Episode 78: How Sales Assembly Built a Community Helping Sales Leaders Succeed

What keeps a community together and growing? Learn how one organization does it successfully.


Matt Green, chief revenue officer of Sales Assembly, shares how the idea came about to start a resource and peer community specifically for sales leaders at tech companies in Chicago, and how Sales Assembly keeps the community relevant for its members.


Chris Davis: 00:24 Welcome to another episode of the ActiveCampaign podcast. I’m your host Chris Davis. On this episode, I have Matt Green of Sales Assembly and he discusses how they built a community for C-VP and C-level sales professionals. It is something that I truly enjoy listening to, because if you’ve worked in a startup, you know how scary it can be sometimes taking on a new job where you are the sole person responsible for the role with not many people to lean on for expertise. So Matt saw that hole, he saw the need, and he filled it with his company, our community company that is a community Sales Assembly. And this episode outlines exactly how he did it, how it functions, and as a user of ActiveCampaign, it also highlights how they’re using the platform to continue to grow their community. So enjoy the episode. Matt, welcome to the podcast. How are you doing?

Matt Green: 01:27 I’m good, Chris. Thank you for having me. How are you?

Chris Davis: 01:30 I’m doing well Matt. I feel when I’m in front of the microphone talking to another business owner or someone in the business space, whatever seems right at the time. So I’m in my zone. I’m in my Zen man and I’m enjoying it.

Matt Green: 01:47 I’m talking to you and that’s all I needed this week. This completes my New Year’s resolution, is talking to you for 2018.

Chris Davis: 01:57 There it is. Well, speaking of me, let’s talk about you and give our listeners a little bit of information about your background and your business.

Matt Green: 02:09 Sure. Well, starting at the top, of course, my name is Matt Green I’m the Chief Revenue Officer of an organization called Sales Assembly, which is based here in Chicago. My background, I spent about 10 years working in sales leadership roles, primarily in financial services and investment banking. Switched to full-time sales leadership roles within venture-backed tech companies here in Chicago and developed a pretty robust network thereof not only salespeople within the venture-backed tech space, but also sales leaders.  But what my partner of the CEO of Sales Assembly, Jeff Rosset, and I noticed, pretty quickly, once we really started working together, was that there was no formal community for sales leaders of venture-backed tech companies here in Chicago, which was interesting, because when you take a look at companies like ActiveCampaign, companies like Sprout Social, companies like Spot Hero, all of these companies, they’re selling different products to different people.

But how they go about doing it is eerily similar. So what Jeff and I decided to do was really just to build this community of sales leaders, provide an opportunity for them to connect with each other, provide an opportunity for their teams to have access to a great network, continuing education resources, tools and knowledge. And that is what eventually became Sales Assembly, which is just turning one-year-old this month. We work with around 60 of the Chicago’s most exciting venture-backed B2B tech companies here in Chicago, including, I’m happy to say, ActiveCampaign.

Chris Davis: 03:54 Yes. And, Matt, you know what? As you’re talking, I know you and I had briefly touched base before the recording, but you said a couple of things that I think would be instrumental for our listeners that I want to kind of detour a little bit and talk about and the first one is you have experience in raising funding for smaller companies, right? And I know a lot of people may be looking at starting a company, and they may know if they should pursue raising funding or not. They may not understand at what point is it even a viable option? What pointers would you give to our listeners, that have a business, that could potentially work with someone like yourself or in a capacity of someone who does what you do to raise funding? What are some of the things that you looked for in those businesses?

Matt Green: 04:56 Yeah, that’s a great question. We, to be clear, my background is not in venture capital, which is when most folks, when they’re looking at raising capital for businesses, especially any business that’s related to tech in this day and age, they’re looking at raising venture capital. What we tended to look for, on my side of the equation, was something that would be a tech or be it some other type of service business was actually a viable business. A business that had revenue, a business that focused on profit, a business that was smart about how they went about spending money. And if you’re asking for my personal opinion, what I see in the landscape right now, you have a lot of entrepreneurs, tech entrepreneurs that are, they read the blogs, they read these success stories from the venture capital space and they’re sort of sold on that dream of how easy it is.

You know, “Hey, if I put together a great pitch deck, I’ll be able to go out and raise a half million dollars. Once I raise a half million dollars, I’ll hire a couple people, put together an even better pitch deck and then go out and raise a couple million dollars.”  And people, entrepreneurs, the mistake that they make, from my perspective, is a lot of them focus on raising just to get to the next race. And again, I’m not blowing smoke. You know, one of the more impressive aspects of watching ActiveCampaign grow over the past couple of years is this really intentional organic growth that you guys have experienced and that your CEO, Jason, and your sales leaders, like Adam Johnson, have really focused on that organic growth. You’re building a real business as opposed to building something on paper that you could go out and raise money against.

