform. I’m a one-person team on day zero of my customer success journey. Why do I get a platform? I have no idea what I’m doing.”

Justin: Yes, it’s like, “Oh, Genesys looks great, but what am I going to do?”

Jennifer: Exactly. Then people were like, “Oh yes, go get your team to do this and do this playbook.” I was like, “I have no team. It’s just me.”

Justin: My team? Right, yes. [chuckles]

Jennifer: Yes, I was looking around. I have no team. I just realized there weren’t a lot of resources out there for startups like myself. As I was figuring out my own footing by talking to other folks in the Bay Area, I’m lucky enough to be in a place where there is a lot of people are down to get coffee, I started realizing that there is a need for a resource to help startups figure out what customer success looks like as startups.

That’s actually how I started writing the book- is thinking about, “Okay, what really matters when you’re a super small company where you just started your customer success?” In fact, you may have just started your company. How do you start thinking about customer success, in a way that is not overbearing and, in a way, that doesn’t overwhelm you? That’s why I wrote the book and how I started my journey.

Justin: Absolutely, I love it. Here on the Support Automation Show, we, after intros, get into the topic of support automation. I’m very, very clever in my transitions here but– [chuckles]

Jennifer: [laughs]

Justin: That phrase supports automation and can mean a lot of different things to a lot of people. I always start every interview with this because it’s interesting how everyone answers it slightly differently. When you hear support automation, what does that mean to you?

Jennifer: I think support automation, in general, especially in the world of customer success, which I’ve run customer support teams in the past within the customer success team, so I know there’s so much synergies there, I think support automation is really about two things. First is increasing personalization, and the second is increasing team bandwidth. I’m saying increasing personalization because you’re able to reach a lot more people more quickly in a way that’s more nuanced. For example, previously, let’s say, the human limit is I’m able to send 100 emails a week that have 5 unique fields, but with automation, you can literally send millions of emails in a week that have infinite unique fields. I made those numbers up but you kind of get the idea, right? [chuckles]

Justin: I don’t think you are off, yes. Directionally correct, right? [chuckles]

Jennifer: Exactly, directionally correct. That’s currently the first part of increasing personalization. I think that second part, which is another huge thing, is increasing team bandwidth. I think the more that I can extract the things from my team that are repetitive, the more my team can spend time pushing things forward, creating more brain space to think more creatively. I just think it’s a win-win for the customer and the company.

Justin: There is definitely a symbiotic relationship between automation and bandwidth, and what’s interesting is that in most instances, well-implemented automation is able to not just create bandwidth for the human capital inside an organization, it also makes the output of that team seem like there’s more people involved in it than there is, right?

Jennifer: Yes.

Justin: You’re point on– It’s not just the number of emails, it’s also the amount of personalization. It’s like an M times N type benefit. What’s interesting, and this comes up a lot, and I’m curious about your perspective on this, is that automation has a little bit of a negative and scary connotation to it at times. People think it’s everything from robots taking over a position on a factory assembly-line, to now intelligent document processing or robotic process automation or some of these other AI technologies replacing white-collar knowledge worker-type jobs.

Why do you think people continue to maybe have some of that pushback against automation? What’s your recommendation for customer success and business leaders to bring automation into their teams and avoid some of that trepidation and pushback?

Jennifer: I think as a lot of things, it’s all about framing. How do you introduce something like automation? Oftentimes, what I’ve found works best is framing it as, “Hey, I see you as a human being that has a lot of really great ideas and a lot of great thoughts, and you can add so much more to the company, let me take that stuff that is boring you, that you don’t like doing. Let me take that stuff away, so you can do more, and maybe even do more in less time, so that you can spend more time with your family. You’re not working at 8:00 PM on a Friday.” Little things like that, so you talk to them.

I think this is just the customer success side of me, like what they value and being able to show, almost like presenting that business case of why automation can really help them. I think on the manager side, I know you didn’t ask this, but on the manager side, I think when people say, “You need to add more automation to your team,” I think it can be scary because automation there’s no playbook for it.

It’s not like, “Hey, do this one thing, and that will work every single time for every single team in every single company.” It is different depending on your customer, depending on what your team processes look like.

