Bridge the Gap with Brett Ungashick

EPISODE 107

Alex Cullimore: Hello, Christina. 

Christina Amigoni: Hello. We know it's Friday because that's when we do podcast recordings, right? 

Alex Cullimore: It’s apparently our podcasting. We should start releasing on Friday, so it's consistent for people. 

Christina Amigoni: We probably should. It's not like we're ever going to record on any other dates anyway so. 

Alex Cullimore: This is our one available day. It’s what happens. 

Christina Amigoni: Yes. 

Alex Cullimore: Today, we just had a fascinating conversation with Brett Ungashick. He runs the company called OutSail, and it's fascinating new type of – basically, it's a new approach to enterprise software sales in the HRIS department and kind of a cool broker model for the plethora of options that people have out there. Just the way he's approaching sales in general, and the way he's thinking about trust and how to kind of create that and create actual, like really turning value and improving how people are doing this. It feels very human and very validating to kind of see this work. So it's really exciting to see what he has done. 

Christina Amigoni: Yes, it is very exciting. I mean, we geek out with him for sure because of our experience in HR software. So it is kind of fun to geek out after being out of it for a few years and knowing that we speak the same language and just know where the skeletons are, know what's actually going on behind the curtains, and understanding what the customers need. I love the approach of building the trust and focusing on the trust and how he explained the shift from when all the tools came out, and they were all flashy and shiny. People went to technology choices first. They looked at the tools before they looked at other things when they wanted to switch payroll and HR softwares and now how that wave has changed to almost back. I don't know if there was a back but about the relationship. The tools are – they're all similar. I mean, there's not that big of a difference. But it's really about the relationship and building that trust first so that especially him and his company can be on the same side of the table as their customers and also on the same side of the table as their vendors. So they are in a very unique position where they're bringing these two sides, and both sides trust them to help them out. 

Alex Cullimore: Yes. Nobody thinks about that. Creating value on both sides is super interesting. It’s a great value-add for both parties here and really removes that obstacle of like just trying to force a product on somebody and when you can get that kind of middleman that actually has the trust on both sides, where both parties can really truly benefit from this. So it's cool to see a model like this out there. I hope it takes place and starts to really take hold in other markets as well. It's right disruption. 

Christina Amigoni: It is. It definitely is. Yes. Kind of like go from the human relationship and human trust first. Then you can match whatever needs to be matched. So, yes, enjoy. 

Alex Cullimore: I hope you enjoy this conversation with Brett. 

Christina Amigoni: Yes, enjoy. 

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Alex Cullimore: Welcome back to this episode of Uncover the Human. Today, Christina and I are joined with our guest, Brett Ungashick. Welcome to the podcast, Brett. 

Brett Ungashick: Yes. Thanks for having me, guys. I'm excited to chat. 

Christina Amigoni: Hi. Thanks for coming. 

Alex Cullimore: We're excited to have you on. So give us a little background on you, who you are. What brought you here? What's your story?

Brett Ungashick: Yes. That's a great question. So I am the founder and owner of OutSail, but that is definitely not where the story starts. So born and raised in Kansas City, worked in technology out of college. So I took my first job in San Francisco and worked at LinkedIn. But I think the reason that I wanted to get into technology is mostly just to be closer to entrepreneurship. I grew up with a family business. My grandfather started business, so I kind of saw firsthand what that looked like. In college or in high school, I started a car washing business. So kind of from an early age, I always liked that independent approach and did something similar in college. I started a bike rental business. I'm going out and working in technology with kind of – it seems to be where a lot of entrepreneurs and kind of open-minded business people are gathering. I did that for a couple years. I realized I was not cut out for big corporate enterprise technology. So after a few years of doing that, kind of found my way to, hey, it's time to start my own business and see where that takes me. So we're about five years into that journey. I think we got some pretty bright future ahead, so looking forward to it. 

Christina Amigoni: That’s awesome. 

Alex Cullimore: That's a great story. 

Christina Amigoni: Yes. 

Alex Cullimore: You said you're interested in that, and you understood that like maybe the big corporate space wasn't for you. What were your keys? What led you to walk out on your own?

Brett Ungashick: They say people don't leave the company. They leave the manager. I think I was like definitely a shining example of that. I mean, LinkedIn, especially back in 2016, it was like the peak of tech mania and low interest rates and just money and perks everywhere. Linkedin was definitely at the top of the list. So from a perch standpoint if that's all you were looking for, it had everything that you could look for, right? I mean we had this unbelievable cafeteria. We had these air-conditioned, Wi-Fied shuttles taking us to and from the campus. Everything about it was beautiful. But I think the two things for me were what can I do that's actually impactful at a place like this, and everyone you talk to and everyone that you kind of network with, it's just data course. Put in your five years. Rise the ranks. It's very kind of structured. It wasn't as dynamic and fast-paced as kind of Silicon Valley might have seemed on the outside. It was kind of probably five years too late, at least at that company, for that sort of like rapid rise and a lot of exciting opportunities. So I think that part of it was just structurally always going to be a challenge and probably was going to lead to like maybe not a 5 or 10-year stop here. But then you couple that with a management experience that didn't go great, and then that kind of accelerated that timeline pretty quickly. 