Chris Davis: 06:54 Yeah. Yeah. And it’s important, because a lot of times people mistake making money for a sustainable business model.

Matt Green: 07:04 Correct.

Chris Davis: 07:05 Right. You can make money for a time selling a particular product or service and that be good for now and later it’d be different. So it’s really important to build that, to focus on that model and make sure that it’s sustainable, make sure that you know what it takes to grow, make sure you’re able to react, and a lot of times, anticipate the market, because those are the things that take the players out, the ones who are just playing business and not officially doing business.

Now, tell me a little bit about Sales Assembly. What kind of caught my ear is how you guys came together and just, “You know what? I want to build a community,” and we hear this word community a lot, Matt, it’s pretty much everywhere, but when you talk to people who have done it, there’re all types of little steps or strategies that they’ve used. And I just wanted you to give the listeners some insight on can you talk about the first stages of the community, what it looked like, and also talk about some of the phases throughout building it that you kind of battled, is this going to work or was this just a good idea in my head?

Matt Green: 08:22 Yeah, no, great question. And I think it makes sense to start and focus a little bit on the why, and from that standpoint, why Jeff Rosset and I started building this is we were working together at a venture-backed tech company that unfortunately hit some struggles and, he and I, we, of course, left, but as a result of that we wanted to connect with other people like us. We wanted to connect with other sales leaders in the venture-backed tech space, really for the purpose of exchanging feedback, exchanging best practices. And we realized that, “Hey, we’re all kind of doing the same thing in the same space. Why don’t we learn from each other?” So we went out there and we started looking for a meetup group or some sort of association that we had assumed already existed that we would be able to join.

And we realized pretty quickly that one didn’t exist. So that’s why we decided to create Sales Assembly.  As far as what I think has made us so successful over the past year, going from, of course, having zero companies as members to not only having around 60 companies as members, but 60 of the most exciting, most prominent B2B tech companies, companies such as ActiveCampaign, but also large companies like LinkedIn and Braintree is really focusing on, to your point, people talk about community a lot, but when you really peel back the layers of that onion to focus on what is going to provide value to the community. It’s not just getting people together. It’s about being really intentional about why we’re getting together, and about the learnings that we’re going to take away after we get together.

And that’s one of the things that Jeff and I were very diligent about from the very beginning. If we’re going to build a network of all the VPs of sales and chief revenue officers from the biggest tech companies in Chicago and the surrounding area, we understand that they’re not going to want to be a part of a community necessarily, just so that they could say that, “Hey, yeah, once a quarter we’re going to go out to beers and chitchat.” right. We want to make sure that we were providing opportunities for their continued personal and professional development, so that’s what we focused on straight off the bat. And once we started getting a larger and larger group of these sales leaders together, we quickly realized that no matter how big or how small their company was, no matter how large or how small their sales team was, they were dealing with a pretty consistent set of issues.

Issues around continuing education for their sales team. Issues around hiring and recruiting and retaining top sales talent. Issues around trying to decide what marketing stack they should invest in. Should they invest in ActiveCampaign or some other type of marketing automation software? What type of CRM was right for them? So what Jeff and I again started focusing on was being really intentional about building out solutions, continued value ads that would address all these questions and concerns that these sales leaders all had as a byproduct of their companies and their sales organizations growing at such a rapid pace.

Chris Davis: 11:56 Nice, Nice. I mean you knew the market, you were the market, so you understood the pain. And I think when I listened to how you formed it, you were very specific. We like to throw out the term niche, but you were very targeted in who you wanted in this community. It wasn’t like, “Hey, all sales professionals, aspiring and established, you are very, very strategic.” Say, “Hey look, we want high-level sales professionals with venture-backed startups.” I mean that is very, very targeted. And I think when you do that and you understand your market, it’s easier to connect with people who fit that demographic and actually build value. So now as Sales Assembly is approaching its one year and, and standing strong, have you seen that the companies are also acknowledging the value of their sales professionals being in the community?

Matt Green: 12:56 Oh yeah, absolutely.  We provide, and to get down to a granular level, we have, I’m focusing again on that cliched term community, prior to sales assemblies, as I mentioned, you didn’t have an opportunity for VPs of sales or CROs to connect with each other, but that lack of community extended all the way down to the business development representatives, the account executives, the account managers, Just like a VP of sales, if you are an account executive at ActiveCampaign you may not know any account executives that are two blocks from you at Sprout Social or any account executives that are two floors below you at PowerReviews. But there’s so much that you could learn from each other, right. And that there’s that communal knowledge that can be built when we get a lot of account executives from these B2B tech companies in a room, and allow them to exchange ideas, exchange best practices.

