GTM 137: The Biggest Business Turnaround You’ve Never Heard Of & The Growth Levers to Pull When Things Go Wrong
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Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage venture capital firm in New York that has backed category-defining companies such as Chief, Alma, K Health, Latch, Alloy, Dandy and Vestwell.
Before joining Primary, Cassie was Chief Customer and Commercial Officer for Marigold (formerly known as CM Group), an Insight Partners roll-up of marketing technology software including Sailthru, Campaign Monitor, Delivra, Emma, Vuture and Liveclicker; Cassie assumed that role when Marigold acquired Sailthru, where she was Chief Revenue Officer (and managed L&D/Enablement!).
Prior to Sailthru, Cassie served as VP Marketing & Analytics at Gerson Lehrman Group (“GLG”) and as VP Marketing & Growth for Savored (acquired by Groupon). Cassie’s time in tech dates back to 2006, when she joined TheLadders.com as an early employee and managed marketing and analytics for the company’s subscription business. She began her career as a tech and media analyst at Citigroup Global Corporate & Investment Bank.
Discussed in this Episode:
The turnaround story of Cassie’s time at Sailthru and overcoming scaling challenges.
How to rebuild and regain customer trust after technical failures.
The importance of leadership alignment and transparency during times of crisis.
How to effectively use Net Promoter Score (NPS) and what it really tells you.
The value and impact of Customer Advisory Boards (CABs) in driving customer-centric growth.
Why executive compensation should align with key business metrics for better team alignment.
Creative tactics like video mailers and regional user groups to engage customers and drive product adoption.
Highlights:
07:53 What happens when commercial scale outgrows your technical scale.
15:53 Driving alignment through northstar metrics and incentives.
22:16 The best ways to measure customer trust.
34:10 Tips on setting up a Customer Advisory Board (CAB).
52:48 A fantastic multi-media mail campaign.
Guest Speaker (Cassie Young):
Host (Scott Barker):
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The GTM Podcast
The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
GTM 137 Episode Transcript
Scott Barker: Hello, and welcome back to the GTM podcast. Appreciate you all rocking with us for the next hour or so. I am, you know, very, very excited to have this next guest. This is someone who personally gives me a lot of energy every time we have a conversation and, uh, has just been an incredible partner, both to the fund, uh, and to, uh, operator, uh, one of the companies that we’re both involved in.
I am joined by Cassie Young. Cassie, welcome.
Cassie Young: Thank you so much for having me. Uh, and I am equally excited to be here. I think I can safely say that I’m a longtime listener, first time caller, uh, and thrilled to be on the podcast with you today. I think we’re going to have a lot of fun
Scott Barker: Awesome. Awesome. Very excited to dive into it. Um, you know, super quick bio for the listeners. So Cassie is the general partner at Primary Ventures. Uh, just an incredible early stage venture firm. Um, and like a lot of my You know, favorite, uh, VCs out there, um, has deep operator, uh, experience as well. She was the former chief customer officer at CM group and was also the VP of marketing and analytics at GLG, uh, tons of great.
You know, startup experience and then at larger companies. Um, and I think what got me so excited about this episode, as we were kind of chatting through what we wanted to discuss, um, I think sometimes in podcasts, we can fall into the trap of always sharing our wins and everyone wants to go and tell the story of, Hey, I went from 10 mil to a hundred mil ARR.
And here’s all the amazing things I did. Right. Which is awesome because we can learn a ton from that. Uh, but sometimes I know when I look back at my personal journey, I have learned more from my losses and the things that didn’t exactly go my way. Um, and you have been kind enough, uh, to, uh, kind of pull apart, um, a difficult time, uh, that you had.
And so I want to just dive right into it. And we’re going to talk about some growth levers to pull when. Everything kind of goes wrong and you’re just not working.
Cassie Young: A comment, you know, I think it’s a, I know there was a little bit of kind of chuckling on both of our ends when I suggested this topic and my head immediately went like, where are you driving improvements in a business? But you and I both know. Every business goes through those growing pains, right?
I say the life and times of a startup company is the S curve. Do you know what I mean? Where you’re riding high and then you stall out or maybe it’s worse than an S curve and it really kind of dips into the valley. But, you know, I tell people, if you think you’re in a business where there’s not those pains, I have very bad news for you.
It’s that. You’re so far removed from the nucleus of decision making that you actually don’t know what’s going on. So one of my favorite things to talk about to your point is like the battle scars, you know what I mean? That you get from the tough times because I think it just builds this incredible muscle memory that you can carry with you into the great times or any circumstance.
And that could become a real professional superpower for leaders.
Scott Barker: totally, yeah, couldn’t, couldn’t agree more. And those are the skills that you acquire when you go through those hard times. Yeah. When things are all rosy again, you know, you take that same attitude and mentality and you can really push on the gas, uh, cause you, you have this almost like a PTSD from when things weren’t good.
So when times are good, you really relish in them and know to take them.
Cassie Young: Totally. And I’m now at the point where I’m like 10 years past the real thick of what we’re going to talk about. So I, I’m, I, everything is on the table, right. To be discussed because it’s no longer some confidential story or any customers’ feathers are going to get ruffled about it.
Scott Barker: Yeah, I love that. Yeah, the scars are no longer open wounds, so we can get,
Cassie Young: For sure.
Scott Barker: Awesome. Well, let’s, let’s fly you back. We’ll build a little, uh, uh, time travel machine and, uh, take you back. You’re at a company called Sailthru that ended up getting acquired.
But before that happened you were facing some challenges. Do you mind just kind of setting the table of where you’re at as far as a company at that time?
Cassie Young: For sure. And, you know, I’ll really take you back to when I joined this business. So when I joined the business, it was a high flyer, right. From a top perspective, you know, it was an interesting time. It was 2013 in New York city. You know, we like to say at primary that the global financial crisis was the single greatest tailwind for New York tech.
