343: Digital Marketing Academy, with Jacqueline Cook

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Did you know that Conquer Local has its very own Digital Marketing Academy? It’s a game-changer because the SaaS industry changes under our feet.

We have Jacqueline Cook (Jackie), Chief Strategy Officer at Vendasta, on the podcast to discuss the strategy behind the Conquer Local Academy. After some research and listening to digital marketing agencies and entrepreneurs from different areas of the world, there was a realization that there was a need in the space for a digital marketing academy. It needed to be all-encompassing of various digital solutions that intertwine frequently. The Academy is built into a culture that embraces a community that agencies and entrepreneurs can grow and learn in. People learn differently; some learn by reading about it, and some want to watch videos at 2 am. The Academy was created to accommodate different learners in the way they want to learn and on their time.

Keep the conversations going in the Conquer Local Community.

She works with the CEO to shape Vendasta’s long term strategy and to align both the culture, organizational design, and company metrics toward those long-term objectives. Jacqueline works across a number of diverse teams to execute cross-functional initiatives, collect and share key customer insights, and test new initiatives to drive Vendasta’s growth levers. She is also the General Manager of Vendasta’s high-growth mid-market customer segment, which currently contributes over half of the company’s revenue and includes marketing, sales, success, support, and four product teams. Most recently, Jacqueline played a major role in Vendasta’s $40M growth funding round, which marks the single largest technology investment in the prairies since the Canadian Venture Capital Private Equity Association (CVCA) started collecting data in 2013. Jacqueline is an alumnus of The Next 36 Entrepreneurial Institute, Canada’s premier entrepreneurial leadership initiative. During the program, she co-founded and was CEO of Triumf Mobile Rewards: a tablet and Smartphone-based platform for small and medium-sized businesses to customize their own loyalty rewards programs. She has been a speaker at events such as Tejo Talks, sponsored by Canada’s Embassy to Portugal as part of Web Summit, TEDx UofS and WE DAY, and has represented Canada at the 2010 G8 and G20 Summits, the 2010 APEC Summit in Japan, and at the 2011 G20 Young Entrepreneur Summit in France.

Jacqueline has been a recipient of CBC Saskatchewan’s Future 40 under 40 and a YWCA Women of Distinction Award and serves on the board of Co.Labs, Saskatchewan’s first technology incubator. She was recently named as one of Betakit’s Canadian women in tech worth watching.



George: It’s another edition of the Conquer Local Podcast. Joining us this week, Jackie Cook is the Chief Strategy Officer of Vendasta. We’ve been getting a lot of questions around what was the birth of the Conquer Local Academy. What was the birth of this community concept where we have the podcast, we have the conference? We have now this resource called the academy and then forums. A place for partners to go and ask questions. We’re gonna bring in Jackie, she’s responding for this at an executive level in the organization, and we’re gonna drill her. We’re gonna ask a whole bunch of questions around what problem were we trying to solve. And I think that will really help our listeners understand what the resource of the Conquer Local Community and the various modules are and how you might be able to use that to benefit your organization. Jackie Cook, Chief Strategy Officer of Vendasta on the Conquer Local Podcast. 

George: Always like getting Jackie Cook on the show, Chief Strategy Officer at Vendasta. And we’re gonna talk strategy today.

Jacqueline: Let’s do it.

George: And I’m excited to talk about this strategy because it’s something that you’re super passionate about. Let’s set the stage. The stage is your 30,000 channel partners spread all over the world, dealing with four million local businesses or end-users. And sometimes it might be like herding cats. So how do you build an ecosystem where that group of channel partners feels supported? Do they have places where they can go to collaborate? They can, I really believe that this kind of sets the stage as to what we’re going to talk about today, doesn’t it?

Jacqueline: Absolutely.

George: How big of a problem is that for organizations as they start to scale and they have this two-tiered kind of customer base that they care about. You care about the reseller channel that you’re using, and then you care about the end-user? It’s not that you care about one more than the other, but it really, it causes this huge pain point that needs to be solved, doesn’t it?

