The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 6 months ago

170. Building a Company from the Ground Up w/ Zach Rego


This week on the Sales Hacker podcast, we speak with Zach Rego, VP of Sales & Marketing at Unstack.

Building a company from the ground up comes with its set of challenges: calling hundreds of leads, setting up the website, and learning skills as you go. With the right vision, and keeping an eye out for professional opportunities in your current job, you can position yourself for success.

Show Agenda and Timestamps

  1. Show Introduction [00:10]
  2. Unstack Explained & Insight into an Early Stage Company [2:33]
  3. Zach’s Professional Background [8:21]
  4. The Sales Development Representative Role [15:56]
  5. Running a Marketing Function & Advice for Building a Company [18:09]
  6. Zach’s Biggest Influencers [20:53]
  7. Sam’s Corner [23:14]

One, two, one, three, three, everybody, it's Sam Jacobs. Welcome to the salesacker podcast. Todayon the show we've got Zach Rego Zak, is a VPS sales andmarketing and unstacked. He's a great sales leader. He talks about building SDRteams. He talks about something that you can do to change your career todayand how to get the most out of your job today, and he alsojust talks about, you know, building a company from the ground up,because that's where unstack is and its growth trajectory. So great conversation. Beforewe get there, we want to thank our sponsors. We got three.The first is outreach out which has been a longtime sponsor the podcast. Theywere the first sponsor and they've got a place now where you can learn howour out which does outreach, how they use their own tool. Learn howthe team follows up with every lead in record time. Learn how a teamruns account based plays, manages reps and so much more using the very ownsales engagement platform. Everything's backed up by data from their customer base. Whenyou're done, you'll be able to do it as well as they do.Had to outreach thatt io forward, slash on outrage, to see what they'vegot going on. We're else is sponsored by pavilion, the community formerly knownas revenue collective. Pavilion is the key to getting more out of your career. Our private membership connects you with the network of thousands of like minded peersand resources where you can tap into leadership opportunities, training, mentorship and otherservices made just for you. With a pavilion membership, you'll build deep connectionwho appears. Access a full suite of training and certification programs for sales,marketing and customer success and, unluck, over a hundred different job opportunities everysingle week, share between members in a trusted and private setting. Go tojoin pavilioncom to learn more. And then, finally, ambition. A Great Companyand I'm I would say friends. I would say friends. He's notmy best friend, but friends with their founder. But every sales leader feelsthe pressure to predictably close more deals. Take control with ambition and end toend sales management software platform that sings with your crm and existing text act toturn overwelming data into realtime goal tracking and instant recognition for your team. SeeY brands like Fedex ATP Waste Management Outreaching the Phoenix Suns used ambition and checkout exclusive offer for salesackers listeners at ambitioncom forward slash salesaccer. Now, withoutfurther ado, let's listen. My conversation was Zach regoy. Everybody, it'sSam Jacobs. Welcome to the SALESACER podcast. Today on the show we've got ZachRego. Zach is the VP of sales and marketing for a really interestingcompany called unstack. Before that he was the gem of words dreams agency business. He's also the host of the zero to a million podcast. We're excitedto have them on the show. Zach, welcome to the salesaccer podcast. Sam, thank you so much for having me. We're excited to have you. So first part of our conversation is typically learning just a little bit moreabout where you work, the company where you work. So what is UNstack? Yeah, on stack is a no code marketing platform really meant toempower marketers to build and scale digital businesses. So we work mostly with SASS foundersand marketers and other digital products, so folks that are selling ebook orcourses online. But really our core, our core customer is a Sass marketeror founder, and what do you do for them? It's, you know, it starts with a website just because that is their digital presence. Thatis kind of their digital real estate and footprint that drives the demand to theirproduct. But it's scales from just a website into landing