Building Through AI Uncertainty With ChurnZero
Startup Builders and BackersSeptember 12, 2026
26
00:25:3323.41 MB

Building Through AI Uncertainty With ChurnZero

What happens when founders can build faster than business buyers can adopt?

In this episode of Startup Builders & Backers, I speak with YouMon Tsang, founder and CEO of ChurnZero. YouMon has built four companies and completed three successful exits, giving him a candid perspective on category creation, B2B market timing, AI adoption, and the confidence required to continue when the outcome remains uncertain.

YouMon believes entrepreneurial founders often run ahead of the market. They see the technical opportunity, create a new category, and then discover that business customers need time to understand the problem, assign an internal owner, approve a budget, and decide what evidence they require. He now sees a strong case for arriving second or third, when buyers recognize the category but remain open to a better answer. It is a useful counterpoint to the startup belief that being first automatically produces a lasting advantage.

We also discuss how AI is changing customer success. ChurnZero works with customer teams focused on retention, expansion, and customer experience. Automation has supported go-to-market teams for years, but agents can now handle decisions and tasks that once required manual review. The important question is when software should recommend an action, when it should complete that action, and what information it needs before the result can be trusted.

For YouMon, the answer begins with data. He separates customer data into facts and information. Facts include contract dates, spending, and points of contact. Information includes call transcripts, emails, product documentation, and knowledge about how the customer uses a service. An AI system needs both to produce a useful recommendation. A clean account record cannot compensate for missing conversation history, while a detailed transcript is of limited value if the system has the wrong contract or contact data.

That combination also affects timing and empathy. Customers quickly notice an automated message that arrives at the wrong moment. YouMon argues that poor timing usually exposes missing information or a badly designed workflow. The language of an email can be tailored, but an empathetic message sent at an inappropriate time remains a poor customer experience.

Trust must be earned gradually. YouMon compares today’s AI agents with the earlier adoption of rule-based automation. Teams initially asked a person to approve each message, then removed that checkpoint after the workflow repeatedly behaved as expected. Organizations can take the same approach with agents. Some may permit immediate action, while others will keep a person in the loop until the business has enough evidence to feel comfortable. The right boundary will vary by company, customer, and consequence.

Founders selling AI must also recognize that buyers require different forms of proof. An early adopter may try an interesting technical answer with limited evidence. A fast follower may want a strong demonstration and one or two customer examples. The wider market will expect social proof, controls, and clear evidence of success. A founder therefore needs to understand where the buyer sits before deciding which argument, metric, or reference will earn confidence.

The conversation closes with YouMon’s view of entrepreneurial uncertainty and a personal story from a difficult fundraising period. Before another investor meeting, he looked in the mirror and changed the question from whether someone would invest to which investor would be lucky enough to join the company. The business had to earn support, but his posture changed from asking for permission to presenting an opportunity he believed had genuine value.

Do founders gain the greater advantage by creating a category, or by arriving later with a better answer when customers are ready to buy? Listen to the episode and share your thoughts with me.

Useful Links

[00:00:00] Scale Your Business With Agentic AI With Limited Risk With Denodo's AI Data Layer, Your Agents Are Provided With Real-Time Company Data And Guardrails For Company Protection Create The Business You Always Dreamed Of With Denodo And You Can Do That By Simply Visiting Denodo.com To Learn More But Now Back To My Guest What Happens When A Founder Moves Faster Than The Market Is Ready To Buy?

