Jessica Ryker is the Senior Sales Enablement Manager at Latch.  In this conversation with The Collaborator, Jessica will focus on running team of one strategic Enablement as a team of one,  operational success, and more.

In additions, Jessica discussed:

1️⃣Setting up a learning quota.  Set aside 10-20% of your time each week for learning activities.

2️⃣Enablement needs to collaborate across the business and identify where you can most effectively help the business.  For example, in here work at HelpSystems in 2020, she started an Enablement Advisory board to help drive alignment, identify the right work, and uncover what each team was doing on their way to achieving these goals.

3️⃣Aligning the buying journey with the sales process – why, how, what.

Audio Transcript

The Collaborator
into 2021 episode one today with Jessica Riker. Jessica, how are you?

Jessica Ryker
I’m well, how are you, john?

The Collaborator
I’m fantastic. You and I were chatting before before we dove on this, which is always the case. And I was just I wanted to remark that I still I love that mug that you’re drinking out of.

Jessica Ryker
It is my all time favorite. So I am from Minnesota. I was born and raised here. And I have the Twin Cities Starbucks mug because I I love it so much it has pieces of of Minnesota, Minneapolis, Minnesota, and then also St. Paul. Because of course, we are a town of two cities. And so it’s nice to have both of them together.

The Collaborator
I love that. Tom, tell us a little bit about you know yourself. I know you’re in between roles right now.

Unknown Speaker
Yeah,

The Collaborator
we’re a new one, but also by herself, Jessica.

Jessica Ryker
Yeah. So I am just leaving position as a sales enablement manager at helpsystems, which is a cyber security and automation company. And I do not have an IT background. So that was that was a fun learning experience for me. And in just a few days, I’ll be starting as the senior sales enablement manager at latch, which is a smart access company. And it’s it actually sounds like a really wonderful place, the people that I’ve had the opportunity to meet so far have been amazing. So I’m very excited to get started.

The Collaborator
No, that’s awesome. And you mentioned, you don’t have an IT background, you have the most interesting backgrounds. We all have interesting backgrounds. Your lawyer, so you know that I am wild to me, I don’t think I’ve ever run into another lawyer doing enablement, which is probably good, because I can see you, you know, taking the trials on the sales manager one day, and that cross examination, I don’t know how how does it shape your view of enablement, though, coming from that background?

Jessica Ryker
Well, so the thing I am most grateful for my law background for, especially in enablement is being able to think in the most strategic ways in terms of what where are we trying to get in the next year, three years, five years, but then being able to break that down into the most tactical. And so when you think about the strategy for enablement, how you’re going to deploy your resources effectively, what do you need from other groups in order to be successful, that is where my legal background has really come into play. And while that isn’t lost, specifically, that is absolutely a skill that has to be on point in order to be a successful attorney. And that has lended itself very well to an enablement career, it, you have to be able to flex, especially as a solo practitioner, which I have been for the last year and a half, you have to be thinking in the big picture, all the way down to the smallest job aid, putting together the playbook. Who do I have to work with? What am I chasing in terms of goals? And so that’s been, I think, the biggest help in in my legal background,

The Collaborator
I think I think that’s definitely huge. And even just, I don’t know what your legal experience was. And obviously, I should say, obviously, I’m not a lawyer, but I see them on TV all the time. And they’re always reading and writing and doing that stuff. If there’s truth to that, that must have had some amount of help and assistance in terms of how you research and approach the role as well.

Jessica Ryker
Yeah, I in order to be successful, you have to be constantly learning constantly, you can’t ever sit back. So I when I was practicing, I did administrative law, which is I it’s a wonderful experience, because it’s it gives you a lot of really great background on how to go in front of a judge and how to argue where, you know, most young attorneys do not get that opportunity. And I did and because it was administrative, I also had the chance to travel all over the country and, you know, try cases, just about anywhere. So that was a really beautiful experience. And because you have to constantly stay up to speed on what’s happening in your field. And what you practice in. The same thing is also true of enablement. So, you know, one of the things I picked up from a former boss of mine at Thomson Reuters, which is the connection between my legal background and enablement. Yeah. One of the directors there, his name was was Matt Edsel, he used to talk about a learning quota. And he used to talk about it with sales reps. And of course, no sales leader has ever been like yes, I want to make that particular quota. But for me, it is absolutely vital that you know, 10 to 20% of my time is spent learning and getting smarter because there’s so much changing and so much new data and information that’s been coming in in the enablement field. And especially as a solo, you have to stay abreast of what’s happening within the field within the industry, constantly trying to learn more about how you can be the best possible asset to your sales teams. So I think about it from that perspective is, you have to always stay up to speed on what’s happening with the law. But the same is true of enablement. You have to be curious and always wanting to know more.