Christina Amigoni: It’s funny how it always comes down to people. 

Brett Ungashick: I wish him well in case he's listening here. 

Alex Cullimore: So tell us a little bit about OutSail. What does OutSail do?

Brett Ungashick: Yes. So OutSail is a company that helps businesses shop for new HR software. Sort of the through line from what I was doing to what I'm doing now is I used to, again, be a software sales rep, calling on HR professionals. So I would reach out to HR leaders and try to sell them our solution. I was really curious about like how can we get better at this. How can we get better at this? I remember like constantly A/B testing different messaging, seeing what would work. I’m trying all these different tools, all these different like handwritten letter. I mean, whatever it would be, just like throw stuff at the wall and see what works. This thing that you kind of kept running up again, so it's like at the end of the day, it's a needle in a haystack approach. It's very much just spray and pray. It's mass messaging. That was really the only thing that worked, and that was kind of depressing. Then there was an example of one customer that I would like think about quite frequently that I called her because we had to do 60 cold calls every morning. I called this woman and clearly caught her at a bad time because she just kind of starts yelling at me, and I think there might have been some curse words. But I just said, “Hey, I'm so sorry. I must have caught you at a bad time. The reason I'm reaching out, you guys have these three open roles. It looks like they were posted over a year ago. We have this tool that helps people find candidates. I'll try to reach back out another time.” Two weeks later, she was a customer of LinkedIn. So what was really fascinating to me about that experience was her pain point around recruitments and I can't fill these open roles was low as just down at the bottom of her list. Her pain point around salespeople won't stop freaking calling me was way up at the top. There was billions of dollars of venture capital going into solving that recruitment problem for her. But there's really weren't that many people that were trying to solve that top problem of like what I just thought of as like vendor fatigue, right? I know as much as I try, the best I can do to get a hold of these people is just be an obnoxious, high-volume sales rep, right? I see from her perspective what that looks like is this is really irritating. This is actually one of the most irritating parts of my job. There was this real clear issue there that wasn't really being accounted for. So thinking about OutSail, the genesis was just what would it look like to really build a service that's centered around the buyer and not be selling software from the salesperson's perspective but kind of thinking about it from the buyer's perspective. Originally, the idea was, hey, what if we built a plug-in, and your email inbox would be really clever where you get a salesperson's outreach. You click the plugin, it slides out, and it says, “Okay, here's what the vendor does. Here's the pros and cons. Here's kind of their side customers. Here's how much it costs. Do you want to meet with them or tell them to get lost?” It kind of workshops that idea. When I say workshops, I mean, literally, connected with, I think, 10,000 HR professionals on LinkedIn, asking them, “Hey, can you spare 15 minutes? I'll send you a Starbucks gift card. We want to run this idea by you.” Kind of over time, this is back in 2018, like first few months of trying to start the business, I just got a lot of feedback that kind of took that initial seed of an idea and said, “You know, what would be really helpful for me is when it came time to buy software, if I had a resource that I could trust that gave me great information and kind of walked me through that process.” So that's really what we tried to build up from there. 

Christina Amigoni: It just reminded me that we actually need to talk to you about our HR software needs. 

Brett Ungashick: Always happy to take a look. Yes. 

Christina Amigoni: That's really fascinating. It also reminded me of this presentation, Alex, that I did last year at a key account management conference, where we took some of our own experience with account managers as business owners and having some different tools and things that we use out there. We basically highlighted how different the tool approach versus the human approach is of having those conversations. How the tool approaches – similar to what you were saying from the sales point of view, I was like, “Let me come in and let me tell you everything that we do. And I hope to relieve the pain points that in your list. It's not even on your list of things that you're thinking about. But let me cause a lot of pain just by wasting your time in this conversation that you'd never wanted.” How from the account management perspective, it's like what if we actually spend more time listening and getting curious about what the pain points are and what's happening with the business. Then seeing if we can't provide a solution or not but the reverse. It was kind of funny because we started with a skit on both ends and how different it was. Some of the feedback we got from the audience was like, “Oh, my God. I could do one all the time.” Where I just walk in and I'm like, “Oh, listen to all our new releases, and we've got this and this and this and this and this and this and this.” Fifteen minutes later, I'm still talking, and the client is like, “When can I hang up? I never asked for this.” 