Jacqueline: Yeah, and I think part of that too, is there’s just so much more cognitive load on that. For customers who have been direct channels, for companies who have a direct channel, you teach one customer. But with what we do at Vendasta, it’s learning what are those best practices. Then teaching those to our customers and training the trainer so that they can employ what we’ve all learned to their customer group. So there’s just so much information, and even hearing from our partners’ feedback of how do we keep up. And between the confines of nine to five, the hours that you’re open like I wanna learn, and I wanna understand more. But it’s unrealistic to think that I can sort of be handheld when there are better tools to learn and to digest some of that information.

George: Now the interesting thing is the term LMS, learning management system, is thrown around that acronym quite a bit. And one of the things that you and I have talked about over the years wouldn’t it be great to have a place where we could take something that we teach on an ongoing basis and make it scalable. So that people could come. Because, and the challenge that I’ve had where I’ve been training people face-to-face, and we did a lot of that work in the early years. You’re sitting with a group of sellers, you get to the end of a lesson that you’re teaching and you go any questions? And no one puts their hand up. Because you don’t wanna look stupid in front of your peers. It is typical, although there are questions. So how do we put that learning motion into a place where there’s a safe place for them to land. To ask what they may perceive as a dumb question?

Jacqueline: Yeah, well, and I think that’s the beauty of what this academy provides. I’ve been learning lots from both Sanjay and Cal who are instructional designers. And to think that every learner learns the same way is totally bogus. Some people like to learn by doing, and they wanna dive right in and try it themselves and then ask questions when they get stuck. Some people want to understand by reading and methodically digesting data in sort of a linear fashion. And other people want to see how it’s done, watch someone do it. And so in the academy, we’ve incorporated elements of each one of those styles. But the beauty in being able to take the training in sort of out of the day-to-day conversations is then our team gets to be way more consultative, on how to apply that knowledge. It’s not just about transferring that knowledge to our partners because our partners are busy, and they don’t have eight hours a day to just sit on a phone call and go through everything soup to nuts. But those that really want to dive deep can do it on their own time, at 2 a.m. on a Saturday morning, if they really wanted to, and spend the time to really dive way deeper into concepts that are way more applicable to their business and they can apply in real life. So that’s what’s been really exciting about this.


Game Changer: Kickstarting the Conquer Local Academy

George: Overused term alert, game changer. But I really believe that the ability for multiple users to be able to go somewhere to learn at their own pace. To learn the very latest information because we live in an industry where the world is changing under our feet. So you have to have that constant cadence, but it’s a safe place. It’s a place where they can go and I wanna go back to something you said. You have these two individuals that you brought onto your team that are instructional designers and they’re teachers by trade. Did you ever think you’d get to a point where you would be hiring teachers to support a software company?

Jacqueline: It’s so cool, George. We hired teachers; we’ve hired police officers; we’ve hired all of these, I’m-not-in-tech type of skill sets that are so relevant, so applicable. Teaching is about, our VP of design, Bryan Larson, the master of storytelling, the master of experience, he is a teacher by trade. And I don’t think that’s a weird coincidence. I think that’s, there’s really something about being able to communicate a concept in a way that someone understands in the least amount of time and friction possible.

George: Now I wanna make sure that we get some lessons from Bryan on how to tell that story. Bryan is probably one of the best storytellers that I’ve ever met. And part of it is the work that he does ahead of telling the story to get prepped for that. But it is cool, I was listening to a podcast over the weekend and it prompted me [to think], “Oh, by the way, I need some budget because we need to get a psychologist on our sales training team to help people when they’re going through a slump.”

Jacqueline: You’ve been watching “Billions” again, haven’t you George?

