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From Fake Leads to Firm Ethics: Rebuilding Trust w/ Jerry Van Vort VP of CS @WUWTA

The Customer UnSuccess Podcast · 2025-10-06 · 44 min

0:00--:--

Key moments - from our scoring

Substance score

60 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality10 / 20
Guest Caliber14 / 20
Specificity & Evidence11 / 20
Conversational Craft13 / 20

Jerry Van Vort arrived as VP of Customer Success at a large internet portfolio company to find a deeply dysfunctional operation. The legal vertical had chased growth by flooding the market with low-quality leads sourced through affiliates - many never actually submitted by consumers. Customers receiving these fraudulent leads either received credits (blocked by a broken policy) or faced lawsuits. Simultaneously, the 10-year-old manager was acting as a solo account executive while CSMs operated without metrics, the team suffered from pay stagnation and attrition, and tools like Salesforce were inadequate. Jerry had to simultaneously address the product quality crisis (working with dev teams on validation safeguards and affiliate accountability), revamp the credit policy, restructure compensation, implement tools like Outreach, train staff on cross-selling, and manage constant escalations - including a Thanksgiving call from a client threatening suit. The deeper lesson: the company prioritized revenue growth over customer listening and process design, creating their own growing pains. Jerry now advocates for asking hard interview questions about product quality, customer complaints, and organizational priorities before joining any role.

Key takeaways

  • →Unchecked affiliate partnerships and supply-side growth without quality controls created a lead-generation crisis where fake leads exposed the company to legal liability and customer churn.
  • →A broken credit policy prevented legitimate refunds, compounding customer anger - validating customer claims at scale became operationally expensive and nearly impossible.
  • →Internal dysfunction (no director oversight for 5 years, outdated pay structures, lack of tools, and manager role drift) meant the CS team couldn't advocate for customers or implement fixes.
  • →Customers consistently preferred higher-quality leads at premium prices over high-volume low-quality leads - data that wasn't surfaced until the crisis forced the conversation.
  • →Asking specific interview questions about product quality, top customer complaints, and organizational priorities reveals hidden problems before you accept a role.

In this episode

  1. 1Jerry's Background: From Winemaking to Customer Success Leadership
  2. 2Discovering Fake Leads and Quality Issues in the Legal Vertical
  3. 3The Credit Policy Problem and Validating Lead Legitimacy
  4. 4Organizational Dysfunction: Lack of Structure, Metrics, and Team Attrition
  5. 5Implementing Changes: New Tools, Pay Structure, and Training
  6. 6Managing Escalations and Navigating Ethical Dilemmas
  7. 7Lessons Learned: Questions to Ask When Joining a New Organization

Mentioned

WUWTASalesforceOutreachJoe DeGrandeJerry Van Vort

Guests

Jerry Van Vort

Topics in this episode

Lead validation and crediting policiesAffiliate partnership management and vettingCustomer success team structure and KPIsSales enablement tools (Outreach, Salesforce)Pay and incentive restructuring for CS teamsProduct quality vs. quantity growth trade-offsLegal vertical business modelCross-selling and service discoveryInterview questions for leadership transparencyInternal attrition and retention

Questions this episode answers

What was the fake lead problem at the legal lead-generation company?

The company opened floodgates to affiliate partnerships to meet demand without proper vetting, resulting in leads never actually submitted by consumers. Law firms called prospects who had no legal need, faced countersuit threats, and couldn't get legitimate credits under the broken policy.

Why couldn't the company simply stop selling low-quality leads?

Leadership had committed investor metrics around revenue targets, making it politically difficult to cut 35-40% of business overnight. The organization chose slow policy and product fixes rather than transparency about the scale of the problem.

How did Jerry approach rebuilding trust with angry customers?

He adjusted the credit policy to make refunds more accessible, worked with dev and product teams on validation safeguards and affiliate accountability, and personally managed escalations - including talking customers off legal threats on Thanksgiving.

What was the broader dysfunction beyond the fake leads issue?

The CS team had no director for five years, a 10-year manager handling top accounts instead of managing staff, no performance metrics tracked beyond churn, stagnant pay structures, and inadequate tools - sales got priority while CS was neglected.

What key questions should candidates ask before joining a troubled organization?

Jerry recommends asking about runway, product quality, the #1 customer complaint and how it's addressed, and what one thing leadership would change - if answers are vague, that's a red flag.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains several substantive observations about organizational dysfunction, fake leads, and ethics in customer success, but much of the runtime is spent on narrative storytelling rather than extractable insights. The fake leads crisis yields some useful principles (validating supplier quality, listening to customers, avoiding growth-at-all-costs), but these are presented anecdotally rather than systematically. The cannabis industry stories, while entertaining, are tangential to B2B customer success operations.

there was a leader who decided that, well, let's just open the flood floodgates and let's start selling more leads. And in order to do that, we need to bring in more affiliates
the clients would honestly, they would pay, they would pay more for higher quality leads instead of low cost, high quantity

Originality

10 / 20

The core insight - that companies pursuing growth over quality create downstream customer success crises - is well-established in SaaS discourse. The fake leads case study is specific to legal services verticals, but the underlying dynamic (quality vs. quantity trade-off, lack of process governance, affiliate partner mismanagement) is standard playbook material. The cannabis and wine industry tangents, while unique in setting, don't offer novel B2B frameworks or contrarian takes. Ethical decision-making is presented as refreshingly grounded but not conceptually novel.

we created our own growing pains
it's almost like growing too fast, so to speak, right? Like there was a ton of demand but not enough supply

Guest Caliber

14 / 20

Jerry Van Vort is a legitimate VP-level CS operator with multi-decade experience across multiple industries (wine, cannabis, legal services verticals) and has managed teams, navigated significant organizational turnarounds, and engaged with boards. He has real scars and has built structure in chaotic environments. However, he's not a founder or C-suite executive at a recognized scaling company, and much of his narrative focuses on crisis management rather than building scalable success motion. He demonstrates practitioner credibility but lacks the high-profile scale that would place him in the top tier.