[00:00:30] Well My Guest Today Is The Founder And CEO Of ChurnZero He's Also A Four-Time Founder With Three Successful Exits He Has Learned That Inventing A Category Can Be Harder Than Following Quickly With A Better Answer Especially B2B Software Where Buyers Rarely Move At Startup Speed So Today We're Going To Discuss How Founders Can Build Through AI Uncertainty

[00:00:58] Why Customer Data Still Determines Whether Automation Works And What Buyers Need Before They Can Trust A Shiny New AI Product We've Got A Lot To Get Through Today So Let Me Introduce You To My Guest Now So Thank You For Joining Me On The Show Today Can You Tell Everyone Listening A Little About Who You Are And What You Do? Yeah Hi Neil Thanks For Having Me My Name Is Yuman Sang I Am The CEO And Founder Of ChurnZero

[00:01:26] So At ChurnZero We're A Software Company And We Help Customer Teams Really Get The Best Out Of Their Customers Make Sure They Know All About Their Customers And Everything That We They Know About Them Get Them Through The Customer Experience The Right Way And All This Of Course Means That They Have Great Retention And A Great Customer Experience Awesome Well It's A Pleasure To Have You Join Me Today And There's So Many Things I Want To Talk

[00:01:53] With You About I Mean Customer Success Teams They're Moving From Dashboards And Alerts And Alert Fatigue Towards Autonomous Customer Growth Systems It Feels Like A Bit Of A Movement And A Bit Of Excitement Here But What Changes When Software Can Recommend And Complete The Next Action What Is The Real Big Change Happening Here? Yeah You Know I Think Automation Has Been Around For A Very Long Time For Many Go To Market Teams

[00:02:20] Right So Whether You're Sales Or Marketing Or In This Case Customer Success Automation Has Been A Big Part Of It And So Teams Have Gotten Comfortable With Decision Making Happening For Them Now Of Course You Know Now There's Just A Higher Percentage Of Them The More Nuance Things That You Thought Were Impossible To Automate Are Now Being Automated

[00:02:42] So What Changes? Well I Think There's A Real You Know Thought About When Do You Actually Have The Software Due To Recommendations? When Do You Have It Focused On The People Instead? When Do You Have It Focused On The People Instead? And Then What is Actually Needed In Order To Have A Good Recommendation Right Because AI While It's Really Smart The More Information You Can Give It The Better The Recommendation You Can Make

[00:03:07] 100% With You And AI Is Only As Reliable Of Course As The Customer Data That Sits Beneath It So Which Reporting And Data Quality Problems Should A Company Or Somebody Listening What Should They Be Fixing Before Introducing Agents? Because I've Been To What 15 Tech Conferences This Year Agents That's The Topic In Every Single One Of Them So What Should They Be Doing First? You Know It's Interesting Over You Know I've Been At It For 10 Years

[00:03:36] One Of The Biggest Issues Around Having The Difference Between A Successful Implementation And Unsuccessful Implementation Of Almost All All Kinds Of Workflow Software Is Really The Data Is Really The Data And It's It's Surprising We Continue To Have This Conversation But If You Just See How You

[00:03:54] Know Companies Are Run You Can You Can See That Data Can Be A Problem They Get Stale You Know The Matching Process Is All Fraught With Errors But That's Really What You Have To Fix I Mean It Is It Is A Brutally Uninteresting You Know Task To Fix Your Data

[00:04:14] But There's Nothing More You Know More Relevant To Getting Great Information That's Fixing The Data So If I Were You Know What I Tell My Customers Is Not Only Do You Have To Fix All The Facts Right So I Think You Know If You Think About AI There's Really Two Major Pieces Of Data One Is Your Facts So Customer Start Date How Much Are They Paying You Who's The Point Of Contact Those Are Facts And Then There's Information Right Information

[00:04:44] Information Would Be Transcripts From Your Calls And Then There's Information E-Mails That You Have Back And Forth With Your Customers You May Have Information About Your Product And Service And How To Use It And Those Are The The Pieces Of Information Together That Really Makes For Great AI And I Think What's Happened Most Recently Is That It Used To Be The Facts Were The Most Important Thing Now You Have To Add The Information Right So The The The Call Transcripts And The

[00:05:38] And When We You Know When We dunno When Our Customers And Ourselves When We Hire For These Roles On And Let's Just Take Customer Success Managers You Know When Look At The Job Description From The Beginning Of Time Right It Was Always Very Aspirational Right You Have To Be Con consultative, right? You have to be curious. You have to, you know, be able to learn about your