But even with that, it was all consumer tech. So 2013 was sort of this era. Where you started to see the 1st B2B enterprise software businesses being built here and sailed through was 1 of those early businesses that we sold enterprise marketing technology solutions. So think personalization and your emails on your websites and then your mobile applications to consumer brands.
What happens when commercial scale outgrows your technical scale.
And so I joined the business as it was. Closing its series B round on a really great upswing. And, you know, my first year there was just sort of continued growth that we can talk more about in many ways. But we hit real scaling challenges with the business, right? So it was there for a while.
We closed a very successful series C process and then our commercial scale, I think, eclipsed the technical scale of the business, right? And we had real challenges with stability. Right now, um, in businesses, like consumer businesses that are sending emails, that is a huge fraction of the overall revenue that they drive right from their digital channels in general.
And so when that channel becomes unstable, it very quickly erodes customer trust. And so we had just an amalgamation of challenges 1, which is our ability to scale the systems to support. Sense of it. We’re talking about organizations like the Washington Post sending breaking news alerts, right? And breaking news is like an arms race to see who gets into the inbox first.
Right? But we also supported e-commerce brands and, um, you know, daily deal and flash sale brands, etc. So we had some, some scaling challenges and then we had just like. A smattering of things that were annoying and poorly timed, right? The data center that we used was closing, right? And we had to go through a data center migration in the throes of all of this.
And we believed we could do that on our own. And hindsight is 2020. And we probably should have brought in, you know, someone who had done that several times over to help us with that challenge. But it was this amalgamation of challenges that we hit. That ultimately drove a really sour downturn for us in terms of customer churn in terms of reputational overhang in the market, because we all know that buyers learn about solutions from other buyers.
Right? And I would say detractors are 10 times louder in the market than the promoters are. Right? So you had churn, you had growth. And, you know, quite frankly, we even hadour challenges in terms of employee retention right through this challenging period. And so that kind of sets the frame for where it is.
You know, the headline that we’ll get to in a moment is that we did stabilize the ship, but it was a multi year journey to go and do that. Um, but I think you and I agree to be fun to sort of really break apart some of the things that we had to think about to rally the organization around getting back on better footing and Some of the tactics we employed both internally and externally, you know, with our customers and our prospects to help us on that journey.
Scott Barker: Yeah. I’m excited to dive into the tactics that ultimately kind of righted the ship. Um, and you know, I think one of the hardest things to come back from is when social proof referrals, word of mouth starts turning sour, right? Whereas companies, as humans, like, you know, reputation is what people say behind closed doors and if they’re saying negative things and you don’t have control over that and you outlined it, it can be a multi year journey to get that trust back.
You know, you, you start losing that trust and, uh, it, it can be a slippery slope. What was the first thing that you kind of identified? We’re like, okay, we’re in trouble and we need to. make some serious changes right now and like, what got us here? We can’t keep doing the same thing. Was there sort of a catalyst or was it just all these things start happening?
Um, but was there a specific moment? Oh,
Cassie Young: The data center migration was definitely a catalyst to a lot of what happened here, but I’ll actually say it wasn’t amalgamation of a number of different things. And one interesting nugget I’ll share is that. In an enterprise software business churn is a lagging indicator, right?
Because if you’re on an email service provider and you’re a scaled business, it’s not like you’re going to churn this week and be migrated onto a new platform next week. So, while churn materialized to kind of showcase the problem that actually lagged by several months, right? The leading indicators that we were using were things like net promoter score, and you can argue the merits of that promoter score all day long, right?
But it is a good, just quick litmus check right on the sanity of how you’re doing with your customers. And to give you some sense of it, you know, we, we. Really leveled up our customer insight to kind of NPS practice work and the throes of all this happening. And I think the NPS that we were recording during this era to give you a sense of the magnitude of the problem was negative 26, right?
Which is I describe worse than your cable company. Right? So I’m comfortable sharing that now because we then went on a journey where we We improved it by more than 50 points. You know what I mean? In the years to come, and that’s what I’m proud is, you know, professional accomplishments is what we were able to go and do, but that gives you a sense of sort of the level of severity.
And so that was a really helpful leading indicator for us. Because if you just looked at the board deck, the problem was kind of hiding out in the background for a little bit. If you talk to people in customer support, they would tell you, well, we’re on the front lines, right? We know exactly what’s going on in the business.
And, you know, that’s a little bit of a. Spoiler alert for where we’re going to now not net out on this, which is, you know, just rallying the entire organization, right about the importance of customer trust. Right? I very frequently say customer value is enterprise value, right? And there are really 2 ways that you unlock customer value.
1 is you show up and you are a trusted partner. The second is that you enable those customers to achieve their own business growth, right? We always say we want to know how the champion ultimately gets promoted in their job, right? Because that helps us to be better at our job.
And so, you know, our huge talk track to our team at the most macro level was to listen, if we do everything in our power within financial constraints, of course, to make our customers successful with this platform. We would have to catastrophically screw something up not to succeed as a business. So we need to go and do that, but that’s hard, right?
Because we had a very technical, exciting product, product, a set of products, really. I mean, we were investing in data science and predictions long before, you know, the current era of everything that people are talking about in AI. And when you take a deeply gifted technical team and tell them that, you know, you have to be focused on stability, right?
And customer centricity and existing roadmap. It’s hard, but it was a long term bet, right? I mean, to give you a sense of it. At one point, I was very fortunate that, um, the CTO of our business, Tom Janowski, um, ultimately became, like, My I said my work husband and right hand partner, and it’s unusual, I think, to have the CRO right in the CTO very closely aligned.
But Tom and I were incredibly closely aligned. And at one point in time, you know, he said, my commitment to this organization is that 70 percent of the sprint team resources are going to go to existing customer needs right to help right size what needs to happen here. And I’m oversimplifying to a certain degree because yeah.
Roadmap is one part of the problem, right? I indicated before core stability was a major need of ours. So, you know, many of our investments were things like investing in an S. R. E. right? Like a reliability engineering team, right? Just given the scale of the data that we were working on, but none of it would have been possible without our work.
