Powerful steps for starting a sales enablement career

Katie Williams is the Sales Operations and Enablement Manager at Sandler Training. In this session, Katie joined The Collaborator to share why and how she made the transition into Enablement and what her first four months have been like since starting a sales enablement career.

1️⃣She shared how her interest piqued when she had the opportunity to be involved in non-L&D projects in her previous job.

2️⃣She shared her outreach across the community, noting the number of supportive enablers who provided her with rich insight.

Katie also discussed her journey through job hunting and how she has approached the first four months in this new career.

If you are considering starting a sales enablement career, you should give a listen and follow Katie’s advice.

Give a listen and remain curious.

Audio Transcript

The Collaborator

Hey, if you pay attention to the show, you know the last week, Katie and I got started, and my network blew up. So that wasn’t Katie’s fault. But she was so generous and good natured about it that she’s come back today to share her story with us, Katie, tell us about yourself.

Katie Williams

Thank you, first of all, john, for having me. And you know, last week just gave me more time to prepare. So hi, everyone who’s joining in. I told john, this is the first time I have ever done something like this. I’m usually the one asking for expertise. So for john asked me to come and share my thoughts on growing and sales enablement. It was such an honor. So john, first of all, thank you. So my name is Katie Williams. And I started in sales enablement, in January of this year. So not only did I transition industries, but I transitioned to a completely new career. And my first manager title. I’m a one woman team right now and all throughout the pandemic and virtual working. So just a little bit of change for myself this year, but I’m loving it so far.

The Collaborator

You’re getting the fire hose of change shot right in your face, and you are smiling. So that’s a very good It’s funny,

Katie Williams

I I told my friend who’s not in business, she’s in health care how I kind of like, jumped right in the middle of a tornado, right? So if I started any earlier, might have been easier any later, I might have been catching up and she goes, but you’re meant to be in the middle of our tornado. You’re right I am and and that’s why I’m in sales enablement. And that’s why I’m excited to be with Sandler, we’ve pivoted so well throughout, you know, the virtual times and transitioned all of our services and our products remotely. So we’re changing, we’re helping our clients change. So being able to enable our sales team to help enable others it’s kind of a loophole, right. It’s like enablement, within enablement. But I am loving it.

The Collaborator

Now what what inspired you to make, not one change, not to change, but to make all these freakin

Unknown Speaker

in first place?

The Collaborator

for punishment, now, I know you’re not crazy, and I don’t believe, for punishment. But you made a lot of changes when you go down this path.

Katie Williams

Yeah, my background was previously in learning and development. So I focused in sales, but a lot of it was, you know, onboarding and traditional learning and development projects like LMS integrations. And so what inspired me was actually a month before the pandemic, a senior leader at my organization, over l&d left. And that is when there was this huge opportunity for me to partner with executive leadership on rolling out new KPIs and identifying a technical workflow in our CRM to manage prospects and accounts that are and I started to get my hands in this more strategic elevated project management stuff. And I just fell more in love with that and out of love with training, you know, hours upon hours every day, even if it was virtual. Right. So I loved what l&d gave me because that perspective is really helpful going into sales enablement.

The Collaborator

Yeah. strong foundation.

Katie Williams

Yeah, good foundation. So I just wanted to, you know, do something a bit with a wider impact, right, and more strategic. So that’s a transition. But I love the search. And I remember we talked like, a few months ago, right? And I was like, tell me more about sales enablement. Right. So it’s funny that it was only just few months ago that I was trying to learn if it was the right place for me. And here we are.

The Collaborator

I’m so I’m so stoked for you that you made the leap. Because you know what life you got to take some of these chances and just see what happens. And so far, it’s going great. But before we get into how it’s going for you right now, tell us a little bit if you don’t mind, what was the job hunt bike? I haven’t looked for myself in 47,000 years. I exaggerate a little bit, but not by much. What What was it like searching for a new enable a job? Let’s just start there.

