Building a Business Case for Enablement HeadcountIn this conversation with Devon McDermott, Carissa Thomas, Director of Sales Enablement at Pendo.io, will shares her insights on how to build a business cases for enablement headcount.

And, how to grow an enablement function from a team of one to a team of many–including how she built an enablement center of excellence and prepared her organization for the implementation of a robust enablement ecosystem!

Along with the many brilliant insights from Carissa on how to build your business case for Enablement headcount, she shares how she prepares the organization with the mindset to make hiring conversations much easier.

Are you looking for a place where you can learn to apply Enablement based upon where you work, your challenges, your culture?  Join the Trust Enablement Community to bring best practices and insights to life in your business.

Audio Transcript

Devon McDermott
We are live. So Hello everyone. Welcome to coffee collaboration and enablement the team of one edition, where we talk to and learn from enablers who are currently operating as a team of one and others like our guest today who started as a team of one and came out on the other side. I’m your host, Devon McDermott, former solo enablement practitioner, current member of an incredible enablement crew at PR Sato, and today we are joined by the wonderful caressa Thomas to learn about how to grow and enablement function from a team of one to a team of many. And I want to welcome corissa to coffee collaboration and enablement. Hello.

Carissa Thomas
Hi, Devin, thank you so much for having me. I’m so excited to be here today.

Devon McDermott
We are thrilled that you’re here. I we had the opportunity to catch up before our conversation today. And you are just an enablement all star, I’ll say so I do. I want to get right into it because you have so much to share. So if you wouldn’t mind to get started, tell us a little bit more about you. So your current role, how you got into enablement, all the good stuff in between

Carissa Thomas
sounds great. Um, so yeah, a little bit about me, I am currently a director of enablement with pendo. We have, let’s see, let me think six of us on the team currently, um, honestly, six months ago, we had one on the team. So we’ll get into all the fun of that. I’m I’m based in Raleigh, North Carolina. I’ve been here for about 12 years prior to my current role, I was actually at Red Hat, where I spent several years in enablement and operations. So I spent quite a bit of time in sales ops and kind of landed or ended up in enablement, just through the virtue of you know, figuring out along the way, all of the things that I knew I really enjoyed and that I was, you know, best at and proud most proud of. Prior to that, I of course, spent some time selling and, you know, that’s really what landed me here is, you know, we talked about this a little bit of at one time, but when I was in sales, like all I ever wanted to do was share anything excellent that I found that was happening for me personally, I was like, Oh, my gosh, everybody needs to know how to do this. How can I help everybody else do this as well, you know. And then same thing, like that’s kind of what led me to sales operations. And then just wanted to expand that a little bit further into enablement and all of the things. So yeah, that’s kind of how I got here. Much like anybody who is in enablement, there’s no single path. It’s just kind of like how you get here.

Devon McDermott
It’s like the it calls to you like you’re over here. But what I want to go back, but I love and I love how different all of our backgrounds are, because it really like it shows itself in the way you build programming the way you build your teams. But it’s so cool that there isn’t just like this direct path. And again, like, finds you, so spoiler alert or not, because you did tell us but you’re no longer a team of one rekt. But when you were a team of one, can you tell us a little bit about like, what were some of your core responsibilities when you were a team of one and one? Like, I guess add on question, were you promised headcount when you joined? So let’s go responsibilities and then send the promises that were shared?

Carissa Thomas
Yes, of course. Um, so you know, my core responsibilities were I mean, I don’t know I can’t think of honestly anything that wasn’t my responsibility when it came to enablement. Whether it was onboarding, ongoing training, product releases, product training, skills, training, sales, kickoffs, General communications, running all hands, running all hands for each of the teams individually. You know, working, of course, incredibly cross functionally across the entire organization to just, I used to just call it like a call for content, like, what is going on in this world in this organization? And what does what do my sellers need to know? So it was a little bit of everything, and then also systems management. So I was responsible for managing our CMS or LMS Call Recording tools. We now have an enablement platform as well and then of course, all of the tools training as in addition to that, so yeah, it was it was literally I can’t think of anything that wasn’t included in my responsibilities if I’m being honest. Oh,

Devon McDermott
that is a lot. I’m getting a little like nervous just hearing about it. But um, because the answer may have just answered it. A question may have just answered itself, but what Wouldn’t you consider to be the hardest part about being a team of one beyond being tasked with? A Yeah,