You know, alignment of the executive team, and that wasn’t an overnight phenomenon either, right? There was a lot of deliberate work done by, I live through a CEO transition at sale through and, um, our, our second CEO, Neil Lustig, I think was taught me as an executive, a master class on what it meant to really drive alignment in the executive function.
And I credit his leadership with a lot of what we were able to achieve, um, you know, in, in, in the years of driving the turnaround situation.
Driving alignment through northstar metrics and incentives.
Scott Barker: How did you ultimately get that alignment and even a step further, like excitement to go and solve these unsexy problems? Like you mentioned, like going in and fixing stability is like, it doesn’t usually get people out of, out of bed. They want to build new, exciting features. And same with this idea of customer centricity.
You know, it’s like, it’s almost like a. A throwaway word, um, and a lot of people talk about it, but you then have to shift that into like real world tactics and get people excited about, Hey, this long journey we’re going to go on. We might not see the results for six, nine, 12
Cassie Young: that’s right. Yeah. And I would be lying through my teeth. Scott, if I said, oh, we were really good at getting everybody excited about this. Right? So, but we had to think about how do we get smart about it so that we are able to retain a critical mass of really smart employees. And I think the way we thought about it was.
We have to just educate them and be transparent, right? That what they’re going to learn in this journey is a skill set that they will carry forward on the resume into any other job that they go and take. And so our commitment was, we will explain the P&L to you. We will explain what the board cares about.
We’re an extremely transparent culture. Our CFO, Marty would regularly do, you know, the SaaS P&L walkthroughs of our business. We always did public company readouts. Of our board meetings, right? To bring people along because we thought, you know, if there’s sort of short term pain here, how do we help people maximize, you know, their learnings from it in a way that benefits their personal balance sheet right in their resume?
So that’s really how I think we brought people on that. And that’s sort of my style as a leader. I was saying transparent to a fall. I’ve definitely had my wrist slapped, you know, a handful of times, but I’d rather air on that. I do think it builds loyalty from employees in tough times, but the more pragmatic answer to your question is, and it goes back to my point about transparency.
We aligned the organization to the metrics that mattered most and we were consistent about it. Right? So the way I often talk about this is, you know, like any organization, we had a monthly all hands meeting on the 1st slide of every monthly all hands meeting for 5 years. It was exactly the same. Okay. And it focused on three big buckets of objectives, right?
We said there’s three things that we need to do really well. Number one is we need to grow our business. Number two, we need to be a trusted partner. And number three, we need to operate predictably and responsibly right on the finance side. And so there was a corresponding sort of North Star metric within each of those, right?
So grow our businesses, exit ARR, because that’s a function of both the new logo and the install base, right? Okay. Be a trusted partner for us was NPS, not because I think it’s the goal gets the gold star. But because, as I said before, ours was in the toilet, right? I need it to be addressed, right? And then number three for a while was a net burn target for us.
And ultimately, once the business became cash flow positive, it evolved into an EBITDA target. So everyone in the organization knew these were the three things that we cared about most, right? So. If you are the leader of the support organization, I’ll pick on that because it’s, you know, a lane that rolled up to me and I’m not actually picking on them, but no one cares that you have 100 percent of the customers sat on ticket resolution.
If your gross churn is terrible, right? So just get people fluent in what I call the first team metrics that matter for the business. But the most impactful thing we did without question was aligning executive compensation to those metrics. So every executive around the table, including myself as a CRO, had an extra kind of purse that came from traditional commission pay, right?
But everyone around the table had a bonus that was tied to. Those three metrics and you really haven’t seen behavioral change in an organization until you see what happens, right? When your technical org has, you know, a third of their bonus being derived by net promoter score, for instance, right? So I always say, I believe that no team will be fully aligned if their compensation plans are not.
I think that’s really just. Important reality of business, but in terms of the broader, you know, staff, I really think this rallying cry and over education about the metrics that mattered were counted and, you know, holding ourselves accountable to driving improvements, but also to owning when we made mistakes, right?
And same thing with our customers, quite frankly, like. Um, you know, I ran our customer advisory board for a number of years, and one thing we did with our cab, which was, you know, 10 executives at a time is we always opened it up with the state of the business, right? Where we’d be very real with them around what was going on.
Get their input. No one wants the dog and pony show, right? Your customers don’t want it, and your employees don’t want it. And so I think you get a lot of. Credit just for showing up and being real, but you have to make progress. You can’t just say, you know, everything is on fire, right? And we’re not gonna, you know, make in rows into solutions.
Scott Barker: A lot of great stuff there. I think more. Even very early stage startups, maybe even more important at the early stages is be that transparent with your, like SaaS P&L, uh, you’re also just getting more, all your employees are getting more financially literate. They understand the business better. They feel like they’re part of it, uh, even more.
So I think that is a great
one for
everyone to steal.
Cassie Young: We say this all the time, like the simple cash in cash out, right? And we have portfolio companies that have shared. Oh, when we actually walk our staff through the very basic cash flows of the business, suddenly all these ideas start to percolate like, oh, wait, well, we don’t need to spend on x, you know what I mean?
It’s just, it’s amazing what happens where you bring people along on the journey and they see the ramifications on runway, et cetera, particularly in the early stage
Scott Barker: Totally. Yeah. Maybe we don’t need that other event sponsorship that hasn’t driven any revenue. Maybe we don’t need, uh, this additional headcount that I just wanted to build my team. Um, and I, I like this idea of, you know, 5 years, the exact same slide, like people just, they start ingraining that in absolutely everything that they do, uh, regardless of, of role.
The best ways to measure customer trust.
Not to derail us too much, but you’ve kind of, and I think this is common, but NPS, not the greatest way to measure things. Have you since found a better indicator of this kind of customer trust and how folks are feeling about your product, feeling about your business?
Cassie Young: So in no particular order, um, What I found way more powerful than just looking at net promoter score is an absolute number was how you’re able to slice and dice that data. So to bring this to life, you know, we ran a longer format MPS survey 3 or 4 times a year, right?
