How L&D can drive business impact with Cassie Young, General Partner at Primary Venture Partners

Dan: Welcome to L&D in 20, your go to resource for all things workplace learning brought to you by Go1. I'm your host, Dan Haywood, Chief Customer Officer and industry veteran. Today we're going to be speaking with Cassie Young. She's a general partner at Primary Venture Partners. That's the world's largest early-stage VC firm with a billion dollars in assets under management right now.

Before joining Primary, Cassie was the Chief Customer Officer and Commercial Officer for Marigold, a role that she assumed when Marigold acquired SailThrough, where she was their Chief Revenue Officer. She's passionate about advancing women in the executive suite and in 2023 launched a series called ‘On the Business’ to help C Suite and VP level women in software level up their P&L fluency and boardroom skills, and that's served over 500 women to date.

So welcome Cassie.

Cassie: Thanks for having me, Dan. I'm excited to be here.

Dan: Yeah, super great to have you here. And so what I'm really excited about is kind of the flavor of our topic today. And I know it's one that, you know, the team of L&D professionals kind of are often fighting with or tackling. And that really is like the role of L&D in driving kind of both top line and bottom line for the business they work for and also delivering for their customers.

So, the first question I'd like to ask you is, I know you've got some, really interesting kind of experience here and some views. So, tell me a little bit about how you see L&D's role in driving revenue.

Cassie: Absolutely. So I always like to paint this visual of any organization of a Venn diagram with three key stakeholders, right?

And the three key stakeholders are the company itself and the needs of the company. The needs of the employees and then the needs of the customers, right? And so, the intersection of those three things is really small, but when you're in that intersection, it's really powerful. And the reason I paint that visual is because I actually see L&D being the tip of the spear of what sits in between those three things, right?

Because, you know, as you and I were talking in preparation for this podcast, I said to you, I think people often forget that the number one way to drive enterprise value is to drive customer value and you drive customer value right by enabling your team to be able to help your customers achieve their business objectives and outcomes.

And if L&D is doing their job correctly, again, they are the ones that make that magic happen and accelerate the rate of learning and people's ability to go and do that.

Dan: Yeah, that's great. And so when you think, about that kind of practically in the workplace, what tactics or strategies have you seen indeed L&D leaders use to, to achieve this?

Cassie: Yeah. So a number of different ones in, in no particular order, so I can run through a few and we can double click on any of them that sound interesting. So, you know, I think the first thing is you need to have a command for your own businesses, P&L, right? The profit and loss or the income statement of what's going on.

So how your business makes money, are they making money? Right. And, you know, one really interesting thing that's going on in the world right now. And I should preface this by saying, I spend most of my time in the B2B software world. So a lot of what I, oh, pine on is going to be, you know, pertinent to that, you know, I was just reviewing sort of average benchmarks for 2024 and across the board, you know, median year over year, ARR growth is down for software companies, median net dollar retention rates are down.

That's important because retention is your cheapest form of growth. And when growth slows. All eyes turn to efficiency, right? And how organizations can get more efficient at what they do. And I bring this up because you said it at the onset L&D helps enable both the top line and the bottom line, right?

So in the top line, they are working with sales. They are working with customer success to help. Hopefully mitigate right decayed growth right on what's happening, but at a minimum they have to be helping with efficiency right and how they help teams to work better or make sure that they're focused on the right tasks at hand, right?

And you know, one of the things I talk a lot about with respect to L&D is I talk a lot in business at large about this risk of the swim lane trap, right? And what I mean by the swim lane trap, it's actually inspired by. You know a phrase that was coined by Patrick Lencioni who wrote books like the five dysfunctions of a team and the advantage And Patrick Lencioni talks about this concept of first team or team number one, right?

And the idea of that is the more senior you become, your first team is your team of peers, not your functional swim lane or your direct report. So, if you're a software CMO, your first team is not the Head of Demand Gen and Head of Brand, it's the CTO, the CFO, right? And all the people who sit around the executive table.

And the reason I give that, that primer is, swim lane is when you celebrate what's happening in your second team, irrespective of what's happening in the business at large, right? So the example I always like to give with this is I once sat in a board meeting where a CMO was celebrating the fact that quarter over quarter.