Carissa Thomas
yeah, I mean, the workload in and of itself was definitely a challenge. But at the end of the day, we’re all only one person and we all only ever have 24 hours in a day, and Lord knows we’re not going to spend all of them working. Um, so that was a challenge. But honestly, the hardest part for me, was just not having another person to ideate with to bounce ideas off of to just, like have a person, whether it’s a peer, whether it’s a direct report, whether it’s even, you know, a direct manager at that point, and not having another individual in the entire organization who was doing what I was doing was really, really challenging. It just felt very isolating a lot, you know, like, you’re on this world of you’re in your own, and you’re kind of like, on this island, doing your thing and driving as much as possible forward as you can. But then you’re like, Where’s my buddy? You know, like, Oh, my gosh, I think I have a great idea. Is this a great idea? Or is this not a great idea? I don’t know.

Devon McDermott
But is it? And how do I know? And it’s so true. And something we talked about quite a bit when we connected. And I loved the way you said it, because you just said it right out of the gate. And it was so natural, was building a team without having a dedicated enablement team. So you talked about how you created a team of cross functional partners in your organization? Can you tell me a little bit about how you went about doing that? And sort of like built your little community without having the direct support?

Carissa Thomas
Yeah, exactly. Well, um, definitely, you have to surround yourself with partners, and you know, folks who are really driving a similar agenda to yours, of course, which is enabling the field in some capacity. So I definitely made sure I was focusing really, really heavily on building relationships, understanding the needs of the organization, and what else is going on in the organization, and communicating and I was really, really transparent, especially like with product marketing, and with product operations, like, Hey, I don’t have a team, like you all are my team. So let’s work on this together. And like, teamwork makes the dream work. You know, and I was very fortunate that I had such an amazing group to partner with, even though there was nobody else, you know, directly reporting into enablement. But, you know, it was really like, all hands on deck, regardless of who you’re reporting into, and what you know, functional organization you’re under, we’re all working towards the same common goal, which of course, is to make sure that we’re getting all of this amazing information into the hands and the brains of the sales team and making sure that they know what to do with it so that everybody has a great experience, our customers have a great experience, our sellers have a great experience our CSM have a great experience, like it’s, I say, oftentimes Equal Opportunity enablement for all, you know, like, it’s just, it’s just part of like, I guess, in my DNA, but yeah, I think you know, what makes it, what makes it possible is extending like that team, to your cross functional business partners, and your sales leaders and reps and, you know, anybody in the organization because again, we’re all here to do the right thing, and to make sure that the team is getting what they need, and that they’re supported. And, you know, I think a lot of it just comes with openness and collaboration and transparency. And just like, let’s, let’s face it, you know, like one person cannot do this on their own. So it really does take a village, you know, to help out

Devon McDermott
Yeah, and I love that like uniting, like, we have the same goal. We are here to help each other, amplify each other’s work, make great teams successful. And I think starting there, it’s like you’re building that trust, you’re building this, like unified force, when

Carissa Thomas
Yes, trust for sure. For sure. And like knowing that you can depend on one another and knowing where to pick off up where the other one leaves off, and like how best to work with one another. And even though you know, like, everybody’s an individual. So understanding what other people’s strengths are, that you can really kind of capitalize on and work best together with it’s, it is it’s really about, like building relationships, and just understanding you know, just understanding how people work and how you can help each other.

Devon McDermott
Yep, I love it. It’s so true. And when those groups are divided, and I think I think all of us have probably been in that situation. It makes everything so much harder, and it’s wastes so much time. So it’s like come together make it work be a unified force. So the internal team that you build is amazing, but obviously like, we want to grow the enablement function and so we talked about this too. I A lot of folks will ask me in our, you know, in our enablement world, okay, so what’s the right ratio of sales or CS reps to enablement professionals? Or how do I know it’s time to add more folks on my team? And my answer, which is not you know, terrific is it’s not that cut and dry. And an enablement function needs to be designed to serve your company your business needs, you have an incredible approach to this. So if you could share a little bit with us about your vision for building out your team, when you were a team of one how you knew it was time, like, what were the indicators? And how did you think about that structure?