So the short answer to your question is yes, we’ve heard from not only the sales leaders that their teams are more efficient and more effective, that their teams come back from sales assembly workshops and training sessions that we do on average once a week or once every other week with some really tactical learnings that they could implement in their business. But we’re also learning that at that VP and C-level, as I mentioned before, that there is considerable personal and professional development that these folks are experiencing. And again, providing them an opportunity to connect with each other in a form that didn’t exist before. So that, that has become really tangible.

Chris Davis: 14:43 Yeah. That’s amazing, and those who work in the startup space, probably this podcast resonates more strongly with them, because it doesn’t matter what position you’ve held, because the startup space is so new in terms of how people are approaching employment. I mean I worked for my first startup a little over four years ago and when I accepted it I was just, “Is this a real job?” Right? Because we were so used to the big corporations having the stable jobs and providing a means of living and as a married man of three kids, I couldn’t, I couldn’t play. So I remember going through that thought process, “Is this real? Are startups real?” And it just goes to show how, one, how new this space is, and when you start talking to professionals within the startups, everybody’s trying to figure out what’s working, what has worked so they can quickly get to what will work in that startup.

Matt Green: 15:47 Yeah. And that’s one of the things that Jeff and I talk about a lot. Both just between us and with other people. I mean, a lot of this might have to do with the fact that Chicago is such a, we have had a, from a tech ecosystem standpoint, we have had a good amount of success over the past 10 years, but it’s still relatively young when you compare it, obviously, to the behemoth of Silicon Valley.

So we think that we started Sales Assembly at the right time where not only the market was mature enough, but at the same time it wasn’t too mature where the sales leaders, the CEOs of all these tech companies’ sort of became insular and said, “No, no, no, we don’t want to share ideas. We don’t want to connect with each other. We just want to be here and grow our own company and demolish everybody else around the area so that we can be the only winner,” that’s not the attitude that’s pervasive here in Chicago, and in the Midwest in general, which again, is another reason why Sales Assembly, I believe has been so successful over the past year.

Chris Davis: 16:58 Yeah, that’s good. No, that’s really good. When you, one last question on the community, when you look at how people are engaging in the community, are you finding the value that they get is from the ease of connection online with like-minded individuals? Or, are you seeing them getting the most of the value from your workshops and events that you put on?

Matt Green: 17:19 That’s a great question. I would say that, if you had to choose one, it would definitely be the latter. It would be via the in-person workshops and events that we put on, but at the same time, we do have a pretty robust online forum for the sales leaders where on the weekly basis, they’re trading messages. They could be these grand strategic questions about, “Hey, we are, our company is toying with building out an account based sales strategy. I’ve never built that before. I’m open to any feedback.” Then you’ll have six or seven VPs of sales that have built strategies like that before basically saying, “Here’s our playbook,” so you’ll have opportunities for those types of grain strategic connections, but also something as banal as, a couple of weeks ago we had the VP of sales of a company here in Chicago reach out on the forum and say, “Hey, the annual renewal language in our contract keeps getting redlined by our prospects legal department and a holding up our sales cycle. What ideas do my counterparts in this forum have?”

And by the end of the day, he had six or seven other VPs of sales that had basically just cut and pasted their contracts saying, “Here’s language that works for us.”  If you’re a VP of sales of rapidly growing venture-backed tech company in sort of similar to your background, Chris, or my background, you made that transition into this tech company from a large organization where you had unlimited resources where you couldn’t have walked to the bathroom without bumping into another person. That was a VP level that you could exchange these types of questions and feedback with, that type of community is invaluable.

Chris Davis: 19:15 I can’t stress enough how thankful I am that you went ahead and created this, because I think you’re actually blazing a trail for many other disciplines, areas of disciplines to do the same, because, like you said, as long as you’re in a space or you’re around people who are not of the mindset, “Let me destroy you. Let me keep all of my knowledge and just destroy,” which we really should not be. Because when we talk about competition, I say this all the time too, to most of our users, “You’re not really in competition with the next business unless you’re on like Walmart, Target level.” There are so many people in need of help that we could all help to our maximum capabilities of our businesses and still leave a good share of the market unserved.

Matt Green: 20:05 Absolutely, couldn’t agree more.