George: Absolutely, he’s one of the most important people in the C-suite on that show. But it’s interesting here I am as a sales leader used to have this lens of, no get off your ass go talk to customers, that’s how you sell more. And then we interviewed Jason Forest, a few podcasts back where he talks about the fact that sales is such a mental game. I think I’m gonna misquote this but it’s something like this, there’s no other business in the world where we get punched in the face all week long. And then you have one win on a Friday, and you’re like, “Wow, this is the greatest job ever.” But the rest of the week has just been failure after failure after failure. So it’s interesting as we look at the skill sets that are needed to pull this whole thing together. What was the impetus or where was the analog when you were thinking about we need an academy, or we need more than just an LMS?

Jacqueline: Yeah, I think that’s really important to go into George, I’m glad you asked that question. There was a perfect storm of events brewing. So on one hand, as you obviously and many of the listeners know, Vendasta raised around $240 million in the summer of last year, and that was to accelerate the growth of our organization. And what that meant is we were going to be going from about 300 to about 500 people in the span of under 12 months. And so, especially in the sales organization, rapid growth in bringing people on, and sales you can’t, as much as we try to systematize it and create a process around it, you gotta know a lot. You gotta understand our customers deeply, you gotta understand our products deeply, the market deeply, how to support our customer experience or customer journeys, there’s a lot to ingest. And the biggest fear in that acceleration path was taking some of our top members off the front lines in order to train the next crop and we simply couldn’t do that. To decrease efficiency and attain the targets that come along with raising a big round like that. It just didn’t make sense. And so on one hand we had, how might we grow Vendasta at the pace we need to hit this next milestone. At the same time, what we were noticing was that a certain segment of our customers as we sort of move down market and brought on different types and segments of customers, they didn’t often operate at the traditional nine to five, Monday to Friday. A lot of them were either moonlighting or overseas or out-of-office hours. And so to give them the support that they needed, was just unrealistic in a one-to-one method. A third compounding factor was, this is really interesting too and we’ve seen this for years is when we say something to our customers, with the most endearing intentions. We’ll tell [them], “Hey, if you’d send out these freemium solutions, and incubate and marketing automation.” They’ll take it with a grain of salt, understandably as I do with any software partner that I use. But when another customer of ours tells them that exact same thing, it’s amazing how they employ and how they trust. And so part of the academy and the community is also about how do we get our partners teaching new partners how to be successful with the Vendasta platform. And for us to really just get out of the way. And the last thing I’ll mention. And again, this is a perfect storm of all these events was there was this thing called the COVID pandemic that happened. And just like every organization around the world, we were forced into a remote work style. And our partners were forced into a remote working style. And a lot of them, unfortunately, had business slow right down to a halt. And so what we saw is this increase in engagement really is from our partners and for their customers who also had closed signs on the doors. They said, I finally have time to learn this stuff. I finally have time to understand what my digital doorway looks like. Or as a partner understand what my stack looks like and really where I can be taking advantage of efficiencies or cost savings. And so we put really all hands on deck not just to create remote tools so that they could continue to operate remotely, but also so that they could learn and soak in all of the knowledge that we had been building and that we’d been making available to them and their customers over the last three to four years.

George: We’ve been interviewing a number of people during the COVID time and one of the things that this forcing function that COVID was for organizations was the ability to stop the whirlwind. And I’m quoting from “The 4 Disciplines of Execution” Chris McChesney, Jim Huling, Steve or Sean Covey, not Stephen Covey. Great book around, same basic principles of John Doerr’s “Measure What Matters”. But it’s this idea of you’ve got your job, and your job is the whirlwind. And the whirlwind keeps you away from the things that you know you need to do, which is I need to go digital with my organization so that we can conduct transactions online. I think a lot of businesses wanted to move towards e-commerce. But the whirlwind kept them from doing that, they were doing other things. Then there’s also this thing of, well, I should learn more about what I could do to better serve my customers through digital marketing, but the whirlwind sucks me in it. And as business owners and entrepreneurs, I think that those business owners have two whirlwinds. They’ve got the whirlwind of their business and the whirlwind of their family life as well. And then what’s left over is this learning component. So COVID comes along, we got lots more time on our hands. We actually are learning ways to be more efficient. You think about sales reps getting in a car driving across town, client declines the meeting. You just wasted the commute time, the meeting time, everything and you’re sitting here going oh over COVID I was doing remote meetings and I was able just to stack them in and talk to way more people. So it’s really interesting how this, you said we had this event that occurred. 