The Collaborator
I mean, you’ve been a team of one for you were a team of one for what a year and a half.

Unknown Speaker
Yeah.

The Collaborator
How do you know taking those that quota concept? afford a little bit, I guess I want to ask you a couple of questions. Yeah. How do you successfully do enablement as a team of one because I think the vast majority of enablement professionals are teams of one, right? And, and first tackle that, but then I want to come back and touch upon if it’s okay. How did you keep learning? Because there’s so much there’s both an overwhelming amount of information and enablement. And not nearly enough. Yeah, in my opinion, but talking about those concepts as a team of one to be successful, you know, the different photos.

Jessica Ryker
Yeah, so what I found to work for me, and I think, all enablement professionals strive to do this. So what I would do is add help systems in 2020, for example, I looked at what are my business’s goals for this year. And, you know, I looked at where could I have an impact in helping us to meet those goals, because it’s more than just sell more. Which is, of course, the goal of any enablement, professional who’s in sales is you want to sell more better customer experience all of that. But for me, you know, we wanted at helpsystems in 2020, to really boost our cross selling, I mean, helpsystems has 120 products and a huge product bag. And they’re still siloed, in terms of who can sell what

The Collaborator
that makes it even harder than

Jessica Ryker
it makes it much harder. And so with that in mind, thinking that we want to improve our cross selling ability, I needed to think critically and creatively about what impact I could have. So you think about the business’s goal, and then you think about what you might be able to do to support that. But the other side of that is, I could not do hardly anything on my own. I depended on other people to get work done. So I had incredibly close relationships with my sales leaders, with my marketing directors, with the product strategy leaders, and and our CRM team, or it group had to have those close relationships in order to be successful. And so one of the things that I am so glad that I did was I started a sales enablement advisory board. And what that allowed me to do was to say, Okay, here’s the business’s goal. What are you doing, to get there? How can I help you do that? And how can you help me also help us achieve those goals? Right, so it was very collaborative, it was very open, in terms of what are we all chasing? And even

The Collaborator
in that advisory board, Jessica, you know, what kind of role?

Jessica Ryker
So I had every sales leader? Well, not every sales leader, excuse me, I had the top layer, sales leaders, because again, this is a very strategic initiative. And it’s much more high level than than tactical. So I had my general managers and my managing directors of sales. I had our VP of product strategy. I had our pre sales engineer, leader. And I also had all of our marketing directors. And then I also invited our services VP. So it was Yeah, and so it was a very, it was a very great, it was a really good group to get together because they all came with different perspectives. And so often, I mean, I’m sure you’ve seen this, but you know, there’s a lot of departments that just don’t seem to talk enough to each other. And so I consider enablement to be the bridge to help connect all of those people

The Collaborator
together between those different teams.

Unknown Speaker
Exactly.

Jessica Ryker
It can be Yeah, and so I, I found that that an advisory board was very successful in making sure that everyone was talking everyone was communicating about where they are with their goals, what their focuses are. And because we had so many different product groups, and leaders that were representing those product groups, they all had different targets to meet. And so we had to think creatively about how we were going to do something big, like improve our cross sell initiatives.

Unknown Speaker
Yeah,

Jessica Ryker
with all of these folks. And so when it taught when you come to when you think about how to be a successful solo person, it’s you have to get every single stakeholder in the room and bought into you. Because it is about buying into you as the person and your vision, but also seeing how you can deliver. And I think it was a big part due to keeping everyone in the same room, constantly bringing it back to where’s the business trying to go.

Unknown Speaker
Yeah.

Jessica Ryker
And then also helping others to meet their goals that made it so much easier for me to be successful.

The Collaborator
Did you find people were getting surprised by some of the things that they would learn? And what I mean by that is, I often find, oh, I’m talking to the customer success team. And they’re doing project they’re doing this project that nobody knew about what we’re hearing, it’s the same thing done. Guess why? Why don’t you guys start talking nothing to do with enablement, per se.