It was probably a 4 or 5 minute survey that asked. Lots of supplemental questions. In addition to the classic, you know, NPS question and a lot of the really powerful insights actually came out of what happened when we did the regression analysis between how people answer other questions and then, you know, what their NPS score was.
And I’ll go through some specific examples in a moment. But before I do that, I would say you also have to run the same analysis for net retention rate, right? I actually just spoke at this event yesterday, and I said to this room full of software executives. If you slept through high school statistics, I have really bad news for you.
Regression analysis actually does have a time and a place scale business, right? And I call it. The sticky drivers of the business where you can map customer attributes or traits and tie it directly to net retention to understand if there’s a statistically significant relationship, right? So, for instance, at sales through, we knew that customers who attended a live training program with us, right?
We’re 30 percent more likely to renew than those who did not. So that became a churn mitigation strategy for us was if we had a high risk customer. We would even consider flying them to the closest training to get them invested in that. But going back to NPS, this is a place where, of course, we asked for ratings in terms of perception of stability, right?
We asked for ratings around perception of ROI and the magic was unlocked when we look at the relationships between these numbers, right? So, for instance. One rating scale we give customers was on a scale of one to five, you know, uh, rate Sailthru’s ability to increase your customer LTV, right? We’d always have an ROI customers who rated us a four or five, their NPS curve and their net retention curves were literally like 30 points higher than the other segment.
Right? And so we said, okay, well, this. This is actually, we need to do a better job reiterating customer value. And we launched the Wednesday weekly report that hit the customer inboxes that summarized all that we did for them. And people, of course, argued our attribution, right? About what we did. But I’m like, I’d way rather have the inbox, like the message in the inbox.
With the economic buyer so that we’re top of mind, right? And here was the craziest thing of all that we learned from this. One of the questions we asked was actually a list of all of the features that we had released the prior quarter. And we said, yes or no. Do you know, did you know about this product release?
The second question was, if you knew about it, did it have a material impact on your business? Okay. And here’s what’s wild. 50 percent of the customers said they had no clue about the product releases, which is actually total BS because because we were an email platform, we sent the release notes through our own system and half the people who said they didn’t know about it, open the email and read it, right?
So it just goes back to this thing that you need to hear it seven times. But that cohort of people who said, okay, we know about the product releases. Literally their MPS score was 44 points higher than those who did not. But there was no material difference between whether or not it had a major material impact on your business or not.
So perception was the reality of how the roadmap equals innovation. And so the takeaway from that was, hey, this is a huge product marketing opportunity. We have to be beating people over the head, right? With what we’re doing and the enhancements that we’re driving and I’m picking on, you know, roadmap examples.
But the same type of analysis could be done with stability, right? Or things. That customer’s experience, et cetera. Now I’m talking about the analysis that we were able to do. And we were at the point of 400 customers, right? So, you know, we had some degree of scale being able to do that. But I always say, even for early stage companies, like what’s your hypothesis on the drive, the sticky drivers for the customer and how do you drive to those behaviors, even as early as implementation, right?
Like it’s, you don’t want a customer to just go live. You want them to live with all of the things that you know, we’re going to drive meaningful outcomes, if that makes sense.
Scott Barker: Yeah. Makes total sense. And, fascinating learning. It’s so funny. We all live in sort of bubble. And we think because we’re so obsessed with this new product launch release date that we’ve been thinking about for weeks and weeks, and we’re like, Oh, we sent out the comms, everyone’s going to know exactly about it.
And it’s rarely, rarely the case. And. Communicating with your customers can be so difficult. Like you said, you have to say it like seven times. Once you had that, that learning of like, Oh, people don’t actually know, even if they’ve read the email, what levers did you pull to make sure that they did know?
Uh, was it sending, just sending more emails? Was it the live training that you mentioned?
Cassie Young: It was, we had to, you know, you have to be customers where they are. So we tried a little bit of everything, right? We did a, you know, since its sales are not a goal theme, we did this, like, shift by sale through monthly recap. And then we forward the email again to everyone just so it, like, didn’t accidentally get archived.
We put in product alerts around what was going on, and then one of the most powerful things we actually did, and all credit to this is to the amazing head of CS who supported me at the time. Ellen Turchilla, you know, she challenged me and said, in addition to this executive level, you know, advisory board, I want to launch these regional user groups that she called rugs.
And the idea with the regional user groups was that, Yeah. She would bring the non economic buyers together, and she would invite customers to give presentations on how they were using the product in a compelling way, and then have the product team do a deep dive into the road map with this way bigger audience.
Now, that’s a set of people who don’t get invited to the events because their bosses get invited to all the events, right? And. That was a program that we were really able to scale. We would do them in major markets like New York, London, San Francisco, LA, et cetera. And we could bring, you know, 50 plus people into a room at a time.
Customers felt smart and flattered that they were presenting it, but then they heard about it from other customers. And then they also literally heard about it from someone on our product team on the stage, right? Preaching that gospel.
Scott Barker: I like that. I like that. I’ve always been a huge proponent of get your. Customers to sell for you, uh, or get your founders to sell your you actually also asked this question of, like, how did we know right where things were going off the rails or on the rails? Maybe you kind of hit the nail on the head. Referral is the dream pipeline source, right? The deals close at higher win rates and they close faster. Right? And, you know, I think when we did the math.
Cassie Young: Referral deals closed at four X, the win rate of a BDR source deal, right? Um, and so the name of the game became, how could you drive that program? That’s really hard to do when you don’t have customer trust. And so another kind of indicator for us, when we started to see the rebound of referrals, right, we knew we were on the right path and honestly my tried and true hack for any organization is the referral.
I’ll give it out for, for, uh, for free here is, you know, the NPS question says. On a scale of 0 to 10, how likely are you to recommend us? And then a bunch of people give you 9s and 10s are promoters. And people don’t go ask them to refer, right? So the number one thing we said was like, let’s find all the 9s and 10s and call them up, right?