pages, testing,analytics, dashboard and contact insites, content and all the things that assass companyreally needs to thrive online. Is kind of all in one and on stackare our goal is to make those tools work seamlessly together, which historically theyhaven't, which really slows down the velocity of sales and marketing teams. That'scool. So in some ways it's almost like a marketing driven square space.So it's easy to create a website, but you got attribution and leads andall the things that you need to actually grow your business with on stack.Now that, yeah, square space is kind of the small business, youknow, local small business, where the digital SMB and start up tool thatreally allows you to market online. So...'s really good analogy. Awesome.How long has the company been around? The founders started on it close totwo years ago. We really haven't been in market selling for a little overa year. We've kind of did a product hunt. Launched last summer.That was kind of our big coming out party and and it's really been paddledto the metal since then. So we're coming up on a full year ofreally sales and marketing pushing, pushing this thing. Cool, awesome. Soyou're running sales and marketing, but it's a small team, if I'm notmistaken. How big is the company? Very small. So we are fourteenemployees, about to be fifteen. So so still very early stage, butit's been a lot of fun. And so you know, and I thinkit's probably a useful question since you're also the host of of the zero toa million podcast, but when you take a job and the company is soearly stage and you're running, you're going to be, you're in charge ofhelping them build and grow revenue, where do you start? How do youget the the engine going? What are the first set of activities and thenhow does that change over the first six to twelve months? Yeah, soit's a good question. You started the interview process by making sure the COfounders are bought into your vision and and you're really well aligned on where thecompany is going. Who the target customer needs to be and I did probablyeight months of due diligence and you know, grant, the cofounder, did eightmonths of due diligence on me as well before we decided to work together. Because it is going to be a long, difficult grind. So youwant to make sure that you're really bought into the Vision on both sides.But I started by hitting the phones. You know, I've run a lotof our demos. I've sent a lot of emails to every new lead thatcomes in and I scrub each of them individually along with, you know,a sales rep or some of the marketing team now, but from the jumpit was very hands on, mostly to get a feel for where these leadscoming from, which ones are most interesting, what features are really resonating, whatSTART DEMO SS be? How long should our demo be? How dowe make it so we don't need to have a demo long term? Soreally trying to get my hands into all of that. And then the nextstep is how do you automated right? So I can't do that forever.So you start really looking at what tools can we use to either automate emailworkflows and sequences when should those come into the fold? And then what featuresand product on boarding can we change that kind of become the most sticky inthe free trial experience that people just want to keep going and that's something we'rereally diving into now. So a lot of the first eight months or soI was I was working on refinding that marketing process, for finding that salesprocess. Now it's I know what makes people tick after running close to six, seven hundred demos. What is that real feature on boarding in product experiencethat we need to nail and we're working on that over the next few weeks. So what have you learned after, you know, to your point right, seven hundred conversations? You've talked to a lot of different people. Whatwas confirmatory about the product and really the market and the pain that you suspectedbefore you joined? And then what's what's one or two things that you knowyou had to were new, we're surprising to you in some way. Yeah, you know, it's hard to have a wedge to kind of get yourproduct into the company's door when a lot of folks are coming to US startingwith a website. A website is a big project that is overwhelming and it'susually multiple stakeholders and it becomes something that's very big and it takes a longtime to plan for. So one thing that I was really surprised by wasour sales cycle is a lot longer than it should be, and that's afactor of just what we're selling and also how we were marketing it. Soone thing that we're starting to think about and shift towards