Carissa Thomas
Yes, totally. Well, I will echo what you just said, like, there is no silver bullet, there’s no ideal ratio, there’s nothing there. It’s It’s so dependent on the business, the organization, the priorities, growth, like just there are so many variables that there’s no possible way you could ever say that, you know, a ratio of X to Y is ideal. So a little bit around my approach and how I, you know, just started thinking about the vision for our enablement team as it was growing was really just like, honestly, every single project I worked on every single program I executed on every single initiative I always was thinking about, well, what if what if it wasn’t just me? How, how in this like wonderful world, would we create some specific roles, some specific responsibilities, and really, like disperse this out? So it really like it was through every retro I did, it was a lot of reflection and a lot of like thinking about the future as well. And really just understanding what is the future of you know, insert whatever organization in my case, pendo? Like, where are we looking to go? Where are we looking to grow? are we focusing on, you know, a really heavy product? Is there a lot of methodology? Are we onboarding like crazy? Like, where? Where do we need the most help? And what would this look like? And how do you build out the vision? So, um, you know, I always like, take a lot of lessons learned, like I said, I do a lot of retrospectives, and think about and, and share with others, like, what worked, what didn’t work? And what are we going to do in the future. And oftentimes, every time, the future was always about, what are we going to do with these additional resources that we know are so imperative for the business. So it was a big, you know, ongoing effort of getting consistent buy in from sales leaders getting buy in from Product Marketing, like, Hey, guys, imagine what it would be like if caressa had another counterpart in enablement, and how much less how much more you would be able to focus on, you know, what you’re really doing and less on, you know, kind of the enablement portion of it, and what that might look like. So it was really just a culmination of a lot of information over a period of time, and then just building out what that ideal future state looked like, again, based on what the priorities are for the business, like, I think that’s so important that we all think about, like, enablement is not just revenue, it’s not just success. It’s not, it’s so much bigger than that, because we’re part of the entire organization. And it’s, it’s just so imperative that we think about it from that lens. And as we’re building out the future, and I ideating and establishing what that vision looks like that it’s really drafting into some of the biggest business initiatives to ensure that we’re aligned. And also, that’s how you get these, you know, headcount approvals in place.

Devon McDermott
Absolutely, and I love how you use those partnerships that you talked about establishing of like, Hey, this is gonna help you this isn’t just like, Oh, caressa gets more people, this is gonna help those challenges that you shared with me when we were building our relationship. We’re gonna we’re gonna we’re gonna solve it together. So I love the setup. And let’s talk about the internal sell. So we talked about, you know, you’re talking to your the team that you’ve built. And I feel like the internal sell to leadership is probably the most challenging piece. So how did you go about selling this vision for headcount and team growth? And who were the folks in your organization that you targeted for that conversation? Or what I imagine were conversations?

Carissa Thomas
Yes. So I definitely went wide here just to ensure that I had, you know, good line of sight from everybody into not only what was going on and enablement at any given time, like what were we What was I working on, but also making sure that everybody had visibility into what we were looking to accomplish and where we were looking to go and grow. So Um, as far as the, you know, like internal sell, it was very multi threaded. It was honestly a really long sales process, in retrospect. But honestly, and I mentioned this a little bit before, every single quarter when I would run through my QB Rs, I would review what we accomplished. I keep saying we because now we are a team. But what I accomplished what we I do say we because it was it was so much more than just me again, you know, like I could never, like, take responsibility for all of the amazing things that happened, even though I happen to be the sole practitioner and enablement. But nevertheless, I’m taking a look at accomplishments, what worked, what didn’t work, and then mapping out what are we doing the next quarter and always, always, always, including additional headcount, like, here’s what we’re looking to accomplish, here’s what I know I can achieve. And here’s what I’m setting out to earn agreeing to do for me as an individual, however, with an additional headcount, this is what this might look like. So using that as kind of the lever to initiate the conversations, but also have that ongoing, so it wasn’t just a one and done. This was, of course, with the executive team with the revenue leadership team, with, you know, everybody there, but it was having these conversations very, very regularly. And consistently, like I think consistency is key. But it was it was a long process for sure.

Devon McDermott
Yeah. And ongoing. Like, I love that you mentioned like, Yeah, we got you’re gonna get this headcount, well, it doesn’t end there. It doesn’t satisfy the needs. There’s so much work to be done. So it’s just it’s an ever growing ever developing process. Yeah. I, I think I commented this too, but like, you are so process oriented, which I love. And I feel like probably most of our fellow enablers are very process oriented. But I imagine it was not perfect, right? So I don’t know that you delivered your business case. And they said, yes, you get five people. What were the objections that you came up against? And how did you manage those?