To go and do that. But they have to have the trust in the core product for their willingness to go and do that. And that just took us some time, you know, to ultimately repair. And during that period, because we kind of skipped over the period of like, Okay. Really doom and gloom, technical outages and things like that.
I mean, one, it all kidding aside, it really did build this resilience for me. Right. I had an amazing customer success person on my team who was on the front end of receiving some harsh comments from Hallmark, right. When we had delayed sends on mother’s day, right. For me, so you don’t want to be in that conversation, but it builds this muscle.
But again, you have to own it with the customer and take them deeply behind the scenes. And so one of the reasons I was so grateful to have such fantastic technical leadership in the business is they would go on site. They were willing to meet with the technical stakeholders of our customers and explain exactly what was going on or what.
Types of innovations we were investing in to, you know, accelerate our send speed and we wouldn’t have been able to do that. Do you know what I mean? Without that partnership. I think it is so monumental that you have an aligned executive team in a difficult time. I think, you know, you can kind of hide a misaligned team when everything is high flying.
And I think businesses crash and burn, right. When there’s the second of, you know, a challenge, nevermind a crisis. If those teams are not aligned, when that happens,
Scott Barker: Yeah. Yeah. Definitely have to, you know, completely own the mistakes when they happen. You know, that’s what people want. They want to feel heard. They want to get your side of the story fully and completely, and then understand the steps you’re taking to address it, and it’s also a time to like to build. I guess, like, trust. Like, sometimes when, you know, bad things happen, you almost get, like, trauma bonded by it. You’re like, okay, well, we went through tough times. This person was still a trusted partner to me. They were honest. They had my back and they’re trying to fix it. And if you can turn those around, those will become your most loyal customers.
Cassie Young: 100%. I’ll tell you a story. I mean, I’ve been out of sale through for five years now. One major episode that we have was over Thanksgiving, Black Friday weekend, which is the Superbowl of email. And I mean, it’s like the joke of my family. I was like being yelled at in three different mechanisms by different company executives
Scott Barker: As you’re cutting the turkey.
Cassie Young: was a special memory, but, but all kidding aside, the COO of one of our customers, every Thanksgiving, I haven’t worked there in five years, text me. And it’s always like, remember that Thanksgiving that we spent on the phone together, you know what I mean? So it is, it’s, it’s like all kidding aside, I think if you do right by people, do you know what I mean?
You absolutely can write the ship, but I think the executives have to lead by example on this stuff. Right. And, you know, for me, when I was on the operating side. And I preach this gospel to all the portfolio companies. It was a failure, a failed day for me. If I was not with a customer and those, those days were few and far between.
And, you know, I used to remember we had a number of different offices around the world. And my assistant used to say to me, when are you going to pee? Right? When I was in San Francisco, because she’s like, you’re just going from customer to customer. And I’m like, that’s, that’s the old, that is how we advance value, right?
Is. Yeah. To meet with these customers, to understand their core needs. And that’s just not a me thing. Like our CTO did it. Our CFO was an executive sponsor on certain accounts. Right. And I think really well oiled executive sponsorship programs are a great way to get the full team thinking about it and cascading it back.
Scott Barker: Yeah, I think that was really hammered home to me during my time at Outreach and I would see Manny Medina’s calendar, Mark Casaglo’s calendar and a bear. It’s like, are the top of the top of the organization. If you looked at their calendar, it was. Kind of scary. It was 10 to 12 customer meetings, like every day they were in front of customers and then they, you know, at 7 PM would go do their real job, you know, running the organization.
Tips on setting up a Customer Advisory Board (CAB)
And that is how we were able to grow so quickly during that time period. You mentioned the customer advisory board and it’s something I haven’t actually talked about a ton on this podcast and it’s really important. When do you advise your portfolio companies to set up a cap?
Is it too early to do that?
Cassie Young: don’t think it’s ever too early. I think it’s that you set the expectation that it will evolve, right? So one way to go about that is to say, you know, I’d love for you to participate and commit to doing it for the next 12 months, right? And then 12 months from now, we’re going to reimagine what this looks like.
but I think in the early days, it can be massively helpful for getting feedback on key work streams in the business, right? One of my favorite advisory board hacks was to actually show the executives a sanitized version of a QBR, right? And say, if you got this in your inbox, like tear it down, tear it apart.
Like, what do you actually care about at the sea level of what’s going on? And we would get amazingly valuable insights from that. Right. And so, you know, even at the early stage, I think, you know, there’s a slightly nuanced version of that, but it is the, what do you care about? How do we stay top of mind?
Why are you going to buy from a startup versus, you know, the old adage of no one ever got fired for hiring insert IBM, Oracle, Adobe, whomever, right into that statement. And so I’m a huge fan of it. In fact, you know, a primary, we do a good bit of incubation work and, you know, one of the incubation teams here, Assembled an advisory board when they were running down an idea to green light that they’re going to persist on the other side of this business.
Now, coming into company formation, which I actually wouldn’t even thought to do if it was a genius idea, and those people might not even all become customers, right? There’s no right or wrong answer to this question. I tend to be partial to keeping the customer advisory board to your actual paying customers at scale.
Some people will say they’ll bring in a dream prospect to help push it. I think there’s other forums to do that, but to each their own. I think for early stage companies, it can be very common. Do you know what I mean? That you diversify because you may not have that many customers in terms of people who come in, maybe you give them a little bit of equity.
Bbut it’s like, I don’t think people talk about advisory boards enough period. And I was actually just thinking for my, um, tactic talk newsletter that this spring, maybe I should do something like a longer format piece on structuring effective cab meetings could be a good one.
Scott Barker: Totally. Yeah. If it’s not talked about, I think there’s, there’s different forms of kind of advisory boards that serve different functions too. I think you can have like the advisory, your advisors that are more like, these are going to help your company grow. I’m also seeing this like a new sort of.
Kind of like almost like an influencer advisory, uh, board that very small amount of equity, or even you just put them on a pedestal through content or media or some sort of incentive. And they’re like, they help you with distribution. So the one is like execution.