Katie Williams

Yeah, I mean, it’s interesting, because enablement, you see all these studies, right? It was like, I think I saw like 13% of companies had enablement five years ago. So it’s growing so rapidly, and I could be misquoting that. But so the first struggle I found was there were so many titles that had sales enablement in them, but I wasn’t sure if it was the true sales enablement that I was looking for. Right. So it’s like, you almost have to work your way backwards. You can’t have titles you can’t depend on applications. And it was honestly I barely had job alerts set up because I was just totally hyper focused on networking with enablement people. So I joined the sales enablement squad. That’s how I met you, I joined, you know, different sales enablement groups. And each person I met introduced me to the next person who introduced him to the next person. So that’s how I started to find out about jobs was I met a leader who had something coming up soon. So I stayed in touch with them. And then actually for scalar, specifically, there was a VP of sales at Sandler who reached out to me inquiring about my previous company, using Sandler. And I said, I can’t help you. I don’t have a budget or decision making power, but you can help me. And you know, we stay connected, and Sandler had no sales enablement at that time, right. So she said, Oh, you should look into these companies. And then probably a month later, I sent her my resume, like I sent you to look over two days after that. She said, guess what? Her first sales enablement and Operations Manager opening is, is just posted. And I talked to the manager and he would be open to someone like you. So it really was like timing. I don’t want to say luck. But of course, luck, and just not networking, the network, but networking with a purpose and not letting them go once you meet them.

The Collaborator

I love that because this community is one of the most giving and collaborative communities I’ve ever had the honor to be a part of. people really are, most people are genuinely interested in helping out. Which is, which is fantastic. And I think you get the best advice possible in terms of the networking with purpose. That’s I guess, that’s key right now, I think. But I love that.

Katie Williams

Yeah. You know, it’s like, it’s funny, like, especially if you’re trying to transition to industries, it’s not like you can really depend on your resume to tell your story, right. I was gonna say, yo, took over.

Unknown Speaker

Did you read your resume? Or did you? Oh, yeah, I

Katie Williams

reworded it like four times, right, the more I learned about sales enablement and the foreign networks, and I think especially going from learning and development, being able to like, quantify the outcomes from the things that I was working on is where I struggled with the most. But that’s where telling the story and walking through everything with people in person, or at least virtually helps kind of bring the story to life with resume is kind of a

The Collaborator

guide. I love that. I love that so much. Now, I’m going to ask you something and no pressure here. I know Devin McDermott was on? Yeah, he’s a couple of days ago. And we were talking about team of one. And that That woman is so friggin smart. My brain exploded. I was awesome. I don’t want I just want to ask you, what’s it been like for your journey so far? First time enabler. Yeah. The company’s had an enablement. Team of one. What’s that journey been like for you? And how have you approached it?

Katie Williams

I think, gosh, my approach has, I think completely changed from from day one, right? day one, I was thinking, Okay, I gotta come in, and be told what enablement means here. Right? So I’m trying to figure everything out. And maybe definitely a little bit of imposter syndrome. Like, Oh, my gosh, am I able to keep up with these projects, I’ve never done so many of these things before. And then it’s just kind of morphed into. I’m reading, essentially, all these different strategies and projects. But it feels like I’m a part of deciding what my role is going to be, if that makes sense. So it’s not me being cold. It’s like, there’s just so much autonomy and flexibility. But of course, with that much autonomy and flexibility, you have to learn how to manage yourself, you have to learn how to communicate when you need help, or when you want to want feedback, right? So I think it’s just having the patience and having the grace for not everything to be figured out. And once you dive into that mindset, it becomes a lot easier.

The Collaborator

I love that. Have you found in my opinion, and I should have asked it differently. But in my opinion, the key is tying it to the business metrics and outcome. Yeah, whatever you pick, has that been a part of your strategy? I should have started with that.

Katie Williams

Yeah. Interesting. I know earlier, we talked about how I’m kind of, you know, enablement within enablement. But we also my division is only a few years old within Sandler. So we’re almost like this startup within a larger successful, very well known organization. Right. So it’s funny because it’s like all these loopholes. But so we’re redefining a lot of our like our sales process, even as we’re looking at how we can tweak our sales process and we’re rolling out new KPIs. So I’m tying in my role, with all the changes that strategically are being done within our division in order to scale So my role is definitely aligned with all of the things that are needing to be done to scale. Like we have all this great content, right? I mean, like years and

Unknown Speaker

years. I mean, I’m sitting there going, Yeah, of course

Katie Williams

crapload of this great content. So now I’m coming in trying to figure out how do we organize this? And how do we standardize it with some flexibility here and there, but really just enable people to take Sandler to the next level, especially within our division that works on larger accounts.

