Taylor: [00:00:00] Welcome to Successful, where we break down the essential elements of leading Customer Success strategies. This podcast is all about uncovering blind spots, pushing beyond typical best practices, and tackling those out-of-bound topics for CS leaders that are key to our success. So if you're a CS professional seeking to innovate and adapt in an ever-changing landscape, join us on this journey to be more successful.

I'm your host, Taylor Johnston, VP of Customer Success at Vitally. Earlier, I sat down with Monique McDonough. She is the Chief Operating Officer at WorkTango and is an expert on building and growing high-performing teams. We talked about how to empower CSMs, hone their skills, and put autonomy back in their hands. I learned a lot from Monique, so let's dive in.

Monique, welcome. Thank you so much for spending time with us today. You have a really unique role. Tell us a little bit about [00:01:00] yourself and your work at WorkTango.

Monique: Thank you, Taylor. And thank you for having me here. This is really exciting to be here. Yes, Monique McDonough. I'm the Chief Operating Officer here at WorkTango. We're an employee experience company, so focused on HR technology. I've been here for about three years. We're a high-growth company, which means that roles oftentimes ebb and flow. As you kind of move through your journey… When I started, Customer Success was the biggest component of my job, but I also had partnerships, revenue operations, and people in culture, which has been very cool having people in culture at an HR tech company.

So I can see our product from both sides as a Customer Success organization and also as a customer. And over time I've picked up sales within the organization and I also oversee opportunities to move customers to better-fit products for them.

Taylor: In today's conversation, we're going to be talking a little bit about CS leaders and any of those folks who want to lean into that business, that revenue side more, and how they can empower their team to really help customers get better at their craft. And I have [00:02:00] always known that you've had this just ability to take on different challenges and really run towards the opportunities regardless of background or specific role fit. So, you know, we don't see it right now, we will more in the future, a lot of folks in the C suite, particularly in the COO role or the CEO role, that have that specific Customer Success background. So I'd love to hear how you feel like having that customer background has helped influence or, you know, made you successful in your current role.

Monique: Well, yeah, I mean, it's absolutely imperative that you understand what the customer experience is like and what they value, right? The vast majority of an organization's revenue is going to come from its existing customer base, not the acquisition of new customers. It's important, but it's probably not the primary driver for most organizations.  And so having a foundation to understand what's important to customers, how to help them understand the impact of what you're helping them do and deliver, what that has on an organization [00:03:00] is critical. And, you know, one of the things about my role here that's so important is at an HR tech company when you have people in culture reporting up to you and you see the world from a customer's perspective, it helps you understand how to architect a better customer experience. So, being able to see and have a passion for the customers and a mission to help them be successful. That's been hugely helpful in our growth strategy and thinking about how we can do more to help customers succeed.

Taylor: That's amazing. Well, I know you've mentioned you've been in the role for three years, and about two years ago, you talked about how WorkTango decided to go through a strategic shift where commercial responsibility, so that revenue side, was assigned to both the CSMs and the account representatives. So, can you tell us the rationale behind the move and what the intended results are?

Monique: One of the things that we found was that our retention rates, while good, weren't necessarily improving. And when we unpacked where our CSMs and our account [00:04:00] reps were spending their time, it was on lower impact work. What I mean by that is that they were helping our HR administrators or kind end users in navigating the platform on day-to-day tasks and not necessarily on the higher impact work that allows people to understand how are we helping them achieve their business objectives, what's the impact of the program on their business, what are the critical pieces that are going to give an ROI on the investment.

And so, that disconnect between the work that they were doing, which is really important work, but wasn't aligned to renewal conversations and strong real outcomes. That's what we saw in the disconnect in how we were going to market. So, we made an intentional shift to align CSM and account reps' work to the outcomes that we needed in the business, which was a focus on retention.

Taylor: Yep, we're hearing it all over the place. So you are certainly ahead of the curve doing this a couple of years ago. I think it really does show the power of, in your role, [00:05:00] having oversight of both the customer side and the sales side of it. I think you were able to make some really interesting observations and changes. So in this shift, what are some of the steps that you've taken? You took that move towards this new kind of structure. How did you modify the usual process?

Monique: Yeah, so it's a couple of things. So we had to modify not just the process, but actually the work that the CSMs and account reps were doing. So, we started by looking at the customer journey and trying to architect high-impact moments where we could influence perceptions, program results, and outcomes. And so one of those really important areas was focusing on quarterly business reviews where we talked not about feature and function adoption of the platform, but actually, what were the business results that were happening. We had to train our CSMs and our account reps on how to have those more strategic conversations because you can't just pivot overnight.

You have to teach people how to mature their motion and their craft. And so the book of business reviews was a big part of [00:06:00] that. Teaching them how to have renewal conversations, and how to test for renewal disposition, six months out from renewal, and 90 days out from renewal. Teaching them how to have conversations about negotiation and objection handling.