Jerry is a VP of Customer Success at Wada and uh and many years uh as a VP in in customer success as a whole
I was probably maybe employee 12, number 12, maybe um and then at our peak while I was there, um probably maybe one of maybe maybe 150. Um so we grew pretty quick, and that was probably within like 12 months

Specificity & Evidence

11 / 20

While the fake leads story contains specific operational details (35-40% of leads being fraudulent, credit policy challenges, call center validation costs), the episode lacks hard numbers on impact: no concrete revenue figures, customer churn rates, or timeline specifics for resolution. The cannabis lab story mentions testing regulations and one $20k bribe attempt but provides minimal measurable outcomes. The organizational turnaround metrics are vague ('five CEOs in five years,' went from employee 12 to 150 in 12 months, then down to employee 3). Host rarely pushes for concrete data or timelines.

there was a leader who decided that, well, let's just open the flood floodgates and let's start selling more leads
35% or 40% of our business uh the stuff that we're selling isn't isn't legit

Conversational Craft

13 / 20

Host Joe DeGrande asks generally good diagnostic questions ('What does your runway look like?', 'What's the number one complaint?') and occasionally probes for more detail, but rarely follows up aggressively on substantive claims. When Jerry mentions 35-40% of leads were fraudulent and significant investor pushback, Joe doesn't dig into resolution timelines, financial impact, or specific remediation metrics. The host validates stories empathetically but doesn't challenge assumptions or push for precision. Conversation reads as collaborative narrative-sharing rather than disciplined investigation of cause-and-effect.

And I think, you know, a couple pieces that kind of are great call-outs. One, I think the biggest theme here is it's it's almost like it's almost like growing too fast, so to speak, right?
No, I think that's that's great advice, you know, for the audience

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

customer37organization25success23industry18leads17sure17problem17product16team15cannabis14interesting13process13jerry12problems12sales11different11

Episode notes

We trace how a CS leader uncovered a flood of fake leads, rebuilt guardrails under investor pressure, and chose ethics over easy money - then connect those lessons to hiring, tooling, and scaling without losing the plot. The stories move from legal lead ops to cannabis lab testing, all through the lens of trust and customer value. • discovering affiliate-driven fake leads and broken credit policies • installing KPIs, tools, and training in a headless CS org • pushing product safeguards and partner governance • choosing quality over quantity and pricing for value • handling escalations, lawsuits threats, and investor pressure • ethics under fire: refusing a $20,000 bribe • hypergrowth pitfalls: five CEOs in five years • asking sharper questions before taking a role • proactive learning and problem-led improvement If you got some value from this conversation, hit subscribe, leave a rating or review, share it with someone who's also out there trying to build a better customer success or go-to-market strategy, even if it's messy along the way. And if you want more frameworks, tools, automated playbooks, check out JodasX.com and

Full transcript

44 min

Transcribed and scored by The B2B Podcast Index.

He's like, I got a bag. It has $20,000 in cash. He's like, if you can tell me I'm good to go and I can pass, I'm good. I'll get up, I'll walk away, the back stay is here, and then that's it.

We're we're good. I'm like, you know, honestly, I would, you know, love to do to take you up on that, but unfortunately, I can I can't. I can't uh I have a family to take care of. Um this is too too much of an ethics risk for me.

Um I can't do it. Welcome to Customer Unsuccess, the podcast where we cut out the noise and talk with real leaders about their hardest lessons in cost for success and other go-to-market emotions. I'm your host, Joe DeGrande, and in each episode, we're gonna unpack real challenges from real leaders. Failed tech implementation, a strategy that didn't feel results or difficult to more importantly, we're gonna take those lessons learned and share them with you so that we can avoid those difficult things with your teachers.

So if you're a customer success sales or other go-to-market motions, stick around and hear for the best. So let's dig into it. Our guest today is Jerry Van Bour. He's a winemaker, turned the DT of customer success at Web.

And after crafting fine lines and diving into the cannabis industry, Jerry now leads a customer success team and shares a story of how he uncovered a flood of fake leads and had to navigate those disgruntled customers as a result. He even talked about a bizarre story where he refused a $20,000 at pride. Really enjoyed this conversation. I hope you do too.

Alex Dive. Awesome. Should we kick this off? All right, awesome.

Well, thank you so much, Jerry, for coming on the Customer Unsuccess podcast. Uh those of you who don't know don't know Jerry. Jerry is a VP of Customer Success at Wada and uh and many years uh as a VP in in customer success as a whole. So um I'm I'm excited to hear your stories, Jerry.

Yeah, absolutely not. I appreciate you having me on, Joe, and uh you know, I kind of look forward into jumping into a few uh scenarios. Yeah, no, absolutely. And it's uh you know, I know we had a couple of conversations, you know, prior to the recording, and we hit it's interesting, I guess, the blend of of I guess I guess essentially like your offering and then how it impacts kind of downstream to customer success, especially after post-sales, right?

