SaaS Breakthrough – Featuring Jake Braly

About Jake Braly:
Jake Braly is the Vice President of Marketing at Highspot, responsible for market development and global growth. Before Highspot, Jake led product marketing and go-to-market strategy for Apptio’s top grossing products through its successful IPO. Prior to Apptio Jake held various positions at K2 software, Microsoft Corporation, and IBM as well as multiple startup and early stage ventures. Jake holds an MBA from the University of Michigan and a Bachelor of Science degree in business from the University of Colorado.

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Show Notes:
A Sales Enablement Solution that Sales Reps Love
Awareness and Rapid Maturing Market
Built With Sellers Experience In Mind
Evolving the Messaging and Positioning
Creating An Urgency Factor
Leveraging Own Platform to Make Informed Marketing Decisions
Organic Channels and Personalization via Direct Mail
Direct Mail CTAs
Experimenting: Prioritize On A Continuous Basis
Kanban Boards, Objectives and KPIs
Next In 2018: More Testing, Extending and Amplifying Thought Leadership
Running the Largest Sales Enablement Industry Event In The World
Lightning Questions

DA: 02:12
Hey Jake, what's going on? I'm really excited to have you here, have your company here. Tons to talk about today. I think we have a very, very interesting episode. Something we haven't talked about yet on this podcast, so I really appreciate your time. How you doing today?

JB: 02:26
Good, David. Thanks for having me.

DA: 02:27
Yeah, no, it's our pleasure. Really happy to have you here. And I know we have a ton to talk about. There's a lot of marketing experiments that you guys are working on that really stood out to me. So why don't you just jump right in, give us a little bit about Highspot, who your customers are and what you guys are doing uniquely in the marketplace.

JB: 02:44
Yeah, absolutely. So, we are a SaaS software solution, for sales enablement and we really position ourselves as a sales enablement solution that sales reps love. The core capability of our software is really five primary use cases. So when we think about sales enablement at the core, there's content management and then there are the things that our sales enablement team or practice needs to be able to do to ready their reps. so sales communication, sales plays that bring all of that together and provide direction and sales training. Those are three primary use cases that our product supports. And then finally, all of this is happening so that sellers can better engage their buyers and prospects and we have a lot of technology that helps them do that. Our customers are really sit both sales and marketing teams, which you might think of as the go to market pieces of the business, that really do sales enablement as a necessity for competing in today's market and being relevant with the way B2B buyers are behaving today.

DA: 03:50
So you said, a certain level of awareness. Does that mean you guys are working specifically with, sales teams that already know about tools like this? Is that just where you guys are in the marketplace?

JB: 04:03
So I think if you stand back and look at sales enablement as a practice area, what's happened is there's been a rapid maturing of this market. And so we're five years ago, we might be describing what that means and what that is to an organization. What we're seeing now is that sales enablement is a known quantity in terms of what it means and its importance to a company. And they're starting to in turn, become familiar with all of the software solutions that are required to be able to do that well. And so I think what we're seeing is a really rapid maturing of this market driven by that changing buyer behavior and the fact that we really have technology pervasive in all lines of business now.

DA: 04:45
Totally, absolutely. And I think one of the, one of the things I want to get into is marketing experiments that help you differentiate as that market matures, but it's so interesting to join a market and to see it mature and kind of get that right timing because you're right, like five years ago, it'd probably be a ton of education to talk about why they need this now. It may be more so why you're the best. So that level of awareness has gone up now. When did you specifically join the Highspot team and what was the company like? The customer size maybe at that time?

JB: 05:14
Yeah. I joined a year ago and when I joined we were probably in the order of 80 or so customers and in that space of time we've more than doubled our customers. We've doubled our head count and we've also been able to get really good retention and recapture for our existing customer base. And so, we're obviously benefiting from that timing and market that you described and we don't see it slowing down. In fact, we see just the opposite, that really the need for this kind of technology, is getting kind of a critical mass and seeing a tipping point where, you know, you can envision every organization needing to have this to, to successfully compete in the market.