is, Hey,our wedge can be landing pages. If we can get people building landing pageswith us and using US for a be testing and analytics, then it becomesreally easy to start to build a website because their content, their fonts,their colors, they're branding, their media... already kind of in our platform. So building new page is becomes really efficient. So we're, you know, we're starting to find some interesting ways to just weasel our way into theright people in the organization and get them using US and then expand from there, which isn't how we initially went to market, but it's something we're pivotingto. There you go. That's exactly the kind of insight that is superinteresting that you learn from doing, as opposed to theorizing about what's your background, how did you find this job in the first place? And this feelslike to the point of you know, your conversations about like what's The onboardingexperience? Was a product experience and we were talking offline that this is amarketing driven, kind of in some ways product led growth experience. But isthat your background? You have experience doing going to market in this way,or you know, what were you doing before? One thing I've learned fromevery job that I've had is what I don't want to do next as wellas you know what I what I do want. I want to kind ofbe a part of my next role. But I was in sales. Myfirst kind of outside sales job was selling consulting services to it directors and CEIO'sfortune. Five hundred companies, long painful sales cycle, getting hung up ona hundred twenty four out of a hundred twenty five dials and the one connecthopefully turned into an opportunity six months later. Like those were my days and Ireally quickly learned like I don't want to sell services and I don't wantto sell to it departments. I guess just not who I drive with.So that was my first transition. Then I went to word stream, whichwas a SASS platform. So I knew I wanted to get into software asa service as opposed to selling services, and I loved it and we soldto marketers and entrepreneurs and I loved that like it was just something that Ievery demo was different, you know, I was always learning about people's businessesand how they were making money and I just thought it was every conversation wasso interesting and it made it really exciting to go to work every day asa sales rep when sometimes sales can be a, you know, a bitof a grind. After, you know, eight years there, I moved intoa general manager role leading a department which allowed me to get really involvedwith product and marketing and get kind of out of just sales. It wasobviously a big focus still, but I love the marketing piece. I lovedworking with the marketing team. I learned a ton from the marketing team atWord Stream. They were outstanding and I knew in my next role I wantedto lead more than just sales. I wanted to kind of keep some ofthat general manager responsibility and I also learned that I wanted to go to acompany that was the platform didn't rely on the platform. So wordstream relied onGoogle and facebook because that's where we ingested data to provide our customers value.I knew that my next the next company I work for, I did notwant to work with a platform or a product that relied on a platform.But I knew that I still wanted to be in SASS and selling to foundersand marketers, which is, you know, where I found on stack as kindof a good sweet spot there. How did you find the founders originally? You know, I, throughout my entire career, have always kept aneye on the WHO's raising money. You know what companies are getting a littlebit of buzz here and there. I think venture Fiz or mass challenge orsomeone had wrote something about on stack, and I just connected with grant,the CEO, and send him a message being like I sent this out toa bunch of CEOS when they raise money. Like super interested in what you're building. You know, I've been in MARTEC for x amount of years,mostly doing sales and marketing. If you ever have any questions or want torun your demo by me, I'm happy to review it and some good beout a good email descend? Yeah, yeah, I've done. I actuallygot a you know, an advisory roll out of it with a small startup in Raleigh that's doing very well now that I still meet with the CEOand the BP of marketing regularly. So it's yeah, it's worked for me. It's got me a lot of really good conversations with people, even onLinkedin, and some people take me up on it. And I love listeningto non sales folks that are doing demos because founders are really passionate and theyhave a lot of the pieces to run...