I think that can be a little bit daunting for some folks. I think when it comes to managing that trepidation, it’s all about showing support and being like, “Hey, we’re here for you. Hey, I’m not telling you to change everything– Rome wasn’t built in a day, you don’t have to change it all and figure it all out tomorrow. It’s going to be a process and I’m here for you along that whole journey sort of thing.”

Justin: Right. Yes. When we were going back and forth scheduling this interview, one of the things you had mentioned- and this is great because I have spent most of my time on this show, probably talking to customer success, customer support, and some internal help desk people at mid-market and up, we don’t cover the startup side of this as much as we probably should. I’m really interested in diving into this with you because you’ve literally written the book on it-

Jennifer: [chuckles]

Justin: [chuckles] -and that is automation within startups and the balance of doing things that don’t scale, which is– Startups love to talk about scale, and the balance of doing things that don’t scale in automation, specifically within startups. I would love it if you could double click on that and give us some insight into what a startup specifically has to keep in mind when they’re introducing automation and then speak a little bit on that balance between things that don’t scale in automation.

Jennifer: Yes. That is such a great question, a really interesting point because we’re told at startups to do things that don’t scale, meet every single customer and really get to know them, and understand how they interact with your product, but also figure out how to make it scale later. I think when it comes to automation, you have to focus. You understand what the objective is, and understand what you are trying to accomplish with automation. I think this is also generally something that mid-market and then above folks also care about, but I think startups it is especially important.

For example, the most common thing you’d probably automate as a customer success person and a small startup is email, so figuring out how do you mass send emails and stuff like that. At the same time, it may make sense not to– There’s a balance there. You don’t want to automate all emails to the point where people are like, “Oh, this is, obviously, a bot. I don’t want to talk to–“

Justin: [crosstalk] first name. Yes.

Jennifer: Yes, [chuckles] exactly. Then they don’t feel that love from you and realize like, “Hey, I thought this was a small team. I thought I’m only working with so and so but it feels like I’m getting all these bot messages.” I think what really works well is first doing it yourself and then giving it to a robot and not– Basically, what I’m trying to say is, “Don’t boil the ocean so quickly.” Don’t say like,

“Oh, I want to automate my emails, and then you automate like all your emails.” No, I would say–

Justin: [chuckles] Right.

Jennifer: First try it out, see what works, see what it does, see if there’s any different segments that you can find. For example, if customers that are in America versus customers that are in Europe, maybe they have a different preference of how things are worded. I don’t know. You can make up, literally, any segment you want, and then really figure that out. Once you feel like, “Hey, this messaging really resonates with someone,” then that’s when you start automating it. That’s when you start realizing, “Oh, I think they really like it when I attach this attachment to it,” and, boom, that’s something easy to automate. I would be very cognizant of how I do that.

Another good example of this is check-in emails. Oftentimes people are like, “Oh, I just check in every other week,” then they quickly automate that. I’m like, “Actually, maybe you don’t want to automate that, every single person’s on a different part of their journey. Maybe think about which segment you want to automate first. Maybe it’s those that are doing really well. Maybe you don’t want to send a generic check-in email to someone who isn’t doing well on your platform. Little things like that or examples of just finding that balance between doing things at scale and automating things too quickly.

Justin: Yes. That’s a great point because there are certain aspects, especially in customer success where you’ve got your range of CSAT scores that are coming in. You’ve got cohorts of customers with far more revenue per customer or more likely to turn less product adapt, however you segment all that stuff. There is certainly an optimal amount of low-touch high automation versus high-touch low automation work that you need to think about those segments, and you’re touching on something that comes up a lot on this show, and that is automation.

Whether it’s as simple as an emailer or as complex as a multi-step RPA tool going through 15 different API endpoints and passing data all over the place. You have to have a fundamental understanding of the process you’re trying to automate before you start to automate it. Those processes can be everything from simple things like generating an RMA number or a much larger one trying to get people to adopt a certain product feature.

One thing that’s also wrapped up in what you were saying that I think would be interesting to touch on is, when you have those high-touch moments where maybe it’s not a good idea to automate those emails and you really should send them, how do you recommend– I’m going to stray from automation here a little bit. I think this is a good topic. Especially in the startup sense when we’re wearing a lot of different hats, how do you recommend people prioritize their time for those kinds of things? Do you feel it’s better to batch process that stuff at, I don’t know, 9:00 to 10:00 every morning or do it as it comes up? What’s your thought on prioritizing and creating time for those high-touch moments?