And we see this quite a bit, right? And there's always the the complaints of like, hey, like we're a proper expectation set, you know, what's the new business, but more importantly, like, hey, does is the product or the offering, whatever that might be, really delivering the impact to the customer? And obviously as a CSM or in customer success account management, uh, you name your vernacular, um, are are they able to kind of just keep the chip afloat for lack of a better phrase, right?

Like and making sure that they could navigate those customer conversations. So I know you had some stories around that, and you know, happy to very interested in you diving in. Yeah. Yeah.

Um, I think that that is a is a good point. I think it's something that we you find a lot in customer success. There's always the the little bit of the overpromising, under delivering kind of thing on the sales side that you're you know you're stuck with. Um, but but occasionally, and and it's I think it's a it's an area that you really try to navigate out of and not be in any customer success role is core product issues.

Um because if anyone's dealing with it, it's gonna be you. Um and you know, I'm a decent sales guy, but I you know, it's hard always for like to put my name or put myself behind something that you can't feel 100% confident in. Um, you know, I'm not definitely not a snake oil salesman. Um and I think you know you kind of end up in either two different routes and depending on you know your kind of your sales style or type.

Um and if you you know really like delivering value and you like to see that outcome and see where that you know goes in the customer life cycle, I think that's where you end up in customer success. Um if you drive a lot of joy from just the transaction, then you end up in sales. Um so you know, for me, product is super important. Um, and uh, you know, there was uh a company that I worked for, uh you know, fairly large company, especially in the internet um you know domain space.

Um and they it's really a portfolio of companies all under under a single brand. So uh I was at a company, it's a pretty large company um on the internet space. Um they encompassed a couple different verticals, uh everything from like automotive to healthcare to travel. Um and so I was working in the legal uh vertical um and they brought me on basically because they hadn't had a director of customer success in about five years, roughly.

Um, and so you know I'm a very ambitious person. I like problem solving, and I think that's something that you know most people in customer success, if you're successful, are good at is problem solving. Um and so, you know, kind of coming into a situation where there hadn't been as much structure and they needed you know some leadership and some guidance, um, and they were looking for all that, and that's why they wanted to bring somebody on, um, you know, wasn't enticing to me.

So, you know, I I come on. Um, you know, normally when I go on to an organization, I'm usually pretty quiet. I don't kind of come in, you know, um banging on doors and just you know making a big, a big uh you know, rumble right away. Usually I come in, I'm very observant, I'm you know, kind of gathering information, seeing who the you know key players are in the in the in the organization, who's you know, my A team you know within my um my director ports.

Um and then I kind of start to make moves. Sure. So, you know, it didn't take long though, you know, kind of getting in and getting the feel for the situation and getting the you know the sense of what was going on uh to realize that this team that I'm assuming um really has not has really just been running autonomously as a headless uh machine for the last five years. Um and what's great about the company is that they do a lot of internal promotion.

Um and I I like that when I when you when you go to an organization, you feel like there's a ladder for you to move up. The problem is when you're not bringing enough outside talent in in the mix of all that is that you end up stuck in more antiquated, you know, workflows and ways of managing your team and and growing and evolving as technology changes. And um so the person that they'd had as a director even five years before I got there was is one of those cases where they had moved up in the leadership role.

Um, and so you know, really it just becomes a con for most cases when someone moves up a ladder like that, it becomes a continuation of doing the things they'd done before um and not necessarily changing the map. Um so what I noticed was that everything that had they been doing was really out of place. Um none of the account managers or customer success managers were getting tracked on any metrics whatsoever. Wow.

Um uh the only thing that really was really being tracked was was churn. Um and important, you know, important metric. Of course. Um, but once I started looking into you know, what is everybody doing all day long?

Um, of course, there was a manager under the director. Um, that manager had been with the company for over 10 years. What had occurred was that over that time as a manager, they had all the you know, tier one or you know uh marquee accounts that they had started to uh uh assume. Um, and it got to the point where they weren't even managing anybody, they were just uh uh a top-tier you know account manager, um and occasionally spending time dealing with escalations from the account managers.

Um as far as adding structure, improving, observing the team, you know, setting goals, no time for that. Um and so that was pretty apparent when I got in there. Uh when I started looking at who was making phone calls, who wasn't making phone calls, uh, you know, who was closing tickets, what how long was it taking to close tickets? Um you know, I really realized I had accepted I got myself into a pretty big rat's mess.

Um but I like that's what I wanted. I wanted to get into something that had some problems that needed to get fixed. So that seemed simple enough. Um I started adding structure to the organization, um, you know, creating you know some KPIs for the team.

Um, but in that in that kind of exercise and going through all that, you know, I'm also starting to now, you know, get more purview to client communications, um, listening in and finding out what escalations are going on. Um and as I did that, it started to look pretty quickly that there was a potential product issue. Um and not just a product issue, but some of the the service aspects of that as well. Um, so the main thing that we did as an organization is that we sold leads to l law firms that were needing, you know, potential new cases.

Makes sense. Um and since you know the company I work for has a lot of internet properties, you know, it really is uh a lucrative um aspect of their business because they get a lot of white web traffic, and if they can parley that traffic into a lead that they can sell, then you know, uh all the better. Um the problem was before I got to this organization in an effort for growth or maybe it's exposure or just to you know make investors feel more confident. Um, there was obviously a it's obviously supply and demand.