...a successful demo but they're missing afew of the sales skills that we can really help them out with. Soit resonates well with with founders when they're at that pivotal point of raising moneyand being overwhelmed. Yeah, and it's not. You're not you're offering,you're not asking for anything and you'ren't even asking for a call, which sometimesis the thing that you know, sometimes when people just ask for a calland you're not quite sure why, I kind of, you know, softputting a little bit. You are at words room for a while. Didyou start just as an individual contributor? I did. Yeah, so itwas. It was a very early stage. At that point. I think wehad twelve sales folks to sales managers, and we all, like you know, we doubled that team within me, starting mighty, my kind of hiringclass, starting in the next one, starting. But yeah, we wereall sales folks. There's two managers in a VP of sales at thetime. So what was the journey like? I mean, GM is a fantasticrole. You've got oversight and responsibility for so many different functions. Whenyou think about your journey upwards at that company, what do you what didyou learn and what do you tribute to your success to you know, Ithink mentors, the leaders at Word Stream. While I battled with them a lotand we, you know, we had our disagreements, I think wealways we always found our way to the other side and I think the CEO, when I was a sales rep, Ralpholes, who's on the boarded onstack now and is, you know, still a mentor of mine, wasalways like very open to sitting down with me or any other sales reps andhe did such a great job of like taking sales reps out of the salesseat and putting them into the CEO seat of like Hey, Zach, that'sa bad sale because it churned, and here's when it churned and here's howmuch it costs me to pay you and marketing and everybody else, and here'show much the company lost because that deal turned in four months. And asa salesperson it's like that stinks, like thanks for paying me, but likeI hate that I hurt the company, you know, like you get thatfeeling of like shoot, now I really understand why these clawbacks happen and thisstuff. And he always was open to other conversations. Like I know rewrotethe commission plan and brought him a pitch on like why I think we shouldrewrite it a different way. He actually took some of my ideas and putit into the new commission plan. So it was a really cool environment wherethey got sales folks into a bunch of different parts of the organization, productor marketing meetings or pricing meetings, and it was it made me really excitedabout learning more about the entire business and less about just being an individual contributoron the sales team. That's awesome. And did you build an str teamat word stream. Yeah, so I started as an AE, became ateam lead, managed and sold with like for people reporting to me as ateam lead and then transitioned into a manager. Built that team up to I think, at its peak, fourteen sales reps, with a couple team leadsunder me managing some reps, and then, luckily, a sales manager had leftand left this team that exclusively sold to agencies kind of high and dry. There was just there was six reps. they were very talented, they wereall just kind of there. They didn't have a manager, they werelost and I saw an opportunity to make a move to become a director.I kind of had a director that was above me, that was just alwaysmy boss and I could never get out from under him and this was mychance to do so. So I went to the VP, I gave hima proposal and he accepted it, but it meant I got to report directlyto the VP as opposed to reporting to the director, and it gave mea much larger team, you know, to full teams or close to threefull teams, and after a while I started really taking a liking to theagency thing and redefining how we went to market with it from a marketing perspectiveand it started to really grow. So I grew the agency team to Ithink, at its peak, maybe twelve sales reps and added SDRs to thatas well and started testing that model and it worked. So then we builtan SDR team which ended up reporting to me as well down the line.And what did you learn from I think, you know, there's a hesitate tocall it a debate, but maybe it's a debate. But there's somedebates, there's some conversations out there.

I think you've Scott Lease's a bigadvocate for full cycle reps that don't have SDRs, that do their own prospectingand, you know, start to finish handle everything and then and there's justconversations about whether or not the role of the str is still relevant, stillthe right thing, and whether buyers really like being handed off from one personto an another to another over the course of a buying journey. So what'syour perspective on just the roll of the SDR? Yeah, I agree withScott. Like I I loved being a full sales cycle rep, like Ithought it was. It was, it was nice, it was empowering.I think it increases the velocity of the sale the way we did. Webuilt the SCR team at at word stream was a little bit different than mostthe strs. They're actually managed old, dormant accounts. So we at wordstream we're getting, you know, thirtyzero first actions a month. So thirtyzeronew emails were entered into our database every month. Three thousand of those,let's say, turned into sales qualified leads across just to use round numbers,I'll