Brett Ungashick: I think to your point, there is such a skill in the listening and when it's selling something, building something. I think most of what the feedback I got from those probably hundreds of 15-minute calls with a Starbucks gift card attached to them, most of the feedback that ended up being useful was non-verbal. It wasn't someone saying, “Hey, you should do this.” It was me like delivering a point that I thought was going to be a resonant and them not responding. Then that happened three or four times in me saying that's probably a clue that this isn't hitting their needs, right? They come back try it again. I think there is so much to that where so much of this business was listen for problems and offer to help them and under promise and over deliver, right? He was just like, “We'll continue to add new skills and capabilities and offerings by just simply doing that.” Hopefully, as the company grows, it's something that we can keep core to the business. But like I sold a recruitment software, but I've never sold payroll and HR software. So on day one, I was telling companies, “Hey, I'm going to tell you what the best vendor is for your payroll and HR software, right?” What the initial approach was, “Hey, sitting on demos is really painful. Why don't you tell us which vendors you want us to evaluate, and we'll kind of look for some that also looks similar. And then we'll type up the notes for you and share our thoughts.” That was just, “Hey, I'm not trying to over promise anything other than I have some time on my hands, and I can type up a nice little synopsis.” You do that enough times. Then pretty soon, you're like, “Okay. Now, I've done this a dozen times. I've seen a lot of demos. I've learned how to ask the right questions.” Then these became more comprehensive reports. It takes a life of its own. Now, I do feel like I can walk into companies and tell them what's a good ideas and the bad ideas of their own software. But I think, again, just kind of that start small, look for a problem, offer to solve it, and then see where that takes you, is a really fun way to kind of grow things. 

Alex Cullimore: That seems just like really applicable to all kinds of arenas too because you can – obviously, HR software is a huge one. That's one where we were doing HR for a little bit or HR software. There's like 5,000 different questions you need answered as you're trying to figure out how to like solicit a vendor and which one's the right one. Of course, every vendor has their own need to try and sell their solution, and it's hard to know. So that's a really cool model. It seems like it'd be a great approach for any kind of like – especially enterprise sales of just generally like, “Hey, I don't even know what questions to ask. But I know we need this.” 

Christina Amigoni: Well, it's true. With something as complex as HR software as we've learned is what matters. What the pain points and what matters too in the software itself depends on who you're talking to in the company. The CFO has very different needs than the benefits specialists, which are completely different from the recruiter, which are completely different from, you name it, the CEO or the HR specialist or even the employees. So if you go down the path of talking to one person when you're selling, you don't really get the picture. You get, I don't know, one percent of what the actual need may be. 

Brett Ungashick: Yes. I think one thing that's been really fortunate about the model that we've been able to build is I think, again, that whole perspective shift that I had from selling software, where no matter how complicated I try to be, how much I try to connect with someone, I'm always across the table. I'm always someone that is just inherently not fully trustable, right? Just because I'm employed by vendor X, right? That's just always going to be impossible to overcome. Now, like because of this model, because of the way like the incentives have been set up, companies do trust that like at the end of the day, we're here to just help them succeed or help them make a good decision, get the right information, do what's best for the organization. It's crazy the amount of force that comes with that, right? There are so many times where I'm having this conversation with companies, and they're so transparent. They're so open. I’m like, “I would have killed for this when I was in sales, if they would have just opened up and told me about it.” Not so I could take advantage of it. Just so I could like really try to help solve their problems. But there is just something about like you can't do it from the other side of the table. It really has to be from their side of the table, and they have to believe that. Because of that, to your point, then you can really start to weave together like the full story from the whole company. You're not just getting that one person agree to take a sales call with you, and you're just driving on that train. But you're hearing from a lot of people. They're being comfortable. They're open. Then you can really start to be more of a consultant and really kind of help them out. 

Alex Cullimore: I mean, this is a great like middle-of-the-table operation. You're kind of on the side of the person buying the software and on the side of the vendors as well if they can get their product across. It does seem like it then kind of incentivizes them to try and get their product to a place where it would be easy to sell within like that broker system. How are companies reacting for that? How are vendors reacting to that?

