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Sales Enablement PRO Awards 2022: Cultivating a Culture of Mentorship in Enablement

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Congratulations to Sales Enablement PRO Award winner Sheevaun Thatcher from RingCentral. Learn more about the Enablement Mentorship award recognition below.

Sydney Lee: I’m excited to announce the winner of the 2022 Sales Enablement PRO member award for people’s choice on enablement mentorship. Congratulations to Sheevaun Thatcher, VP of Digital Learning and Enablement at RingCentral. I’m excited to be here with her today as she shares how she led enablement at RingCentral, while continuing to be a mentor and resource for the larger enablement community.

Sheevaun, I’d love for you to introduce yourself, your role and your organization.

Sheevaun Thatcher: I am Sheevaun Thatcher, I am the VP of Digital Learning and Enablement at RingCentral.

SL: Again, thank you so much for being here today and I’d love to get started on the topic of the impact of your efforts at your organization. To start off, how have you structured RingCentral’s enablement function to become a critical arm for your organization’s success and how do you measure the effectiveness and success of teams?

ST: The sales enablement or enablement team has transformed fairly significantly in the five years that I’ve been here. When we started out, which is early 2017, there was just a very small group of us, only three. We now have about one hundred and forty, but with the three, we recognized that through very little discovery, we needed to do two things right away. One was to create an effective, new hire training for sellers; the second one was to have a one-stop shop for content or any of the materials they might need – assets – in order for them to be able to do their job. The onboarding at the time was two weeks sitting in a room, having subject matter experts come in and simply turn their back on you and read their slides. This wasn’t effective. It was a total fire hose, nobody maintained anything. From the content perspective, there were ten, fifteen versions of the corporate deck. The competitor information was all on the laptop of the person who was doing the analysis. It just wasn’t centralized and made easy. That was our first set and once we did that, we really started to transform how enablement supported the selling efforts and how sellers actually went and did their jobs. After that we focused on the leadership part of it, which was ‘how do you teach selling mangers how to coach their people through the sales process’. Not how to be leaders per se, but how to coach their people. Many of them had come up through the ranks, had never had any type of management coaching and there was just nothing that they could turn to. That was 2018, to get that done. The program there was called Lead, which was very, very effective; we still use it. 2019 was when we really started looking at things like social selling, or what we call modern selling. Where we could use the social capabilities that are out there to help with our prospecting, to help with our research, with our customer support, whatever it was we needed it for to take advantage of those tools. Then 2020 of course was pandemic. So it was hybrid, what are we going to do, how are we going to manage, how are we going to transform. Over this time period of course the team is growing and growing. The one thing about enablement, from my perspective, is it’s a business within a business. I’ve got investors, I’ve got stakeholders, supply chain and because of that, when you give the investors back what they want, they give you more investment. With that we were able to grow the teams; as the sales arms grew and became more successful, enablement grew as well, so the team grew and grew and grew. Three years ago, I put a proposal together, to bring all of the various enablement and support teams in the company together into one group. It took three years for that to happen, but in December 2020 I got the go-ahead to do that. That is when I was able to pull channel, pull customer training, pull curriculum design, digital design, pull all the sales arms, be it pre and post, together into one group and that became the Digital Learning and Enablement team.

SL: Absolutely, that’s fantastic. I’d also love to know, what initiative was most impactful to the success of the RingCentral enablement team this past year. What specific behaviors resulted from the implementation of your initiatives?

ST: This is going to sound kind of interesting, but I think the main initiative that we had that was very successful, was a program to look at employee happiness, for a variety of reasons. One, of course, is the great resignation and we wanted to make it the great retention. So, how do you do that? By figuring out, what are people motivated by. People wanted a sense of safety. There wasn’t a lot of safety out there in the world, so what could we do as an enablement force to give them that feeling of safety? Not only within their work environment to make sure they had everything they needed, but also in their personal environment. How could we make sure, that they were going to be safe? And this affected all our stakeholders. Our stakeholders, and when I talk about customers I mean our employees, our partners, as well as our actual customers, and our programs transformed for this happiness angle to be added in there. We actually have a survey that we run every quarter, to find out – from our sellers’ perspective – how we are doing. That allowed us to identify gaps very early in the pandemic, so we were able to change the customer sat, the e-sat in such a way, that we increased it by twenty percent in a very short amount of time, just because we listened.

SL: Absolutely, I love that. What was the biggest challenge your team faced and how did you overcome it?