There's a lot of demand for these leads. Um, law firms, it's almost in limited demand. They'll take as many leads as they can as long as they're good cases they can close. Makes sense.

Um uh the problem is that it is the quality of the leads and our reality to source them all. So somewhere along the lines, there was a leader who decided that, well, let's just open the flood floodgates and let's start selling more leads. And in order to do that, we need to bring in more leads. And if we are maxing out our own properties, then we have to use affiliates.

Um, so that's the course that they went prior to me coming on board. Um, the problem was is that not too long after this happened, that leader left and the new leader came in, and I'm assuming at that point did not review the current process and realize that there wasn't a lot of checks and balances in that deployment. Um, so what I was finding was uh that a lot of these firms were complaining that they were getting leads that were never submitted by the consumer. They would call the lead, they'd say, Hey, I don't know why how you got my phone number.

I never, I don't, I didn't have a car accident, or you know, I'm not getting a divorce, or whatever it may be, I don't need any uh legal assistance. Um and not all of those calls where they would call someone and solicited would have that response. Sometimes it's in some cases, it's even another lawyer that they'd called uh that says, I'm gonna sue you guys for calling me without my permission. Wow.

Um so then we're getting the the call being told that we're gonna get sued. So or I'm gonna get sued, either or sure. Um so it really turned into a pretty big snowball pretty quick. Um and part of the problem was not just that the service was broken and that we're selling leads that were never submitted by the consumer, um, but their crediting process.

So we have a credit process in place to um address leads that were you know not submitted by consumer, um, you know, disconnected number. We have some criteria there. Um, but the way that criteria was developed really did not uh play into the advantage of the what the issue was. So they would submit for credit, not get credit, and then they'd end up paying and getting stuck with these leads that that are are truly not submitted by anybody.

Wow. Um so one of the first things I had to do was try to put a band-aid on the situation, um, was address the credit policy. So we you know initially made some credit policy adjustments to try to make it a little bit more convenient so if they are getting these leads, for the most part they can we can get their money back, um, but it's not guaranteed. Um and the problem is it's a huge cost for the company to validate the leads because we're sending all these off to a call center to then call and validate what our clients are saying is true.

Um the problem is if we couldn't get in touch with them, how do we validate? In that sense, so that was a big aspect of it was you know the inability to validate the claims made by the client so then that we can credit them for something that they are validly credited for. So um that obviously caused more contention, but we did make some improvements to the credit policy that helped ease some of that tension. Um and then I was immediately servicing all this information, you know, to my leader, which uh reported directly under the COO of the full organization.

Um and at that point we started having a lot of more dev meetings and then trying to really work with a product manager um to you know suss out what kind of you know uh securities and fill safes can we insert into you know our process to have more legitimate uh leads that we're selling. Um and then as well as you know, what kind of you know, our partnerships, our channel partnerships managers with these affiliates, like you know, how are we policing them? And you know, what are what are the consequences to them for uh providing us with you know leads that either they sourced or they acquired somehow that are validly not legitimate?

Um so it took a lot of tough discussions and there was some pushback at the top. I mean, I think when you're in an organization, I think either private or public, especially one that relies on investors, you know, you have metrics that you've given to that you're gonna you're supposed to achieve. Um so to go and say, like, hey, you know, 35% or 40% of our business uh the stuff that we're selling isn't isn't legit, we need to cut it up, we need to cut it back. Like it's kind of a non-starter.

You can't almost you can't almost go that route. So um you're in a bit of a conundrum. Um and I mean the challenge really is for the most part, the clients would honestly, they would pay, they would pay more for higher quality leads instead of low cost, high, you know, uh high quantity, but then they had to spend a bunch of their time going through and and and chasing the tails. Um so you know, there there was there was some options there um of what could have could have happened.

We could have just cut the floodgates off, increased the price, and then I think they would have been happy as well. Um, and then we would have felt better ethically. But um we that really wasn't the option that I had to play with. So during probably the next six months, you know, we're really interesting, you know, as we're trying to make these rapid changes in development.

And in a normal organization, um, you know, for that organization at least, but and what I've seen in a large organization is for the most part, the dev teams don't move as fast as they do in certain startups. Um so you know, you're sitting there pulling your teeth out, you know, dealing with problems every day that you're having to, you know, uh talk clients off the ledge for, and while you're just kind of twiddling your thumbs, hoping that they can get the you know resolutions in place quickly.

Yeah. Um the great thing about the organization that we're you know that was in was that since we were in multiple verticals, we did have teams and with different skill sets that we were able to kind of parlay into the conversation that um really assisted in ramping up in expediting um the resolution to this issue. But um but yeah, it it was it was definitely an interesting challenge to go through. Um and then in an antiquated team that you assume, there's there was more than just just even that.

So there's the product problems, there's the structure of the team problems, and then obviously the big thing for the team really was attrition. Um I couldn't even get people to stay in the team um until I got there. They were having a lot of trouble keeping people and even hiring anybody because they hadn't updated anything with their pay structure in probably five or six plus years as well. Um and because there wasn't anybody to advocate for them.

Sure. Um there was no director, there was nobody there, and jail manager was just looking at two doors of a purview to really pay attention to individual teams. Um, so you know, I had to also spend a bunch of time mapping out and building a new pay and incentive structure, um, and then had to advocate for getting new tools brought to the team. Like that maybe sell sales was sales was was was the queen.