DA: 05:58
That's fantastic. So you've almost doubled growth or you did more than double of customer size, you grown the team. Sounds like growth is amazing. When you joined a year ago, I'm not sure when the company was founded, but when you joined a year ago, what was like the company like, what was the major pain point that you guys were trying to face and why bring on a VP of marketing at that time?

JB: 06:18
Yeah, so I think, you know, the company really in earnest started going into market and about 2014 and just like you said, at that time, I think there were still some education to do, but the timing was good. The team and the founding team, Robert Wahbe, our CEO, along with the rest of the technical co-founders really had a vision around building technology to make sellers profession and what they needed to do by giving them the content that they needed when they needed it. And that was really the core of the idea and the technology was really thoughtfully built from the ground up with that seller experience in mind. Because if you think about CRM and if you talk to sellers about how they feel about CRM, you're not going to get warm and fuzzies. And so having a solution that was intuitive, useful and worked in the all of the areas that sales reps were already working was really important and that has allowed us, I think to be in a great position now fast forward several years where we are starting to get rapid adoption, with our existing customers and great, acquisition of new customers as we continue in this market.

DA: 07:32
So a lot of product evolution in the early years and then bringing someone in to help then to market and acquire more customers is basically kind of what that journey was. And when you came in and you're coming into a product that's maturing heavily, it sounds like from the engineering side you're adding in features and stuff for the sales reps, what is it like for you to come in and start looking at the landscape, starting to look at, okay, this market is maturing, this market is getting more competitive, how do we stay different and how are we unique? What does that look like from your position itself as the VP?

JB: 08:05
Yeah. You mentioned kind of messaging and what are some of the things that I observed a year ago when I came in and, and how I evolved, and one of the things, because we were such a great technical, offering with an incredible team that developed the technology, what that translated into is a lot of incredible technology that we were also trying to communicate to the market at that time along with the education. And so my job was really to evolve that messaging and the positioning in two different ways and I think, you nailed one of them, which is how do we uniquely stand out from a lot of very noisy other solutions in the market and rapidly evolving solutions. So that was a primary. The other one was how do we evolve from talking about product and technology to talking about business outcomes, business impact and, and really buyer persona pain points.

JB: 09:05
And so over the last year, I feel like we've made great progress on both of those fronts. If you think about marketing messaging really coming to life, via our website, that's where you'll see a lot of that new positioning and messaging and the positioning and the differentiation that has really helped us is where our roots started and that's why I wanted to give you the visibility into the focus that we've had at Highspot on the sales experience, in the sales user experience because ultimately that drives sales adoption and you have to have sales adoption and usage of a product like ours in order to be successful. And so the position that we have is we are the most loved sales enablement solution. For that, that user that matters so much which is a sales rep.

DA: 09:58
Does that mean that you are on calls with a lot of the customers to learn? I guess not just about product, which sounds like maybe the founding team came from sales and they already had an idea of the pain points. Is it just that constant communication and understanding like what are you actually getting from our product? What is the value that each feature is standing out for what each feature is doing for you? Is that how you then translate into better languaging or what's that process like?

JB: 10:29
Yeah, so I think, you know, actually our founding team is largely technical and background. Robert, our CEO has a, has an extensive technology background but has also spent time in marketing which is unique I think for a business leader. So it, it really did require an evolution in terms of, look, we understand some of the core pains around, the need for a solution. What we, what we had to evolve was understanding what are some of the business reasons and business rationale that's going to make somebody take action and make a purchase. And so you're absolutely correct, it requires talking to a lot of people in the space, both practitioners but also executives, both sales and marketing executives understanding what their pain points are, why something like sales enablement, our solution for them would be important to them. And then working to really show them how it ties to very significant business impact and results. And for us, that means competing and winning in today's market. And I, every business leaders thinking about that. Right.

DA: 11:40
That's very, very, very, very tough. So it sounds like you, are you working together with customers to create case studies or winning campaigns that you can then utilize on the website to say, hey, listen, Highspot is the best because of x customer story where he went down the exact same journey that you're on and was able to 10 x the results or something like that. Is that kind of the major way to stand out with results in that area?