[00:06:04] customer needs. You have to understand your customer's work. You have to study, you know, the industry that they're in, right? And all those things, you know, were the things that we hired customer success managers for, and we've never used them that way, right? Even though that's what we want, we use them more for really the technical day-to-day, the administrative part,

[00:06:28] and so in many ways, we should be hiring exactly the same way we've always wanted to hire, right? This aspirational hire, but now with AI handling those routine things, it's up to the humans now to do the work that we hired them for to begin with. So in many ways, nothing's changed. We're just going to use them the way we've always intended to use them. And I think when businesses first start

[00:06:53] adopting AI agents, there's a certain trust element going on here. And what should an AI agent be allowed to do independently for a customer? And which moments still require a person who understands that relationship maybe to be in the loop and step in? I know it's a bit of a balancing act, and maybe the trust need to be built over time. But how do you see this? Yeah, Neil, I think you're right. I think the trust, by the way, trust being built over time,

[00:07:20] I think is the important phrase there, because that's what we would have said seven years ago when it came with just automation, right? Where, you know, just trigger a message out. There's a static message. Oh, it happens when the customer, say, hasn't been using your product for two weeks, right? So that's a new automation. You know, customer success managers sort of had to get

[00:07:49] comfortable with that like seven years ago. And so what we often will say is, what a human, like we didn't use this term, but put a human in the loop at first, right? So every time it triggered, it asked the human for permission to send it along, right? And once you got comfortable with it, you could sort of take out the human and the, you know, and the automation will take over. It's very similar now, right? So

[00:08:14] agents that we provide for our customers, we give them the option of just firing automatically, right? Based on, you know, some, some attribute or get a human in the loop, you know, say yes, yes, no, no, until you feel comfortable that the agent is doing the right thing at the right time. So I do think, you know, and by the way, of course, agents are doing more and more sophisticated things.

[00:08:38] And there may be a time where in fact, it makes, it could make better decisions than a human can in the moment, because it, it really can absorb so much more information more quickly. But until now, I think the comfort level is really what dictates, you know, full automation between sort of human and the loop. And by the way, that's different for every organization, every organization has their level of comfort. And again, a question for leaders listening here, how should they better

[00:09:08] distinguish healthy automation that is improving customer outcomes from maybe automation used mainly as a short-term headcount measure? A big difference here between the two approaches? I think there, there absolutely is a difference between, you know, affecting top line outcome and impacting say the bot, you know, the profit margin, right? The expense line. By the way,

[00:09:34] I think both are really important. So I wouldn't say, you know, I wouldn't say one is better than the others. In fact, in many cases, when we talk to our customers, you know, some of them don't own the outcome, right? They actually are servicing the customer. And so for them, it's really a bit of a cost center. And so if you are a cost center, guess what? Your number one thing is to really, you know, focus on minimizing the headcount to provide the best customer service, right? So

[00:09:59] that's, I think that's a fully good way of thinking about AI. But in the end, you know, what, what the company really does want is the best customer outcome, right? That would normally be retention and expansion because why, you know, your modern company wants growth over, you know, values growth more than they value earnings, right? And so, you know, I would say depending on what

[00:10:25] your company, what your department's goals are, you know, if it's top level retention or is a cost center, your AI really does have to service that goal. And on a personal note, as someone that has built what several software companies, I've got to ask, when you look back, what have you learned most about timing a new category and what should maybe founders listening today understand about building around AI? Has much changed since you started out?

[00:10:54] Yeah. Yeah. Well, you know, maybe I'll, I'll comment. I mean, the question is the right, right? What's, what have I learned about timing a new category? Um, you know, I'll focus on B2B. I've been in B2C and I've been a B2B companies. So, you know, but lately it's been B2B. I think B2B, um, I think most entrepreneurs are faster, uh, in their innovation than a B2B category can handle.