Brett Ungashick: Yes. It’s a great question. I'd say, by and large, it's a really positive reaction. I think it's pretty easy to see why. I mean, I think my experience, again, having that sales experience was really helpful because I talked to these vendors in like sales operations terms, right? Talking about lead flow and how quick they are to close leads and what their average customers. Just using their language to kind of bring them to the table has been really helpful. The way that we've positioned our broker model is we'll take a commission if you are selected by one of our clients, and only take that commission after you've been paid yourself. So from the vendor perspective, they're like, “What's the downside,” right? This person's just going to send us leads. If they don't work, we don't pay them a cent. If they do work, we're just paying them from our winnings, right? Just from like our profits. So from their perspective, it's kind of a no-brainer. I mean, I think what I really find fascinating is kind of where the market seems to be heading. So over the last couple years, we've seen just a complete degradation across all vendors on the service side. There's these big macroeconomic trends, right? HR tech had huge tailwinds during the pandemic. Companies that never invest in HR tech all of a sudden couldn't get to their filing cabinets and needed to have things in the cloud. So there was this huge tailwind. But also, companies started getting more complex, right? So if you were a customer support rep that just pick a name called ADP, generally, all of the questions you were getting, if you're in the Colorado office or about Colorado regulations, then you can know that stuff. But now, everyone's multi-state. A lot of companies are multi-country. So you've got more customers than ever before, and they're harder than ever before. Then we've got a great resignation where people say, “All right, I'm out of here. This work isn't worth the trouble anymore.” It's been really truly industry-wide that we've seen service really collapse. In my position, my belief is that I don't think that it's ever going to fully recover. I think what we'll probably see is a lot of these vendors that historically were both software providers and service providers are going to move more towards just software. That's kind of been the enterprise model than like what Workday does, right? Workday, they're going to study the software. But don't expect them to kind of pick up the phone and tell you how to process payroll in Texas, right? That's not who they are. They’re like, “We’re a tech company, and then we have this whole ecosystem around us that they'll be the service layer.” I think we'll see that more and more in this industry and that getting back to kind of how do vendors feel about this. I haven't spoken to like to see how companies know exactly. But I do think that the market is taking us to a place where they're going to be selling just software and focus on software. They're going to want ecosystem partners, people that can do great selection work like we do, people that can do great implementation work like our partners. I think that's going to be a really rich growth there as the vendors kind of recede and say, “Hey, we might lose some revenue by pulling back from services. But our profit margins are going go way up because we're just going to be selling software, and we're not going to be doing that low-margin service work anymore.” 

Again, I think there's just going to be a lot of growth in that services layer that surrounds these tools. 

Christina Amigoni: Yes. That definitely makes sense. The one thing I see is from a product perspective, if these companies become so detached from the actual user. Because they don't do the implementation, they don't do the selection, they don't do the customer service, how do they even know if the product is still working, if it's meeting the needs of the market and of the users?

Brett Ungashick: That's a great question. I would love to look at like what work they've done to stay close because I think people do like their platform. But I almost think that part of what makes them an outlier here is that their system is like 100% configurable. So if you give company an entire toolbox, then they'll kind of build it themselves. Maybe you don't necessarily have to be listening as closely because the customer and the service partner will figure out the details. I think that it's really interesting more in the mid-market where they don't give you these unlimited tools. They kind of have to build some structure into them and some rules and some limitations. How will they know what things to put in there? I do think that there's things about you'll hear the term technical debt quite a bit. I think that's a real thing in this industry for a couple of reasons. It takes a long time for someone to become a large trusted payroll vendor. You can't do that overnight, and it's really slow, unsexy development that has to be done. But no one's excited about making sure all the tax codes and tables are all accurate. So the names don't go for that much and they're usually older platforms. Even though – again, Workday, who's kind of the flashy one in 2005. I mean, they're older than the iPhone. So there's this age that's required. You kind of have to be a certain age to be in this industry. But then there's also so much that's changed in our work life that there's now these next-gen platforms that we're seeing come out that are way more flexible, way more dynamic, way more built for the world of work today. They've got contractor management built into because so many people are relying on contractors more. They're built for global companies. They're built for non-linear reporting relationships. They're built for Integrations. Like all these things that these older vendors are going to try to catch up to. But they'll never be able to because they have these anchors behind them of kind of how things are built in that technical depth. There's this push-pull of like the old guys have all the experience and the trust and the reliability. The new guys have all the dynamism. It's really hard for one to jump into the other lane. I don't really think that can happen overnight for either of them. 

Alex Cullimore: Yes. It's super interesting. So there's basically this – oh, man. It's like the advent of things like LinkedIn, where you can have 10,000 InMails in a day, and you can be blasted by salespeople, and you can be blasted by all the – it seems like a prime spot to move. Then to your point, Christina, about getting that customer feedback, it's almost like an extra service you could offer or maybe even charge the vendors of like, “Hey, here's what we heard before they didn't select you.” Or, “Here's what we heard before they did.” 

Brett Ungashick: Yes. No, it's a real thing. We're going to launch the software platform this summer that we're really excited about. Right now, it's going to be really focused on just enhancing what we already do, right? It's going to digitize that, kind of build your requirements, see which vendors match you. Then we've built this whole suite of what we're calling evaluation tools, where you get your team in there. You've got shared score cards. You've got shared notes, apps. You put all of the documents that you got throughout their sales process in each vendor's folder. So really just trying to organize and kind of give tools so that companies can do a good job without having to really think about it and prepare for it and hire some project management experts. That's the focus. But the reason I bring that up is because we're looking at designing right now, okay, what comes after that. I think it's really fascinating to say like let's track the satisfaction levels within these platforms at a really granular level and see. I kind of have a vision of, okay, each time you log a ticket, like do it through the OutSail app. Then we'll keep track of where those went and if they got closed and how happy you were with those. A lot of companies show up to their end-of-year review and, “Hey, do you want to resign the contract?” They're like, “Yes, I guess so.” But instead what if they showed up with, “Here's our report for the year, and actually we had 42 tickets. Sixteen of them are still unresolved.” Now, you're having a much more strategic conversation. Then to your point, like that's valuable data for the vendors too. If we can start flagging this to them in real time and say, “Hey, these are the high-risk customers, and they can be more proactive.” At the end of the day, there's just a lot of adversarial buyer-seller actions, and it happens even after the sale is made, right? Buyer or user or vendor, whatever it is. But it's just we're against each other. Hopefully, we're trying to just bring both parties together a little more transparency, a little more technology, and definitely some people in there as well because I don't think tools are going to get us all the way. 