They were getting everything they wanted. Sure. Um, but uh success did not, and we were you know really lacking. We really just had Salesforce.

Um, and uh that's not uh uh a great customer success tool in itself, but uh solely. Um, you know, so you know, we sort of bring on things like outreach, which really helped in the email cadence and communication, um, you know, reducing a lot of the time spent there just checking on clients. Um, so and then a lot of training for the team to get them up to speed uh with and then as well as cross-selling. Uh there's obviously lots of different businesses with even just the legal vertical that we had for services for, but a lot of team members didn't even know what those services were or how to speak to them.

Yeah. Um so you know, I think there was a lot of interesting challenges there, but I think the biggest one was really just dealing with clients that um I remember, you know, even on Thanksgiving, I'm in the store getting some last-minute uh groceries, and you know, uh I was on vacation that day even that but I I had a team member call me and say, hey, I'm getting you know, I have an escalation right, I I need you to jump on with the guy's literally threatening to, you know, file suit.

Wow. Um and so lots of talking people off a ledge. Yeah. Lots of it.

No, that's that's definitely a lot to unpack. And I think, you know, a couple pieces that kind of are great call-outs. One, I think the biggest theme here is it's it's almost like it's almost like growing too fast, so to speak, right? Like I think you kind of called it out in the beginning, right?

There was a ton of demand but not enough supply. And that's kind of essentially the the well was dried up, right? So they kind of not without much, you know, essentially like a deeper research and understanding of like what the process should look like, they kind of just went full reactive mode, which you know, even in like a CS side, as far as like if you're reactive, it's gonna lead you into a lot of troubles as opposed to being a little bit more proactive, right? And they were not auditing and creating a process for those partnerships.

So process is a big piece of this as well, right? Like it seems like understanding, like, hey, who who exactly are we partnering with? Can they get the job done? And then also, too, like it sounds like I guess would you agree it's also a little bit of like customer listening, so to speak, because I think also you mentioned about like cut you know, the feed like the feedback from the customers, at least again, more of their reaction to it was like, hey, we wanted more quality over quantity, is that right?

Yeah, absolutely. I think that's the best way to put it is that you know, we created our own growing pains. Yeah. Um, and we didn't need to go down that path.

Um, it looks nice, and we have something shiny that says I can make more revenue. Yeah. Um, but really, I think without investigating that further, especially with you know involving the clients um in that in that discussion, you know, you can lead yourself astray, and that's kind of what we did. And you know, reality is that we could have really increased the the quality of our current product and then increase the decrease the price.

Um you know, obviously, even then you're gonna get some blowback from clients whenever you do a price change, especially if it's an increase. Sure. Um, but you know, I don't think you're gonna get threatened with suits. Um, you're not gonna you know have a lot of the issues that you know you're gonna run into when you go a more nefarious route.

No, 100%. I think um yeah, to avoid a lot of uh headaches that that you experience, I would say taking a step back is kind of the it's it's a good first step in this case. Developing that process. And then also too, I think it goes back to like the value of the product, right?

I think that's a key theme here too, because once you start to focus, like you said, like on that quantity versus quality, it's almost like no matter what you're charging, it's like, okay, now the customer's already perceiving this, hey, this is uh you know inferior to whatever you name your data provider that there's tons out there, um, that you know, they're just gonna essentially jump ship and or in this case it looks like files too. But hopefully no one else experiences that.

But um but I'm curious now. So like now that you've experienced this, right, Jerry, like you you had a lot of learnings, right? There was a lot of downstream impact, right? You mentioned attrition, keeping employees, um obviously customers, right?

It's it's kind of a domino effect. But I guess like now having this background, I guess like how have you changed your mindset and the way you approach things coming in as like a new person coming in, right? Because that's common, right? And I think it's very smart.

A lot of organizations should be thinking about like having a new set of a fresh set of eyes of someone coming in to from a you know a bird's eye view. But what is like I guess like your take on now how to avoid those, you know, essentially or just get even more aware of those, you know, those challenges so that way it doesn't get deeper and deeper into the hole. Um, I mean, I I guess if you're look if you're in the situation like where you're applying for a role and you're looking for you know some more feedback, it's hard to really get a company to get those skeletons out of their closet in the interview process, um, with the fear that maybe scaring you away.

Of course. Um, so I think how you ask that question is gonna be super important so then that way you can convey confidence to you know whoever you're interviewing with for a particular rule um that you know you do like these challenges, you do like to solve these problems, um, and that honesty goes a long way. Um but you know, even then I think you know you're always gonna kind of walk into a few things that you know got swept under the rug or um you know weren't totally foreclosed, you know, to you before you got on into the role.

Sure. Um but I think you know not asking the questions is it's just gonna be a disservice to yourself. Um so you know, one of the qu you know, one of the questions I always ask, even just for like a startup, is you know, what does your runway look like? Um so you know, there's certain key questions that you need to ask.

Uh I think for any organization of what's the product quality? What's the number one quite you know complaint that customers give you? Um and how do you address it? Um, you know, if there was one thing that you wanted to change around the organization to improve its success, what would it be?

Um so I think asking the right point of questions and not just being the interviewee, but also an interviewer during your interviews um would hopefully shed enough light. And honestly, if you don't get even an ounce of clarity from those questions, um, then maybe that's enough of the red flag already uh to give you a sense that maybe there's something that they're they're hiding that you know you're just gonna end up getting yourself into a mess. Um but yeah, I think that would probably be you know the best way just to start off the conversation to see if you know what you're getting into before you get into it.