Learning at Your Own Pace in Your Own Way: A Recipe for Success

George: What are you finding in the early iterations of the academy around feedback from learners? And what are you, ’cause there’s two customers here. There’s the learners and then there are the people that are delivering the information. And I think there’s frustration on both ends. The people delivering the information and doing the teaching are saying, and I’ve said this, this is why we did the podcast for God’s sakes. If I have to train on the customer journey one more bloody time, and so we were like, oh, I’d like to learn the customer journey. Listen to these five podcasts, where one I pontificate. The other four, we bring in experts that validate why the customer journey is so, it’s scalable.

Jacqueline: Yes.

George: But it’s more than scalable, because scalable is our win. But for the learner, it gives them the ability to learn at their own pace.

Jacqueline: And in their own way.

George: In their own way.

Jacqueline: At their own pace, but also on their treadmill or when, or the other brilliant thing, and we’ve had a lot of feedback right at the beginning is now I don’t have to train my staff on Vendasta. I can plug brand new people into this ecosystem. And that frees up time in my day to do things at the strategic level as well. And a lot of this was so yeah, selfishly, it was really about, how do we scale this but more than that, and it was way more than that. It was how do we teach people, take all of this tribal knowledge inside of the brains of George Leith and inside of the brains of frontline folks that have worked with tens of thousands of partners. And share that in a way that people want to digest. So it’s really about, I can grab off the shelf what I care about, rather than I have to sit here and just listen to whatever the person teaching wants to tell me about.

George: Well and one of the other big challenges in this space that what I like about having a hub or an academy that you can put the content is that the bloody stuff changes. And one of the challenges we had is we’re going to go over here and we’re gonna do this course. And then the very day that you get the course finally produced and populated, wherever you’re gonna put it. Google changes their algorithm and everything that you have in there has to be redone. And that is a struggle for the teacher. And it’s a struggle for the learner. That was another problem that we believe we’ve come up with a bit of a solution through this methodology in the system.

Jacqueline: Yeah, and that’s always held us back from this. You know that, George,  is like why do we bother putting in the effort if it’s just gonna change right away? Hello, that’s why we’re in this space. That’s why we’re all in this space, is because it moves so quickly. And we can keep abreast of these things and we can share that knowledge so our partners can keep abreast of all these solutions and changes and ecosystems. I mean, that’s why local businesses and large businesses and massive enterprises need help with this stuff is ’cause it’s not static. And it does change frequently. So yeah, we did get a lot of pushback internally just on what happens if this becomes out of date? Well, at least it’s this current, and at least we have something because the alternative is nothing really.

George: Well and the alternative is confusion. So first off, now we’ve got these lessons, okay. I’m a big proponent, as you know. But then, there was another magical thing that kind of occurred when we gave this ability to have a forum where the various people that were taking the courses could start to interact with the very people that develop the courses or would be developing the next course or others that had taken the course and start to have that communication. And that really was the ah, the magic moment for all of us when we started seeing these layers of communication. And I think it made us respect the level of responsibility that we have for our customers because you could just see how serious they take everything. And we knew that, but when you read it, and you see the comments, and then you look at the timestamp, and you’re like, that was at 3 a.m. That person was either in South Africa and it was their morning, or they were really up at 3 a.m. losing sleep over this question that they had. And that’s why they reached out into this community or this forum.