Cassie Young: You just pay them cold hard cash. It’s funny that you call them influencers because when I was at SalesReel, I called it our micro influencer program, right? And to be honest with you, our view, and we wouldn’t do this with existing customers because we didn’t want there to be a conflict of interest, but particularly in the CMO role.
There’s so much turnover that you always have these people that are free agents with amazing Rolodexes. And so we said, you know what, like if you walk us into a deal, that’s not in our pipeline right now. And we had very clear verbiage around deal registration, right. And what would count. And we close that deal.
We’ll give you 10 percent of first year ACB and that math works right at this particular enterprise. And I always tell the story of someone who walked us into a million dollar deal where. There were like a dozen vendor RFP going on that somehow we had been left off of. She got us a courtesy meeting. We end up winning this deal at a million dollars.
She gets a hundred thousand dollar check from us. She was literally chasing me for the check because it was going into like part of a down payment for a vacation home that she was buying. And guess what happened the next week? She opened up her LinkedIn. She’s like, give me all the target accounts. You know what I mean?
But she had to check in the pocket and was incentivized to go do that. I think now, I mean, I’m dating myself. That was probably like seven years ago when we were employing that tactic. Like everyone’s caught on a little bit, but it is, you know, I think in places that are hyper networked industries, it still works really well.
Scott Barker: Yeah, it’s caught on, but not to the extent that you would think I’ve always liked the whole, my whole journey through SaaS. It was like, why don’t we do this? And there was a pushback at my time at outreach anyway, it was like, ah, like they’re going to send us the customers that we’re going to win anyway.
And we don’t want to pay, but it’s like, we already have our. Sales development team, like prospecting into this, we’re already running ad campaigns. Like we are spending money. Why don’t we spend it once it’s
Cassie Young: To our earlier
conversation, referral deals close faster. Do you know what I mean? There’s just so many mechanics, you know what I mean? Of like the core unit economics of the deal that are attractive by doing it that way for sure.Scott Barker: Yeah. Um, so I think the incentives for like those two style of advice reports are fairly straightforward. You could do, you know, cash for influencers, for people that are closer to the business, like true advisors, you know, it’s usually equity from a cab perspective, your customers, how did you incentivize them?
Was it just like access to. Early road access. It was accessible. We did not give them equity in the business. And I mean, we made it really fun, right? So our customers came from not even all over the US, right? We had customers in Europe who were with us as well. And we met twice a year. We paid for them to come to New York. We went to a great hotel.
Cassie Young: We did a fun event and dinner, et cetera. But it really was, you know, priority access and we would do our best to prop them up at other events. Right. So, you know, people always talk about conferences and, you know, the cold hard truth, as you and I both know, is no one wants to hear from a vendor at a conference, right?
They want to hear from the customer who’s using the tool around what they did. And so that cab group was sort of our go to that if we were going to do a large conference sponsorship, we’d get those people on stage, right. And we’d help them build their brand. We’d help with, you know, their presentations.
So we would do wild things like. Even with our video testimonials, we would say, you know what, we’re going to, um, show up at your office in LA with a glam squad. Do you know what I mean? Or you can get like your hair done, your makeup, whatever for this video. Do you mean that it’s going to be like your brand thing about this amazing marketing program that you did?
So we tried to find those little hacks, but the headline was we helped those people build their own brands. And that by extension, it helped us because sales was part of the narrative that they were, you know, sharing around how they, you know, accelerated their market.
Scott Barker: Yeah, that was kind of the, the sales hacker playbook back of the day was just, all right, we can get all these great people to give us their content and we’ll put them on stages and a pedestal. And that’s going to help them in their
Cassie Young: I mean, it’s so funny how you can ask someone for a case study and they’re like, no. And then you’ll say, oh, will you come speak at this conference in front of 1500 people? And it’s a guaranteed yes, because they look really good. They always crack me up. That was our exact move at the, we created the sales engagement podcast at outreach, not for distribution. We didn’t care who listened to it. We could have like 10 people listen to it. What it was, was yeah, ability to, if we couldn’t get a case study with X, Y, Z huge company, but we invited them on the podcast.
Scott Barker: Well, you can infer, cause I’m talking to you and saying how amazing our partnership is that you’re probably a
Cassie Young: I love that. Um. It worked, it worked really well. And then we would also invite prospects on too. And it gave a chance to, to meet with them in a non commercial, uh, kind of environment, which was cool.
Scott Barker: I kind of sidetracked a little bit there on the customer advisory board. Um, any other things, you know, I’d sail through that kind of drove you to customer centricity and ultimately to getting into a healthy, healthy space.
Cassie Young: Yeah, lots of little hacks around the margin is what I’ll say. Right? So, you know, let’s talk about engineers for a moment. Engineers don’t want to hear from the life cycle marketing director. Do you know what I mean about what they’re doing? Maybe they’re interested in that, but they want to understand the fruits of their own labor.
Right? So one program we ran, for instance, was, you know, we had a technical stakeholder at every customer, right? If not a small team of them, you know, We would bring the technical stakeholders into meet with the sprint teams that built products. They were deploying and the engineering teams love that right of just kind of understanding.
Okay. This is the limitation of the historical data import, right? Or whatever it may have been, but they can have a much more technical conversation. So we did that. Of course, at a macro level for good hygiene, we always brought in, like, Okay. Customers speak with the whole company, right? We probably did that on close to a monthly basis.
And we would ask them the tough questions right around, you know, if you could change something about the product tomorrow, what would it be? All that fun stuff. So that was one idea. I mean, other kinds of tactical things in the trenches were, you know, we required everyone at the manager level and up to do regular shadowing of the support desk for a week.
So for half a day for an entire week, they would sit down and that was actually a great way whereengineers would sit shoulder to shoulder with support agents, and they’re like, why don’t we just fix that now? You know, you and I both know that it goes into, like, the queue and the backlog, et cetera, but it’s just very eye opening when you go and run that playbook compensation.