The number of closed won deals that were sourced by marketing had doubled, but what you wouldn't have seen on that board slide was the fact that this business had shrunk. Okay. And this guy is celebrating this fit. And so to bring it back to L&D, I think one trap you see a lot of is people talking about, well, we launched this many training programs and this was the completion rate and this is the frequency of using the content.

But if the business hit, is it hitting its goals? None of that matters, right? And so it's this alignment to how do we accelerate the business's ability to hit revenue plan, to hit margin plan, and how are we measuring every single initiative or activity that we launch to ensure that it goes and does that, right?

And we can go through examples of how you might do that and where I've kind of seen some wins on it, but I think far too often there's swim lane kind of vanity metrics versus, Hey, what, what is it that we did that fundamentally advanced, you know, the business's ability to hit its plan.

Dan: Yeah. And I'd like to, maybe we can dive in there actually.

It's a great, great kind of topic to jump in to. So, if you think about kind of drawing that, that, that line between kind of L&D initiatives and financial impact, kind of what, what advice or, you know, what examples do you have in terms of things that you've seen?

Cassie: Yeah. So I'm going to maybe split track this answer.

So I have lots of examples and I'll take through a few of them. But before I go into the examples, I'll say this, you know, so often businesses are focused on sales training or customer training. And it's, so we're going to educate you on sales process and our med pick methodology and all these things that are.

Incredibly important. Far fewer organizations educate people on a P&L or what I call customer value chain, right? At the end of the day, your way to drive customer value is to make sure that your champion right in your customer account can get promoted, right? So. What are they trying to do? Who's codifying the business drivers of your customer and leading a strategy education on that.

Right. And so I think point number one is actually understanding the brass tacks of how your customers make money and how your business makes money. And even if we think about your business, you know, if you think about something as, as simple as, well, you know, our sales playbook is we want everybody to sign, you know, annual contracts paid up front in advance, right.

And it's just like, that's the way it is. Well, why is it that way? Well, the reason for that, right, as we both know is because if you collect all that cash up front, it gives working capital to the business. That's not always described. And so one thing I always say to L&D people are like, buddy up with your CFO, right, kind of help explain the context of what's going on in your business and then bring customers in to talk to the team around how they make money in their business, right?

Because if you're not fluent in that language. You're not going anywhere. But if we think about specific examples to a business, I always talk about this, this framework, and I don't have a very sophisticated name for what I call it. I call it my sticky drivers framework. And the whole idea of the sticky drivers framework is, what are the activities in a business that accelerate key metrics?

So let's, let's pick on an example. Let's say that we want to study what customer traits or behaviours drive materially higher net dollar retention rates, right? That is an analysis that should be run. And when we identify what those activities are, and we'll go through some examples. The enablement team should be focused on accelerating those activities, right?

So for instance, when I was at SailThrough, uh, and this is a pre COVID era, right, we ran these really big live training days. We called them StoneThrough Academy and we ran them in our various key markets. And, you know, these were full day kind of hands on keyboard training sessions where you walked away with new use cases of the product.

And we ran a regression analysis that ultimately showed us that customers who attended a live training day were 31% more likely to renew than customers who did not, right? And so the name of the game for the enablement team was like, well, how do we get as many people as possible to a training day?

And quite candidly, if we have a churn risk, do we just want to. Suck it up and pay for them to go to one right if we know that it's that much more likely that they're going to renew right and there's countless examples of this you know I could think about it on the product enablement side where you could cut that data for customers who use native integrations right have a net dollar retention rate that's X percent higher than customers who don't.

Well, then how are you leaning in on the product enablement right to ensure that customers are following that behaviour? And so I think everything kind of has to come back to this. So what, uh, what you're doing, and even if we pick on like my favorite of all, just good old fashioned sales training, since that's what a lot of L&D orgs do, you know, so often I hear this like, well, we accelerated ramp time, right?

Ramp time isn't sorry. Sure. What's the business impact of that, right? If someone becomes fully, you know, quota carrying in half the time, do the math for people, right? What does that mean in terms of the amount of pipeline generated this year of the incrementality and bookings generated this year? I think, again, it comes back to this.