[00:11:22] Yeah. Right. I think that's absolutely true. I think most entrepreneurs are really into innovation. They really want to push a category and B2B and, and businesses are just slower to adopt. And whether that is inventing a new piece of software, whether it's, it's dragging your customers into using AI, a typical entrepreneurial founder will be faster. Um, and so I think the timing is, you know, like one,

[00:11:50] one of the things I've sort of decided because I, I feel like that's me. I feel like I'm too fast. I would rather, I would rather actually not be first in a category. I'd rather be second or third in a category. Uh, cause I think being first in a category, uh, is really tough. Um, you know, I've seen a lot of, I've seen a lot, in fact, most winners of a category are not first. Most winners of a category are the fast followers to second. And you remember them maybe as being perfect.

[00:12:18] Salesforce maybe was not first, although, you know, you, but they survived, but there were plenty of companies before Salesforce to try to do what Salesforce did. Yeah, completely agree. And of course, customer success software can identify risk earlier, but customers could react badly to outreach that feels automated or intrusive. And I would imagine in both our personal lives, we've come and encountered things like this. So how can teams

[00:12:44] preserve empathy and timing as the system and agents keep taking on a little bit more work at a time? How do we perceive that, um, protect that empathy and, and timing that has made it so successful over the years? Yeah. I, you know, it's interesting. I think timing is probably the, the, the thing to focus on. In other words, you know, if you're going to get a piece of automation, um, bad timing

[00:13:09] is very obvious to see. It's like, why are you sending me this now? Right. Um, and so bad timing is either will lead to, to, to, you know, and you, you would say, oh, that's either a bad decision by a person and that's no great, that's not great. Or they're putting me in some kind of automation that's badly designed. Right. So I would say timing is the thing you have to fix. And of course,

[00:13:34] to do great timing, you really need a lot of good information, right? Uh, cause oftentimes bad timing is, is based on the system, not having the information and the workflow of not using great information in order to send the, uh, um, send the automation in terms of empathy, right? That's a design problem. Uh, you know, and that's, it's hard for a machine to be empathetic. Uh, but you can certainly

[00:13:59] write the right email. You can have AI customize it for the situation. Uh, and so you should be able, that ought to be, that's, that feels solvable today. Uh, timing, you know, also feels solvable, but if you fix the timing problem, it feels like the empathy problem, uh, can follow pretty easily. Yeah. That's such a good point. And for any founders listening that are maybe selling AI into

[00:14:24] established companies, what earns confidence fastest? Is it technical proof? Is it a narrow commercial result, a measurable impact, strong controls or evidence that the employees will actually use it? What kind of metrics or what wins them over? Yeah, that's, that's a great question, Neil. So what, uh, how do you sell AI into existing companies and yeah, what, what matters? I would say, by the way, you, you, you sort of almost went through, um, uh, what, what is

[00:14:53] that? You and I have been through that. It was the, um, the, the cycle, the hype cycle, right? Uh, and so I would say, depending on different parts of the hype cycle, different folks, you know, uh, need different things. So for instance, if you are an early, uh, those, there's the folks who, who will try things, all you need is a interesting technical, um, a problem

[00:15:19] that you have a solution for, right. And people will try it. Those people will try it. That's all they need. Uh, they, sort of the people who are maybe fast followers. So a little bit, they will take a little bit of risk. Um, they'll want to see some proof, like, but just a little bit, right. So maybe one or two customers, uh, maybe I'll, I'll, I'll, I want to, I want to dig in on a demo and that will give it a try. And then there's the majority, uh, folks and those folks,

[00:15:45] if you want to sell AI to them, guess what? You need a lot more, right? You need lots of proof, lots of social proof. You're going to have to show me that you have strong controls, right? And then also evidence of success, right? So there's sort of, as you move, uh, through this cycle of buyers, right. It does change over time. So yeah, think about who your buyer is, where they are in the cycle and you really do have to bring, um, you know, a different set of, of, uh, proof for them.