As I said before, the alignment of that was huge for us. I also just think that co-mingling of the teams was huge. And what I mean by that is. Um, and this is a great way to reward your superstars. Things like when we need to do a pipeline brainstorm. Well, more often than not, it’s like commercial leadership gets in a room to figure out how to drive pipe.
We said, well, what if we bring the best sellers, the best solutions, engineers and the best and they’re invited to come in this room and help us brainstorm where we want to. Go with it. I think that was huge. And then similarly, like telling sales, you should be coming to your customers. QB ours, even if it’s 2 years later, because 1, you need that network node, right?
For your referrals. And 2, you’re going to get these amazing stories that make you a better seller in the 1st place. So a lot of that co-mingling and we really. It was about the people we hired, right? Who had to be bought into that strategy. And I feel really grateful that I think we had a lot of boots on the ground to subscribe to that, right?
And it really did feel like a team. There wasn’t finger pointing between sales and CS when times were touching that that’s, those times are tough, but that that’s a credit right to the leaders who were over each one of those functions, you know,
Scott Barker: Yeah, they did that then I imagine the employee retention kind of took care of itself because that was one of the things you mentioned at the beginning. We had kind of had this churn problem, customer trust and then employee retention. Was that ever a. Um, a focus, or was it, Hey, if we take care of our customers and they love us, people are going to enjoy working here again.
Cassie Young: It was both, right? I mean, we definitely lost employees, right? When we found fell on hard time and I would get on my soapbox and I think some people, I still have some folks who work at my org who make fun of me and send me texts on this regularly, where I have this rule that I call the no hangover rule.
Like shit happens and I don’t want to hear about it. You know what I mean? Like once there’s a plan to get an action and resolve it, like it’s really not well spent on me, right? It’s the number one rule of working in my org. Um, but you know, I would get on my soapbox and explain what we talked about at the onset.
If you don’t stay at a company during a time of challenge, you do not build the muscle memory and it will happen again in your career. So totally up to you, right? If you want to tap out, no judgment to go and do that, but I guarantee you, like if you don’t do it here, you’re going to do it somewhere else.
So I put out my saleswoman hat, right. As I was trying to pitch people on that, it didn’t work all the time, but it worked sometimes, but I would say the people who stuck around. Really stuck around by the guy I look at, you know, we ultimately sold as part of a private equity roll up and in late 2018, there were a ton of people who were with the business who had been with us for years, who had really just kind of seen it in and out.
And, you know, the proudest thing for me as a people manager is just seeing what all those folks are up to now. Right? And they did kind of carry that with them and, you know, translated it to something positive. The number of VPs and Cs that have emerged out of that squad is fantastic.
Scott Barker: Yeah. And you better believe that in every interview since, uh, leaving sail through they, they bring up the hard times, you know, that’s like the perfect thing to showcase.
Cassie Young: That’s right. That’s right.
Scott Barker: That’s what people want to see. And, uh, the no hangover rule. Does that mean you can be hung over? You just can’t talk about it.
Cassie Young: That’s right. That’s right. That’s exactly right. You can’t talk about it. Um, you just made me think of something else. I had an amazing colleague, um, after the acquisition at CM group, which is now called Marigold, but my colleague, Ethan Zubeck, there had a great line that I always use, which is to your more literal question, pros play hurt, right?
That was the big line at the sales kickoff every year, right? Which I thought was a good one. Yeah.
Scott Barker: I like that. I like that. Um, I want to double click on something because I thought it was a really good, um, tactic and I want to make sure that we highlight it for the listeners and make sure I got it right. Um, I think this idea of shadowing the support desk is really interesting. Did you have that just for?
Managers on the go to market side of the business, or were these managers across the entire organization? Even the people team financed the entire organization, it really, I mean, support is a hard job. I, but it’s such an important job, right? Because it’s the tip of the sphere of like the really frequent, um, interactions with customers. So no, it was required in any function in the business.
Cassie Young: And I think that served us really well.
Scott Barker: Cool. And so you would spend a day every quarter
Cassie Young: You would spend half the day for five consecutive days. I can’t remember if we did it once or twice a year. Yeah,
Scott Barker: Cool. I think that is something everyone should follow. It’s like, you could almost do the same thing. You
could like shadow support and shadow like sales development would
Cassie Young: Right. I mean, you’ve probably heard that Starbucks requires every employee, even at corporate, to go be a barista. Right? I mean, I have friends who worked in the post MBA program at Home Depot who worked on the floor of Home Depot. You know, it really just feels a totally different type of customer empathy when you go and do that.
Scott Barker: Yeah. Yeah. I like that a lot. All right. This has been awesome. I could probably pick your brain for four more hours
Cassie Young: Like, I always, I always love chatting. It’s always a blast. Yes.
Scott Barker: It’s the best. Um, but I do have to get to the final two questions and these are the same for every episode. They are intentionally vague, so you can take them any way you want.
The first question is what is one widely held belief? That revenue leaders or founders still believe to be true that you think is bullshit or no longer serving us.
Cassie Young: Hiring for quota capacity. This drives me crazy that I’m still talking about this because I feel like I’ve been preaching this gospel for a long time, right? We’ve all been in the bit where it’s like, we need to add 10 million in bookings and each rep can do 1 million. Therefore we need to hire 10 reps.
And it’s like, well, show me the business where a hundred percent of them are hitting quota number one, but way more importantly. Where in the hell is that pipeline coming from, right? And we see this trap all of the time as businesses rapidly grow the go to market team ahead of the pipeline. As you and I both know, even the best AEs on the planet hate prospecting, so there needs to be a plan in place, right?
To future proof the pipe coverage. So it drives me crazy when I see this in models. I’m like, it’s just like a totally antiquated way of thinking. Yeah,
Scott Barker: Yeah, huge. I’ve been told by many. Smart founders looking back like, you know, sellers don’t create demand. They turn the demand into revenue. So you can’t just, you know, let them loose with this big quota. What’s a, what’s a better way of doing it in your eyes?