Christina Amigoni: Yes. It’s definitely true. I mean, having been on the vendor side of things, a lot of the creating that bridge, so realizing that we're on the same side. It's not us versus you or you versus us. It really came down to the humans and the relationships and the customer's feeling that we're on your team. We're not on our team. We're not here to make your life more difficult. We're not here to sell you more stuff. We're just here to make sure that your payroll goes smoothly, and your life is fine, and you don't wake up in the morning wanting to pull your hair out because you're going to have to log into your HR software. But those were definitely, at least from my experience, having a lot of customer-direct relationships through implementations and change management and even support. It was all about the relationship. It was creating the relationship from the human to the human. Then one of the two humans leaves and takes another job. Then you start from scratch. It really doesn't matter what the software does because now it's a whole new human looking at the software from their perspective and their view and what they're expecting and whatever their filing cabinet of past experience is. So now, you've got to start back from one conversation at a time and rebuild it. 

Brett Ungashick: No question, yes. We asked a survey of every customer. We kind of do our intro call and get to know them. Then we have them fill out this survey and just make sure that we have a lot of data about what they're looking for. Truth be told, I feel like I've done this so many times that after the first call, I can almost build the recommendations already. So the survey is a little superfluous. But it does two things. One, it just kind of makes the users show some buy-in, right? It's a five-minute survey. But if they can’t complete that, then it's like a red flag for me of like, “All right. Are they really going to be able to convert a payroll system? We'll see.” Another great thing about it is it gives us a really standard data set. 

Alex Cullimore: I think slightly more than five minutes. 

Brett Ungashick:I think that data set – yes, exactly. Yes. It’s just the first test along the way, exactly. But, yes, within that data set, what was interesting, I was pulling this for a webinar next week. This past year, users have shared that. So we're asking, “What are the reasons that you want to switch?” The number one reason is customer service. Before that, the number one reason was capabilities. I think that's really fascinating that companies are searching their technology providers not because of the technology now. It's been surpassed by people. It's like at the end of the day, these are technology tools. But, again, and the technology is not the number one reason that they're leaving these platforms. That's the first time that that has shifted. Again, I'm not sure that's going to change back. I think we're kind of going to have to reconfigure this model a little bit. 

Christina Amigoni: Yes. People have changed. Don't switch because of the technology. They don't buy technology because of the technology either. I mean, we've gone through it. When we were looking for our HR software and even other tools that we use, it was really about how we felt with the people we talked to. The technology, they’ll – 90% was all the same anyway. But it was more about when I actually have a problem or where I have a direct question, are you going to answer or are you going to tell me it depends? Are you going to find the solution and understand where I'm coming from? Or are you going to give me a boilerplate script? We can tell which one is which. 

Brett Ungashick: Yes. It’s something that I've thought a lot about with as we've developed like scorecards. We're really teaching companies how to evaluate these tools is like what's the right amount of human element to account for. At the end of the day, again, you are buying technology, and it can go too far the other way, right? You've had people that buy the wrong system, just because the sales person was really connected with them. Or my favorite example was someone was telling me, “Yes, I really like this software platform.” I said, “Why?” “Because I was really –” I didn't think it was a fit for them at all. She said, “I really like their colors.” It's like, “Oh, no.” So definitely only this need for more rigidity of like make a decision on sort of the facts and the code and the capabilities. But also, like they'll come to us and they'll say, “Well, person showed up to the first meeting, and they had the wrong logo, and they didn't read in the notes we sent them.” They still need to account for the human side of it. It’s kind of like an interesting like how much of that should it make up in your overall evaluation. I think that it definitely shouldn't be zero. We probably need to minimize it a little bit more than what has happened historically, where it’s just like we're a salesperson, and I connect more. 

Christina Amigoni: Yes. That’s definitely a huge like we've been on the receiving end of being and like having the discovery call. Then they come back with the presentation. First of all, the presentation has nothing to do with what we need. So clearly, they did not listen or even evaluate, use critical thinking about who we are as a company, where we are in our stage of the company, and telling us that they did all this research on our website. This one company was actually pretty historical because they did all this research on our website. Then they came back, and they were trying to sell to us leadership development programs. I'm like, “Did you not know that that's what we do? I think we're going to take care of our own leadership development programs. We're not going to outsource that. Why am I here?” But it was also the same thing. They had this huge like 25-page PowerPoint, and they had the wrong name company on it. It wasn't us. So I was completely confused because I'm like, “Why is there somebody else's company name on this PowerPoint?” 