[00:16:14] And before I let you go for everyone listening, churn zero, tell me a little bit more about what you guys are working on, what excites you and what the rest of the year looks like for you as well. Yeah. Uh, so, you know, we work with customer teams, um, you know, this, so we're talking in the summer, late summer of 2026. Um, you know, what the whole industry has been dealing with, not, not just ours, but the whole go-to-market industry, all software, uh, probably since the beginning of

[00:16:44] 2026 is really like the, uh, I call it the fog of Claude. Um, and, um, you know, it's, it's been an interesting year. You know, if you, if you think about the first six months of 2026, Anthropik, who makes Claude groove revenues more than the size of Salesforce, right? It grew more than an entire Salesforce. So you can imagine like, you know, you're an industry and everybody,

[00:17:13] imagine everybody who uses Salesforce today, you know, so think about everyone who's used the Salesforce today. They actually all bought it this year. Everyone just bought it between September and June. So you can imagine sort of the distraction, uh, of sort of that type of technology landing all at once. And AI is even broader than that. AI is, it's a tool set. People don't, you know, can put a lot of imagination into a Claude and figure out, oh, what can I use it for

[00:17:41] this? Can I use it for that? And so the first six months has really been this unprecedented, unprecedented, unprecedented time of experimentation. What can it do? How am I going to use it? Uh, and it's, um, it's actually been really fascinating to see, you know, our prospects and our customers sort of on one hand, it's like, okay, what can I do with this? What can I do with churn zero? And I think a lot of us are facing, um, you know, that moment now, as you've, you know,

[00:18:08] the SaaS apocalypse, uh, came, uh, and it's now we're hearing that it has, it has ended. Right. And so that, you know, that means to me, and I believe this to be true, um, that, okay, we, we, we figured out the experimentation. We figured out what is, you know, we're generally starting to understand what is good for and what it's not good for. And then now we can actually get back to, you know, um, moving forward rather than, you know, experimentations.

[00:18:34] So can we take that as official? The SaaS apocalypse is done now, right? Founders can breathe a sigh of relief around the world. So, I mean, it, I will say the other thing, right. Is that AI will not stop. Uh, it is incredible. Um, you know, as an entrepreneur, this is probably the most, um, the most uncertainty I've ever seen in the space. And so as a founder and entrepreneur, like really, this is your time

[00:19:00] to embrace it, right? You could fight it. You can fight the uncertainty. Um, just don't do it. You have to embrace it. You have to ride the ride and you, nobody knows where it's going to go. If someone thinks they know where they're going to go, they're wrong. So it's just, you know, using your best entrepreneurial skills, your, your frame of mind, and really like be as agile as you can. I think it's the, it's, it's the, it's, that's what, uh, you know, I will recommend all

[00:19:27] founders do over the next 18 to 24 months. Cause it's still, it's still kind of rock and roll out there for sure. Yeah. And for any startup builders or backers listening and anyone in the startup community listening to you today, it's very optimistic message here, especially that entrepreneurs can move so much quicker in this space than the, the large enterprises. I, it is important to recognize here cause we see a lot of doom and gloom and a lot of noise around, but

[00:19:53] it is an exciting time to be an entrepreneur, isn't it? I, I think it is the most exciting time to be an entrepreneur. It's, um, you know, the uncertainty is, is, is scary for a lot of folks. Um, but, you know, I would say that, you know, you know, sometimes you, sometimes there's situations that, um, will distinguish like, okay, am I, am I really an entrepreneur versus not? And then by the way,

[00:20:19] this is not a value judgment. We're like, I think, I think people have very different skill sets. Uh, people are, are more appropriately built for, um, you know, different types of organizations. And that's, that's wonderful, right? Cause we need all those types of people. Um, but oftentimes when everything is booming, right? Um, there's a lot of new entrepreneurs that, but it's sort of when, um, things are either busting or things are changing. That's when you're like, okay, like who has the