Jessica Ryker
Right. But it is about those connections. Yeah, absolutely. It that that did come up a lot. And it, it started to diminish a little bit when we, when we really started to get some traction with the advisory board. And so yeah, exactly. And so I took it upon myself to kind of update everyone on what was going on across the business. And I invited folks like our customer marketing group to come in and talk about what they were doing to help push cross sell initiatives. And, you know, again, where are my business goals? How are we getting there? How are we serving the sales team? You know, we we focused really on sales initially, but I and I imagine that the the focus at health systems in the future will continue to expand to customer operations to services and support and continue to be customer enablement as well as sales enablement.

The Collaborator
Yeah, you have to broaden that you have to broaden that, that who you’re supporting, and all of that as you go forward. Exactly. Now, this was wonderful, really, really wonderful, Jessica, but one of the things I know you and I wanted to talk about, was, you mentioned a real focus upon operational success. Yeah. It’s really a foundational element of what you’ve been doing and thinking about for the last year, at least. What is that? What does that even mean? You know, what does operational success mean to Jessica?

Jessica Ryker
So I am, I don’t have experience in sales operations, other than as a, as a as a way to help enable our teams. So the way that I think about operational success is how can we improve the productivity of our sales reps, remove barriers, remove roadblocks, and also enforce good process, which sometimes feels counterintuitive to the productivity. So one of the things I did at the beginning of 2020, is we launched an updated sales process, one that was also aligned to the buying journey. And any, you know, anyone in sales enablement, knows to your core that thinking about your buyer, and where they are in their buying process is absolutely necessary to ensure a good sales process and a good experience for the buyer. Your salesperson knows where they’re at and knows how to help them, they will have a better experience.

The Collaborator
Much better than saying to the customer, we’re not gonna you’re in the purchase stage in my CRM,

Jessica Ryker
exactly. It doesn’t work, that customer does not care.

The Collaborator
You’re not care. And if they do, they’re probably not a real customer. They’re just plant.

Jessica Ryker
Exactly. So. So connecting those two, helps see significantly in terms of helping to get the mindset and I think of a lot of enablement as change management to because you are constantly driving people forward. So when you think about it, from that perspective, we launched this new sales process aligned with the buying journey. Every process is now standard. Now you have to also continue to push for that. And continue to push for that process in ways that aren’t just a piece of paper or aren’t just a training call. So, as we were upgrading our CRM system, we’re upgrading our CRM or they will be excuse me, they’ll be upgrading their CRM system to mimic the buying journey. Love that. Right. And so when you think about it from that perspective, now you’ve got the mindset starting to change with the reps, because now instead of thinking only about, oh, I am in the negotiation stage, or I am in the evaluating stage, or whatever that is, doesn’t matter. Now we’re thinking about it from the buying perspective. And so that’s what I mean about operational success. How can we make sure that we have all the right data? Yep. Or capturing all the right data? How can we make sure that CRM is our single source of truth? And how can we make sure that our processes are also aligned to the way we want our sellers to sell, and that aligns with our that makes that aligns with methodology process, the good best practices that we instill over and over again, you have to also make sure that that’s part of their day to day, and not just a sales meeting?

The Collaborator
remind people so your team of one, you were team of one? Yep. And the team, and I’m assuming this wasn’t just Jessica’s bright idea, it was it’s a good idea. But I’m assuming it was part of a team coming together and saying, look, we need to align along the buying journey. This just makes sense. How did you as a team, or are you individually if you’re another enablement team of one, and I want to replicate what you’ve been through? Yeah. How do I start to think through aligning to the buyer journey? Because a lot of us are sitting here going, Well, my CRM system has these seven stages. And none of them have to do with how the buyer works. How would you recommend people start down that road that you’ve traveled,

Jessica Ryker
do the research first. So part of that idea of learning quota is making sure that you understand in depth what the benefit is, because when you believe it, you start to bring others on board. And so what I mean by that is when I sat down and met with sales leadership, and I said we’re going to align our sales process to the buying journey. Yeah. Why does that matter? Well, it matters, because studies have shown that just the simple act of having a buying journey, be part of your sales process improves your revenue goals by 12%. Crap, you

Unknown Speaker
pull that data.

