Designing The Post-Sale Customer Journey With Gainsight's Caitlin Quinlan

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This is a podcast episode titled, Designing The Post-Sale Customer Journey With Gainsight's Caitlin Quinlan. The summary for this episode is: <p><span style="background-color: transparent; color: rgb(0, 0, 0);">While everything in sales and marketing funnels is measured and instrumented to ridiculous levels of detail, it's easy to forget about the post-sale customer journey. That's where </span><span style="color: rgb(0, 0, 0);">Customer Success Operations teams come in.</span></p><p><br></p><p><span style="background-color: transparent; color: rgb(0, 0, 0);">CS Ops hasn’t always received the same amount of time and attention that Marketing Ops and Sales Ops have, but it’s making its presence known now.</span></p><p><br></p><p><span style="color: rgb(0, 0, 0);">Our guest on this episode, Caitlin Quinlan, is the Senior Vice President of Revenue Operations at Gainsight, and she has helped design every aspect of that customer journey</span><span style="color: rgb(0, 0, 0); background-color: transparent;"> from post-sale responsibilities and hand-offs to retention forecasting. In our conversation, Caitlin and I talk about the evolution of CS Ops, the way she debunks myths about Sales and CS compensation, and she outlines the 2x2 grid that Gainsight uses to segment its customer base.</span></p><p><br></p><p><span style="color: rgb(3, 28, 51);">Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp; review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts</span></p>

Sean Lane: Hey everyone. Welcome to Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. Stop me if you've heard this one before, a hyper- growth company is laser focused on acquiring new customers, their growth rates, their bookings, everything in the sales and marketing funnel is measured and instrumented to ridiculous levels of detail. People are arguing over multi- touch attribution models and win rates. And then, you get to the customer part of the customer journey and it's a barren wasteland, devoid of any types of measurements or metrics. This story, while still common, is actually starting to disappear, and the reason for that is the rise of customer success operations teams. CS ops hasn't always received the same amount of time and attention that marketing ops and sales ops have, but it's making its presence known now. Everything from post- sale roles and responsibilities, to customer handoffs, to retention forecasting, are living in this critical function. I wanted to talk to someone who is living and breathing this evolution every day, and I found that someone in Caitlin Quinlan. Caitlin is the Senior Vice President of Revenue Operations at Gainsight, the customer success platform. Who better to talk to about CS ops than someone who is both responsible for CS ops and her company exclusively works with CS teams every single day? In our conversation, Caitlin and I talk about the evolution of CS ops, the way she debunks myths about sales and CS compensation, and the two- by- two grid that Gainsight uses to segment its customer base. By the way, you should just outright steal that grid, when we get to that part of the episode. Let's start though with the emergence of CS ops and how Caitlin has positioned that function within her own larger RevOps group at Gainsight.

Caitlin Quinlan: I've been doing ops for about 10 years, and in that time, I laugh because my title has gone from plain operations to sales operations, to business operations, to sales strategy, and then RevOps for pre- sales, and now RevOps for the entire go- to- market. And specifically, in CS and customer success, we've seen it rapidly develop over the last few years in tech, as these new teams emerged to address a newer part of the post- sales motion, which is related to a business model where a customer can leave you at every turn, versus staying in your install base forever. And so, as we've seen that role expand, there's also a mandate to ensure that you have the entire customer journey tied together. So, for a client that is helped before they come into the sales cycle, shout out to Drift because that's something that you guys all enable, helped during a sales cycle, and then helped after the time you become a customer. And from an ops perspective, there's a greater importance of tying every strategic decision you make in your go- to- market together with your peers. So, early funnel all the way through renewal. And if the customer journey doesn't paint the picture for you, another way that I personally like to look at it, because it's tangible to me as a math person, is you think about fast growing companies. Very quickly, your renewable client base is two, three, five times your incremental sales booking. So, it's definitely something of focus.