Alex Cullimore: That's the customer side of the five-minute survey test. You're like, “I don't know if I can do that.” 

Brett Ungashick: They're dropping very strong hints for you. 

Christina Amigoni: Yes. That was one of those like, “I don't really care how good your tools are or your services. That's it. You're done.” 

Alex Cullimore: To your point earlier, like you never know on the other side of the table. It’s just there's a certain barrier of trust. You know what their incentives are. You know where they would like it to go. You know that's their general goal. Even if they're very friendly, even if they have most of the questions, unless they actually start being like, “Look, I don't think we're the fit for you,” it's hard to be like, “Yes, I totally can trust this person.” Which isn't – it's not a bad thing. It's just that's just the structure of the relationship, like you're saying. I'm curious, you've got a very interesting broker kind of model in this. I'm curious, as far as OutSail goes, what would you say is like the philosophy of the company and the philosophy of how you'd like to see it go?

Brett Ungashick: I think that my kind of big mission vision for the company is companies rely on software more than ever before, and we're not getting any better at buying and implementing and running our software platform. What we want to do is bridge that gap and say we need technology. It's not going anywhere. But let's make sure that we are doing it the right ways and really trying to build out like what are kind of foundational principles about making smart software selections and smart software deployments. To me, I think it's – and this is something I believe since the beginning. it's always going to be a human and a tool-driven approach. In between working at LinkedIn and starting OutSail, I worked for a tech company out in San Francisco that was – and we were still in the recruitment space, and we're trying to build this tool. It was myself and an engineer. We were trying to kind of like launch a startup within the company. The engineer just firmly believed that like we could create this product, and people would use it and be so user-friendly that we would not need to have any people help the users through it. But what we're trying to do is trying to help people at the end of their med school residency get matched to the hospital they're going to work at next. What we found is like with big decisions –maybe with small decisions like finding a new t-shirt or something, you can go tech-only. But with big decisions, even at kind of the height of Silicon Valley Mania of 2017 or whatever it was, it was like there are certain things that just aren't going to get fully automated. What we found was life decisions about where I want to upgrade my family, the tech is definitely going to play in this. But we ultimately realized and what their business realized is like they had to go out and acquire essentially like a staffing firm to then use that technology but then provide these experts who do this for a living and coach people and help them through these transitions. Yes, I think that example always stuck with me. So these big HRIS purchases that we're talking about, these fall into that same bucket, right? These are big decisions that impact entire companies. They're hundreds of thousands of dollars at times, maybe millions. That's the type of thing where as we want to make companies better, like I'm excited about the software that we're building. I think that's really going to help. But I also firmly believe that like no one's going to do a good job with a self-service-only experience. So trying to weave together like when's the right time to bring in experts and how to put them into this process and really try to make it a full experience for companies of like people on demand, technology on demand, and kind of trying to figure out what the right blend of that is. I think also the people doesn't have to be just us, right? There's a time and a place for speaking to someone that's a vendor, right? They know that product way better than I ever will. There's also a time and place for speaking to peers. So like trying to bring all the different people into this while also kind of creating this technology guard rail that keeps people moving along is sort of how I can see us achieving that vision of like better software outcomes. 

Christina Amigoni: So how are some of the ways that – now that you've seen all the skeletons and probably like most of the vendors’ closets, you know where the real pain points are or some of the things that the vendors will gloss over or not speak about because they know they're going to fall if it actually comes up. How do you keep your objectivity of the vendors?

Brett Ungashick: Yes. Yes. That's a good question. Okay. I'm not afraid to tell a customer that one vendor is a bad fit. I think one thing that we're pretty clear about with everyone is that there's no perfect system. So kind of the philosophy that I've come to is let's try to tease out what are the most important things for a business. Try to really define that. These can't be small fine-grain details like the colors of the platform or – but it’s got to be – it could be big things. It could be service. It could be cost. It could be we're a lean team, and we need something that can kind of augment us. Whatever those big, big things are, like trying to establish those, trying to keep those top of mind, and then just telling them throughout the process like, “To the best of our ability, we're going to tell you the good, the bad, not good with all these vendors.” There's going to be things that aren't perfect about some of these. But a good selection is going to be you going through that process and figuring out which ones have strengths that match up with your biggest needs and which ones have cons or weaknesses that you can live with. If that happens, like that's a good selection. Again, that's where I don't think of necessarily. There's certainly a bar that I have of like certain vendors where I'm like, “Sorry, But like I can't ever be confident enough in what I'm seeing here, the overall picture. Not just the software but maybe the team, the financial position, whatever, that I can't bring out. But if it's above that bar, then it really is just like I really want to understand. What are you good at? What sandbox do you play best in? I think one thing that really probably frustrates vendors the most is like we're really strict about like size of companies that we're comfortable putting certain vendors with. Especially, you're very excited, for lack of a better, word sales reps that want to go win out that big deal. We come in, and we're like, “Hey, their average customer size is down here.” You're taking a risk if you're going to be kind of on the 99th percentile of their customer base. That's just something to keep in mind. So that's definitely one thing that I always try to do is like put some of those pieces together to make sure that I can feel comfortable if a client makes a certain decision. I think that one other thing we'll do for an objectivity standpoint is we'll disclose our commissions to our clients, so they know exactly how much we stand to make from each vendor. Generally, it's about the same across the entire market. Just something to build that trust and let them know that like, “Hey, just because you're not paying us, and we're going to get a commission on the back end, you're really not going to see that happen. We don't want you to think that like anything that's not controlled to your goals is taking place here.” 