JB: 12:05
Absolutely. I think, there's an urgency factor that we want to create and actually I think has already created in the market, but I think it's tying sales enablement to that urgency and helping the market understand that, that's the message that you'll see. And so for the first part of our fiscal year, we've been in market with a, what we call modern campaign or a modern theme program. And the whole idea around modern is to really expose that idea that like, look, you're doing it the old way. You're doing it wrong and if you're doing it the old way, you can be sure that your competitors are starting to move away from that. And ultimately that goes back to the, this is the way that you have to win deals and be competitive in today's market to have sales reps that are equipped with the content on there already at their fingertips when they need it, where they need it for immediate buyer engagement interaction.

JB: 13:01
If you don't have that, then you won't be able to successfully compete. And so this modern campaign for us is really focused on those big change factors that are driving this, the modern buyer, which is about new and different behavior, moving very fast, consensus driven sales cycle. A modern sale seller. And so what does the sales rep have to look like and do to be valuable in that process because most of that decisions happening before you even talked to a sales rep. and so what's the value add and the need that it's required to be a modern seller. And then to the last point that you made, we have the modern company component of it, which we think of a modern organization and yeah, we bring that to life through those case studies where companies who have adopted this and are doing this are winning companies and we can very clearly tie that to the business impact and results. So I think you're spot on in the ways that you're thinking about how we bring that theme to life and help drive some of that urgency.

DA: 14:01
That's fantastic. And it sounds like you really try to do more than tell, you try to paint the picture. You try to show what the product does and why you need to evolve to a certain level. So you've, you've literally laid the path of what they need to understand and see themselves as and maybe what they're aspiring to do and then showing the benefits of that. Your product can do that because you are the right company and here's the results of other people. So that sounds like an absolutely incredible marketing campaign. Since you've joined over the past year and I'm just going to fast forward here, what, what in the actual campaign types, like this modern campaign or what type of experiments have you seen that have actually stood out in this more competitive market now? Is it, you know, are there certain channels that have worked best?

JB: 14:47
Yeah, I think, you know, the one thing that we're kind of all coming to realization around, as modern marketers, is that a email as a channel is, has become a very difficult channel to break through the noise and the, you know, there's been a lot of focus within the industry around account based marketing. And while I think that that's incredibly valuable, I think it needs to be appropriate for any given organization and where they're at within their industry and what they're offering looks like, what their go to market looks like. And so, so for Highspot, you know, we very much believe in leveraging our own, our own solution to drive our own go to market. And a lot of our testing has been done via content that we're using within our own platform and the ability then to get analytics to inform. Okay, well what changes do we need to make, what sales content is actually a) getting used by our sales force and more importantly when it's getting used, what's being engaged in what's being engaged successfully and so that actually helps drive a lot of that kind of iterative testing, that we do in our own go to market.

DA: 16:00
Oh, that's fantastic. It's always so great when you can use your own product to learn to market and then in turn it kind of completes the flywheel of, you know, fixing your product the way you need it and you are basically your own customer, your own campaign. You can kind of optimize for that. Now with acquisition, now you're talking about direct selling with acquisition. Have you guys done any type of outbound channels, like a direct mail or something like that?

JB: 16:27
Yeah, so if you think about our outbound side for our go to market and our business, we absolutely have a marketing outbound motion and all of those channels and we also have more of an account based approach to tele prospecting and account development. And so, that was really the comment around using our own platform is primarily around that, that account based selling outreach and that motion on more traditional marketing channels. I think what we're looking at there is, you know, we, we very much focus on acquisition through organic channels because we think it's most important that you have to capture a prospective buyers that are nearing the point of consideration and intent. (...) That's right. And so we absolutely try to get the highest level of intent and awareness first and we do a lot of that by focusing on our organic and search engine optimization or around that. In terms of other communication channels that we leveraged for inbound lead generation. As I said before, email, and this is a statement on both the outbound selling side, but also an outbound marketing is just become very noisy. It's difficult to really break apart, get attention. And so we have looked more as a direct mail as a way to help us break through and do that and to bust through the noise a little bit in a more personalized way.

DA: 18:01
What kinds of things have you seen that have one in direct mail? It's one of those forgotten channels. People don't talk about it as much, but I've been talking to more and more marketers who are saying exactly what you're saying. Email is getting cluttered. People are trying all these different channels and direct mail has become a winning channel. Again. What have you guys taken away? What has been a major win on your end?