ST: The biggest challenge the team faced was getting people to be comfortable in this hybrid environment or getting people to be comfortable in doing selling and talking to the customers and being curious and working within this video stage. For example, I am very well-trained on looking at the camera. If I was looking at you, I’d be here. That’s where you are on my screen. Teaching people that you can’t connect by looking at someone on the screen – especially these ones where you can get fifty people in a big gallery and you’re trying to respond to somebody – as long as you keep looking at the camera, you can keep eye contact. Things like using your hands. I’m not sure if you’re aware, but psychologically, if you show people your palms, they get the sense of safety right away, because you’re not carrying a weapon. It goes back to the days of the saber-toothed tiger, which is ‘am I safe?’. Again, it’s a big issue that has come up, consciously or unconsciously, and what we were doing is teaching people how to be comfortable in this new environment, how to forgive, because we all have things going on. As I started talking, my son came in the door, I heard the door open and shut and it’s like ‘okay, it’s happening there’. Dogs bark, children run through rooms, spouses, it doesn’t matter. It’s the forgiveness of ‘I’m making a human connection’ and that is how we need to communicate at this point forward. And to listen, to really connect with that, because that’s very hard to do if you’re not sitting over dinner or playing a game of golf or the things that we were used to doing, we just don’t have that ability.

SL: That’s great. How do you align with other leaders at RingCentral to continue to invest in enablement?

ST: As I said a little while ago, it’s a business within a business, so each of my leaders has a main stakeholder. For example, on the sales enablement side I have Sarah and her main stakeholder is the CRO. Those two are in lockstep with all the programs that are needed. They evaluate them quarterly, they talk daily about things that are going, what he is seeing or what he is hearing and what we are seeing and what we are hearing, that we make sure we identify the gaps, that initiatives are created for those gaps and that we actually measure the impact. That’s really important. What are the initiatives, how are we going to implement them and what is the impact those initiatives have? We do that on the sales side, I do that on the customer training side, we talk a lot with our professional services leaders, we talk a lot with our customers and it’s saying what’s working and what’s not. Because it’s not all about RingCentral and what we do and ‘we’re fabulous and why wouldn’t you buy us’. Instead, our conversations are much more around what is it that you really need, what are you really being challenged with, where’s an opportunity that you see. We don’t like getting into competitive fights, that just becomes future function and frankly, buyers don’t care. Buyers want to make sure that you hear what their issues are and that you can come to the table with solutions that will really work for them and then help them through that whole thing. I like calling my sales enablement team personal trainers for just that reason. There could be bar tenders, where somebody comes and says, ‘I have this issue, solve it‘ or ‘this issue, solve it’. They may be very similar, but we’re doing a one-off all the time. I like it more that we are personal trainers in that we actually work very closely with these leaders and say ‘what exactly is it that you’re trying to solve. What is your end goal, how can we work a plan to get there and then let’s work through it together’. That is how my teams work. If a major problem comes in, we swarm to the problem, regardless of what division it’s in, determine who should be working on the problem, release everybody else – instead of having these fifty-member committees trying to solve something that could be done by two or three people. It’s that approach that we’ve taken.

SL: Now I want to move on to this topic of the importance of mentorship in enablement. To start off, what role does mentorship play in a person’s career and why is it important?

ST: In the case of sales enablement, mentorship is huge. There is a big, big gap in enablement right now. You either have to really experience people like me and others that have twenty, thirty years. It may not have been called enablement at the time, but that is really what we’ve done. We’ve suffered the slings and arrows, we’ve been there, we’ve done that and we have the gravitas to go in and actually affect customers from the high level all the way down. Versus enablement folks with three or four years, or maybe five years of experience, who have some, but are still fighting that upwards battle. Having mentors allows us to go to the ones that don’t have as much experience, or in fact have them come to us and say, ‘here’s the situation I have, what would you do?’ Now, mentoring is different to coaching. Coaching is when I would sit with somebody and they say ‘here’s my issue’ and my response would be ‘what have you tried? What else have you tried. If you had the opportunity to do something and resources weren’t an issue, what would you do?’ So it’s helping them uncover it themselves, whereas mentoring is ‘hey, I’ve done this, this is what I’ve done.’ So mentoring allows you to do it quick, get it done and try it, because as I like to tell people, I know the ten ways to do something and they all work, but there are two ways that work better than others. So it’s giving that back. That’s why it’s so critical, because in enablement you don’t have the time to always sit back and try to make something perfect. Sometimes it’s ‘we need to make it really good, we’re going to get it eighty percent done, we need to pull the trigger, we need to get it out that door and that’s really important’ and mentorship really helps with that, because you can get the answers really fast.