Christina Amigoni: Totally understandable. Going back to their needs and what's the best match and just the integrity and the honesty and transparency of here's the real picture. 

Alex Cullimore: Yes. It's really interesting how you present yourself to that. 

Brett Ungashick: Yes. Hearing the cons. They’re always happy to talk about it with the other vendors. But I'm like, “Yes, this is what we have for you guys.” “That's not true.” I’m like, “Oh, well. The last 10 customers told me it was true, so I don't know.”

Alex Cullimore: That's kind of the brilliance to the model here is that this is a great play on all the angles. I mean, yes, the vendors might not like to know that their cons are being put out there. But, I mean, this is how you build the trust in a relationship. Vendors can be frustrated at not making sales. But speaking from personal experience, we've seen what happens when you sell what you can't actually deliver. It's not a good fit for you either. I understand the desire for the sale. But, man, that can really backfire. That could be a reputational hit. That can just drown your support staff. There can be a thousand issues if you make the wrong sales. So there's actually huge benefits for the vendor to not be lined up with the wrong customer too. 

Brett Ungashick: Completely. Yes, yes. I think that, again, I kind of talk about vendors and salespeople like a little bit tongue-in-cheek. But there are ones that do a great job. Even though they'll never fully be on the same side of the table as the buyer, like they can get pretty darn close just by being super transparent. I tell sales reps this a lot. The number one thing you can do is, one, be really honest. When someone comes in and says, “Hey, here's the things we're bad at,” immediate trust. Immediate through the roof like customer wants to learn more from them. Then just like educating too. I think a lot of people take for granted that buying software is not someone's day job and teaching them things, right? Teaching them things about how they can run their process better, questions they should be thinking about. There's value in that and not in the, “Oh, I heard this one stinks,” but like just a higher level, more consultative questions. I've seen those things work really well, and so I think – again, I joke about some of the more aggressive salespeople. But there are ones that do a really nice job. I think those are the ones that our clients like working with. They find the right matches. They disqualify customers that aren't going to be a good fit and those ones that it is easy to build trust with, right? So I know that like we can bring them into opportunities as customers, and I know that they're not going to sell something they can't do. If they are a great fit, I know they're going to take great care of the client. That's pretty invaluable. 

Christina Amigoni: Yes. We definitely experience that on our side. They want to see on transparency and just them being the first ones to say like, “Listen. At your size and what you need, we're not the right fit right now. Call us in a few years, but you’ll be wasting your money.” 

Brett Ungashick: So powerful. Yes. 

Brett Ungashick: Recently, we had a conversation with someone. It was software-related where we thought we needed a service. They were like, “No, you don't. You don't need our service yet.” Like, “Let me just give you some free advice. Call on us when you need to, and we'll chat. But you don't need to hire us.” That only incentivizes us to go back to them when we are at that stage if we ever get there, where we do need to hire them. But we'll be first on the list. 

Brett Ungashick: Right, yes. If a friend asks for something in that realm, you could be like, “Hey, check them out.” I think they seem to really trustworthy, so yes. It's tough because of salespeople will oftentimes. They're judged by the quarter, judged by the month. So it's hard to believe that five years from now or three years from now or maybe next quarter, this will come back around in some way, shape, or form. I think it is a little bit of like a leap of faith where someone in a sales organization to operate that way. I believe it works out, and I don't know if I have the data to say so. But I like that approach. I like it when people do it. 

Christina Amigoni: Oh, for sure. Yes. It's a little bit our own approach too, even with our clients. We try to be very direct and very transparent. We tell them like, “Listen. If we don't go down this path and the needle doesn't move, we'll tell you to fire us because we're not doing our job. We’ll be the first ones to say you need to get rid of us and go different directions. We can't help you.” There's something to it, long-term vision. 