JB: 18:23
We haven't, if you think about more kind of traditional tactics like clutter busting and having something show up on the desk. Those are great. I think it's successful when it gets attention. That's success number one, but I think what we're finding is you don't need to just grab the attention. You need to grab the heart and for us, a lot of our direct mail campaigns, we try to give something personal, whether it's a, you know, a bottle of wine or a some some unique hot sauces from our region. Something that that actually says, yeah, we were thinking about you and you uniquely. It's not just kind of a marketing shtick that we've put out on somebody's desk, and that just becomes another piece of marketing collateral so that the more personal feel that we can bring to it, I think has shown really good results for us.

DA: 19:17
And so just to kind of reference for any listeners, you're doing this in almost an ABM style method where you're going out and you're doing prospect research of like the perfect target customer, right? And then you're saying, okay, we want to find these 10 people will be perfect prospects. You're then investigating them, learning more about them, finding a product that would fit them based on likes, interests, trying to get their attention to then, open a conversation with a sales rep to learn more about the product, but you're going more as like a direct method. And the direct mail piece is a direct like ABM outreach.

JB: 19:52
That's exactly right. I mean we, we very much leverage hand written cards. Again, anything that can, that can be more personal, better. And you know, there's only so much that you can do at scale, but at scale you can, you can do different things as well. It might not be the same level of personalization, but you can still convey a personal touch and the kind of outreach that you're doing. And for us, those, those type of direct mail campaigns have been most successful. And it's got to be tied in also to an integrated motion. And when I, when I say an integrated motion, I mean it's not just a marketing channel, but it's marketing channel also that is brought to life through all of the sales and demand marketing that's happening around it as well.

DA: 20:42
That makes sense. I remember we were actually going to do a campaign type very similar to that and we had our target list kind of laid out and we started going through and making notes of different things that people would be great (inaudible). And one of the ideas that we had was to create custom pillows with quotes that those people said online and all of our target market people were influencers that we wanted to get in touch with the thing that we didn't. And it was really cool. It came out really nice, but we didn't actually match them up because we couldn't. We didn't know the best way to then have the campaign call to action. So when you guys are sending these gifts, yes, it's great. You get in front of them and your brands that are like, oh, this is great, this is awesome. What does it call to action to get them back to, you know, create that relationship or open the door to then get on a call with them. And then of course, are you thinking of it as a longer sales cycle? You just opening that door for a relationship or are you going pretty hard after saying, listen, we'd love to have you sign up for our product for a trial like on the first call.

JB: 21:40
Yeah, and it depends on the kind of campaign we're running. But where we've seen the most success and partly this is because of the nature of our business model and who we're reaching out to, that that call to action really is a response and it's a response, to an individual or it's a, it's a response, as a call to action, in terms of requesting a product demonstration. Those are really two of the primary calls to action. We're not going and sending somebody to a unique landing page for the most part. Those have not for us and what we're doing always ended in the, in the right kind of conversion. But there's certainly a place for those. And I think, you know, like your pillow story's kind of funny because, you have to have some ability to close the loop on it. And if you don't have room in the box for the primary thing you're trying to do, which is your CTA, then yeah, it's going to be very difficult to tie a ROI to your direct mail efforts.

DA: 22:45
I think it's a really great piece of advice that you're just looking to create the relation to look for a response, a call, you know, reach out, just something that opens the door for that connection. You know, we definitely had the thought of do we do custom landing pages? There's all those different things. And it brings me to my next question, which is, when do you know for you guys, like how are you doing testing to know when it's time to move on to another experiment? Are we changing a channel? Like what are you like, what becomes the benchmark for when you need to break out and try something new?

JB: 23:16
Yeah, we, so the way that we, we have tried to get a little bit scientific about our growth testing, but we're not trying to over architect it. And we do have kind of an internal committee that takes a look at our growth tests on a weekly basis and prioritizes them. And so we have a lot of ideas and demand for different tests that we want to do across the business. And we try to do is prioritize running no more than three at any given point in time and for each one those tests, we have very defined goals and hypotheses that we're trying to get to and so it always varies. I don't think there's a, how we don't necessarily have a, how we know it's time to try the next one. More so we look at all of the tests that we could be doing and we prioritize them on a continuous basis.