Sean Lane: Yeah. That inflection point, when you hit that as a company where all of a sudden you have more renewals and more upgrade and expansion, than what you're bringing in from new business, that's the moment. And oftentimes, people realize that too late to say," Oh, we have to change the way we think about this." So, I'm curious with that 50, 000 foot view in mind, how do you set up your CS ops team at Gainsight, in order to address all the different parts of the customer journey that you just mentioned? Is there a dedicated function for CS ops? How do you staff that?

Caitlin Quinlan: Yep. So, my team for operations is across the go- to- market and I resource CS ops and the company resources CS ops, the same way you would sales ops, for instance, it's not a part- time thing, which is something people sometimes think. And it's analytics, enablement, process and systems, just like sales. And so my rev ops org, is centralized and reports into the CEO and I have designated teammates whose titles reflect the leadership team that they most often partner with. So, for example, customer success, analytics and strategy. So, that is intended because planning for CS now is just as robust as planning for sales.

Sean Lane: CS ops is not a part- time thing. If you take nothing else from this episode, take that, CS ops is not a part- time thing. Caitlin talks about her team being responsible for tying every strategic go- to- market decision you make, together. And that's really where I wanted to dig in with her, the place where I often see tying those decisions together, fail, is at any handoffs in the customer journey. Handoffs create friction, they create gray areas for who does what, they create opportunities for things to fall through the cracks. So, how does Caitlin and her team design that journey to avoid all those pitfalls? For her, it all comes back to what she calls operationalizing outcomes.

Caitlin Quinlan: So for us, the priority is first, how do we operationalize the outcome that that client wants? And tying that through each a part of the customer journey, is what makes it smooth for each of those handoffs. To go back a little bit, it starts with the client's goals at the beginning of the sales process and obtaining them through qualification, and then making sure that when you get to close, those goals are clearly articulated and can be realized by the professional services team as they implement and onboard your customer. And then, as the CSM gets involved, they know clearly what outcome they're driving, that the client wants to see, we call these verified outcomes. Those verified outcomes are put into the health score of the customer, so we can tell how that process is going and it also helps us forecast and plan expansion, something that we would use for customer success segmentation.

Sean Lane: Got it. And so, if you're going to use that to segment your customers, can you tell me a little bit about what that means? How do you take those verified outcomes and then use that to segment the customer base? What does that mean?

Caitlin Quinlan: Yeah. So, ex- consultants or current consultants will love this. We actually, our segmentation uses a two- by- two grid. So, this is how we prioritize focus of the CS team with our client base. The horizontal axis is about white space, expansion and potential, and this is based on what additional products that might be relevant to that client and what their current usage of entitlements that they've already purchased is. Along the vertical axis, we plot that health score. And so, that includes the verified outcomes and it also takes into consideration the average deployment. So, are customers assigning and consuming all the license they were entitled to? And adoption scores, are the users using the software in a healthy way?

Sean Lane: Got it. So, I'm literally drawing the quadrants over here as you're talking about that. And so, inside of the health score, on that vertical axis, there's the adoption that you're talking about. Right? And then, also those outcomes, how does that work? Are all of those things playing an equal part in that health score? If I wanted to do something similar at my company, how should I think about those different components you mentioned?

Caitlin Quinlan: Yeah. I'm glad you phrased it that way because you really should think what works for your company. So, certain elements will weigh more heavily, but that is in part designing the health score for your customer. So, once you have that, the health score itself is the same across the axis.

Sean Lane: Okay. Got it.

Caitlin Quinlan: So with that, the goal is really maximize the potential for expansion. Of course, at the end of the day, that's a goal for CS. And then, also make sure that we're serving our clients in the way that they want to be served. So, not pushing on anybody where it may not make sense. So, when grid ends up... So, as you're drawing it in your head, that upper right is the expanding customers, very high priority. The lower right, they have lower health scores, but lots of white space, that would be a second high priority. And then, you have your upper left is following that. And then, lower left has the lowest likelihood to expand. In some cases, there's lower touch there and we may have CSMs for instance, owning the renewals, instead of sales.