Chris Davis: 20:08 It’s important to understand that collaboration is really the key and when you have somebody like yourself and your partner that have honed in on that and created an environment for people to more easily collaborate, in between the events and just really be able to further their skills in their profession, it’s great, I love seeing it. Real quickly, you guys have started using ActiveCampaign and I would imagine a lot of your marketing is to the … do you do your marketing to the companies with the VPs or do you go directly to the VP and C-level individuals?

Matt Green: 20:48 A little bit of both. It’s primarily the ladder, but at the same time, again, going back to our focus on just building the community in general. We do tend to err on the side of hitting more targets versus less, so I’ll put it that way.

Chris Davis: 21:07 Good, good. As far as what that process looks on the back end, I would imagine it’s not an just an easy, “Hey, join my group,” if they say, yes, there’s probably some nurturing that goes on.

Matt Green: 21:20 Believe it or not, I know that there’s a lot of nurturing simply because A, let’s be honest, we’re a year old, so that there is some consideration to be made there. But again, going back to what I mentioned a couple moments ago, what we really have to provide is some sort of value, and that’s where ActiveCampaign has really been instrumental in the facilitation of us providing value on a consistent basis. In providing a program that’s ease of use is so simple that even someone like Jeff or myself, as unintelligent as we are, could obviously get our heads around this and build what we believe is a relatively robust marketing program for a company that’s as new and as small as ours.

Chris Davis: 22:14 Yeah. Which is exciting, because you bring to the table a unique use case of where you’re using the automation to truly facilitate a relationship to join a community. Whereas a lot of our users, there’s a product on the other end. I’ve recorded podcasts where there’s a service that you want someone to sign up for, but to see ActiveCampaign see Marketing Automation be used in the sense of getting somebody into a community to further their career, to be better and collaborate it’s always good to see.  With that being said, Matt, I want to thank you so much for coming onto the podcast. Where can people connect with you and find out more about your company?

Matt Green: 23:01 Yeah, great question. Our company website is salesassembly.com, and, of course, they’re more than welcome to email me directly at mattatsalesassembly.com. I’m one of those guys that I love meeting everybody, so if anybody wants to reach out to me, I’m happy to buy them a cup of coffee or, of Course, you could always look me up on LinkedIn and connect with me there.

Chris Davis: 23:24 Great. Great. And all of those links in that information will be in the show notes. Matt, thank you so much. I appreciate you taking the time and coming on and helping provide some insight and value to the audience, man.

Matt Green: 23:38 No, thank you Chris, and thank you for everything that you and ActiveCampaign continue to do. You’re really a benchmark here in the city of Chicago. We’ve loved watching you grow up.

Chris Davis: 23:47 Thank you, man. We appreciate it. And I’ll see you online, Matt.

Matt Green: 23:51 Oh yeah.

Chris Davis: 23:54 Thank you for listening to this episode of the ActiveCampaign podcast. I hope this was enlightening in terms of showing you the power of getting focused with building a community. I mean Matt knew to a tee, not only who he wanted to build a community around, but he was also very intimate with their needs. So with that formula, with those dynamics at play, it’s no question why and how sales assembly is as successful as it is, and a lot of times when it comes to community building, we see people try to take the broad approach and get as many people in as possible and then try to worry about how to actually get value out of it later. So I enjoyed hearing a targeted approach of a community that’s adding value to individuals in their professional careers as they continue to work in the startup space.

If you are new to the podcast, this is the time where I extend my personal invitation to you. Yes, you’re listening for the first time. This is your invitation to join the listener-hood of the ActiveCampaign podcast. We’re available in iTunes, Stitcher Radio, Google Play, SoundCloud, anywhere where you can download a podcast, type in the ActiveCampaign podcast, and we are there.

So make sure you’re subscribed, so you don’t miss out on a new episode, we release them every Friday. And while you’re there, please leave a five-star rating and a review, that helps us get the word out. It helps validate us, quite frankly, quite frankly, that people are not only listening to the podcast, but getting value from the podcast. So if you could do that, that would be greatly appreciated. If you’re stuck with ActiveCampaign, I have not found a business that could not benefit from ActiveCampaign. So if you’re stuck, it doesn’t make sense for you to stay stuck.

We have too many resources readily available to you to help you move forward, and one of those resources is our Success team. You can sign up for one-on-one and talk to a live success member about ActiveCampaign in your business at activecampaign.com/training. And if you want to take the more self-guided approach and learn on your own at your own pace, at your own privacy, without talking to anybody, you can do that as well with the Education Center, activecampaign.com/learn, you’ll find podcasts, guides, videos, webinars, manuals, help documentation, any type of information that can help you learn how to leverage the platform. The Education Center is here for you. This is the ActiveCampaign podcast, a small business podcast, to help you scale and propel your business with automation. I’ll see you on the next episode.