Awesome. No, I think that's that's great advice, you know, for the audience. And I think also that advice in general, it's always just for understanding like true objections or or true problems, right? Whether it's with a customer or or interviewing for a position, asking and kind of listening to people's responses in kind of the undertones.

I think it's it's super important to kind of get the the true answer. Um you know what's interesting, Jerry? I know we had on our on our prep call, we're talking about kind of like more personal interests. We're talking about like, you know, even the wine industry, um as well, and then also you have actually background, obviously, in the alcohol industry as well as the cannabis industry.

And I know we were talking about a couple of different stories of interesting challenges that you've experienced along the way. And I I can't can't recall if they were CS related or it were just you know go to market in general, but I know you know there's some interesting stories that you know the audience would probably love to learn and like some of the challenges there too, because it's always interesting. Yeah, no, absolutely. I so you know, um, and even just like with the last the last scenario with uh the company I was just talking about, yeah.

Um a lot of things kind of roll into like ethics. Sure. And you know, like on the customer side success side of things, you have a lot of opportunities sometimes to um make decisions that you know impact obviously the customer or an organization, and you know it's you end up in a weird spot on a fence of how much of a customer advocate am I, or how much of an employee of the organization am I? Um and it gets tough because you really do, in your role, need to be the customer advocate for the organization, you know, pushing that agenda across all the different channels.

Um, because the more customer-centric an organization is, you know, the easier is to sell the product, the better the product becomes, the less support issues that you have. And at the end of the day, the more customer-centric you are, the easier job becomes because you've improved the process and resolved a lot of issues, and then you face less of those on the support side. So um, but interesting though, in the cannabis industry side of things, so I got into that um after you know being in the wine industry.

Uh, you know, we I start was tracking trends in the wine industry and seeing some decline in beverage consumption. Um, and then there was a lot of regulatory changes in a lot of states going legal with cannabis. So um I thought it was kind of like the pick and shovel movement of uh a whole new growing industry that has just started into bloom. Um, you know, in that's a billion-dollar industry.

So uh I figured I'd get in and get my feet wet early. And so I made a transition from wine into cannabis. Um and from winemaking actually to you know now customer success. And um, you know, everything I'd kind of done had had customer success aspects of it.

Um, especially in working a lot of small mom and pops, you end up wearing multiple hats, and you know, post-sales service is a big portion of that, especially as a winemaker. Um, any problems in the wine, any problems with anything, you're the one the person that that made it. So um best to answer that. Um, you know, post-sales education series and things like that.

So uh very, very translatable. But um, so got into the cannabis industry, um, ended up getting a job for what was and I think might still be the largest network of cannabis testing labs in the world. Um, and so it's a very niche thing. Um, and given there's a ton of new regulations and each state has its own regulations, there's not like an overarching federal regulation because it's not federally legal yet.

Yep. Um it there's a lot of nuances that occurred. And so with that, uh the company I work decided to work for uh wasn't only just a lab, but was a software company. So it developed its own laboratory information management software, and then we would franchise out the brand and the software to licensees.

Um so we would license out the product and the the services that you know we perform, all the methodologies for the testing and everything as well. Sure. Um and so we not only went through the cannabis regulations, but we went through like the FDA, the the FDA came out with a uh um a hemp, the hemp bill. And so hemp became something now that was able to be grown legally and then had its own process.

Though the process for you know regulated cannabis, as in like you know, the stuff that has THC that's gonna get you high, is different regulations than what the farm bill covers with um hemp. So regulated cannabis, you buy in dispensary, uh that's gonna be tested for uh uh depending on the state, uh, regulation is different, but usually it's gonna be like the cannabinoids concentration, like the THC, the psychoactives. It's gonna be like, you know, uh you know uh yeast and mold or um mycotoxins, which is the byproduct of the yeast and mold, um, heavy metals, pesticides, things like that.

Um hemp, though, doesn't have any of those requirements. They only care that it doesn't have THC and it's not gonna get you high. Um so we were doing some testing for the now rolling out of the hemp testing requirements um now that the farm bill is released. Uh so we went to a farm, we did random sampling of his plants, and we brought them back to the laboratory to run tests to verify that they're within the legal limits.

Um, and unfortunately, you know, they came back as not in the legal limits. Um, and this guy had acres, because it's an outdoor growth, so acres of cannabis. So um, and this is his first uh harvest of hemp, so obviously a lot of investment in here. Sure.

Um, and so he calls me, he's like, How's how's the test going? Well, I'm like, Well, not looking too good. He's like, Okay, well, uh, maybe I should come in for an in person meeting. I'm like, Okay, yeah, sure, come on in.

Um so he comes in and he's with his girlfriend, and you know, I mean, this is a really interesting industry to work in, Ricardo. You know, the people you work with from suits to you know, deadheads to everybody, it's really interesting. But so the guy comes in, um Um, and you know, he we come he come into my office, he sets his a bag down, and then he's like, So, you know, I hear we got a problem. Like, well, yeah, it doesn't look like you're gonna pass uh testing, so you know, we really gotta work on you know some preemptive testing down the road.

So we're doing this way in advance, so you're not ending up in the situation in the future. He's like, Well, I can't end up in the situation now. And he's like, I got a bag, it's setting, I just sat down, it has $20,000 in cash. He's like, if you can tell me I'm good to go and I can pass, I'm gonna I'll get up, I'll walk away, the backseat is here, and then that's it.