The Collaborator
Okay, so you you went, you found some great data that backed it up, you shared that as part of the case that you were building and explaining.

Jessica Ryker
And then you back it up with how you’re going to help your reps to get to that 12% improvement. So it’s not just about so here, I’ll show you what we did. So, right, we have our sales process, buying journey and selling journey. So it’s not just about here’s the process, here’s what it looks like. But it’s also how do we continue to instill this over time. And so I put together a plan for how we were going to launch how we were going to reinforce that information and knowledge, how we were going to continue to keep it in front of folks. And then what I also did that I think a lot of enablement folks do, too, is I focused on sales manager enablement first. Amen. Because our managers are going to be meeting with these people every day, I can’t be in front of 150 reps. I can’t it’s impossible. I depend on them.

The Collaborator
You were better at your job, you could be in front of all 150 reps. Jessica. I’m kidding. Of course. Yeah. support that you have to scale, you have to find a way to scale yourself out. And the manager level is a smart way to do that.

Jessica Ryker
Absolutely. If you have, if you’re able to bring your sales leaders and your sales managers on board, and they know it like the back of their hand, and they believe in it. They will do the same thing for their reps. And so

The Collaborator
how did you? How did you enable them? I don’t mean detailed an essay at the super, super detail level. But how did you enable How did you convince them? And then enable them to start to roll out these pieces as you went forward?

Unknown Speaker
And then already Yeah,

Unknown Speaker
you know, yeah,

Jessica Ryker
most sales leaders already know. Yeah, what the right decision is or what the right idea is, and a lot of times they coach to it without knowing. And so, when you think about imagine a situation where your rep has has a deal in the upside forecast, not committed yet, but it’s an upside. Okay. Or best case?

Unknown Speaker
Yeah,

Jessica Ryker
whatever you might call it. How do you know that that’s in the proper forecast? How does your rep communicate to you that that’s the proper forecast? Is it about what they’ve done? Or is it about where their buyer is what their Learning from their buyer what they learned and discovery, how they know they’ve reacted to a price in conversation. It’s about the buyer, right? Always, if it’s just about how the rep feels about the deal. That’s bunk. And every sales leader knows it. So it’s Yes, it’s about pulling out statistics, talking about what we’ve learned as a sales industry. But it’s also reinforcing what they already know to be true. So when you come to the table, and you say to sales managers, we’re going to align our sales process to the buying process. And a lot of them are going well, what’s the point in that? Well, not only is there a lot of money on the table that you’re not taking advantage of, and there’s greater opportunity out there, if you have your rep start to think this way, but you already coach your reps to do this, this is about standardizing that process, so that it’s easy for the reps to remember. And it comes to their mind more often. And now you have a rep who’s thinking instead of where am I at, but where is my buyer. And when you do that, you’re able to help them move that deal through the journey faster, that sales cycles that can shrink, depending on how well you’re able to coach. And I know you’re all amazing coaches. So it’s really just about taking what they already do what they already know to be true. And reinforcing it. This is one of the other ways were being a lawyer and being really good at having those kind of leading people to water can be helpful.

The Collaborator
I kind of I kind of saw the lawyer mind working there. You know, he’s guilty. Let me explain to you why.

Jessica Ryker
Right. But you know, and it’s also fairly consistent. You know, a lot of times people know the right answer, but they don’t, they haven’t made the connection in their mind yet. So it’s just about helping them to make that connection. And you know, it, you’re also going to have people that also already know that this is the right idea, they’ve already thought of it they already understand. And it’s just about calling it out and giving them a way to do it. So that that was how I approached it as a as a solo with managers. Well, let

The Collaborator
me ask you this at latch, you’re gonna start a latch? Are you going to be the first enablement person there?