Carissa Thomas
Yeah, well, you’re right, I am super process oriented, because well, it’s just how we operate efficiently, and how we get things done, and not reinvent the wheel every time. You know, when I look back at it, and like, think about it, I didn’t like come out of the gate with the big grandiose, you know, business plan or business case around headcount. It was very organic, but I did follow a process. And in doing so that’s really what allowed me to work as a team of one for as long as I did. Um, and it’s honestly, like, it’s a blessing and a curse sometimes, right? Like, if we think about what I was able to accomplish as a sole practitioner on the enablement team, a lot of times I would get feedback from the executives from sales leaders, from whomever like, well, you’re doing such a phenomenal job, you don’t need additional heads, you know, like, Okay, if you’re performing, and you’re producing as a team of one, why would we Why would we throw extra money towards this? Or why would we invest more into this team, when you’re already doing it? You know, yeah, um, so I attribute that in a positive way to the process that I did have in place, in terms of, you know, just building out the case itself, I would say it was very organic, like I said, and it was being persistent and continuously, like, over and over and over. And time and time again, they knew that chrissa was not going to stop asking, and she was not going to stop building a case for why we need this support, why we need this investment, why this is so imperative to the business. Because it is it’s so much more than just enablement. Like, we’re not here to just train like there’s so much more that happens as a result of it. So I’m just making sure that we were bringing in, you know, all of the outcomes and the great things that we’re going to happen as a result of this. And I often think as well about not just quantity, you know, like, we as an individual can pump out however many programs or projects or whatever it might be, but the quality is not always there as well. So it’s about ensuring that, you know, you’re elevating that and including that as part of the case as more of the qualitative components of it outside of the actual like, here’s what’s going to get done. So I would say, um, yeah, the objections mostly were, I mean, also let’s not forget that we were in the middle of a pandemic for a portion of this so we weren’t actually hiring for a period of time. So you know, there’s that um, but I would say, you know, over and over again, it’s persistence is what pays off you know, and just like, like I said, knowing that I’m not going anywhere, and I’m I’m going to get this team we work people,

Devon McDermott
here’s why. Yes, and I and it’s that curse to like you said, we are used to doing it. So you’re you’re producing, you’re doing a great job. But like showing them, there’s so much more that is possible, like the holistic full program, not just like a training or a certification or a coaching. Like, yeah, it changes the game, and I think I’m able to share that that’s backed with data is is key. 100%. So we talked about the plan, business can’t plan business case, what would you consider when you were building your plan to go to leadership, like the must cover topics, and we talked a little bit about, you know, current state future state, but if someone was sitting down in front of a blank Google Doc, to build out their business case for headcount, where would you tell them to start? What are the areas?

Carissa Thomas
Yeah, I would say before you even open up that Doc, start, well, you can use this doc in collecting the data, but it’s really about having the information like going out and being resourceful and like literally doing discovery, honestly, and getting feedback and making sure that you understand from, you know, the leadership team’s point of view from the reps point of view, like what do you need to truly understand about the business and about the team to define your needs. So I would say start with that, like, go out, collect data, have all this information in this, this too, is very organic, this is things that you’re doing every single step of the way, right, like through retros through what’s working, what’s not working through QB, Rs, whatever it might be. So I would start with that, and then I would get really specific So start with a specific ask in terms of who the next hire would be why this individual it’s based on, you know, the velocity in which or the volume in which we’re, we’re growing, right? So we’re hiring X number of, you know, reps over the next you know, couple quarters or whatever it might be so onboarding, I mapped out the job description for every single headcount that I was requesting, what are their key focus is going to be how much of their time will be spent in segment versus on global programs. What does this look like in terms of the org chart like I literally mapped it all out because again, throughout the way I was there along the way I was thinking about well if I had somebody else to focus on this area of the business or this area of the business, this is what this would look like. Um, so I was very very specific and what that was the other thing that I always made sure to include is well what happens if we don’t hire so we talked a little bit about this like thinking about Okay, well here’s what I know I’m signing up for next quarter Well, what are the consequences to the business if we don’t bring on this extra head we’re gonna continue to just you know, move at this rate, we’re not going to be moving up. So this is really, really huge, I make sure that we’ve got that included. And then of course, contrary to that, what are the great things that are going to happen you know, to the business as a result, and thinking even bigger than, you know, just for sales leaders or customer success leaders or reps themselves, but like the overall experience, imagine how this feels for our customers when we have a go to market team that’s fully enabled and we’ve got the proper resourcing and staff in place to make sure that we have consistency and how we’re going to market such a phenomenal experience for our customers and at the end of the day, that’s what we’re aiming towards, like we want our reps to have a great experience we want our customers to have a great experience. So getting like really you know, focused on those big positive business outcomes for the business as well. Those are a couple of the things that come to mind for sure. Um, I personally did not start with a template of any sorts like I didn’t have anything that I was like Okay, here we go. I’m going to fill in the blanks, but I will say I did Google a lot of things and I just made my own Um, so yeah, the World Wide Web is your friend definitely get out there. There’s a lot and also network like us, like all of us are great sounding boards. I can’t tell you how many people in the enablement world I reached out to and I was like, how even even not from like building a business case necessarily, but like, I need a sounding board when you are operating as a team of one, extend your network reach out, everybody is so phenomenal. And that’s what I love about this industry. And like just being in this role in this capacity is how helpful everybody always is. Um, but yeah, in any case, now I’m just rambling, but I was kind of getting excited.