We're we're we're good. I'm like, you know, honestly, I would I would you know love to do to take you up on that, but unfortunately, I can I can't. I can't. You know, uh I have a family to take care of, um, and with what I get paid per year, it like that 20k doesn't compensate for like it's just too too much of an ethics risk for me.

Um and I I can't do it. Um, so luckily the guy was nice. And unfortunately, down the road, even though we he ended up failing and had to they had to destroy all that crop. Wow.

This is like probably like a half million dollars investment just bulldozed. But because of the ethics that I had displayed in that moment, later on down the line, he actually reached out to me and tried to offer me a job. Um, so it goes a long way. It goes a long way, I think, being ethical in your decision-making process.

Um that, you know, even if it's not the news the client wants to hear, it it's it's your you know, resolved in that situation and the the trust that they can develop um and how you handle it and how you navigate it, uh, that I think really can come out their side in a in a good positive way. Yeah. Um but that's just one of the like I can go further if you want on some of the stories I had there. No, for sure.

This is this is great. I mean, I think like you know, listening to the story, it's actually interesting. It brought back another story similar to um, I actually visited a a cidery in cidery and the mini winery in New York, and they actually had a similar problem where their their cider had too much alcohol content to be cider, but then it was it couldn't be wine, and they were just in this like essential, essentially purgatory, and they just had just it sitting in the vat, and it just you can't do anything.

Obviously, probably not as as costly as cannabis, but it's uh pretty crazy. It's a good story, but I think it's also too it's a great story because it's uh it's understanding well one you brought up ethics, which I think is actually super, super important too. Like I think a lot of it doesn't come up often in customer success and just business in general, it's maybe just the underlying subconscious sometimes it comes up, but like to kind of be more self-aware about it, right?

Like, hey, what do I do that's more the most ethical thing I could do to better a customer? It's kind of the the main takeaway here. And also too, I think the risk is a big piece of it too, when it comes down to obviously in that case, as a business owner, right? There's that chance that it might or regulatory change, you know, you know, regulations might change and you might need to pivot and then it might be too late.

Same thing applies, I think, even in the SaaS tech world, there's tons of regulations on, I mean, maybe like for instance, like how you should be charging customers in terms of auto renewal, those changes are constant. Um, and you just need to be privy in it um and understand there's always a risk in any of this stuff. Um I think you know, just keeping in mind at the time, I'm curious if you do you do have one quick one and then and then we'll wrap up because I'm I'm always intrigued by these.

These are great. Yeah, yeah. Uh so probably the other you know crazy aspect of working for that organization was you know, just because it is such a new, it was such a new industry, um, there was a lot of money coming into it, um and a lot of easy money coming into it. A lot of investors wanted to get involved because it was a lot of you know it seemed really lucrative.

Sure. Um and so we were able to raise a lot of money. We went through a seed round, a series A, um you know, uh actually got to like a series maybe C. Um and that was probably the more unfortunate aspect of things because we didn't expect to have to raise more money.

Wow. Um but in going through it, so when I started with the organization, I was probably maybe employee 12, number 12, maybe um and then at our peak while I was there, um probably maybe one of maybe maybe 150. Um so we grew pretty quick, and that was probably within like 12 months. So really, really rapid growth.

Um and so you know, when you grow, you make mistakes and things like that. But um one of the you know big mistakes that we made is that we were too busy growing and not enough enough focused on the organization and the growth and how that growth was occurring. So, you know, we made a lot of mistakes in hiring. We made a lot of mistakes in um building out structure and focusing on our core industry.

Um, because at the time, you know, our headquarters was in California. Uh, we were licensing out in our you know methodology and the software across the nation and worldwide. Um and so in licensing out, we had to you know worry about each state's regulations and what they're doing and what they're not doing, so we can develop the methodologies to apply to those particular scenarios in those states. Um, but what we didn't spend up time was even our own, our our core market, our California market.

Um there's other problems in the California market, and I'm sure you may have heard them on the news, but taxes, the rollout of the regulated cannabis industry in California really got kind of butchered um based on too many hands out. A lot of a lot of cities wanted to get paid, counties wanted to get paid, the state wanted to get paid. Um, so just really just overtax the industry and then keep kept people in the black market because of uh affordability. Um but what had happened was you know we faced all these challenges and our our our CEO kept focusing on growth and not structure.

And so we got to an inflection point where you know we were losing money and we kept going back for more at the well, and the well started saying, hey, we're we're not giving you anything until things change. Um and it got to the point where I had an interview with the board and kind of give them, you know, being the customer-centric guy, you kind of have a pulse on most of the organization almost more than almost anybody in the organization. Because you know what's getting sold, you know how it's being sold, you know what's what the customer's asking for, what they're not asking for, what your competitors are doing, what their competitors are not doing, um, you know how other teams in the organization are supporting the customer and the business's growth.

So um, so I was a really key person in the middle of all of that. And so after kind of discussing things with the board, um, they made the decision to uh have some of our investors who had a different class of share uh between common stock and whatnot and preferred shares convert their shares over so that then the board had more uh say than the CEO. Because the CEO was also invested in the company. So they actually ousted the CEO.