Jennifer: Yes. I think first off is always to remember why we have those high-touch moments. I think oftentimes the mistakes I see is I’m doing high-touch for the sake of high-touch and not really realizing that maybe this is a bad time to do high-touch, or maybe this is not the right customer to do high-touch with, and just like being a lot more thoughtful of the time that you’re spending. I think a really great example, and I’m taking this from my book is that we have this idea of QBR or quarterly business reviews, where, I believe, it was Jeff and his team back at one of his former companies and they were doing quarterly business reviews for all their accounts because that’s something that everyone knows to do.

Then they realized that about half of those quarterly business reviews, no one cared, the other people just didn’t care, but it was a high-touch moment. They were spending so much time on it. Their data team was spending a lot of hours collecting the data and making sure everything looks right, but then the customer didn’t care. That was a high-touch moment. That’s like a really great example of how you need to be really, really cognizant of why you’re doing that high-touch moment.

In terms of prioritizing in the day, I think I’m a big proponent of just really getting to know your customers, especially when your seed are series A and just having a lot of different moments, whether that is the kickoff call to like the check-in call, just really making sure that not only are they having a really great experience, but you’re learning something at every single step of the way. That’s exactly why high-touch is so great, is that you’re either building a relationship more or you yourself as a company are learning something that can then benefit something else in the future.

I think just really having that in mind as you prioritize your day, it really depends if you’re like a morning person, a night person, or whatever it is but I think just really remembering what your objective is. It will help you so much.

Justin: Yes. It’s a good point because oftentimes, and this happens in marketing too, you get enamored by the means and not necessarily the ends. A good example of this is I got game-recognized games sometimes and I got pulled into a LinkedIn ad for a planning tool that I was like, “Oh, this one is great.” I mindlessly fill out the form and then read the ebook, the SDR emailed me, I took the call, and I was like, “Wait a minute, wait, wait, wait. Time-out. I don’t need to be spending money on a playing tool right now. I got just enamored with this idea of, “Oh, this would be very helpful,” but didn’t really think about what it was I was trying to accomplish in the first place.

How do you approach automation specifically at Seso?

Jennifer: Yes. I will note that it’s like month one at Seso for me [chuckles] right now, but I think even on my previous company when it comes to automation it’s really, and you were touching on this a little earlier, it’s like really understanding what the process you’re trying to automate, understanding what happens before it, during, and after, and what are some of the edge cases? What are the common edge cases? What are the less common edge cases? How do the edge cases interact with big logos versus small logos? What customer segment that they affect? Really understanding that process, and I think that’s just key.

I think once you figure that out then you have to figure out your team, like what works best for your team or your customers because you want to make sure that the automation works for them and not against them. You don’t want to confuse people after all. For example, let’s say, I have a customer and they love getting texts, but I have customers who hate getting texts all the time. If I were to automate something that texts you every single time something is updated, oh, yes, half of my customer base is going to hate it. Being really, really cognizant of the process and how I’m doing it and- then you can start planning.

Then once you start planning and really come up with a plan, that’s when you– Of course, you do your research and make sure you have the right way of going about it which could be getting engineering on board, getting product on board, or it could be getting a third party, or it could be you working with a Google sheet or a no a low-code or a no-code tool. You don’t always have to buy things which is another great thing about automation.

Then once you figure that out what works best and making sure that you keep going back. Does it achieve the objective? Understand what metrics are you trying to hit. Understand what success looks like. That’s something that we always ask of our customers but we also need to ask of it of ourselves. What does success look like so I know that this project is successful. Then, of course, once you figure that out, you execute it and then you keep iterating on it and making sure that it works, and all that good stuff.

Justin: Very cool. Let’s step away from automation for just a second which– I’m the host in the show. I get to decide when we go with automation.

Jennifer: [chuckles]

Justin: [chuckles] When you were doing the work for your book, I understand you’ve talked to a lot of people in customer success at startups. This is a research, you case studied work here. What were a couple of things that you learned that surprised you, that you didn’t think you would hear from successful customer success leads at some of the places you talked to?