Devon McDermott
Yeah, cuz you’re talking about Where do you start? Do you go to Google? And like, when I think, you know, when I first got into enablement, you would Google it and nothing would come up. There’d be like one article. And now we have like trust enablement, sales enablement. There are so many amazing forums. And to your point, like, I have never reached out to someone who wasn’t willing to engage with me answer a question. How about, we’re so lucky.

Carissa Thomas
I love it. I love it. I can’t tell you how many strangers I got on zoom calls with and I was like, Hey, I’m caressa. Nice to meet you. I have a couple questions. Okay. Yeah.

Devon McDermott
Oh, my God, I couldn’t agree more. So we’re getting close to time I want you to share, if you could share one piece of essential advice that you would give to a solo enablement practitioner who’s planning to grow their team. What would it be?

Carissa Thomas
Yeah, I would say process for the win. process. persistence. Perseverance, I guess all of the peas Yeah, I’m just you know, it’s tough. It’s really, really tough. Hey, we’ll throw in another p patients as well. Like you have to be patient. Okay, so you asked for one essential piece of advice. That’s like a handful of them. But in any case, like follow the process, stay true to yourself, be persistent. You know, be patient, it does not happen overnight. And you you mentioned this in the very beginning, but you were like, I’m sure you were probably promised headcount early on? Yes, of course I was. And guess what, it doesn’t always happen right away. So be patient. But just remember as well that as you are working or contributing as a sole enabler and an army of one as I used to call myself the one woman army. You can’t do everything. So be kind to yourself and you know, really be gracious in knowing that you’re doing the best dang job that you can, and good things will come You know, good things will come be persistent.

Devon McDermott
Yeah. And I loved you shared, something that I wrote down while you were talking is like, as you’re scoping programs, as your, as a team of one, start thinking about, hey, if I had this person, yes, they be doing on this project and starting to document that so that when it’s time for that business plan, or that presentation, you’ve already thought through it, you already have it all mapped out, and you’re not staring at that blank piece of paper. So kind of like planning as though we have this person here.

Unknown Speaker
Yes, exactly. That’s okay. Um, well,

Devon McDermott
I could talk to you for like another two hours. So we may have to bring you back. But um, thank you so much for all of your incredible insights. It was great to learn from you from where I’m sitting, and I’m sure for the audience as well. So um, since we will probably have you back but in the interim, where can our listeners connect with you to learn from you and follow your enablement journey,

Carissa Thomas
of course, by all means, connect with me on LinkedIn, please, please, please, I’m very active there. I also frequent the enablement squad, the Slack channel, or that workspace. So if you’re not out there, jump on, it’s a great way to very quickly and easily collaborate. And yeah, otherwise hit me up on LinkedIn, I would love to connect. And like I said, I love networking and meeting other folks out there. It’s it just like makes my day for sure.

Devon McDermott
I love it. Thank you so much, and for all of the current and future listeners out there. If you have or, currently are in enablement team of one and want to share your experience with others, you can reach out to me find me on LinkedIn as well or in the trust enablement community. But another huge thank you to you corissa Thank you so much, and thanks for joining us, everyone.

Carissa Thomas
Thank you Devin. Thank