Sean Lane: If you caught that at the end, Caitlin's team is actually making staffing decisions based on which quadrant the customers fall into. This can be such a powerful exercise for you to do within your own customer base. If you weren't drawing the two- by- two grid along with me, that was white space potential along the horizontal axis and health or adoption score along the vertical axis. Does your team have something like this? Can you start with a rudimentary version and then evolve it from there? Okay. So, let's say you build this grid and let's see even be generous and say you nail it, the double- edged sword of working in hypergrowth is that your perfect grid likely isn't going to be perfect for long. The product changes. The ideal customer profile changes. Definitions about what healthy even means changes. How have Caitlin and her team kept up with these types of changes at Gainsight?

Caitlin Quinlan: One key part is as we go through the segmentation for CS, there is a necessary step of coordinating with sales. So, aligning what sales' belief about expansion and health of the customer is with CS, and that really helps triangulate where somebody should end up. And that has been a step that has come in over time, where teams maybe felt more separate and then definitely feel more aligned, which has helped a lot.

Sean Lane: One more tactical question I have about that, and sales is going to sell the dream, right? Of what's possible with Gainsight, and what's possible with Gainsight has grown and continues to become even more elaborate. And then, how you actually make that dream a reality post- sale, is a whole different type of challenge. In those handoffs that you were talking about, is there something specific that you guys have put in place or something that you've learned, that actually makes the handoff of those goals and those verified outcomes, a little bit more of a reliable type handoff?

Caitlin Quinlan: It's very tactical. When you think about a qualification framework in sales, for instance, we use MEDDIC, those metrics and decision criteria and compelling events, what you input there, we've tied it to those outcomes that the CS team is focused on. And that is really making sure that that documentation is clear and has common language and can flow through each part of the process. It sounds very straightforward, but you would be surprised how many companies don't share any information, so the customer has a brand new experience and you know what that feels like when you buy something and somebody else asks you," Okay, now that you've bought it, let's talk about what your goals are." That makes no sense. Somebody has just talked to you about what your goals are for the last sales cycle. So, very clear documentation.

Sean Lane: I couldn't agree more. If you find yourself or your CSM team going through a rediscovery process, that is a brutal customer experience, right? And so much of what I think the handoffs between sales ops and CS ops is, is making sure that that information is making it over, and I really liked the point you made about common language there as well. So, when we're doing these handoffs, one of the things that always comes up in the sales to CS world is, what is the behavior that is motivating the folks that are doing this work? And so, that takes us into this world of compensation and so, I'm curious, how do you think about compensating the teams post- sale, to drive some of the behaviors that you've told me are important?

Caitlin Quinlan: Yeah. So generally on comp, I always have two rules, no matter what the team is, who I'm working with, the simpler, the better and presentation matters. So, those are my guideposts to start. When you look specifically at post- sales, I think one thing to call out that's important is the variable is typically less than 50%, which is often what it is for sales. So, you want to make sure that what you're tying to that variable yields a percent payout that is motivating and not too small. If you're getting into four or five, six decimal places, maybe it doesn't make sense. The other thing to keep in mind that I think is important is drive behaviors to the outcome you want, not necessarily just the lagging metrics that are tied to a particular plan. And for CS, we're seeing typically the primary quotas being gross retention rate, so no expansion. Net retention rate, so with expansion and in- period lands and expansion, or what we're seeing increasingly is net dollar retention, which is something growing out of the SaaS world to measure success. And specifically, that's looking at the beginning period customers and calculates the ratio of dollars in that pool of customers without the new ones, and then what they spend over the time till the end of the period.