All skills that CSMs and account reps had, they just hadn't been honed. And so when you start from the customer journey, you kind of work backward to see what those high-impact moments and conversations can look like. And then you train your CSMs and your account reps on how to have successful conversations. That work takes a fair amount of time, but it's really important for the outcomes.

Taylor: How did you go about the enablement process?

Monique: That's a great question. It's a journey, right? It didn't happen overnight. So we picked one key area to focus on first. So, the first one was quarterly business reviews, then we focused on program impact, then we focused on the negotiations, the objection handling, and teaching them incrementally on how to be really good at components of it [00:07:00] was really important. 

We also made sure that when we were rolling out support systems, everybody had a view and an understanding of how the role was evolving so that our other teams within Customer Success could support those conversations. So, our support team needed to have a little bit more of a strategic lens in providing more thorough information for our quarterly business reviews. Our implementation management team stretched to become technical project managers to dip into customer relationships post-launch if there were technical needs that were required. So we evolved not just the CSM and account rep responsibilities, but we evolved all of the Customer Success responsibilities because it's an ecosystem that helps you drive to that outcome.

Taylor: That's incredible. That's incredible. It is a team sport.

Monique: Yes, Customer Success is absolutely a team sport.

Taylor: Yep. So both training on new skills, but also recognizing the limit and knowing when an additional resource is really going to move the needle on the [00:08:00] revenue side.

Monique: Absolutely. And, you know, in an ideal world, we'd be able to do everything but, you know, we are realistic about what we need the work today to be like to drive the outcomes of tomorrow. And so making sure that we're setting our CSMs and our account reps up for success is a big component. And we brought in actually our most seasoned seller to align with that business so that we can have the highest potential outcome.

Taylor: This is an interesting shift, moving an experienced new business seller onto the relationship side. How did you navigate that transition?

Monique: So it was actually a pretty easy decision to get to once we kind of put all the pieces together. So we have very strong relationships with our customers, but in some cases, we've been removed from the ultimate kind of decision-maker through the process of serving and supporting them. One of the things that we've noticed is that the person that we're dealing with day to day may not be the person who actually wants to serve. And I think the reason [00:09:00] why it's so important is because there are so many different ways that we can target our customers across multiple platforms. Let's take her, layer her over with the CS organizations, tap into those existing relationships that she has, and help us build deeper relationships with customers who have more products from WorkTango.

And it's been a phenomenal success for us because we've been able to accelerate conversations. She's got such deep product knowledge and really impactful conversations, and she's been able to see WorkTango help customers in multiple ways, so her experience has just been fantastic.

Taylor: Yeah, that's incredible. I love the, you know, crossing over of different skill sets and bringing new perspectives into the [00:10:00] customer and relationship side. That is fantastic.

Monique: It's also a great opportunity tailor for skill development, right? People talk about how career paths, you know, are sometimes perceived as being linear, and that's not the case, right? When you're at a high-growth organization or any organization that's growing rapidly, you have an opportunity to think about creating different in-kind roles that give additional opportunities for different kinds of work, skill building, and deeper relationship penetration. So it's, it's been a win for the success of the organization and for this individual who's selling in a different way.

Taylor: Mm hmm. Monique, we've talked about enablement. So a new CSM or account rep is coming in the door. How do you help them be successful?

Monique: Oh, that's another really good question. CSMs and account reps who come to WorkTango have skills, right? Everybody has a set of experiences that makes them very successful. Our job is to take them from good to great and to help hone their skills to be even better at their job.

That could take a couple of different [00:11:00] fashions. One, our CS leaders spend a lot of time shadowing calls or even joining calls with our CSMs and account reps to understand how they're engaging with customers, how they're presenting the impact and the ROI of the programs that customers have in flight with us, and really thinking about how to drive and advance relationships and opportunities forward.

But it doesn't just stop with the CS leaders. What we try to do is create a team environment where our CSMs are learning, with and from each other. And they're developing together because everybody comes with a little bit of a different perspective. So what we want to do is make sure that there's a lot of collaboration and best practice sharing that happens in real-time across the team and is facilitated in many ways by our CS leaders.

But we want to make sure that they get one percent better every day—WorkTango’s values. Our job as a CS leadership team is to make sure that we give them every opportunity to get better each day with the skills that they have when they come into the organization.

Taylor: I love that. [00:12:00] So, let's talk about something that I'm sure is on everyone's mind with a new model and team set up in a different way. Can you talk to us about the compensation plan setup? I'm curious what the primary focus is and how you've constructed it.