Uh and the CEO had been drama the whole time. I remember being at a conference in Vegas where uh at the Las Vegas Convention Center, um, the biggest you know cannabis conference in the world, and we're sitting there at the booth, and somebody comes by with these flyers and it's like, hey, is this your guy's a CEO? I'm like, look at it. And it was this whole like one page, like this guy is crazy, narcissist, like just bashing this guy crazy and the company, which I work for.

Wow. And so my name's kind of on it. So I go around like, where'd you find this? He's like, Well, every someone's handing it out at all these like tables for people eating lunch.

So I I go over there and I'm literally taking flyers out of people's hands. And as when I before I get back to our booth after like you know, saving our dignity with all these flyers, this guy who I guess had created them, like literally attacked our CEO at the expo, like at the booth. My my boss, our CEO, literally had to like pull this guy off. The police had to come.

Whole crazy create like who is you did not ex you not did not expect it. Wow. And then uh, you know, so obviously after he was ousted, it was nice to have him gone. Sure.

Unfortunately, they kept replacing him with people who didn't know the industry, didn't know our customers, and you know, maybe thought they were too good to really spend a bunch of time with you know people like me and and other people in the organization to get that to get that information. Wow. Um, or they were just too interim that their focus wasn't really on the company. And so we ended up going through five CEOs in five years.

Wow. So that's fun. Each time you gotta reinvent yourself with each one of them, and you gotta like display why you're important, why you you know, especially when the company at this time is the well's kind of gotten dry and got went through about four or five different layoff iterations and actually got to the point where I was like now employee three of three. So uh I rode the ship down to the end until it it was the Titanic was sinking.

Um but uh I don't recommend that. Um but it uh it was a fun journey though. It really interested. It definitely uh definitely a learning experience.

I guess the main thing is you you never know what you're gonna get, and I guess it's part of you know the startup culture, you know. Again, it's startup problems, so to speak. Not to say that every startup is like that. I think that's a pretty unique story.

Uh but interesting nonetheless. I mean, it is uh it is a learning experience, and it just goes to show you, you know, um what a turbi turbulent environment, you know, uh a company can have. But you know, it as far as as we wrap up here, Jerry, thanks so much for these stories. These were awesome.

I'm just curious, in terms of like your experience, like where do you go to learn? Like, I don't know if there's any books that you've recommended and you've read in your past or courses or things of that nature, but I'm always curious and ask my guests, like, hey, you know, what is what is something that you always kind of turn to turn to? Yeah, so I'm not always the the best standard proactive learner. Um I do try to always like evolve.

I like learning. Um, I would say I'm a lifelong learner, um, but I always find that I learn best when I have a passion or a problem to solve. Um, so you know, I'm always a passion about customer success. I'm always trying to learn what I can there.

So I'm trying to pay attention to what's going on in the industry. Um spend a lot of time on LinkedIn, reading, you know, obviously articles and you know new things coming out. Um I try to involve myself in any kind of like webinars or anything that, you know, um is hit or miss with those things. Sometimes you're in it, you're getting you get caught in some kind of sales thing and it's not even really educational.

Sure. Um, but I'm always trying to stay in front of the tr the trends, especially with AI. Um, the company I work for now, we have our own AI product, so that's that really kind of you know and reinforces that that need to be aware of the industry. Um but other than that, really, you know, I think I I spend a lot of time whenever I have a problem or a question or something I can't resolve, um, look trying to find out how I can do it better.

And I think that that's better motivation and I have better memory retention when it's something that I'm actually like I can I can put a context behind it. Um and so you know, whenever I find a new or unique problem, or I'm always digging for problems, I'm always trying to find problems. And so, you know, and sometimes there's not even a problem. Sometimes it's just thinking about what could happen or what might happen.

And uh I think that's super that proactive problem solving before a problem actually happens, and that foresight really is is super imperative uh in resolving issues in structure, especially as you're mapping and building things out for the first time. But um, it also drives me to then learn more all the time about what what I could do or what is there when you have an idea, just Google it. Because a lot of times if you have an idea for a platform or product product, either it could be something entrepreneurial you can pursue on your own if there is nothing out there, but more than likely you're gonna find something that's gonna you know meet your needs.

Awesome. No, I love it. Thank you so much for that, Jerry. I think it's I think it's super important.

Also, too, like even I think uh there's so much out there, you know, even like with AI and ChatGPT, Anthropic, I mean there's tons of different things, but you're right, passion is really should be the driver, and I think that's um yeah, it's some great advice. And I guess like uh you know, to wrap things up, where can everybody find you, Jerry? Uh right now I'm just LinkedIn. Um you know, I probably should start like a blog or a podcast or something myself, but um, you know, I yeah, find me on LinkedIn.

Awesome, good stuff. We'll put that we'll put your LinkedIn in the show notes for sure. That way everybody can find you. But thanks so much for the great stories, Jerry.

Really enjoyed our time together, and thanks for coming on. That's a good job. Appreciate it. Anytime.

That's a wrap for today's episode. Thanks so much for listening. If you got some value from this conversation, hit subscribe, leave a rating or review, share it with someone who's also out there trying to build a better customer success or go-to-market strategy, even if it's messy along the way. And if you want more frameworks, tools, automated playbooks, check out JodasX.

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Quick note before we wrap this podcast is for educational and informational purposes only. The ideas and opinions shared here are of my own or those of my guests, and don't reflect the views of any current or former employers, clients, or partners. We might reference tools, platforms, or companies, but nothing shared here should be taken as fact, endorsement, or criticism. Do your own research and always consult your team or legal counsel when making any business decisions.

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