We get stuck on the vanity metrics of just. Utilization and usage versus really tying it back to what it's doing to the top and bottom lines for the business.

Dan: Yeah, I love that. Really challenging ourselves to think about that connection and you know, in a far more strategic way. I think one of the things that you shared previously that I kind of really, really stood out to me and obviously, you know, and as a Chief Customer Officer, you talked a lot about kind of not only L&D aligning with their own business objectives, but making sure that they understand how they're helping.

Their customers grow their business. Could you share a little bit more about some of the things that you've seen here?

Cassie: Absolutely. And so maybe I'll give like a pragmatic example to try to bring this to life. I talked before about this idea of customer value chain and maybe to back it up. It's actually a fun little story.

So, in my role at primary, I interview a lot of senior leadership candidates for our portfolio companies. And anytime I, um, interview a CCO or a Senior Customer Success leader, I always say there's three core jobs of a customer leader. I'm going to list them out, which I will in a minute. And I want you to stack brain how you do on these, right?

And number one, right, is what I call the procedural, right? And these are things like the account segmentation and QBRs and all the stuff for how you run the business. Number two is the commercial, right? Of how you're going to grow the install base. And number three is customer value chain. And I leave that very vague just to see kind of what bait they take on it.

So let's define a little bit about what I mean by that today. This again is how does your, how does your customer base make money? Now you might say, well, all my customers are totally different. Sure, but I would argue that there's commonalities in different segments. So during my time at SailThrough 70 percent of our customer base was e commerce and retail.

There's a lot of shades of gray, even in e commerce and retail. Like I would tell people we had Fandango as a client on one end and then we had Rent the Runway as another one. And you might say those are two very different businesses, which they are, but at the end of the day, if you look at a consumer online business and really think about what their marketing team is trying to do.

Fundamentally, it comes down to five things. Number one, they're trying to acquire customers cost effectively. Number two, once they do that, they need to get them to buy something for the first time. Number three, they need to get them coming back and buying more and more. Number four is they need them to spend more in every transaction.

And five is you got to mitigate the risk of churn. And so we said, okay, these are now the value drivers of how SailThrough CSMs communicate with their customers. Each one of these five things may not be top priority at any given point in time, but your customer surely is going to care about one of them.

And here are like the 50 different things we can do within each one of those value drivers to help you advance the ball in the business. And so enablement played a huge role in this in saying. How do we collect all the customer stories? How do we educate the sales team that this is the vernacular that we use?

But then when the rubber hits the road in the QBRs in the sales process, it's kind of playing that back to the customer. So you look like a domain expert, right? And you hopefully are. But then you say to them, talk to me about how this translates to the business for you. What's going to be talked about in your performance review next year, right?

What's going to make you look like a superstar. But this is like all the information that has to come back right to the enablement team. And that needs to be a consistent language from pre sales all the way through to post. And I gave an e commerce example, but like. You know, I have a portfolio company that sells into dental practices.

There's a value framework you could make for dental practices, right? Like every sort of different business segment, we could talk about how, you know, they ultimately make money. And that needs to be the language that the employees are fluent in and the businesses supporting them.

Dan: Yeah, that's some great takeaways. Thanks so much.

Cassie: Sure.

Dan: So now we're going to move on to the next segment, which is the 60 second budget breakdown.

So I'd love to hear from you kind of the three most important things that you'd recommend L&D leaders spend their money on.

Cassie: Yeah. So, we are sitting here in February of 2025 and I don't know that I could list anything that's not AI related for teams right now. And so I'm going to rattle off a couple of ideas, but I think there's so many great solutions that are in the market right now.

What I want to harp on is two things. One I already said, like growth rates are down, you have to become more efficient. So every business needs to be fluent in AI and how it can make themselves better for enablement and L&D teams. This is particularly powerful because it allows you to really grow your throughout of the number of artifacts and materials that you can ultimately go and deploy.