Jennifer: [chuckles] I think there’s two things here. I think one is more directly the answer, but the first thing that I’ll say is that my publisher did a really great job of making sure that I had no assumptions going into the project. They really pushed me to think– For example, I would be like, “I want to do this. I want to cover onboarding, and support, and X, Y, Z.” They’re like, “Throw that all out the window.” I’m like, “I just worked on it.” They’re just like, “No, it doesn’t matter. Don’t write a single word until you talk to your interviewees.” They just didn’t– They’re just like, “Yes, tear that all away because you need to figure out what’s happening on the ground. You need to figure out what other people are interested in learning, not what you’re interested in talking about.”

I think that was really great because that meant everything was a surprise in some sense or everything was just like really interesting and examples, and stories, and all that really good stuff. I think one thing that comes to mind, not surprising but something I wish that they had a better answer to, was I asked some question around the words of sometimes at a startup you always feel like you’re always firefighting. There’s fires here, there’s fires there.

I remember talking to someone who has a much more established company. Definitely not like series C, series D, series E, I think even IPOed at some point. She was like, “That never stops, Jen,” and my heart sank a little. It surprised me. I was like, “Wait, but you guys have so many more resources, teams, and processes, and there’s still fires.” She’s like, “Yes. That happens.” I think it really– It surprised me in a sense that I thought it would not be [chuckles] but– I also hoped for a different answer but that’s the case. It also gives me a lot of hope that customer success will never be boring and my job will always be interesting because there’s always something more to solve. There’s always other things to personalize and make even better, and I think that’s just really exciting.

Justin: The scale of the problem solving may go up but the amount of problem solving doesn’t change, right?

Jennifer: [chuckles] Yes.

Justin: It kinda reminds me once I was talking to a Salesforce rep and I was– I like anybody in sales and marketing and increasingly, customer success at this point too. I get very frustrated at Salesforce very easily.

Jennifer: [laughs]

Justin: Shout out to Salesforce. I asked our sales rep I was like, “Just shoot me straight. How is Salesforce inside Salesforce?” She was like, “It’s a mess.” I’m like, “Okay, good.”

Jennifer: [laughs]

Justin: [chuckles] I feel better now. I really can’t thank you enough for your time Jennifer and this has been a fantastic conversation. Let’s start wrapping up here. Thinking about getting back to automation, the two questions I like to sort of always end the conversation with, and the first one is if you were going to give a piece of advice to a business leader who is looking to get started on bringing automation into their place of work, what’s the one thing you would tell them to make sure you get this right before you get too far down the road?

Jennifer: It can all be summarized but don’t boil the ocean. Big piece of advice includes a lot of smaller pieces of advice like starting small, prioritize your time, see if it’s actually working or not. Also, thinking creatively and not just to throw money or people at the problem but really use that noggin and nog inside your head. As much as automation is automatic, it only exists because we thought about it and we’re thoughtful about it or should really. That’s the advice I would give to people. It’s like don’t rush yourself

Justin: That’s good life advice in any scenario. When you think about the future of technology, and automation, and customer success, what excites you the most?

Jennifer: I think what excites me is that we’re really only scratching the surface of it right now. I think a good chunk of automation is a lot of if this, then that automation. I think it’s just going to be super exciting when we can get to that next level of much more complex logic and not just huge if, then, then that statements and having things that can actually think for us. That’s just going to be huge and I’m really excited for it.

Justin: There’s a certain amount of power you can do with nested if functions inside of Excel. [chuckles]

Jennifer: [laughs]

Justin: Excel’s good for that kind of stuff but you’re right, the true AI getting into everything from sentiment analysis and much deeper level thinking in decisioning on things versus, to your point, if Z’s score is greater than X, do Y. This has been a great conversation. We’re going to close it out with my quick-fire around. You have the distinct advantage of being able to answer this question in a great way. What’s the book you most often recommend to people?

Jennifer: [laughs] The book I most often recommend to people is my own. I talk to a lot of startups in the world. Actually, yes, in the world both across the country but also overseas. I think there’s not a lot of resources for startups out there so I really do recommend my book The Startup’s Guide to Customer Success, available on Amazon and others. If I can’t say my own book, I think I will also recommend No Rules Rules which is by Reed Hastings and Erin Meyer. I think it really helped because as much as Customer Success is about figuring out the customer journey and all that really great stuff, a good aspect of it is employee culture. I think that book really helped me to better understand the power of having really good team culture and how to unlock people’s brains, energy, and motivation. Having that is just super important. That’s another book I recommend.