Monique: Yeah. So, the compensation plans have changed over time, and that's intentional because Like I said earlier, this is a journey of moving from an orientation that was very much service-focused to one that is both service and revenue-focused. So, in the first year, we rolled out incentive plans that had a team renewal component to them. So across CSMs and account reps, The full book of business because we wanted to create an environment where our CSMs and account reps were sharing what was working and that they were asking each other for help at times when they were struggling.

So winning as a team sport was really important and we had the renewal component that was initially two years ago as a team goal. What we've been able to move to over time is something that is much more segment-based, and [00:13:00] eventually we'll move to something that is portfolio-based. But we've also created incentives for growth, and growth can come in several different ways.

It can come in terms of price increases on the renewals that you negotiate, so there are kickers for that, including multi-year agreements. So, the more price increases and the longer the contract duration, there's a bigger kind of incentive in place for the individuals who are transacting that business. There's also a growth component, and growth in our world takes two different flavors, upsell and cross-sell. At the time we incented growth, upsell, and cross-sell differently, so there were different targets for each that were aligned with our annual operating plan. We noticed that it created additional complexity that our reps kind of struggled with. In terms of trying to make it easy to understand what the targets were, we actually overcomplicated the plan.

So this year, we have growth plans that include price increase, upsell, and cross-selling all together in one target. And we've empowered our CSMs and our account reps to go after and find growth in whatever way works [00:14:00] for their particular book of business. They have loved having the latitude to go and look at their business strategically and figure out how they're going to achieve their outcomes. That's been really, really incredible.

Taylor: It's incredible. That's incredible. You know, related to this, you know, you talk about portfolio management and I'm curious if you feel like there are other advantages in this shift towards, you know, maybe thinking about account-by-account and instead looking at your entire book of business and saying, all right, I'm going to create a path to growth, as you called it. What other advantages are there that you see for that kind of strategic approach versus individual account by account?

Monique: It's critical, right? Without a more strategic approach to your book of business, what we find is that CSMs and account reps manage their book out of their calendar, meaning they're kind of looking one or two quarters out at the renewals that are in front of them and trying to spend their time shoring up business that's in the line of sight versus the overall health of the [00:15:00] portfolio.

And we have lots of tools that we put in place to help ascertain customer health. But what we want to do is empower them to look at the business and figure out where their time is best spent when they're looking at the overall outcome. So the book of business reviews, which we do quarterly, gives us an opportunity to do just that. And then they can look at their book and say, okay, where do I need to lean in to stabilize? Where do I not? Spend as much time, right, and just kind of put things on a nurture path. Where do I think I have the highest potential for growth? And I want to really lean in there and try to identify the cross-sell potential there. Then in some cases, identify who are those accounts that, quite frankly, we're just never going to win. And so we're going to spend as little time as possible because there is no turning back. And I think that has been really helpful for our CSMs in particular to figure out you can't spend All of your time equally across all accounts.

So how do you spend your time with the accounts that have the highest propensity to grow, or do you have the highest propensity [00:16:00] to be able to move towards a yes at renewal and potentially growth?

Taylor: Such an important lesson. I think it's so easy when you get to your point, a book of 30, 40+ accounts, just reacting to what's coming in the door and living by your calendar. I think too many of us are guilty of that for sure.

Monique: So one other point on that Taylor, which I think is interesting is for our account reps, they have larger books of business, right? So they might have a hundred to 120 accounts in our tech touch world. You might have 250. And so you literally just can't go account by account. So you need to have information and data to help you figure out who's healthy, who's unhealthy, and where I need to spend my time.

Taylor: Yep. You mentioned data. How do you all use data to help the CSMs be more strategic?

Monique: Oh, Taylor, that's such a great question. So, in our support model, we've got a Customer Success team that includes support, it includes an enablement team, and it also includes a technical project management team. So, [00:17:00] we have always-on support for customers if they proactively want to come to us. But when we think about our outreach to customers, we want to use data to identify two big variables. One, where is there risk in the business so that we can intervene earlier? And two, where do we focus on growth opportunities?

So, for those organizations that are using our product with really strong results, we can think about expanding that partnership and time is the most valuable quantity that we have. And so helping our CSMs and our account reps, regardless of the size of their book of business, figure out where their time is best spent to shore up retention or to influence growth is really important.

Taylor: Like we all think there's nothing worse than just a check-in call with a customer. So leveraging data to figure out where you need us, here's where I'm going to come to you because you're signaling to me that something is off or something is great is a super smart way to go about it.

Monique: Right, we should always have a purpose for every [00:18:00] conversation, and check-in is not one of them. So we're either solving a problem or strategizing on an opportunity, but check-ins can be emails. Let's give everybody time back.