DA: 24:04
That makes sense. Do you guys have a time that you sit down and just come up with ideas or is that part of the organic process as you look at things like KPIs and stuff like that? Are you just thinking, that would be cool to try something different like this and you just writing them down and then in the strategy session you're organizing them?

JB: 24:19
Yeah, that's exactly a good description. We use a Kanban board and for any kind of new idea, which might happen organically in any, in any venue, we can forward it off to the length that automatically it to the incoming on the Kanban board. And then those get groomed into. And more fleshed out, and as we determine we want to run one, then it would get a full, I'm kind of one page, a synopsis and objective doc that we would then put in place before we actually started the test so that we can come back to it and determine if it was successful or not.

DA: 25:00
I always find this interesting. How do you guys come up with your objectives if you just kind of pull it from previous data, but if it's new, if new experiment, how do you know what the objective can actually be?

JB: 25:12
Yeah. So for a specific, there's the broader objective which always has to tie to our corporate corporate goals and so, you know, the ideas that we have fall into those different theme buckets. And we have very specific ones. Like engaging influentials is a big strategy for us. And so we have different tests that we want to run. It would, it would fit within that category. But then as you're going into specific test with any kind of larger objective area to get to an objective for that specific test, we do have to look at historicals, we have to make some assumptions. If we don't have a historical run rate, if there's external benchmarks, we might want to look at those or it might just be a test that were, you know, the hypothesis we don't know, but we're, we think and hope it would be like, like this. And then we determine how close or how far we are from that once we put a test in flight.

DA: 26:06
That's awesome. And do you guys have like a set marketing team KPIs? Are you doing KPIs on a per experiment basis? So it's like we have to have unique KPIs for our direct mail campaign versus you know, another campaign.

JB: 26:20
Both. Yeah we do. So we have, you know, my team has goals that we want to accomplish on a quarterly basis and for the year. Everybody on my team has quarterly objectives and KPIs that are tied to that. And then I think the level down from that would be some of the very specific campaigns, tactics, tests that we're running, would each have unique objectives for my team. Those tend to fall, within three areas, are we regenerating leads, are we regenerating quality and velocity, so really conversion and velocity, and are we influencing and impacting revenue that's active and in the pipeline. And so they all tend to ladder up to those, which of course are shared goals that we have for our organization.

DA: 27:08
That makes a lot of sense. And that's all set by leadership, the general overall ones.

JB: 27:13
That's right. Yep.

DA: 27:14
That makes sense. Awesome. Well that's really super solid and really great advice across the board. I love how you guys are doing this really strategic, experimental process and how you kind of layered this out and I love the idea of these cascading KPIs all the way through the organization and looking forward, I guess the rest of 2018, which is crazy to say there's not many months left. What are you guys going to do to stay competitive? Stay relevant. Do you see marketing evolving anywhere? Do you see experiments going a certain direction?

JB: 27:46
Yeah, I think we have made a dedicated focus and the focus is working for us, which has really been positioning ourselves as a thought leader within the sales enablement space. And so what that means and looks like as high quality content and thought leadership, it looks like best practice sharing. I think from a technology and channel perspective, we have more testing and things that we want to do around interactive video, formats, mobile formats and things like that. And so I think as a marketing organization, those are kind of the areas within the business that we're focused as a company, how we expect to remain competitive and relevant in this market is really through leveraging all of that thought leadership, but then extending and amplifying it through the thought leadership community, which includes all of the industry, subject matter experts and luminaries who have large followership center are influential in this space. And so that those relationships are also very important to us. And I think we'll continue to be increasingly so for what we want to do in the market.

DA: 29:01
How are you guys pretty much nurturing those? Are you doing events, stuff like that, like private,

JB: 29:08
We have a sales. Thanks for teeing me up. We have a sales enablement soiree is an event that we really build as an industry event. It really is the largest sales enablement industry events in the world and we're doing that September 27th and there we have a great roster of those exact profiles. But we also will have a lot of people that are putting this into practice and practitioners to share what they're doing, how they're doing it, etc. So that's a big venue and that will continue to be. But outside of that we engage with influentials in a lot of different formats. That's probably the biggest investment that we have throughout the year though, to bring all those people together.