The Collaborator

So find like a lot of your sellers, because there’s so much content, they struggle to find it all. Is that part of the early challenges?

Katie Williams

Yeah. And we’re going through right like a brand, we want to be able to brand ourselves working in these larger accounts and being the enterprise division while still staying aligned with the very well known sailor brand. So it’s not only figuring out what content is most relevant, but of course, updating it to represent where we want to go as a division.

The Collaborator

I love that. And I’m just going to interrupt for a second. Bob does this throughout, you know about the interview part of the process. He’s wording, the resume getting calls and not having the background? It’s hard to get in in the first place. I mean, I think you kind of found the same thing. It took a lot of work to get involved.

Katie Williams

Yeah, I mean, I could put a month, a month, timespan on it. I started looking in June. And then I started at Sandler in January. So it took about six months. I mean, of course, in the pandemic, the employment rate was up and down. But yeah, it took me about six months. But I’m glad it took me that long. Because I remember hearing of things thinking, Oh, that’s it. That’s what I want, right? But then because I continued looking, and maybe someone wasn’t hiring at the time, helped me figure out what was actually best for me. And just ask more questions and find more stuff out.

The Collaborator

I love that. And I always tell people this, and it’s so relevant. you’re interviewing the company as much as they’re interviewing you. Oh, yeah. He is in line with yours. Otherwise, you’re stepping into a bunch of landmines, that it’s not good for either one of you. So right, that’s asking a lot of questions. And Bob Britton, the Sherpa himself said, when you get started, you need to utilize a racy chart. It will help a time. I agree with Baba, I love building those raci documents. I’m not Yeah, I’m not the best at it. Because my brain always explodes between who’s actually accountable who’s. But it’s a great exercise. And if you get the right people together and work through it powerful. So I agree with Bob as well.

Katie Williams

Yeah. Charter has been on my list,

The Collaborator

right? And ask you what things have you. This is not a pass fail question. There’s no casting.

Unknown Speaker

I know. What What

The Collaborator

kinds of things have you done? foundationally so far, yeah, versus running around and tackling a lot of projects learning, which is all important to do to Katie, what sort of foundational things have you done so far?

Katie Williams

Yeah. So so far we are, we’ve been vested in high spot. But that kind of ties in to figuring out what content lives where and, and previously, it was uploaded from like a desktop, right? So we got to get it in SharePoint. So it can have its one source of truth. So getting high spots set up as long as our CRM, so we invested in a CRM about two years ago. So ensuring that all of the data in there is relevant. And everyone is trained on how to use the system, and then the analytics piece. So those are some things I’ve worked on, we’re also doing an integration. So training the team on the difference between teams, and SharePoint, and Dropbox, and high spot, because now that we’re virtual, you know, we’re so grateful that we were able to get set off in teams and continue to communicate virtually, but I think probably a lot of companies can relate. We now it needs to come together, there has to be a rhyme or reason where files are and where we’re communicating, right. Otherwise, it’s just difficult to keep track. So those are the things that that I’ve worked on so far and set up so far. And looking forward, we’re going to look even more into just ways that we can ensure adoption of these great tools and great processes. But when you say building the foundation, we really are are starting at the foundation.

The Collaborator

That’s awesome. What’s been some of the early things that you’re feeling like were really big successes or even small successes versus challenges. What have been some of those as you’ve gotten started, Katie.