Justin: Very cool. What’s the best productivity tip or productivity hack, scare quotes for anyone not watching the video, that you’ve ever heard that has stuck with you and you still use?

Jennifer: I don’t know if it’s a productivity hack per se, but something that my former manager told me and I think is something that I also encourage my team to do a lot, and is, just ask. Ask the question. Oftentimes I see folks, including my own team, myself, my previous self, I’m sure in the future I’ll see this again, they get scared to ask questions. They feel like they can figure it out themselves if they spent three hours on it. No, that’s why we’re a team. Just ask, [chuckles] you’ll probably get the answer way faster and maybe learn some new things along the way. I feel that’s always the best productivity hack.

Justin: It’s amazing what you can get by just asking, isn’t it? My brother gave me this piece of advice once, and I think it’s very similar. I love the way he put it. He’s like, “Justin, if you ever have a problem with your car and you take it to Bob’s Auto Body, and you have a question, call the number and ask for Bob.” I’m like, “Okay.” He’s like, “Just ask for him. When you get the guy and you get the person who’s directly involved with it, and you just ask him questions. People will help you.” I think that’s really good because it’s forgotten a lot, especially in a startup environment, you and I both know this, working in startups, you put a lot of pressure on yourself to succeed. You’re a small but mighty team, et cetera, et cetera. You’re right, just asking is, as simple as it is, is a lost art.

If you could recommend a website, blog, Slack community, LinkedIn group, Facebook group, real-life meet up if we ever get to the point where we can do those easily again, for customer success folk, what would it be?

Jennifer: Yes, there’s so many wonderful communities out there, but actually we’ll go slightly deeper. I actually would say that it’s not necessarily one site or one program, but rather to take advantage of the mentorship programs within each of these communities. I’m a mentor myself at some of these places and I also help run mentorship programs at some of these places and I can’t believe what I’ve seen come out of it. The learnings that you get, and the experience that you have is just far more superior than just reading a blog, reading a site, and not to mention, you’re also building a network, you’re meeting people. Meeting humans and that’s what we do best thing, sure thing. That’s actually what I recommend is, find that mentorship community within whatever blogs.

Justin: Yes, whatever it is.

Jennifer: Yes, whatever it is. I think that’s probably the most powerful thing to do.

Justin: Very cool. We’re going to end with this one, if you could take anybody in customer success, business, career, life, generally, out for either coffee or cocktail, depending on the time of the day, and just get to pick their brain for an hour, who’d it be?

Jennifer: Oh, wow. I think there’s so many great people out there. I probably would want to choose- probably some badass women leader at some CEO tech company. The first thing that came to my mind was Susan Wojcicki, who was the CEO of YouTube.

Justin: Yes.

Jennifer: Hopefully, like Sheryl Sandberg. Of course, there’s other leaders that are outside the tech world that I feel like I can definitely learn from. I think everyone has– I feel like I can also just learn from everyone. I’m just that type of person. I’m always down whether it’s your 1st day in customer success or your 10,000th day. I feel like I can always learn from everyone. I think it could be anyone, but there’s so many people. [chuckles]

Justin: Yes. Jennifer, this has been a wonderful conversation. For the listeners out there if they want to find out more about you or Seso, where can they go to get that information?

Jennifer: Yes. I’m super available on LinkedIn. I always love to nerd out on customer success with folks, talk about the book, talk about customer success at their companies, work with them and their team, all that really great stuff. LinkedIn is the best way to find me there or you can find my book on Amazon. If you want to learn more about Seso, you can go to

Justin: Jennifer, thank you so much for coming on the Support Automation Show and you have a wonderful weekend.

Jennifer: Thanks for having me.Justin: The Support Automation Show was brought to you by Capacity. Visit to find everything you need for automating support and business processes in one powerful platform. You can find the show by searching for support automation in your favorite podcast app. Please subscribe so you don’t miss any future episodes. On behalf of the team here at Capacity, thanks for listening.