Jessica Ryker
I will be second, sorry, I will be the second enablement person, and they had an enablement person before. But they were a bit green, I think, yeah. And so they wanted to bring someone in that had more experience, and could kind of just jump in and hit the ground running. And because I have done this, as a solo, for a year and a half, jumping in as a solo, again, and getting started, is not a far stretch. So I’ve done it before I can, I’m excited to hop in and do it again. And the company is growing like crazy. And so I’m really looking forward to coming in, it’s gonna be a huge focus on onboarding, they’ve got a ton of new reps starting this year. So

The Collaborator
ask you, how do you determine how do you determine what the focus is going to be? How are you going to focus your own efforts for the first month or two? You know, coming in new brand new to the company? team of one again, more or less? Although some some stuff new to build on? Maybe not? How are you going to approach it? Jessica? I,

Jessica Ryker
I’m gonna do a lot of listening and asking a lot of questions. But at the same time in it was a rigorous interview process. So I met with a lot of folks, including the CEO, sales leaders, operational leaders, and one of the things they asked me to do was to put together kind of like a 30 6090. So I’m, I’m you got already, I’m already there. So I know that in the first, in the first bit, it’s building out a sales training program, not only to upskill existing reps, because they’re shifting from a hardware sales team to being software sales folks. And it’s it is a little bit of a shift. And it’s just about getting comfortable with that motion and feeling good about that. And so it’s defining the sales messaging for the product and the solution and really leaning into that, to get people feel uncomfortable about being software sales people building out their sales training program, both for upskilling. And then for onboarding, and creating content like playbooks buyer personas, the the like really like the crux of good enablement work. And then over time, we’ll be focusing on knowledge management, go to market strategy, channel enablement, because they do have channel partners as well. So in the first year, that’s kind of the scope but I fully anticipate that there’s More, I don’t know that there’s more that needs to get shifted and bumped around in the priority. But yeah, that the first 30 to 60 days is going to be a lot of listening a lot of learning and providing as much value as I can, knowing what little by then I’ll probably know. And also getting to know the product as best I can as well.

The Collaborator
Perfect, perfect. What happened we talked about Jessica, we’re almost 30 minutes in our Yeah, you’re like, geez, john, I wanted to share this is one point is two points, anything you want to share before we part ways,

Jessica Ryker
you know, our focus today was talking about operational success. And one of the things I want to make, I want to say is, a lot of times we think of sales operations and sales enablement as two entirely separate entities. And I want to break that down for folks, you may have a lot of things that you depend on operations for. But your job is an enablement, professional, especially if you’re a small team, or a team of only yourself, your focus on operations can make the biggest difference for your sales teams. Because when you focus, even if it’s something as simple as removing a few clicks within the CRM, you will get a lot of really positive feedback from your sales team, you will start to gain the kind of attention and trust that you really want to have. And so don’t set operations aside as something you don’t have to worry about or you shouldn’t think about it is vital to the success of enablement. And you you have all of the all of the resources at your disposal to do it. And so that would be my my one final comment is don’t shortchange operations, because it is absolutely the thing that has helped enablement be successful at helpsystems. And I will continue to focus on it as I move forward in my career.

The Collaborator
I love that, especially as especially as a small team and exactly what you said there, Jessica, I see. So often, you might be hired in as enablement. But that includes helping out with the CRM or other places. And your job is to make sure that sellers have as much time to sell successfully and then with the information they need as possible, right operations needs to be considered as part of that. And ultimately, I think operations and enablement and enablement are two sides of the same coin. It’s about helping sales. So we’ll have both and some will not. And that’s okay.

Jessica Ryker
And when you’re a solo, sometimes your operations, enablement training and anything else they can throw at you. If you are a solo, make a charter to defend your time. And don’t be the fixer of all broken things. Fix the things that have that make an impact on business goals.

Unknown Speaker
And that is

Jessica Ryker
the only other thing I’ll say about that. Because it is easy to fall into a trap of being a solo person, and there’s so much work to do.

Unknown Speaker
It’s so easy.

The Collaborator
always easy to be busy. It’s hard to have an impact if you don’t put thought into it. So I love that last bit of wisdom that Jessica planted out, make sure you’re working upon things that have true business impact, because we can all be busy being busy all day long. For simply being busy, and it’s not actually helping anyone. Nobody cares.

Jessica Ryker
Exactly. Exactly. And if you can’t depend on results, your or your people buying into what you have to bring to the table. You’ll never be successful.

The Collaborator
Exactly. And you’ll be looking for another job doing something else. Right. Remember that? My free good time today was wonderful. Thanks, john. Wonderful to chat. Great to chat if people want to reach out and ask any questions. Should they just reach out on LinkedIn?

Jessica Ryker
Absolutely. I’m an open book.

The Collaborator
All right, awesome. Thank you, everybody. Thank you, Jessica for helping us kick off 2021 Take care.

Unknown Speaker
Thanks. Bye