Katie Williams

Yeah. Oh, gosh. So I think that really probably my first success was actually really good lesson learned. So we, as I mentioned, we’re reorganizing all of our content. Not only What clients See, but also internally what people used to do their jobs. And it’s funny because my boss at the time asked me to create an architecture of this content and how it can all come under a certain umbrellas, right? And so I remember I was like, This isn’t right, that there’s no way this is right. Like, we had a call, I had looked at it 1000 times. And I was I was confident, john, that it was wrong. And we got on the call. And I showed it to him. And he said, it was completely what he was thinking as well. So I was totally right. Yes, very few edits. But and that was a small win, and probably more of a psychological women and anything else, because it’s like, sometimes you’re so much harder on yourself. And you’re actually like, can do a pretty good job if you give it a good effort. So that was a good lesson learned. And that enabled us to then go to the next phase. And so because of that, we’re able to start training on high spot very soon, right how to use it and have a rhyme or reason for everything. So I mean, that’s going to enable people to do their jobs, because, you know, we want people to not have to think about where things live, or if it’s the most updated document, or ask questions about it, right, we want to just allow them to, to use it and succeed and help our clients. So that’s probably one of my biggest wins another we started, I started

The Collaborator

to see this, Katie, sorry, real quick, those to you. That’s awesome. You brought all these amazing skills over to a new career, and you were probably unsure about which ones actually we’re going to help you out. And, and right, there is a great example of it paid off, all these skills came over and you were able to get the job done. So I love Sorry to interrupt you, but that I just want to know, that’s

Katie Williams

fine. I it’s funny. It’s like I, I even learned more about kind of what my goals are and how I like to work and what my Why is. And I saw a stat the other day that was saying that 50% of revenue comes from 20% of sales teams. But we know that right? There’s the top performers, a lot of the times they hear the team and then other people just don’t get ramped up. And that’s my why. Right? Like, it shouldn’t, it shouldn’t be only the 20%. succeeding, right, and it shouldn’t be the leaders depending on only 20% of their team. So just bridging the gap and giving everyone whether you’re a new, an experienced salesperson, you’re given accounts, you’re not given accounts, the same chances of succeeding, because that’s that, I mean, I know true, because I’ve seen it in other organizations I’ve worked for, but that just has to change. I love that. I

The Collaborator

love that. Let me ask you, I actually have an interrupted one second. Now please read again, he’s doing tech is tricky. You have to adapt it to it, it doesn’t adapt to you. Yeah, your processes to the tech stack, which creates other issues and can pull your attention away from your core competencies. I absolutely agree with Bob it can be that can lead you down several rabbit holes. And yeah, maybe in a few months to have you come back on and talk about what rabbit holes you’ve experienced as a result of all of this. Um, let me ask you this. So what are the what are the challenges or successes did you want to bring up?

Katie Williams

Oh, gosh, well, I think success was, you know, just bridging the gap between everyone virtually I started something called make it happen. It’s kind of a recognition program for people who hit a certain criteria in a new deal or a deal worth a certain size. And that’s just bringing everyone to I think virtually Ray, everyone’s working on their own and the commodities maybe God and and we want to be able to encourage not only recognition and congratulating each other, but tell people why we’re winning deals, right? Like, what did you do? Where did it come from? So just bridging the gap in terms of that communication to is really helpful. So I’m proud of that I’m proud of standing up our CRM. I mean, again, it’s only two years old, and we started training on it right before the pandemic, and then everyone went virtual. So the adoption hasn’t been super high. But now that we are, you know, working on how to, you know, adjusted and train the team on how to use it, and then showing analytics, hey, here’s the analytics we can pull from the system to help you know, what’s working and what’s not. So I’m proud of just, I can’t say like, some days, I feel like I’m a digital marketer. Some days I feel like I’m a data analyst. Some days I feel like I am a trainer and other days I feel like I’m a program manager. And so, you know, being okay with the role and the priorities and the strategies fluctuating timelines, like everything was bad. Yeah, don’t get married to a timeline because 90% of the time, you know, bottlenecks come up. So I think it’s, it’s fun. I like variety. Again, I like to be in the middle of, you know, change and and empower people. And I was thinking about my role. And I’m almost two things. Number one, I’m the sweeper. Right. So we have our strategic leader team. Yep, amazing ideas, they’re thinking 10 steps ahead of the game, right. So I think of myself as the sweeper behind them, making sure everything stays clean, and it’s working. And it’s getting adapted, because they got to go on to the next big strategy or big idea, right. But then, besides the sweeper, xv the energy, right because if a sales team is going through a lot of change, or any organization is going through a lot of change, they have to understand why this is happening, what’s included in it, and I not only got to bring energy and my training, but I’ve got to bring energy to what it’s going to do for us. So I think I think no matter what I’m doing, whether it’s digital marketing or some other role that day, sweeping and bringing the energy is always my, my main goal.