Cassie Young: I actually think it’s really marrying the top down and bottoms up pipeline, right? So what I mean by that is the bottoms up or like, what are the actual deals that you have? But the top down is actually built out of the cohort analysis. I actually just did a tactic talk on this last week’s newsletter on the importance of using cohort analysis for out periods to really understand the pipeline coverage.
What’s the go get that you have to get from there. I’m not saying for a moment. You should live in a world where sellers are drowning in pipe covers, but I think there’s a happy medium. Do you know what I mean? Where they have to do a little bit of work, but you don’t run the risk of they come in and they’re going to immediately leave because they have nothing to work because you’ve hired five people at the same time.
But I’m a big believer in like, Do the cohort math, regardless of whether you’re high velocity or enterprise. See where that nets you out and sanity check that with the, uh, with the, I
Scott Barker: Yeah. Couldn’t agree more. Are you, I’m just curious. Are you seeing, um, something I’m kind of noticing, are you seeing the rise of the full cycle AE again in your portfolio?
Cassie Young: would say, you know, in the early days, sure. Cause we’re first check in, but I do think as organizations grow in scale, no. And I’m a huge believer in not having the full cycle AE. I’m a big believer in the classical account management function. I mean, I think there’s a time and a place for, you know, when it’s an account manager versus when it’s CSM versus when it’s more procedural renewals manager, I’ve also.
Done a little bit of writing on that. Um, but I think for early stage companies, like you, you need it. Do you know what I mean? Your resource constraint, it’s helpful to maintain that relationship. It’s good product feedback. Um, but I would say for scaled companies decidedly, no, right. You want those people focused on new logo coverage so that you really have great throughput of new logo velocity.
Scott Barker: Yeah, for sure. I think it’s just, it’s a tough ask, you know, to have someone prospecting, creating the pipeline in the demand, closing it and then cross sell upsell. It’s tough. We specialize for, for a reason. Um, and I think getting away from that is a bit of a disservice and now with technology. Two, you can, yeah, throw in like a GTM engineer in there and they can do the role of like a few sales development folks.
Cassie Young: Sure. Yeah. But I do think like, I mean, just look at the numbers, your go to market efficiency numbers will go out the window, which I mean, if there’s an overemphasis on, you know, managing and install base set, and again, there’s always exceptions, there’s nuance to what I’m saying, highly strategic enterprise logos with obvious additional BU’s, like, there’s a lot of shades of gray of what I mentioned, but in general, I like the new logo.
The AE’s really focused on new logos. Yeah.
Scott Barker: All right. My final question, and I call this one, the, the silver bullet question, I think, uh, your turnaround story outlined in a, in a great way, how there is no silver bullets, you know, you win the war by doing, you know, a ton of tiny little, you know, battles, but, um. The question is what is one go to market tactic or strategy that you’re seeing right now that is working, uh, across the different portfolio companies that you’re working
A fantastic multi-media mail campaign
Cassie Young: So this is a fascinating one and I actually used it when I was an operator and AI has just made it infinitely more scalable, which is video mailers. Right? So we did video mailers and sailed through a kind of an ABM basis, right? Where, um, you know, we were trying to break into bed, bath and beyond R. I. P.
right? For 1 example, right? And, you know, we, um, we would sort of do these kill campaigns where. Our two biggest competitors were Oracle Marketing Cloud and Salesforce Marketing Cloud. So we would do these videos that were really hitting home the points of how we were differentiated against some of the pain points of those solutions.
And so we would send a piece of mail where when the person opened it up, it was a pre roll video of me. Right. And so one day, Scott, I had to stand in a room and say, hi, Scott. Hi, Max. Hi, Jason. Hi, Molly. Right. And then the rest of it built out now with AI, right? It’s way more compelling, but we have a number of businesses, particularly companies that sell into SMBs.
It’s a great way to get their attention. I always only thought about it for ABM because it wasn’t cheap. I think those mailers in total, all in cost was like 50 bucks a mailer. Really amortize all the expense of it now. I haven’t looked at it recently, but I’m sure the costs have come materially down, but, you know, we, we know people who are doing it with dentists, right?
And other sorts of S and B type businesses. And it’s a great, just different way to capture someone’s attention.
Scott Barker: I like that particularly with you, you mentioned dentists. I could see that working really, really well. And like these verticals that just haven’t, haven’t seen anything like
Cassie Young: And there’s so much like the direct mail stuff, like I remember someone telling you this story of like the early days of ZocDoc. I don’t know if this is like urban legend or accurate, but to get doctor’s offices attention, they would send direct mailers and x-ray envelopes. There’s so many of these hacks in the go to market world.
Yeah, totally.
Scott Barker: I love that. That’s, that’s probably my favorite thing still to this day about go-to-market. It’s just those little creative things that you, you test and you try and you’re like, wow, that just 50 XR response, right. You know, with just these tiny little things that you can optimize. Um, and so how folks could action that.
You know, there’s a million and one AI video platforms. So you don’t have to say, Hey, Barbara. Hey, Joanne anymore. You can kind of just set up your talk track. It will customize it for you. And then you’re physically sending, um, an actual like video
Cassie Young: little kid that had studies and stuff like that. Yeah. But it actually was a little artifact with a bunch about the brand and case studies. And when you load it up, it has a play button on it. When you hit play, my face appeared. Right.
Scott Barker: I love that. There’s probably even like, yes, you could schedule now on, there’s probably like a QR code with the calendar. Yeah, all the things. I love that. Hyper, hyper tactical. Well, Cassie, thank you so much for the time. It was a blast as always. And always a pleasure.
Appreciate you. And I know you’re just coming off a 4-hour portfolio review. So I hope you don’t have a meeting right after this. I’m praying your calendar is a little less chaotic after this, but I appreciate you, and to our listeners,I say it every week, but listening is one thing, executing something totally different.
Hopefully we gave you some ideas, tactics, strategies that you can bring into your own business and we’ll see you all next week.
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