Taylor: That's the gold standard, right? Us all having maybe an indicator that tells us directionally which way to go and then layering on top of the expertise of the CSM or the account rep to say, all right, I see this as an opportunity. So, those paired together. Nothing better than that. I do also want to go back a little bit. You mentioned earlier leaning into the business of your customer, and I'd love to hear kind of your thought process on how this idea of helping your customers get better at their craft influences how you think about Customer Success.

Monique: So part of this starts with the onboarding process and asking them, validating what we've heard in the sales process, what it is that you want to achieve enrolling out a program. So, benefits of our program could be improved employee retention or [00:19:00] improved NPS from your employees, improved customer sat—there are lots of ways that you can think about what the program results are, but it's really important that we understand what each customer wants and then architect an experience back from that. So, if you know what your customer needs to deliver, to look good, right? We want to help our customers look good.

We want them to have a good program impact. That orientation allows you to make sure that you're solving the right problem for that customer. Also, it can help us to guide them on best practices, right? Customers who want this outcome typically launch their program in these ways. We can be consultative and help them with as little lift as possible, stand up a program, and put it on autopilot. Then if we're coming back to our quarterly business reviews and we're saying, here's what you told us was really important. Here's what we've done to help you get there. How are we doing? You have an aligned conversation. And so you're part of a team, not part of a vendor-customer [00:20:00] relationship.

Taylor: So important and what we're all striving towards—to understand and articulate back to our customers that you are achieving the results that you set out to achieve with us. I've heard you, you know, even today, Monique, talk so much about this theme of, you know, empowerment. So looking at the business and empowering your organization to make interesting decisions, to move a model in a different direction, empowering the CSMs to really think strategically about their book and chart their own path towards growth. Then also, empower your customers to be able to say, this is why I am here, why I am a customer. Help me get to my objectives. Is there anything else on this thread of empowerment that you wanna share?

Monique: Look, at the end of the day, our CSMs, our account reps, our folks in support, our folks on the implementation team, right, they talk to customers all day long, and it's important that you find ways to synthesize that feedback and that input to make sure that you're making the right decisions. So, if somebody in support [00:21:00] identifies a problem or a theme, it's okay.

Take that data, work with the product team, stand up a fix, and just go ahead and make that work and just help them to see not just the individual issue that they're seeing, but collectively all of the feedback that we're getting from customers. Let's make sure that we're solving the right problem, but go ahead and fix it.

You know what's best. So, really thinking about individual contributors and especially frontline managers owning the problems and finding ways to resolve that. One of the things that I found incredibly helpful and is really important for any CS leader is to make sure that you are listening to calls actively, and that you're actively conducting calls with customers so that you have a real sense of what it's like on the front lines and working with customers. To help identify issues proactively as a leader, you can surface or identify issues, but working with your teams to solve them is the important part, right? I can bring lots of ideas, but at the end of the day, they're the ones [00:22:00] who are going to know what will work and what won't work for the given situation.

Taylor: I love that. Going straight to the front lines, they have the hardest job and a great job and we can support them even better every day just by joining some of those calls and listening in and being a part of it. Yes. Monique, this has been fantastic. Thank you so much for sharing your insights. Before we let you go, we'd love to do some quick hits. So I'll jump right in if you're open to it. All right, let's rock and roll. So what do you wish you could spend more time on in life or work?

Monique: Wish I could spend more time taking care of myself, right? Like work comes first, family comes first, me sometimes comes second. And so that always ebbs and flows. I jokingly say I'd love to spend more time sleeping, but I think I'd probably rather spend more time running an extra mile or two during my workouts.

Taylor: Hey, sleeping is great [00:23:00] too. What part of your work life do you wish you could automate?

Monique: Updates. Any kind of readout and updates. We have a lot of it automated, but there's still kind of those insights that you have to put your time together. That takes a little bit more time. I like the creativity of it. I wish I could do it faster.

Taylor: What's one habit or routine you follow that's had a positive impact on your life?

Monique: Regular working out. Right? Finding time a couple of days a week to make sure that you are keeping yourself healthy is really important.

Taylor: Is running your go to?

Monique: Running is the easiest. I love biking, right? And I'm actually a triathlete. So trying to find time to do all three of those swimming, biking, and running while also kind of having the job I have and having a family with the age that they are, it's a little challenging.

Taylor: That's amazing. It's funny, you're actually the second person we've had who was a triathlete. So really a popular one. Thank [00:24:00] you so much for sharing, Monique. Thank you so much for your time. This has been an incredible conversation.

Monique: Oh, thank you so much for having me, Taylor. It's great to connect with you again.

Taylor: A special thanks to all of you who tuned in. If you enjoyed this episode and found value in our conversation, don't forget to spread the word to your Customer Success friends. And before you go, I'd love to hear your thoughts. Find me on LinkedIn at Taylor Johnston, and leave us a rating and review on your favorite podcast platform. Your feedback means the world to us. See you next time.