The Collaborator

I love that, you know, Bob Britain’s on fire here. So I’m gonna I’ll share this too, because Bob is super smart. He’s far smarter than I will ever be. So I’ll share this to start when starting off categorize your efforts into short, medium and long term wins. Very small. Yeah, short term wins, you know, within a sales cycle. Medium short, medium term wins in two to three sales cycles in long terms and longer. Focus on those short term wins the first and again to the capital. bigger projects. Yeah, the guy’s a genius. So I’m gonna say yeah, Bob now, but he’s right. Those are really smart tips. Let me let me skip ahead. There’s another Katy out there. There’s plenty of other Katie’s out there right now we’re thinking to themselves is enablement, right. For me, is this something I want to get into? Do I want to change careers at all? What advice would you give them based on everything that you’ve learned in this in this period of time? to consider?

Katie Williams

Yeah, I think cash first, my my biggest advice would be talk to enablement people, right? Learn from the source, go straight to the source, whether it be me, people are more than welcome to reach out to me. Of course, I’m still a new perspective, because I’m only four months in, but talk to people and just ask questions, right, try to understand what the role looks like and realize that it could look very different, depending on the enablement practitioner. But second of all, I would say, enablement is filled with change and filled with a variety of priorities and projects. So if you’re someone that likes to live, you know, within the box and likes rules and regulations, of course, I like rules and regulations to some degree. But I like to live outside of the box, right. So I think it just depends on people’s strengths, the way they like to work. I’m a very independent employee, and I’m an independent person. But being a team of one, right, I think is in itself. A choice outside of just enablement. So, you know, I’d say just network and understand your strengths first, and then, you know, talk to me, or someone else.

The Collaborator

And I think you summed it up well, especially if you’re in a smaller situation, where you’re, you’re the team of one, it’s a very independent role, you better not care that much about the box, because you’re creating the box. You move one, if you’re in a bigger company, like an IBM or something like that with a really formal and rigorous process, then there’s a box that you’re staying inside, but it’s still, it’s still a creative role and a scientific role. So you definitely want a bit of both. Katie, this is awesome. What did we What did

Katie Williams

I think we talked about everything? I mean, talk to me again, in four months, eight months, and we’ll see where we’re at, but four months and I mean, I’m just so grateful for all the people and they know who they are, who have networked with me and stayed up with me and how my transition is going helped me decide to be an enablement just like you, john. So all the organizations that I’m a part of sales enablement, societies, this sales enablement squad, like I could not do without the village behind me. So thank you so much for having me. And if I could have taught someone one thing today, that would be a huge one.

The Collaborator

Katie, thank you so very much, my friend and I’m excited you made the transition. I’m excited. You’re creating this whole brand new role and opportunity for yourself. So definitely, we’ll have you come back in a few months and talk to us about you know, what’s changed and evolved. I think you’re you represent nice Just yourself but a community of people that are just getting started down this path and and I appreciate you sharing everything that you’re learning and experiencing. So thank you.

Katie Williams

Oh, thank you so much. And if anyone watching wants to connect on LinkedIn, I mean that that new enablement community means so much to me right cuz cuz I’m experiencing it firsthand. So I appreciate you just helping build that community. JOHN, your, your, you know, stuff that you put online and the people that you connect is so valuable, especially to people like me, who are just starting out.

The Collaborator

Well, appreciate it. Take care. And we will talk again soon, Katie, thank you for listening. And I’d say two bits of advice as I close out. Bob dosis Thank you another advice but just follow up Bob does thank you for your thoughts about getting into the field that is hard, but maybe talk reach out to Katie too. I know she’s she’s definitely got the same kind of experiences you have. And Bob Britain Mr. sherpur yourself, you my friend are a rock star and always appreciate you so by all