Alex Cullimore: I’ll say, Adam Grant's book, I was just reading about like I think his originals, but talking about a guy who ended up getting investors and then selling his company to Disney. Both times, he started his pitch with, “Here's the top five reasons you shouldn't invest in us. You shouldn't buy us. Just because like here's our skeletons.” It goes immediately from everybody trying to figure out where the holes are after being like, “Oh, you could get around that hole. That's fine.” 

Brett Ungashick: I love that. That's such a great call. Yes. I think it's a self-awareness too that that shows of just like this person knows where their weaknesses are. They're doing that analysis. They're looking around. I think doing that work, I think it already sets someone apart. I'm sure that's why they're able to build something incredibly valuable. 

Christina Amigoni: So a couple of last questions for you. First, where can people find you? Well, we know where we can find you when we need to talk next week about our HR software needs. Where can others find you?

Brett Ungashick: Yes, absolutely. I'd say use these places. So our website, OutSail, O-U-T-S-A-I-L.co. That's sail like sailboat. Yes, find me there. My email is brett@outsail.co. I am unfortunately zero-unread type of person. So I'll get back to people pretty quickly on email. If anyone wants to chat HR software or tech landscape, anything like that, I'm always open. 

Alex Cullimore: Our final question for you, what is your definition of authenticity?

Brett Ungashick: I was thinking about that once you mentioned that was the final question. I’m not sure coming up with the definition. But there is a feeling thing that I can point to of like feeling fully ingrained, integrated, and kind of behind the things that you're saying and doing that kind of signals authenticity. I think like we've all probably had an example of saying something that we didn't believe or didn't trust. You can kind of feel in your chest that like shakiness and kind of that solar plexus feeling of like, “I wasn't really fully behind that.” I think too many days or too many conversations where you don't feel that kind of integration and forcefulness behind what you're doing or what you're saying. I think that tends to be pretty good education to me that, hey, let's check in on what's going on. I've definitely had that experience, just even within this job, which I've really enjoyed and loved doing. But there's times where I'm like, “Maybe I'm running the exact same meeting over and over again. I'm finding myself just no longer staying at the same enthusiasms.” It’s like, “All right, how do I change this? What needs to change? What needs to come through? Or what do I need to kind of reframe so that I can show up like I hope to.” Not just for the client but just for me so that I don't go through my day doing stuff that wasn't enjoyable. I want to kind of be present in those halls. 

Christina Amigoni: That's awesome. Yes. I like the it's a feeling and checking in with yourself when that feeling shifts. Or it doesn't feel the way you want it to feel and figuring out where it comes from. 

Alex Cullimore: Yes. Like where you used integration as well for the integrated feeling. 

Brett Ungashick: Yes. It's a little bit of a HR tech word, but I think it also applies to like having full mind, body, spirit behind what you're doing. 

Alex Cullimore: Oh, there's whole fields of psychology around integration work. That's fine. 

Christina Amigoni: Yes. I'm sure you can find a way to use data conversion in there somehow and APIs. 

Brett Ungashick: If I had more time with the question, I definitely would have. Darn. 

Alex Cullimore: Well, thank you so much for joining us, Brett. We really appreciate this conversation. It's just awesome to get to hear somebody who's got such a unique philosophy and seeing it succeed and seeing you get in there. So you've been out for five years already. That's like the first huge benchmark for a company that's got some staying power. So that's awesome. Congratulations. 

Christina Amigoni: Yes, congratulations. Thanks for joining us. 

Brett Ungashick: Thank you. Thanks for having me. Yes. 

Alex Cullimore: Yes. Thank you. 

Brett Ungashick: Yes. This has been a great Friday conversation and happy to do it anytime that you guys are available. 

Christina Amigoni: I'm sure we'll want you back. Maybe you and Sam at the same time. We can do a –

Brett Ungashick: Yes. That would be fun. 

Alex Cullimore: That would be fun. 

Christina Amigoni: Oslo and HR software conversation. Let's see where that integration can come. 

Brett Ungashick: We can find it. We can find a connection. Yes, yes. He and I are going to have to do some homework before that call I think. 

Christina Amigoni: Nice. Well, thank you. 

Alex Cullimore: Thank you so much, and thanks everyone for listening. 

Christina Amigoni: Thank you. 

Christina Amigoni: Thank you for listening to Uncover the Human, a Siamo podcast. 

Alex Cullimore: Special thanks to our podcast operations wizard, Jake Lara; and our score creator, Rachel Sherwood. 

Christina Amigoni: If you have enjoyed this episode, please share, review, and subscribe. You can find our episodes wherever you listen to podcasts. 

Alex Cullimore: We would love to hear from you with feedback, topic ideas, or questions. You can reach us at podcast@wearesiamo.com or at our website, wearesiamo.com, LinkedIn, Instagram, or Facebook. We Are Siamo is spelled W-E A-R-E S-I-A-M-O.

Christina Amigoni: Until next time, listen to yourself, listen to others, and always uncover the human.