DA: 29:49
No, it's a fantastic way to do it and nurturing so many relationships and having a live environment. So love that and that's a fantastic idea. Just a really great idea. If anyone's thinking of how do we build thought leadership? So based on time here, what I want to do is I want to flip over to our lightning round questions. Just five questions. We'll go through quickly answer with the first best thought that you have in mind. You ready to go?

JB: 30:13

DA: 30:14
Alright. Pressure is on. Advice for early stage SaaS companies starting marketing today.

JB: 30:20
Test, assess, rinse, repeat, and hiring. If I can get a second one in there.

DA: 30:28
You can. Absolutely. What would you say for hiring? What's the advice there?

JB: 30:30
Oh, it's super, super critical. Early on in the success of a company. Establishing culture and everything you need to be successful. it comes down to people. So put a lot of focus on.

DA: 30:40
I absolutely agree. What marketing skill do you think is vital for teams to improve and build on today?

JB: 30:48
The written word, communication through words, man. It, it's amazing. I think the technology is good and bad and that we've gotten a little bit lazy with our own ability to communicate with written texts and maybe it's the shorthand that we use in Twitter and other social formats, but it's super important. It's almost becoming a lost art and it's a, it's one of those key and unique skills that you just have to be able to find for the people you're hiring for sure.

DA: 31:18
Absolutely. It's a critical piece of marketing and you have to be able to write and communicate with your target audience, be able to speak to them. What about a best educational resource you'd recommend for marketing?

JB: 31:31
Well, I name two here. SeriousDecisions, for us has been a great relationship. I really do think that they have a lot of good thought leadership, but that they have a lot of good tactical advice and expertise to put it into practice. So that relationship has been great for us. I would also say, you know, a marketing professionals should understand full funnel and that's just becoming more and more important and one of the best resources I'd recommend for that is, is looking for a book by a guy who used to work for Alex Shootman who came from Eloqua, called the Revenue Engine and that really decomposes all of the dynamics of the funnel and how marketing contributes to it and I think it's fantastic.

DA: 32:16
That's awesome. I'm going to go on Amazon right after this and get that is called the Revenue Engine. All right, I'm going to pick that up after this. Appreciate that recommendation. What about a favorite marketing tool you can't live without?

JB: 32:29
Oh, I like some Doso right now per direct mail themes and Doso, we use, to basically send an Amazon gift cards, Starbucks gift cards, things like that to prospects. And it's a, it's a way that you can almost wedge a kind of direct mail approach to email in some ways. but for us that's, that's been a fun, can't live without tool, in the theme of direct outreach and personalization,

DA: 32:59
I'm definitely checking that out. We did a campaign where we send out gift cards and I had to do it all manually because I couldn't find it tool itself. Yeah, you just saved my life. What a, what about a brand business or team that you admire today?

JB: 33:13
Yeah, I tend to think in our own space sales technology and one of the companies I think is doing this well is within the sales engagement technologies. So all of those providers that are really making it easier for forward that broad prospecting and broad outreach, from sales development and tele prospecting reps and outreach is a, is a company out here that's actually local to Seattle and has done phenomenally well. We have integrations with outreach, but I, I've had a lot of respect for the way that they built the business and for what they're doing in the market. And I think I hope to see him continue to do great things.

DA: 33:56
That's awesome. And will definitely list all your answers on our show notes and definitely have all the resources linked. I think that's a new company. I haven't heard that one before, so have to check them out as well. So lots of great answers and Jake, I just really appreciate your time today. It's been a real pleasure to have you on. We talked about a ton. We learned a ton. I learned a ton, so I appreciate your time. Yeah, no, thank you so much. Really, really means a lot and have a wonderful day. Thanks again.

JB: 34:22
All right. Thank you for having me and have a good day,

DA: 34:26
All Right. Huge shout out to Jake and the entire Highspot team. What an incredible software and product they're building out. It's an incredible space. (...)

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