I'll say thirty Reps. it was more than that, but you know, that gives them a hundred leads each every month. Well, they canonly manage so many in boundaries at that type of velocity. So that we'vekind of found that there were segments that were getting left behind. After sixtydays, you know, eighty percent of our deals closed if they were goingto close, and after ninety days ninety eight percent of them closed. Sowe kind of said, hey, like sales reps get to hold their leadsfor ninety days and they're going to get ninety eight percent of their lead,their deals, out of it, and the other two percent, like there'ssomething there, but they're just getting left behind and never worked. So webuilt an SDR team to route those dormant accounts to and just do a reallyhigh touch. What was it? Maybe seven calls, seven emails through allof those accounts, just non stop going on and asking them around, andit worked really well. Like we got, you know, we got some incrementaldemos out of it, incremental deals out of it, but it wasjust a way to wake up a database that was getting left behind because thesales rep was always worried about like, what's the shiny new lead that's comingin? Right, that makes a lot of sense. So what's been youknow, you're now running a marketing function, not yet a team, but oneday, but soon it will be a team. Anything surprise you nowthat you've gotten your wish and you get to run you know, you getto run marketing. That that you didn't expect. Yeah, I don't tellanyone, but I know a lot less than I thought I did. Iam very much like a strategy ideas guy. Execution is way more difficult than thefolks that I used to come up with the ideas with and be likeall right, cool, how long will this take? In the big outus a day, but it takes me way longer than a day. SoI'm learning a lot being kind of the doer. But it's fun, Imean it's empowering because I get to come up with ideas and go and dothem without having to ask. But man is it is it challenging not havinga team of a very talented people around you to come up with ideas andbrainstorm with and then have them execute on. And I have that. You know, I've got an email marketer. She's outstanding at amazing content team,but there are a lot of things that I'm still doing hands on myself.That is not not my sweet spot. You asked me to create a displayad. I'm not great at creating display ads. It takes me hours andthey end up looking horrible. So that's where an agency or contractor my canasyinstead ask for budget. Any sort of like principles? You know you've beendo you've been working now for a while. You've built teams. You're now,you know, building a company from pretty much the ground up. Anylessons or key principles around business or your career that you want to share withthe audience, things that sort of guide how you make decisions or how youthink about taking action? Yeah, you know I think the one that Iwas asked to do a long time ago that was an amazing exercise, issit down and write down the job you want in five years and be likethoughtful about it. And maybe it's not a job. Maybe you want tobe the, you know, President or CEO of a company and Start Yourown you know, so you want to be an entrepreneur and start your ownwhatever company. But sit down and write... out, because there are experiencesyou can gain and get paid for in your current job that you're missing rightnow because you haven't written down exactly what you want to do to go andfind opportunities to do it. And that was an exercise I did a long, long time ago and it allowed me to really focus on, like I'mgoing to do my sales job, but I'm going to raise my hand toget involved with X, Y or Z, to get exposure to how we domarketing, how we manage, you know, NPS, how we doproduct development. What the hecks you know agile? When people say that,what are you know? And it really helped me be focused on the thingsthat were going on around me so that I could get experienced to do thenext job and I still haven't gotten the job that I wrote down then,but I'm a lot closer than I would have been if I was just daydreamingabout it. It's a great suggestion and I love that it's about leaving yourjob. It's about their experiences that you're missing out on right now. Sogo, go get them, because they're available to you and you'll get paidto get them, since, yeah, your job spaying you. We're almostat the end of our time together. Last thing we like to do isjust pay it forward a little bit and figure out who are people that areimportant to you. They're they could be former bosses, they could be peopleyou don't know that are just, you know, famous celebrities or famous foundersor something like that, or investors. But when you think about people thathave really influenced you and inspired you, who comes to mind? Who Doyou think we should know about? I think I've mentioned Ralph a couple oftimes on this podcast. He's been amazing all Brian Hanley, the CEO ofreveal mobile, does some amazing work. I'm an advisor for his company,but he's taught me a ton. They're in the MARTECH space as well.Howard Koganformacy of words. chroom another huge mentor of mine. I call himtext him often to just bounce ideas. Most of these guys are very levelheaded, something I am not, so they can usually repackage things for mein a way that makes me think about them a little bit differently. Soall