Jacqueline: We’ve had almost, so we’ve had over 3,000 learners, I believe, to-date. We’ve had over 100,000 hours logged like, the amount of engagement in the academy has been tremendous. Because again, people finally have the opportunity to learn but what you’re hinting at is those community forums, and we’ve launched now the ability for our partners to connect in a safe way and to share best practices and to speak to each other on what they’re learning. And that was always something that we were totally divided on is some of us are like, wow, they might compete against each other. They might be in the same market, they wouldn’t wanna share best practices ’cause whatever. But it’s the exact opposite, and really I think a lot of this came from our Conquer Local Conferences. We had someone and I can’t remember which of our partners said, as soon as we launched this community it was now rather than once a year, I get to connect with the Conquer Local community every single day, 365 days a year. And one of the proudest moments I think of this is one of our partners asked for help on, does anyone have any tips on sales training remote teams? And like four partners just, yeah, I’ve done this here I could, connect with, DM me, yeah, I’ve also done this. And they’re just willing to help each other and they’re willing to share their war stories. And maybe they compete, there’s just so many businesses out there that need help with this stuff that the pros and the positives and the ecosystem overall is outweighing anything we were worried about before.

George: Well, and it was I remember speaking to Amy DeLardi who is one of our partners. She’s okay with me saying her name on the podcast. And Amy has been in the web development business for 20 years. And she has customers that know her and love her in the web development business. But she knew that she needed to solve more of their problems. But she knew for a long time, and then when the community and the academy arrived on the scene, she said what I really needed was that push. Was others who had been there, done that and what it meant to their business. And she said by having those case studies and really having those conversations, it removed, I talk a lot in training about removing the fear of the prospect. And the reason why people don’t make a decision is the fear of making the wrong decision. So then they just are setting this place where they don’t make any decision. And they’re really hurting themselves. And what we’re hoping to do with the courses is to remove some of that fear. I don’t know this oh, they’re in the course now, the question is answered. But then to have that learning validated by actual street level experience, seems to really be the missing piece. Because we had YouTube channels for a long time with lots of training, I can go back and find a Jackie Cook webinar from six years ago. But it didn’t necessarily mean that that learning was leading to motivation. And I’m quoting Sanjay, where he said, that you can teach him something but doesn’t mean it motivates him to take some sort of action.

Jacqueline: Totally, yeah, totally. And I think too some of the feedback we’ve got, especially in the academy is you guys release so often. Like we have 19 software teams, and they are tasked now on weekly sprints. So they release often, there’s always, and it’s never fast enough if you ask Brendan King, right. But to our partners, sometimes they, as much as they read our newsletters and they keep abreast on what’s coming. To be able to digest that in a very structured way on their own time has been really helpful for them to identify like, wow, you mean I have this whole CRM or I have these remote book me now tools or I have all this for free? What, I didn’t know about that before, but people are busy like they don’t have, I delete emails all the time. I just, can’t keep, so the academy specifically is the place that you can see what’s really there and we’ve kept up to date through a sort of academy-first release model, as well as now the community you can see what’s worth really looking in and diving deeper into.


Problem Solving: Forming an Ecosystem to Help Partners

George: So in the strategy that you had for bringing forth this academy, the forum, the community, where do you think you are in the problem you’re trying to solve? I know it’s a bit early, but I think it’s important for people to understand that this isn’t a game changer overnight. It’s a game changer that is going to have a lifecycle. And where do you really think that you are in that lifecycle today?

Jacqueline: Yeah, so the first problem we wanted to solve was, how might we allow our partners who have a little bit of downtime to take advantage of this downtime with them and their staff, and to teach them about the Vendasta platform? The second problem we set out to solve was how do we bring in experts from around the ecosystem and around the world, people that know way more about way more things than we do to help these 

partners of ours be successful. So it’s really about bringing in external thought leaders into this academy. So you’re gonna start seeing way more of that. Next, it was how do we connect and create these magical collisions of our partners to share their own knowledge of what they’re learning with each other. And start to sort of highlight some of the partners that are thought leaders and have been with us for a while or are totally new, and they’re just killing it and finding new tactics and innovative ways to take the solutions to market that we’ve never considered. I think next is, and this is an evolution. I don’t think this will ever stop. We’re always gonna be building this community but something that I’m seeing on the horizon and we’re all seeing is there’s an appetite to leverage each other’s expertise and skill sets. Take Amy for example, or anyone that sells, I just sell websites. But I really know that I need to get into SEO, but it’s not my skill set and I don’t have the expertise there or even something further like online security solutions or accounting, G-Suite. Things that my customers are asking for, that I don’t quite have the capacity. And so this idea of peer-to-peer sharing and being able to hire out the knowledge of the peers in the Vendasta ecosystem is something that, I don’t know, it’s starting to take waves and we’re seeing these collisions and I think we can help enable it.