I have a little bit of a selfish answer to this question and that I am an investor at primary in an uh, an AI platform for go to market teams called OneMind. And what OneMind is doing is they've actually built, superhuman. So think photo real avatars that can engage like salespeople would, right? In terms of inbound BDRs, ride along solutions engineers, and they're having a ton of interesting use cases with enablement, right?

In terms of helping with ramp time, helping with materials, prep, and thing along things along those lines. But I would say in general, any AI tool that can really help people with the throughput, right, of what they're ultimately able to produce by way of case studies, training programs, et cetera, has to be top of mind for me.

And my bet, just to make a controversial statement for a moment, is that I think with the rise of AI in go to market specifically, you're actually going to see a bunch of really traditional categories totally boxed out. Like if I were a betting woman, I don't think learning management systems necessarily exists in three years, you know, because I think there's going to be so much of this groundswell of agentic, you know, things taking on different parts of the work.

Dan: Yeah. Super interesting. Thank you. So, if you move on to our next segment, Lifelong Learnings, we'd really like to hear from you a time or a situation that turned out differently than you expected. And most importantly, what you learned from that.

Cassie: Yeah, absolutely. So I'll probably talk a little bit about my experience at SailThrough. So I've been a primary for five years now, but was at SailThrough for close to seven years beforehand, both.

Pre and to private equity roll up and post and you know, I joined the company during this period of really wild and rapid growth and we went through a bit of a growing pain where our business grew faster than our technical scalability did and we ended up losing a lot of trust with customers. We suffered really horrendous churn and a blow to net promoter score.

And to be very candid with you in the world of enterprise, right? It takes customers months to churn. That was a reputational overhang for us in the market for probably a good 18 to 24 months. And so, we really had to pivot into turnaround strategy mode. Right. And what I learned during that was just the importance of focus and alignment.

And so just to harp on that a little bit further, focus was we had to have the entire company rallied around the fact that we had to rebuild trust with our customers, right? So the next shiny object of the thing that we could release, sure, it was interesting, but basic stability, giving the customers what they wanted, rebuilding trust that way was hugely important.

What do I mean by alignment? And it's directly related to focus was literally, how do you make every function in the business care about that? So one thing we did, for instance, was we looked at our executive team and we said, every executive, this company is going to have the exact same bonus plan. That is tied to the same three metrics, regardless of whether you're the Chief Product Officer, you're the CRO, right, CFO, whatever the role is. And for us it was exit ARR, net promoter score. Not because I think NPS is the best metric in the world, but because ours was in the toilet, right? And we needed to get it out of there. And then third, and this is interesting going back to our conversation on P&L was a cash burn target.

And once we became cash flow positive, we turned it into an EBITDA target. You haven't seen behaviours change until you've seen what happens when you have a product leader where a third of his bonus is being dictated by net promoter score, right? So, it was just this really interesting learning for me around just supreme alignment and alignment of incentives to help people get there.

Dan: Thanks for sharing. Thank you.

Cassie: Absolutely.

Dan: So now we're going to move on to our final segment. Self development hacks.

And so for me, I really love this section. So keen to ask all, I guess, what is your favorite self-development hack, learning resource? Where do you go to grow?

Cassie: Take your CFO to lunch. This is my number one piece of advice for people. You know, we talked about the importance of P&L here, and a lot of people will say, well, I never took a class in this, right?

There's lots of stuff you can read online for it. But the number one way to understand it in your business is ask. Someone on the finance team, it doesn't need to be the CFO to go to lunch, right? And say, help me understand how my work directly connects the top and the bottom line. What is our board asking you about?

And my joke on this, and I, I've litmus tested this with many finance professionals. No one's asking the finance team to go to lunch, right? So they're guaranteed to accept the invitation. And I think it's a great way to just really understand the financial metrics that matter for your business that then allow you to build a more compelling case for the projects that you're working on.

Dan: Cassie, thank you so much for coming on the show today and sharing all your insights with us.

Cassie: And thanks again for having me. It was a blast.

Dan: Thanks for tuning into the show. I'm Dan Hayward, Chief Customer Officer, and that wraps up another episode of L&D in 20. We hope you found today's discussion as engaging as we did.

Whether you're listening on the go or at your desk, we'll catch you on the next episode, and until then, keep learning.