amazing resources, all folks that are very willing to help any you know, salesperson or aspiring entrepreneur. You know, I think, people that I lookto outside of kind of my a eat media network. I think BenHorowitz is just his books amazing. The way he talks about things is amazing. The way he has dealt with challenges and not had kind of a linearpaths to success, with a lot of bumps in the road, and howwe helped dealt with those bumps in the road is, I think, justan amazing and read and story and if you can listen to him as muchas you can, really really sound advice coming from him awesome. Zach,if folks want to reach out to you, maybe they want to buy on stackor maybe they want to just bounce some ideas off you. Are youopen to that? What's the best way to get in touch with you?If you are. Yeah, connecting me on Linkedin. Zack is he achrigourgeo. I'm happy to connect. Shoot me a message, you know,if you're looking for a salesmantor I'm you know, I'm happy to help ona call or career guidance. Happy to help on a call and do whatI can to pay for and help you out. So awesome, awesome,Zack. Thanks so much for being on the salesacer podcast. Will Talk toyou on Friday for Friday fundamentals. Awesome, Sam. Thank you, everybody.Sam's corner. Another good conversation. Really enjoyed talking is Zach Grigo onsac sounds like a really interesting company and I think the concept of, youknow, a square space, but specifically designed for marketers and or specifically designedto capture leans. I've used squares space and great, great company. Theydo good things, but it can be unwieldy. Maybe I'm just an idiot. So I'm really intrigued by what they're building it on stack. The otherthing I liked is just the concept of what you learn when you have hundredsof conversations. That's what Zack's been doing over the last year. So hehad hundreds of conversations and they learn that leading with hey, build a websiteis a big ask and takes a shitload of work, and so they moveto hey, let's get a landing page going, and of course that's probablythe as they said, the wedge. That's probably the right way to engageand talk to a marketer, because marketers...

...are really thinking about lead capture,lead generation a lot, probably more than just like building an entire website fromfrom nothing. So landing pages feel like a good place to start. Thereare other companies that help people build landing pages. So the other thing thathappens sometimes as you shift and involve your positioning is you bump into new competitivesets, but regardless, as a really cool conversation. And then the otherthing is, you know that thing that he mentioned at the end about youknow, hey, figure out where you want to go, figure out whatexperiences you have and what experiences you want, and then look around you where you'recurrently working, because inevitably there are opportunities where you work right now thatyou're not taking advantage of, and all you have to do is ask forthem. Go to your manager, go to your boss and say, I'minterested in learning more about agile and interested in learning what is ruby on rails. I'm interested in understanding more about unit economics. Can I have a thirtyminute coffee with the CFO? And typically I mean who would say no tothat, especially if you're doing well? So get yourself some exposure. Doesn'thave to mean that it's your day job. It just means exposure to new experiencesso that over time you know more and more and your better and betterpositioned to get that job that you ultimately want. So that's my take.Now, if you're not a part of the salesacer community yet, you're missingout. Go there. Go to salesacercom. Any sales professional can join as amember to ask questions, get answers and share experiences with likeminded be tobsales pros. Jump in and start a discussion with more than seventeen thousand salesprofessionals. That sales hackercom. Of course, we want to thank our sponsors.They are three. First as outreach. Learn how outreach does outreach. Headover to Outreacho forard slash on outreach to see what they've got going on. Also, unlock your professional potential. Take advantage of over a hundred differentjob opportunities every week in access a full suite of training and certification programs forevery level and every role. Go to join pavilioncom to learn how to becomea pavilion member. And finally, ambition. Every sales letter feels the pressure topredictably close more deals. Take control with ambition and and to End SalesManagement Software that sinks with your crm and turns overwhelming data into goal tracking andinstant recognition. Go to ambitioncom forward sales hacker. It's all. It's alot of stuff to say, and so, but I will also say give usfive stars. Somehow we have a four point five. It's I don'twho's gonna go to the thing where you rate podcast which is not a thingthat you do it very often, and you're going to intentionally hit for probablysomebody hit three or two. Somebody didn't like me. That's understandable. NotEverybody likes me. It's okay. I'm okay with it. If you wantto get in touch when you can, linkedincom forward lash the word and forward. Mf Jacobs, if you want to email me, I've got a newthat email address Sam at join pavilioncom. Otherwise, I will talk to younext time. My Friends.

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