SL: That’s great. What is your advice to those seeking a mentor in the enablement space?

ST: Don’t expect mentors to come to you. That is something that I see a lot. People saying well, I’d love it if Sheevaun reached out to me, I’d love it if…no. There is this thing called LinkedIn, there’s a sales enablement society, there’s Sales Enablement PRO, there are all these various places that have forums and podcasts. Go and listen, go and talk, go and reach out to those folks, because frankly, my day is jammed. I don’t have time to go and say ‘hey, who needs my help’. More importantly, if someone really cares about their career and they really want to make a difference where they are and have an impact and have thought about it, then I will help anybody. And they know that, I’ve had people reach out to me. Provided you’ve got an idea of what you want, what you really want specific help on and how you think it can impact your business and you’re really serious about it, then reach out. There are a lot of people that will help you, but it’s up to you. We don’t have the time to go look for people. We can reach down in certain times, but most of the time you have to reach up.

SL: Absolutely, that’s great. What is your advice to those who are currently mentors in the enablement space?

ST: Just keep doing it. You have to keep doing it. It’s really interesting. What I’ve seen – and I don’t know if it’s generational or not – but people are afraid to ask questions. The one thing that I say to my team all the time is ‘you are allowed not to know. You’re allowed not to know. You’re not allowed not to find out, but you’re allowed not to know’. I think it’s that fear of appearing not capable or not capable enough or not as smart as this person or not as plugged in as that, that holds people back. And that’s a mistake. You’ve got to keep doing it and as mentors, keep encouraging. If you do want to be a mentor, make it known that you will be. There are a lot of folks that don’t want to approach someone like me or some of the others, because they think they’re unapproachable. That is not the case at all. We love talking about what we do and helping people get better at it. We absolutely do, but you’ve got to reach out to us, and the mentors have to be available as well.

SL: I’d love to get onto this final topic of key considerations for 2022, so first I’d like to know what was your biggest learning in the past year and how will this impact enablement in 2022?

ST: I think the biggest learning is that people can get very, very tired when they have to be on all day, every day. Even something simple like setting your scheduling system for your meetings to be 25mins or 50mins, so that there is that gap. What happens is people don’t consider that there are things like having to eat lunch or going for a walk or just taking a break, biological or otherwise, that you need to do, so be conscious of that. When you start doing that kind of thing, other people will do the same. The other thing is to allow people not to be on camera. I wouldn’t do it every day; I think the connection is really important – like this eye contact is important – but there are going to be days where people just say ‘I just can’t do it’. Okay, don’t do it, that’s fine. Do phone calls again. We’ve learned that there was a study done at Stanford, it was called Zoom Exhaustion and something else, they called it Zeg or whatever it is. It was this study that was done on people being exhausted. It is so much harder to stay focused and be involved in the conversation on video, than it is even on the phone or in person, because you can’t read body language. There are a lot of things that our minds do subconsciously that you can’t do over video, so our brains are hyper-alert, trying to see if there’s anything that I’m missing, whereas normally it would just be flooding in. But when you’re looking through this tiny camera or you’re looking at little images of people, your brain is trying to figure out and make itself comfortable in one way that it can gather everything that it needs, and it’s exhausting. The one thing that I think we learned is to allow people to show up the way they want to show up, when they want to show up.

SL: For our final question of the day. Now that 2022 is in full swing, how are you planning for the year as we continue to face a mixture of virtual, in-person and hybrid work environments?

ST: We’re really doing a lot of very thoughtful discussions around ‘do we re-integrate instructor-led training in person’. Do we even do that, is there value in doing that and if there is, when, for whom, for how long? The world is very different – as we all know, that is an understatement – so what we need to do in order to support not only ourselves for us to be able to do our jobs, but how do I teach my enablement folks regardless of where they are, pre, post, onboarding, whatever it is, how do I make sure I teach them to be conscious of this and then how do we as a leadership ensure that we create the programs that continue to be leading-edge and that continue to really support the environment that not even just our sellers, but our customers are in right now. How do we help our customers deal with this? Our enablement isn’t just that we’re going to create a lead program or a training program to teach sellers about product. A lot of it is more around how do we help people be comfortable where they are right now and that is a lot of what we’re talking about. There’s a lot of EQ going into this right now, to say what’s really working and what’s not.

SL: Absolutely, that’s great. That’s all the questions we have for today. Thank you so much, Sheevaun, for joining us and for sharing your expertise and congratulations again for being our 2022 Sales Enablement PRO member award winner.

ST: Thank you.



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