Sean Lane: Before we go too much further into comp, I want to pause for a quick second and talk about some of the terms that Caitlin just brought up, because there's actually a pretty wide variety of churn and retention terms that get floated around, all with slightly different definitions. So, let's just go with the ones that Caitlin raised. Gross retention rate versus net retention rate. Gross retention, as Caitlin points out, refers to the amount of dollars you retain from your customer base in a certain period of time, excluding expansion. So, if you start with a bunch of customers that pay you$ 100 and those same customers contract by$ 10 and are now paying you$ 90, your gross retention rate is 90%. But let's take those same$ 100 worth of customers and that$ 10 worth of contractions, but now you have$ 20 worth of upgrades or expansion, your net retention rate would be 110%. In my opinion, I think it's really important to pay attention to both gross retention and net retention because good net can hide bad gross. As Caitlin mentions, these measures are becoming more and more popular in customer success compensation plans. So, let's go a little bit deeper on those plans. First, most SaaS companies have their sales plans at 50% salary and 50% variable. That 50% variable is generally too high for a customer success compensation plan. So, I wanted to ask Caitlin if there was a percentage or a benchmark that she typically recommends that people use for their CS team plans, that's still meaningful enough to drive the right type of behavior?

Caitlin Quinlan: I would caveat that I think it depends on the maturity of your customer success team and org and what their mandate is. So, what are their goals? But I think between 25 and 30% is pretty typical.

Sean Lane: Got it. Okay. And then, you mentioned the different retention metrics, right? And a lot of times the net dollar retention and gross renewal retention that you mentioned, those are going to be outputs, right? So, I'm curious, how do you think about the inputs for the team, to make sure that what they're doing is actually leading to solid net dollar retention?

Caitlin Quinlan: Yeah. So, another component we use, that is something that we believe drives the behavior to get to that end result that we're hoping, or that net outcome that we're hoping for, is the verified outcomes. So, this is this client successfully achieving a goal that they've set out related to this purchase. And so, there are several leading indicators. This is the one that we like to focus on. So, for Gainsight, a verified outcome for a client might be getting a better efficiency or improving their retention rate, or their expansion with their customers. It's sometimes difficult because we are a CS company with CSM selling to CSM. So, it might be to meta of an example, maybe a non- tech example would be, like if the client was Peloton, the exercise bike, and it would be a coach from Peloton that was working with a particular user to exercise a number of times a week or get to a specific goal weight, or something like that.

Sean Lane: Got it. One thing that I would feel like operationally would be challenging about verified outcomes is knowing that your customer actually hit their outcome. And so, you've done all the work upfront to capture in MEDDIC what their goals are. You know what metrics you're trying to move. You know what the outcome is. How do you know, at the end of the day, if that outcome actually came true?

Caitlin Quinlan: Yeah. That is part of, in my opinion, the CS role, to make sure they're staying engaged and one way to do that would be staying on a regular cadence. So, when you have executive business reviews, tying everything back to those strategic goals, and if you think about an individual contributor and you think about a company, a company has a strategic plan, that person has specific goals. So, setting up your regular check- in with them and putting their goals at the center of that, is something that they're going to be interested in. So, it can be very straight forward. You'd be surprised, if you ask somebody about the thing they care about the most, they will tell you a lot about that and they will want you to help them work towards that goal.

Sean Lane: And I would imagine, you're incentivizing the right behavior in terms of understanding those outcomes about your customer, because if I'm a CSM and I'm comped on these verified outcomes, I'm much more likely to put those outcomes and those goals where I need to in our systems of record, in order to make sure that my comp is impacted positively by that, right? There's definitely a incentive component to this as well.

Caitlin Quinlan: Exactly. Exactly.

Sean Lane: Got it.

Caitlin Quinlan: That's right.

Sean Lane: Got it. So, we've talked a lot about the different roles that are both pre and post- sale and how you've set up this, both the handoffs, but also the design. One of the things that I've seen pop up in the past is that depending on the relationship and transparency between these teams, if I'm an AM, I might question the motivations of a CSM. Or if I'm a CSM, I might question the motivations of an AE. And people can make jumps and say," Look, I know this person is doing this because I know what's in their comp plan and they're only doing this because they're getting paid on this, or they're not doing this because they're not getting paid on this." Is that something that you've found and is there a way for us to address that within our different go- to- market teams?