[00:20:49] muster, uh, to survive this and get through this. And, and by the way, you can really tell a lot about yourself. It's like, oh, okay, well that that's, that's a little too much uncertainty for me. Let me go ahead and, and, and, you know, get out of the surf. Right. And that's totally fine. Uh, and those of you who are really into it know that that means that you're an entrepreneur. And what would you say to that person listening? I've got to say here, you've had what four, you're a full-time founder. You've had three successful exits, hugely successful. When there

[00:21:15] will be people listening that do have uncertainty, that do have that imposter syndrome that sits on their shoulder saying, are you sure you're an entrepreneur? How do you deal with those negative thoughts when they, they do creep in and do you still get them now all these years later? I don't have any more just because I've done it too many times. Um, but probably my second company, um, you know, one of the things that happened was I was raising money, uh, and I was not

[00:21:42] doing very well. Right. Um, and you know, there's early on and what I did and this sort of what I recommend people is if you're an entrepreneur, like, like what I did before the last, the next meeting is, is I just looked myself in the mirror. It's like, you know, who's the lucky investor. Who's going to get to invest in my company. Right. So I changed around. It was before it was like,

[00:22:09] would you, would you please invest in my company, please? Right. Versus like, are you the lucky person who gets to invest in my company? Um, so I do think like, you know, in many cases, it's just the attitude that you bring to the problem that changes everything. Right. Because I think most, I think most of us are humble people. Uh, we were sort of, you know, our parents, you know, uh, instill that

[00:22:35] into us. And I think there's a bit of like, I, I, you know, I got to kick over cans, um, you know, as an entrepreneur and I would really sort of, you know, so for, for, for most of us who have to kind of get over that, just pump yourself up. Know that in fact, no one else can solve this problem. Only you can solve this problem. Whether that's not true. I think that's an important part of being an entrepreneur. And I think that is a powerful and somewhat inspiring message to end on. And for

[00:23:01] everybody listening, they want to find out more about you, about churn zero, about everything we talked about today. Well, do you like me to point them? Yeah. Thanks Neil. So, uh, to find me, you know, I'm probably most active on LinkedIn. So please, please, uh, link with me, uh, on, on LinkedIn and we can, you know, have conversations on company building or customer success, uh, for turn zero, come to turn zero.com. Uh, we have a lot, by the way, we have a lot of, um, learning

[00:23:26] materials, education materials, uh, both about customer success in general and about AI, uh, as it impacts customer success. So please, uh, please find us and hopefully we'll have a conversation soon. Awesome. Well, I will have links to everything that you mentioned there and anyone listening have got any questions or you want to learn more about churn zero, please go visit. And also feedback to me, let me know your thoughts on anything we talked about today, but more than anything,

[00:23:52] thank you for sharing your story and leaving everyone listening with such an optimistic and inspiring vision for that future. You can do it. Everyone guys and girls that are listening, please go out there and seize the day. And on that note, I would just thank you for your time today. Appreciate you. Thank you, Neil. Had a great time. I think my guest left us with so many useful reminders today in particular, uncertainty is part of a founder's job description. Yes,

[00:24:19] the market is going to change. Buyers will hesitate and the category you worked hard to create might actually end up rewarding the company that arrived second. But what matters is how quickly you learn, how clearly you understand the buyer and whether you can show the right evidence at the right moment. And I think his story about looking in the mirror before an investor meeting also says

[00:24:45] believing your problem is worth solving and presenting that belief with conviction. Fantastic advice. So big thank you to him for sharing his story today. Remember, you can find him on LinkedIn. Learn more about churn zero at churnzero.com. I will be adding links to the show notes over at techtalksnetwork.com. You can leave me an audio message there. Maybe answer this question. How are you

[00:25:10] building confidence while the AI market and the pace of technological change continues to ramp up? Love to hear from you. But that's it. We're out of time for today. I'll be back again real soon with another guest. Thanks for listening. Bye for now.