George: Yeah, not to oversell because I never do that. But of all the initiatives that we have driven forward together over the last six some odd years. It’s the one I am the most excited about because of the ability to see the comments from the user and how it’s really changing the game for them. 



George: That’s really where I see the game changer, the game changer, that old sales training thing of, you gotta focus, if you’re gonna land a plane, they teach you right out of the gate to focus on the horizon. Because if you look at the ground you crash every time. It’s the same thing of outcome based, if you think about the outcome that you want for your customer, and you’re aligned around making them successful, the bonuses just happen, the quota attainment just happens. It’s a crazy thing, there’s a lot of work that goes into that but if you think about that, if your goal is to make that person successful, and that really is the underlying tone of all of these various, there’s a lot going on here. There’s a lot of brainpower, there’s a lot of technology, there’s a ton of money that’s being spent. It’s a big part of the hiring plan where we’re fortunate we were able to raise the money to be able to invest, but when you see the result at the end of the day of the learnings, it really is a cool thing to have a look at. Jackie, always a pleasure having you on the show. I know that there’s been a lot of questions around the academy, the podcast, the Conquer Local Conference, and the forum and how it all ties together with the platform. We’re gonna have this as a resource now where we can send people to hear that vision. And the banter that we’ve had about why we did it and where it’s coming from and what we’re trying to accomplish. I guess now, the next thing is, what if people wanted to offer suggestions? What if they wanted to get a hold of you or any of the team on ideas that they have to help us evolve this massive resource?

Jacqueline: Well number one, I would say join it. I can’t stress enough how brilliant it’s been for all areas of our organization. Our product managers are in the community. Our product marketers are in the community, our sales teams are in the community, people are watching there because they see we’ve actually got rid of software tools that had other channels for customer feedback, and we’re only using the community. So if you wanna get to the right eyeballs on Vendasta task manager and how to improve it, that is the place. As a community overall, I would always love to hear from you guys at any time about the direction or what we could do to make it better or things that we’re not even thinking about. I mean, send me a quick email, jcook@vendasta.com. I’d love to hear any feedback. It’s evolving, be patient with us as we figure this out. We’re just doing it again in the idea that this is a year where our partners really share with new partners and existing partners, their success, their triumphs, and we just get the heck out of the way. And we listen and we support and we do whatever we can. But it’s really about you guys and making you successful. So any feedback you have on that we’re dying to hear it.

George: Chief Strategy Officer, General Manager of the Mid-market division of Vendasta, Jackie Cook joining me on the Conquer Local Podcast. Thanks Jackie.

Jacqueline: Thanks George, take care.

George: Always a pleasure having my colleague and friend Jackie Cook on the Conquer Local Podcast. And a lot of requests to understand more about the online academy. The fact that we are embracing e-learning inside that academy. And to build something that really will enable our partners to be industry-leading in the way that they solve their customers’ challenges. The community forum is going to be that place where you can go ask other organizations that are dealing with the exact same things that you are. And we’re really excited about the early feedback that we have been getting from our partners around the world on the value that they’re finding from the academy. But as Jackie mentioned at the closing of her comments, we really value the feedback and we take it very seriously. And we wanna understand where we need to go to solve as we move forward. So feel free to reach out to Jackie or to myself. And we look forward to getting that feedback as we continue to groom what the Conquer Local Community and its various tenants will look like as we move forward in the years to come. Thanks for joining us on this week’s Conquer Local Podcast. My name is George Leith, I’ll see you and I see you.

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