Caitlin Quinlan: Yeah. It is a common misconception that comes up, that people are working towards different goals. I think a lot of ops people would agree with me on that, and I think it comes from the fact that comp is confidential. I believe it's super important to keep it that way. I don't want anyone sharing other people's comp, but it can make for some gaps and understanding. So, what we do and plan to do, is set up sessions with sales and CS separately, that explain at a high level what the other team's incentives are. The goal here is to ensure that CS and sales feel like they have a mutual plan and a mutual goal, because at the end of the day, your best advocates for new prospects are happy, healthy clients. So, they really are aligned.

Sean Lane: That's a brilliant idea because I think ultimately, you're not sharing the confidential parts that you mentioned, right? Which I completely agree with you is important to keep confidential, but at the same time you are debunking any of the myths that are out there. I think I would say, that ops people would see this as well. You see these myths pop up and they take hold within teams. And so, addressing them upfront and being transparent about it can basically avoid a whole bunch of that swirl later on, about what one team is doing for one reason or another. Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?

Caitlin Quinlan: I would have to say that if NPR was a book, it would just always be the top of the list. But I am currently reading A Promised Land by Barack Obama, which I am enjoying.

Sean Lane: Nice. I think I'm 400- ish pages in. It's a lot, but it's super interesting and I'm always surprised by how transparent he is about what happened and the people that he met with, which is interesting. Favorite part about working in ops?

Caitlin Quinlan: When somebody really sees and hears the analytics trend that you are sharing with them. You might have to say it a few times but when you see their face change from," I hear you," to," I get it." I think that's the best part.

Sean Lane: Least favorite part about working in ops?

Caitlin Quinlan: When somebody asks me and myself to change something as an admin to Salesforce, because they've clearly missed what my role is. I don't even have admin access rights anymore. My team made me take it away like five years ago.

Sean Lane: Oh, that is brilliant. I need to do that same thing. That's such a good idea. Someone who impacted you getting the job you have today?

Caitlin Quinlan: Yeah. Two people who have been very influential to me and have been very helpful to me, Adrienne Germain and Subar Samian.

Sean Lane: Cool. Last one, one piece of advice for people who want to have your job someday?

Caitlin Quinlan: I would say, lean into learning about sales, marketing, and CS because the ability to work and appreciate and understand those functions and the leaders that you're partnering with closely, that appreciation makes for a stronger alliance and relationship with those leaders. And you can serve them better as a strategic advisor than somebody who's just tooling around and helping them create a dashboard.

Sean Lane: Thank you so much to Caitlin Quinlan for joining us on this week's episode of Operations, special shout out to DC for introducing us. Thanks so much for the intro, DC. If you liked what you heard on this week's episode, please, please, please make sure you're subscribed, so a new episode comes into your feed every other Friday. And if you took something away from this episode, you liked what you heard from Caitlin, make sure you leave us a six star review on Apple Podcasts or wherever you get your podcasts. Six star reviews only. All right, that's going to do it for me. Thank you so much for listening. We'll see you next time.


While everything in sales and marketing funnels is measured and instrumented to ridiculous levels of detail, it's easy to forget about the post-sale customer journey. That's where Customer Success Operations teams come in.

CS Ops hasn’t always received the same amount of time and attention that Marketing Ops and Sales Ops have, but it’s making its presence known now.

Our guest on this episode, Caitlin Quinlan, is the Senior Vice President of Revenue Operations at Gainsight, and she has helped design every aspect of that customer journey from post-sale responsibilities and hand-offs to retention forecasting. In our conversation, Caitlin and I talk about the evolution of CS Ops, the way she debunks myths about Sales and CS compensation, and she outlines the 2x2 grid that Gainsight uses to segment its customer base.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️  review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts