Offboarding Done Right: Alumni Networks and Employer Branding with Andrew Hamilton CEO at When

[00:00:10] Hey, this is William Tencup and Ryan Leary, and you are listening, hopefully watching, Inside the C-Suite podcast. Ryan, I got that.

[00:00:18] I did. I spit it out. It's all right. It's a Wednesday. This is what we do. So, Ryan, how are you doing?

[00:00:25] I am wonderful. I'm fantastic. And I'm excited to have this conversation today.

[00:00:29] 100%. Andy, how are you doing?

[00:00:32] Doing great. Excited to be here. Thank you, guys.

[00:00:34] Yeah, no worries. All right. So why don't we do introductions first. Andy Hamilton is the CEO and founder of When?

[00:00:40] I am. I'm the CEO and co-founder of When.

[00:00:44] Okay. And when is the name of the company for those at home? Just got to make sure you understand that.

[00:00:49] We're not playing the, this isn't a Groucho Marx bit.

[00:00:52] Correct.

[00:00:52] This is actually, When is the name of the company.

[00:00:55] It is very confusing.

[00:00:56] No, I actually love it. We did, when y'all, I think you did a round of funding at some point. I can't remember what it was.

[00:01:02] Yeah, it was over the summer.

[00:01:03] Yeah. Ryan, I covered it on our new show and I'm like, the company name is When? And Ryan's like, it's When?

[00:01:10] I was like, yeah, it's When.

[00:01:11] We may have gone off on a tangent, Andy.

[00:01:14] But understandable.

[00:01:15] I'm like 60 seconds.

[00:01:16] I love the name. I mean, it's memorable, which is half the battle with having a company name.

[00:01:22] Yeah.

[00:01:22] So why don't you introduce yourself for us? Tell us a little bit about yourself.

[00:01:27] Yeah, definitely. So co-founder of When and, you know, quick background on When. We're an offboarding solution.

[00:01:34] So we actually partner with employers and our mission is to help employees that are transitioning out of a company have a better experience, ultimately a soft transition.

[00:01:45] And it's kind of that forgotten landscape, the end of the employee life cycle.

[00:01:50] So what we wanted to do was bring innovation, solution and support to people that are going through, in many cases, like a very difficult time in their career.

[00:01:59] So that's that has become our goal is to allow employers to provide a better experience to people.

[00:02:06] It's such an important part of the process that often gets overlooked.

[00:02:11] Really, do you do you dip into alumni like where you're building an alumni network for them or anything like that?

[00:02:17] Or is it more just the offboard? I suggest it's the onboarding process and making because there's probably a hundred solutions on onboarding technology.

[00:02:28] Right. SAS products that are out there either built in the ATS or otherwise.

[00:02:31] But there's not that many offboarding applications, SAS applications.

[00:02:37] Like nothing, which is kind of why we started.

[00:02:42] Right.

[00:02:43] To your question around like alumni network, we've talked about that and I think it's some.

[00:02:47] But ultimately, you know, what we're doing is it's a destination for existing employees.

[00:02:52] And today, like for most companies that aren't using one, the process has been you get an email when you're leaving a PDF attachment with a whole bunch of phone numbers and emails of people you should contact.

[00:03:05] You have no idea who they are.

[00:03:07] And then you get a Cobra letter in the mail that gives you this like crazy.

[00:03:11] Very cold.

[00:03:13] Yeah, it's very stark and it's done.

[00:03:15] Yeah.

[00:03:16] And then you're kind of on your own.

[00:03:17] So, you know, we realized people need more help.

[00:03:21] And like you mentioned, onboarding, you know, there are hundreds of solutions out to make that onboarding experience excellent.

[00:03:28] To help you during open enrollment when you're looking at your benefits and choosing health insurance.

[00:03:32] And then all the point solutions while you're employed.

[00:03:36] But, you know, like Riley said, it's a forgotten landscape end of the employee life cycle.

[00:03:41] And our motto has always been like last impressions are lasting impressions.

[00:03:45] You would never have somebody come to your house, greet them real nicely when they're coming in the door.

[00:03:51] And then when they leave, it's like find your way out.

[00:03:53] Like see.

[00:03:54] So why do we do that to workers?

[00:03:56] Right.

[00:03:57] Because if you want to have an alumni network, you can't treat them like crap on the way out.

[00:04:01] You have to treat them with respect, but also give them support and solutions to help them in the transition.

[00:04:07] Do you think before we get into your story specifically, Andy, do you think this part of the process has been offboarding, has been overlooked because people don't care about it?

[00:04:21] Once you're done, you're done.

[00:04:22] Move on, right?

[00:04:23] Break up, move on.

[00:04:24] Or is it just there hasn't really been a good playbook, a good process or good software, for example, or a platform to help companies navigate that?

[00:04:36] I think it's both.

[00:04:38] I think, unfortunately, and we actually hear this when we talk to some employers still today, is like when the employee leaves, they're kind of dead to me.

[00:04:46] And that's kind of been the mindset, at least within our country, of you're gone, you're forgotten.

[00:04:52] You're not our problem.

[00:04:54] It is very short-sighted.

[00:04:56] And because of that mindset that I know I experienced coming up through the ranks and working at different companies, I think it's just limited the amount of effort around solutions in that area.

[00:05:08] Everyone is so embracing of, oh, we have to recruit people.

[00:05:11] We have to get the best talent in.

[00:05:13] We have to make sure people are able to choose health insurance solutions.

[00:05:16] But there is no like, oh, how do we treat people better on the way out?

[00:05:19] Because the mindset is, who cares?

[00:05:21] They're gone.

[00:05:22] Right.

[00:05:22] They're not my problem anymore.

[00:05:24] Yeah.

[00:05:24] And with the impact now is that everyone has a social media presence.

[00:05:30] And so those experiences, you know, I think it was what, up in the air with George Clooney.

[00:05:35] You know, that you could get away with that in the 70s because like, who's somebody going to tell?

[00:05:42] You laid off, you do a riff, you lay off 10,000 people.

[00:05:44] Right.

[00:05:45] Okay.

[00:05:45] Like, okay.

[00:05:46] So it's a limited exposure.

[00:05:48] It's not limited.

[00:05:49] Everyone's, there's a glass store.

[00:05:51] There's all kinds of sites that rate companies.

[00:05:54] And oh, by the way, everyone's got a Twitter account or whatever type of account.

[00:05:57] You don't even need the rating sites.

[00:05:59] Forget the rating sites.

[00:06:00] Right.

[00:06:00] You just need one good story with somebody crying with a.

[00:06:04] 100%.

[00:06:05] Some type of emotion behind it.

[00:06:06] Recording an exit interview, putting it on TikTok.

[00:06:09] Yeah.

[00:06:09] The way it goes.

[00:06:09] Well, and so that begs the question of like, like you said, with recruiting and onboarding

[00:06:16] and recruiting the best talent.

[00:06:18] That's all in our world, the employer brand and employer branding.

[00:06:24] They haven't thought of the third leg of the stool.

[00:06:27] They thought of the first two legs really well.

[00:06:29] So how do we do the candidate experience?

[00:06:32] How do we do the employee experience or EX?

[00:06:36] Okay.

[00:06:37] But the, you know, folks that are leaving, those, those are, those are alumni.

[00:06:42] Whether they're not you, whether or not it's for cause or not for cause, whether or not

[00:06:45] you chose or they chose their alumni.

[00:06:48] Ryan worked for IBM for a couple of years.

[00:06:50] He's an alumni of, of, uh, IBM and will be until he dies.

[00:06:55] So that's just is what it is.

[00:06:57] And oh, by the way, that's a, that's the third leg of the employer branding stool.

[00:07:01] Yeah.

[00:07:02] And it's so valuable.

[00:07:03] Like you're wearing a, you know, an Aggie shirt right now.

[00:07:06] Like we are proud alumni of the universities we attended or alumni of a lot of different

[00:07:12] organizations for whatever reason, it's not embraced in the workplace.

[00:07:17] But it should be, I'll say this though.

[00:07:19] There is an industry where it is relatively embraced and that is consulting.

[00:07:24] Consultants understand when somebody leaves, that's a potential future client.

[00:07:29] That's right.

[00:07:29] That is a brand ambassador.

[00:07:31] If they want to hire new consultants of quality, they can't have the former one saying the place

[00:07:36] sucks.

[00:07:37] So they tend to take better care on the exit, but they're one of the few industries that

[00:07:41] really focus on.

[00:07:41] I think the second one that's far behind the consulting folks, professional services is

[00:07:47] financial services.

[00:07:48] Cause you see some boomerangs in both in those industries, you see the boomerangs where

[00:07:52] they come back and they're, they're hireable.

[00:07:54] They did a great job.

[00:07:56] They just wanted to kind of do some different things, maybe start a company or whatever.

[00:07:59] And now they want to get back into consulting.

[00:08:01] And it's like, they already know our culture.

[00:08:04] They were great at what they did.

[00:08:05] Like, like this is an easy hire, but that's predicated or predicated a bit on how they left

[00:08:11] the company.

[00:08:14] You know what you should know?

[00:08:16] You should know the, you should know podcast.

[00:08:19] That's what you should know because then you'd be in the know on all things that are timely

[00:08:24] and topical subscribe to the, you should know podcast.

[00:08:28] Thanks.

[00:08:30] You know, that experience that they had.

[00:08:31] Does it matter Andy, how they get arrive at the notion of we need to have a better off

[00:08:38] boarding program, whether it's because they want to protect future customers, future potential

[00:08:43] sales.

[00:08:44] Does that even matter?

[00:08:46] Just have a good program and good things will happen.

[00:08:49] It's a good question.

[00:08:51] I mean, frankly, the shift we're seeing in the conversations we're having, you guys were

[00:08:57] mentioning earlier.

[00:08:58] The newer generation, like Gen Z, like they know that they're not going to take anything.

[00:09:05] They're very outspoken and vocal.

[00:09:08] They will record you.

[00:09:09] Glassdoor is important to them.

[00:09:11] But like you said, like any platform, they are going to drag your brand through the mud if

[00:09:17] it was a lousy experience.

[00:09:18] And that is drawing more attention to off boarding.

[00:09:22] And when we start talking to folks, like we certainly stress, like we're here to help protect

[00:09:26] your brand and reputation along with making sure they have a good experience.

[00:09:30] And that resonates because there is this fear of, okay, this isn't like your parents that

[00:09:36] stayed at a company for 30 years.

[00:09:37] And if they had to leave, like they weren't going to say anything.

[00:09:40] The newer generation, one, they're only going to be there for maybe two and a half years,

[00:09:44] three years tops.

[00:09:45] And you better be careful with how you treat them.

[00:09:48] So you really want to treat them as well as you treated them on the front end.

[00:09:51] Absolutely.

[00:09:52] Or better.

[00:09:53] So that they, and again, if they chose, you don't have to have butt hurt.

[00:09:57] Or it's like they chose to do something different and like, okay, but let's be supportive.

[00:10:02] Like, cool.

[00:10:03] Like you need to go and do this bit.

[00:10:04] Last question that I have for when, before we do some of the other stuff is I think one

[00:10:09] of the struggles, Ryan, for why this isn't as developed as let's say onboarding, pre-boarding,

[00:10:15] if you will, is it's been hard to identify the owner historically of who owns off boarding.

[00:10:22] Who are like, what executive owns this?

[00:10:25] It's HR check, but within HR, who owns this bid?

[00:10:30] And for a lot of companies, it's been the team.

[00:10:34] So it's been, you know, the general manager, the district manager, you know, somebody on

[00:10:39] a team and that, and all of a sudden they can have any experience that they want.

[00:10:43] So there's no standards.

[00:10:45] But they, they literally, you need to have kind of a, I would say a chief off boarding

[00:10:50] officer or VP of off boarding, call it something a little bit more nice.

[00:10:53] But, but the idea that there's gotta be a gal or a guy that owns it, that that's what

[00:11:00] they do and that's what they care about.

[00:11:01] And I think that's why it hasn't gotten to where it needs to.

[00:11:04] And that creates a wonderful market opportunity for when, because it does, it does.

[00:11:09] And what we uncovered and we'll, I'm sure get more into this later on, but there's a massive

[00:11:15] financial component.

[00:11:16] And like you're saying, like nobody really owns off boarding.

[00:11:21] There are areas, whether it's rewards or benefits, CHRO may oversee all of it, but we uncovered

[00:11:28] like there is a financial unlock here because even when somebody leaves the one health insurance

[00:11:34] option that they have to hear about by federal law is COBRA.

[00:11:38] Right.

[00:11:39] So they may be out of your organization, but they still may be on your health insurance plan.

[00:11:44] That's right.

[00:11:44] And the claims coming in from these individuals on average are three times higher than your

[00:11:51] actual employees.

[00:11:53] So all of a sudden, like we're opening eyes to the finance team or if they have a risk

[00:11:58] team and saying, look at your claim comparison of people that work here and people that don't

[00:12:03] work here.

[00:12:04] And this is why we need to start thinking about that exit experience because there's options

[00:12:09] beyond COBRA and we can save you a lot of money, but those people need help finding those options.

[00:12:16] Right.

[00:12:17] They need help navigating.

[00:12:18] You know, it's interesting because I've always thought when, when a layoff happens or

[00:12:24] any of that stuff happens, someone, someone leaves the company, you've got the health insurance

[00:12:31] stuff, right?

[00:12:32] Right.

[00:12:32] You've got finding a new job, right?

[00:12:35] You've got, there's a, there's a plethora of things that, that happen.

[00:12:39] I mean, even so much when you, William, you mentioned IBM.

[00:12:43] Yeah.

[00:12:43] I had a corporate card.

[00:12:45] Yep.

[00:12:45] There was a lot of money on that corporate card.

[00:12:47] Well, that was tied to my name.

[00:12:49] I couldn't get that thing paid.

[00:12:50] It took 12 months to get it paid and it's hitting me.

[00:12:54] Yeah.

[00:12:55] Right.

[00:12:55] I'm getting the collection calls.

[00:12:57] And so I left IBM, not that they care about me, but I left IBM with a really bad taste

[00:13:04] and I was there for, you know.

[00:13:06] It's funny what people prioritize is we need our key card and our laptop back.

[00:13:11] It's like, yeah.

[00:13:12] Okay.

[00:13:13] Well, I've had the laptop for six years.

[00:13:15] You're not going to really get anything out of it, but all right, we'll get the laptop.

[00:13:19] I'll send me a box.

[00:13:20] I'll send it back to you.

[00:13:21] All right.

[00:13:21] Let's go.

[00:13:22] Let's go backwards real quick.

[00:13:24] Andy.

[00:13:24] Let's go back into, let's say high school.

[00:13:27] What did, what was the dream?

[00:13:29] What did you want to be when you grew up?

[00:13:32] I can tell you exactly what I did not want to be.

[00:13:37] My parents were both computer consultants who had their own consulting business together.

[00:13:45] And I listened to their conversations around work and developing software every night at

[00:13:52] dinner.

[00:13:52] And I swore I would never, ever exactly.

[00:13:56] I would never get into computer consulting.

[00:14:00] Hmm.

[00:14:02] Have you ever been to a webinar where the topic was great, but there wasn't enough time to

[00:14:05] ask questions or have a dialogue to learn more?

[00:14:08] Well, welcome to HR and payroll 2.0, the podcast where those post-webinar questions become episodes.

[00:14:13] We feature HR practitioners, leaders, and founders of HR, payroll, and workplace innovation and

[00:14:19] transformation, sharing their insights and lessons learned from the trenches.

[00:14:22] We dig in to share the knowledge and tips that can help modern HR and payroll leaders navigate the challenges and opportunities ahead.

[00:14:28] So join us for highly authentic, unscripted conversations, and let's learn together.

[00:14:33] How did that work out for you?

[00:14:35] I spent my first two years in college studying journalism.

[00:14:40] Okay.

[00:14:41] And I had a moment of enlightenment.

[00:14:44] And that was when I was in a class, which journalism class, but they're talking about the starting salaries for journalism majors.

[00:14:52] I've had this realization.

[00:14:54] And I'm like, are you kidding me?

[00:14:56] Yeah.

[00:14:57] And honestly, the next semester I enrolled in the business school.

[00:15:00] A hundred percent.

[00:15:01] And lo and behold, a couple of years later, I was a consultant for electronic data systems.

[00:15:06] EDS?

[00:15:07] Yeah.

[00:15:08] Ross Brewer.

[00:15:09] Oh my God.

[00:15:10] And more Meyerson too, right?

[00:15:12] At one point?

[00:15:13] Yes.

[00:15:14] And then they were eventually bought out by, or became HP.

[00:15:18] Right.

[00:15:19] Which no one understood that culture match.

[00:15:22] Because the culture at EDS and the culture at HP are completely different.

[00:15:26] Like, absolutely different.

[00:15:28] Like, when it was announced, I remember people in Dallas going, did you get two more different companies?

[00:15:33] My sister-in-law went to work.

[00:15:35] She was at EDS, but then worked for Ross at Pro Systems.

[00:15:40] So she stayed within the family.

[00:15:42] She stayed in the family.

[00:15:44] And I'm not sure what she makes, but she was like employee 12 at Pro Systems.

[00:15:50] So.

[00:15:51] Probably doing okay.

[00:15:52] Probably doing all right.

[00:15:53] She's probably doing all right.

[00:15:54] So what did you do at EDS?

[00:15:55] What was the bit?

[00:15:57] Yeah.

[00:15:57] So I graduated actually with probably more interest in sales and marketing.

[00:16:01] And I did do market research out of school for a company called Information Resources.

[00:16:08] And that was, you know, late 1990s.

[00:16:11] And you had the internet boom going on.

[00:16:12] And, you know, I had that calling from my parents of consulting.

[00:16:18] And that's where I made the shift and went into EDS's system engineer development program.

[00:16:23] And they shipped you down to Plano.

[00:16:26] I went down there for a couple months and went through like a crazy intense boot camp where they teach you how to become a software engineer and how to be a consultant and how to work on site at clients.

[00:16:38] It was wild.

[00:16:39] Like I had never worked that hard in my life.

[00:16:42] It was like 90 to 100 hours a week.

[00:16:44] They're getting people to wash out.

[00:16:46] That's what they were.

[00:16:47] Yeah, yeah.

[00:16:48] You had like a 25% failure rate.

[00:16:51] If you failed the program, you're out.

[00:16:53] You're fired.

[00:16:53] You're done.

[00:16:54] Yeah.

[00:16:55] Plano is unrecognizable now.

[00:16:58] So if you were to visit Dallas, all of that area that was like pasture land back then, all buildings.

[00:17:05] Like you would look at it and go, this is not the same place.

[00:17:08] It is literally not the same place.

[00:17:10] Well, I came back there because I ended up selling a company to Real Page.

[00:17:14] Yeah.

[00:17:15] I was down in Carrollton after that.

[00:17:16] Yeah.

[00:17:17] I did come back.

[00:17:18] But yeah, you know, I worked at EDS for a little over two years doing consulting and learning Oracle, became like an Oracle consultant and was down in St. Louis working for a client there.

[00:17:29] And I did that for a couple of years.

[00:17:31] And then I moved on and actually went to an Oracle consulting boutique firm based out of Chicago because I wanted to get back home.

[00:17:37] But yeah, EDS was good.

[00:17:39] And it certainly set me on my track of getting into technology, learning how to work directly with people to understand their real problems and how to develop solutions around it.

[00:17:51] They had a playbook.

[00:17:52] And the playbook worked at that particular time because you were building up, depending on when you were working, there was a build up to Y2K.

[00:17:59] Yes.

[00:17:59] And so it's like, okay, they had a playbook that worked with clients.

[00:18:03] And sometimes they'd install them and put them there.

[00:18:06] And sometimes they were, you know, come and go and all that other stuff.

[00:18:08] But they had a playbook that worked.

[00:18:10] Yeah.

[00:18:10] It was then an IBM.

[00:18:11] Like they were the two beasts at the time that could develop, you know, young kids and the ropes.

[00:18:17] And it was great.

[00:18:18] Like I really enjoyed my time.

[00:18:19] Yeah.

[00:18:20] Yeah.

[00:18:20] That's like an advanced degree, actually.

[00:18:22] You got your master's degree at EDS.

[00:18:25] Absolutely.

[00:18:25] Yes.

[00:18:26] Sorry, Ryan.

[00:18:26] No, you're good.

[00:18:28] So all these moves, right?

[00:18:30] You're moving around now.

[00:18:32] Timeframe on these moves.

[00:18:34] But were these moves with intent or were you just happy to have another job as you kind of left the previous company?

[00:18:42] That's a good question.

[00:18:43] I would say with intent, but maybe not always like the best intent.

[00:18:49] Like it was certainly financial growth.

[00:18:51] Yeah.

[00:18:51] Like I knew like at EDS, like I'm on the path of being a consultant.

[00:18:55] I went to a like Oracle boutique firm and I knew also like I needed to learn more and get better technically.

[00:19:03] And the company I was at was called Tusk, the ultimate soft, horrible name, but also kind of hysterical.

[00:19:09] Great Fleetwood Mac song, but, you know, horrible.

[00:19:13] So while I was there, it really was like I surrounded with some really smart people.

[00:19:18] It's really probably where I learned how to become a solid solution designer, leading a large project, taking on more that you would get at like a big company with EDS where you had, you know, hundreds of people at a project.

[00:19:31] Like I would be leading a team of like 10 at Tusk.

[00:19:35] And the move through there was how do I get up through the ranks?

[00:19:38] How do I make more money?

[00:19:39] Because like I'm in my 20s and that's obviously important at that age.

[00:19:42] But it was how do I become really skilled?

[00:19:44] I, you know, probably not purposely, but I started becoming really skilled at designing software solutions for clients.

[00:19:52] And at some point that turned into how do I start building solutions?

[00:19:57] So architecting, when you say designing, I want to make sure the audience understand the difference between architecting and coding.

[00:20:03] Yeah.

[00:20:04] So it's a good question.

[00:20:05] So I remember way back when we were going through discovery with a client in Philadelphia, we were thinking about what is the architecture for this massive system?

[00:20:16] My job at the time, like it's funny now, is figuring out MVC, model view controller framework.

[00:20:21] And how do we build a platform around it?

[00:20:24] This was like just as this idea was coming into fruition.

[00:20:28] And I actually remember calling Oracle corporate and talking to some of their leaders about this new tool they designed that would allow you to build MVC software following their architecture.

[00:20:39] Right.

[00:20:40] So it was it was pretty like bleeding edge at the time, but it was how do you have the architecture?

[00:20:46] How do you put a framework around it?

[00:20:48] And then it was actually writing the code and I would write the code, but I would lead a team of us.

[00:20:53] That's fantastic.

[00:20:54] Has that so the question is, has that hindered you or helped you when you started a company, a technology company?

[00:21:02] Like it's helped.

[00:21:04] It's kind of like with kids.

[00:21:06] Like I have a 15 year old and high school and I hear the stories.

[00:21:12] I see the excuse.

[00:21:13] I hear the excuses.

[00:21:14] And I'm like, you can't.

[00:21:16] Sorry.

[00:21:17] No, no.

[00:21:17] So when I'm in a room with like engineers, I certainly can't write code anymore, but I know what they're saying enough to be like.

[00:21:25] No, no.

[00:21:25] That is not the reason you missed like the deadline or why there's an issue with this module not working.

[00:21:31] Like I've been there.

[00:21:32] Like I know how stuff works.

[00:21:33] Yeah, I can see that.

[00:21:35] I can see because I've worked with a couple of CEOs that could crack open a laptop and code.

[00:21:39] Yeah.

[00:21:40] And it's crazy.

[00:21:41] It is crazy to me.

[00:21:43] It's impressive.

[00:21:44] You know, that's a great, that's a great idea.

[00:21:45] Let me see.

[00:21:46] I'm like, dude, are you in, are you actually in your software on your?

[00:21:50] Yeah.

[00:21:51] And I've also seen the opposite.

[00:21:53] You know, guys and gals that don't know, they have a great idea.

[00:21:57] There's a great, but technical lead.

[00:22:00] And so that person kind of handles that side of the business and they handle the other side.

[00:22:05] So the question is with your technical background, but you did say you had a love of sales and marketing at one point.

[00:22:11] Where do you see yourself with the company?

[00:22:13] Like what do you, what do you kind of gravitate to?

[00:22:15] Is it, is it more on the technical side and features functions, you know, that type of stuff?

[00:22:20] Or is it, Hey, we want to go to market.

[00:22:22] Wait a minute.

[00:22:23] Let's talk a little bit about that.

[00:22:24] What are we going to do?

[00:22:25] It's an awesome question and it's evolved.

[00:22:29] When is my third company?

[00:22:31] And my first one, which was acquired by RealPage years ago in 2013, I was a CTO and co-founder.

[00:22:38] Hi, I'm Steven Rothberg.

[00:22:40] And I'm Jeanette Leeds.

[00:22:41] And together we're the co-hosts of the High Volume Hiring Podcast.

[00:22:45] Are you involved in hiring dozens or even hundreds of employees a year?

[00:22:48] If so, you know that the typical sourcing tools, tactics and strategies, they just don't scale.

[00:22:54] Yeah.

[00:22:55] Our bi-weekly podcast features news, tips, case studies and interviews with the world's leading experts about the good, the bad and the ugly when it comes to high volume hiring.

[00:23:06] Make sure to subscribe today.

[00:23:08] Hey, this is William Tenka, Work to Fun.

[00:23:11] Hey, listen, I'd like to talk to you a little bit about Inside the C-Suite, the podcast.

[00:23:14] It's a look into the journey of how one goes from high school, college, whatever, all the way to the C-Suite, all the ups and downs, failures, successes, all that stuff.

[00:23:25] Get a listen.

[00:23:26] Subscribe wherever you get your podcasts.

[00:23:28] And back then it was, I was writing code.

[00:23:32] I was involved in the infrastructure.

[00:23:34] But I was also doing some sales and I was involved, you know, in going to conferences and doing pitches to prospective clients.

[00:23:42] I would say, though, like I did enjoy consulting and programming because I think I'm a natural introvert.

[00:23:48] And I get my energy from solving problems, not from talking to people.

[00:23:52] Right.

[00:23:53] That drains me quickly.

[00:23:54] Yeah.

[00:23:55] So, you know, I think as I started to get more comfortable, first startup and then with the second startup, I moved more towards operations, which got me more like probably my consulting roots of how do you come in?

[00:24:09] How do you think about putting all the pieces together?

[00:24:12] But also looking at finances, looking at how we move the needle with generating revenue and being like the second startup I had done, which was ApartmentJet.

[00:24:22] Me and my fellow co-founder was the CEO.

[00:24:25] The two of us, we were doing all the selling.

[00:24:27] So, like I was forced into that and I enjoyed it.

[00:24:30] But I also really enjoyed the marketing aspect.

[00:24:32] So how do you how do you get into a position where you're talking to somebody, but you get them excited about features within the product that you're building?

[00:24:40] So I certainly grabbed onto that.

[00:24:42] And now, like, as my career has moved on, like I'm not involved in the technology.

[00:24:46] Our CTO would probably kick my ass if I said anything about the code.

[00:24:51] So you want nothing to do.

[00:24:52] Correct.

[00:24:53] I'm not allowed to look at the code.

[00:24:54] Like, that's a no.

[00:24:55] But I'm certainly very involved in all aspects of sales, whether it's the clients, it's investors, it's talking to guys like you guys.

[00:25:03] I enjoy it.

[00:25:04] You're telling the story.

[00:25:05] Telling the story is something like I'm really passionate about now and I enjoy that piece.

[00:25:10] Looking back, it's different than the excitement you get out of building with your hands.

[00:25:15] Now I'm telling the story about what we're building, but I'm not actually doing the building anymore.

[00:25:19] It's a little bit different.

[00:25:20] Yeah, 100%.

[00:25:21] How accurate are you at telling the story?

[00:25:24] And does your team come back and say, Andy, what the fuck?

[00:25:30] That is a great question.

[00:25:31] I love asking that question because I know some people over there will say 90 things that we have no business being.

[00:25:43] Yeah, because you've never been on the other side where they're responsible for coding it, for deploying it.

[00:25:51] It's real easy to just bullshit and it's all vaporware that you're selling.

[00:25:56] 100%.

[00:25:56] Don't see live software.

[00:25:58] Do you just see this demo that we're going to show you?

[00:26:00] Absolutely.

[00:26:00] In this demo environment where we've created everything.

[00:26:02] You have in your head a dream of what you wanted to do and you're selling that.

[00:26:05] So I have too much respect for what my team is doing and honestly too much respect for the people we're pitching to sell them something that doesn't exist.

[00:26:14] It's really important to me that we sell what we can do.

[00:26:18] Right.

[00:26:19] That said, I have to sell and you have to be creative in how you position stuff.

[00:26:24] But we've always been pretty firm.

[00:26:27] We're not selling something that isn't green.

[00:26:29] I think talking to people about releases, like showing them live software, here's how it is right now.

[00:26:34] So let's just crack open one.

[00:26:36] We have their permission.

[00:26:37] Let's go through this.

[00:26:38] It's not a demo environment.

[00:26:39] It's not PowerPoint.

[00:26:40] It's not something we kind of mocked up to make it look greater than it is.

[00:26:43] This is actually looking at something.

[00:26:45] And oh, by the way, we do four releases a year, whatever the bit is.

[00:26:49] Here's what's going on in the next two releases for sure.

[00:26:54] And like letting them know, okay, it's not there.

[00:26:56] Like if you buy this tomorrow and we do the implementation, we stand you up.

[00:27:01] Okay.

[00:27:01] That's not going to be there.

[00:27:03] But that will be there on January 15th.

[00:27:07] Nothing wrong.

[00:27:07] That's salesmanship.

[00:27:09] Nothing wrong with that.

[00:27:10] It's great excitement over something that doesn't exist.

[00:27:12] Or like ultimately being a leader who doesn't care about the software.

[00:27:16] I don't care if it works or not.

[00:27:17] Like I'm here to just sell.

[00:27:19] Yeah.

[00:27:20] And for me being like, it needs to work.

[00:27:22] It needs to work.

[00:27:24] Excellent.

[00:27:24] It needs to be a great experience for our end users.

[00:27:27] Otherwise, to me, it's a failure.

[00:27:29] It doesn't matter if it's a hundred million dollar business.

[00:27:31] Ryan, I think you're a bit, I think that's more with salespeople.

[00:27:34] Younger salespeople.

[00:27:35] Well, I'm not sure.

[00:27:36] Sales leaders.

[00:27:37] They'll just sell whatever.

[00:27:39] Not the person who's built the company.

[00:27:41] Right.

[00:27:41] Yeah.

[00:27:41] Totally.

[00:27:42] Yeah.

[00:27:42] I mean, we've been there throughout the career.

[00:27:45] I've seen the CEOs have that same attitude.

[00:27:47] Yeah.

[00:27:47] Yeah, that's true.

[00:27:48] That is.

[00:27:49] You can name a couple of companies if we actually want to do that.

[00:27:51] Yeah.

[00:27:52] No, no.

[00:27:52] Some of the, I know a few who have gone to that extent and they've really thrown their

[00:27:59] team under the bus.

[00:28:00] But in their minds, I wrestle with this.

[00:28:03] Excuse me.

[00:28:04] I wrestle with this because I think, okay, they need to sell.

[00:28:07] Get it.

[00:28:07] But is there a part of them that's actually believing like, you know what?

[00:28:12] I can sell this.

[00:28:13] I know it's not a massive feature that could be added.

[00:28:16] And Andy is amazing.

[00:28:17] He can get this done in the six weeks that I need him to get this done.

[00:28:21] Yeah.

[00:28:21] Because there's a sales lag.

[00:28:23] Yeah.

[00:28:23] And they know by the time that that happens and contracts go through legal and all that

[00:28:28] stuff.

[00:28:28] That doesn't make it right.

[00:28:29] No, no.

[00:28:29] Ryan, you've heard me say this before.

[00:28:32] There's a book during the Lean Startup Movement that a buddy of mine wrote.

[00:28:36] It was Lean Analytics.

[00:28:38] And in the first chapter, they talk about how entrepreneurs are psychopaths.

[00:28:44] And the reasoning for this whole chapter was entrepreneurs live in the past, present,

[00:28:50] and future tense simultaneously.

[00:28:52] So when there, it isn't so much that they're trying to tell someone a lie, that they're telling

[00:28:59] them that they know that this is available and it's coming, but they can't say that it's

[00:29:04] coming because that's going to ruin the experience.

[00:29:06] Yeah.

[00:29:06] They're squishing everything together into the current time period.

[00:29:10] Right.

[00:29:11] I get it.

[00:29:11] So, yeah.

[00:29:13] First, you did say you sold to RealPage and I know RealPage and there's some executives

[00:29:17] at RealPage back in the day.

[00:29:19] What was the bit?

[00:29:20] What was the company?

[00:29:21] I mean, we forgot to ask you.

[00:29:22] No, that's fine.

[00:29:23] So I was in a multifamily industry, not purposely.

[00:29:27] I just somehow got into that.

[00:29:29] The apartment industry.

[00:29:30] Fell into it.

[00:29:31] Fell into it somehow with our first startup and that was called Rent Sentinel.

[00:29:35] Rent Sentinel was actually the product, but that's what everybody knew us by.

[00:29:39] And Rent Sentinel was a marketing solution for owners and operators.

[00:29:43] And its original purpose was, I mean, it's kind of crazy to think, but there was this new

[00:29:48] platform where people were going out onto looking for apartments.

[00:29:52] It was called Craigslist.

[00:29:54] And owners and operators wanted to figure out how the heck they listed their apartments

[00:29:58] on Craigslist because it was free.

[00:29:59] And so we started building a platform that automated the process to get an apartment listing

[00:30:06] onto this horrible, antiquated Craigslist solution.

[00:30:11] Still looks the same.

[00:30:13] Still looks the same.

[00:30:14] Yes.

[00:30:15] But it's effective, especially people that don't know the area.

[00:30:18] They're moving from Chicago to Philadelphia.

[00:30:20] They've never been to Philadelphia.

[00:30:22] They need to know, by the way, their job starts on Tuesday.

[00:30:25] Like they've got to get an apartment.

[00:30:27] Yeah.

[00:30:28] So first marketplace, it didn't look corporate and you were just doing a transaction with

[00:30:32] an individual.

[00:30:33] I see.

[00:30:33] I can see real page wanting that.

[00:30:36] Yeah.

[00:30:37] Yeah.

[00:30:37] I can see that.

[00:30:38] We built it.

[00:30:39] The first tool with Rent Sentinel that made it really easy for some of the biggest owners

[00:30:45] and operators.

[00:30:46] Smart.

[00:30:47] Of, you know, some of them were public REITs.

[00:30:49] Yep.

[00:30:50] To be able to get their apartment listings onto Craigslist with a couple clicks of the

[00:30:54] button.

[00:30:55] Oh, I love that.

[00:30:56] And then what we did is we gathered all the data around it.

[00:30:59] So we were able to, like, you could log into our app.

[00:31:01] It was pretty wild.

[00:31:02] And if you had a listing on Craigslist for an apartment down in Texas or two bedroom,

[00:31:06] you could pull up, we call that, I think it's like our microscope and our ad microscope.

[00:31:12] And you could see everybody at that moment that was looking at your listing from all

[00:31:17] over the Arlington area.

[00:31:18] Wow.

[00:31:19] It was cool.

[00:31:19] Wow.

[00:31:19] It was like a salesman type tool.

[00:31:22] Yeah.

[00:31:22] But it was pretty slick.

[00:31:24] It certainly worked well in the sales process.

[00:31:25] It was like Zillow in some ways now.

[00:31:28] But you could see the inventory, but also what the inventory costs.

[00:31:31] Correct.

[00:31:32] And then we started aggregating all the rents.

[00:31:34] Wow.

[00:31:34] What the rents were moving for.

[00:31:36] You know, we facilitated basically the ability for large operators to get listings on the Craigslist

[00:31:42] and move those transactions, but also visibility into the marketing side of it.

[00:31:47] Yeah.

[00:31:48] And we could show them the ROI of moving a lot more of your inventory away from some

[00:31:52] of the big listing sites where it would cost them millions per year.

[00:31:57] Yeah.

[00:31:58] Over to this free site Craigslist.

[00:31:59] That said it was a constant cat and mouse game because Craigslist did not want their inventory.

[00:32:05] They certainly didn't want it from the owner and operators to be putting it out there.

[00:32:08] They wanted it from the individual renters.

[00:32:10] So we had to figure out how to get around Craigslist.

[00:32:13] Right.

[00:32:14] Did you stay on with RealPage?

[00:32:17] I did.

[00:32:18] So they acquired us.

[00:32:19] We built the company for about five years.

[00:32:22] It got pretty big.

[00:32:23] I think we had, at the time, we acquired about 50 or so employees, but eight of the top 10

[00:32:29] biggest owners in the country were using us.

[00:32:31] And I think we had over a million apartments on our platform.

[00:32:35] So Steve Wynn, who was the CEO and founder of RealPage, loved what we were doing, acquired

[00:32:41] us.

[00:32:42] We went over our team and we ended up running their marketing division, which included our

[00:32:47] solution, but a whole bunch of other marketing solutions that Steve Wynn had acquired.

[00:32:51] It was a quarter of companies.

[00:32:53] It was great.

[00:32:53] It was a good experience.

[00:32:55] Steve Wynn is in Steve Wynn?

[00:32:57] Steve Wynn?

[00:32:57] Not Steve Wynn, the hotel guy.

[00:33:00] Okay.

[00:33:00] All right.

[00:33:00] Different Steve Wynn, both very successful.

[00:33:03] Both very successful.

[00:33:04] Okay.

[00:33:05] Yeah.

[00:33:06] And Ryan's second company, after you did RealPage, you stayed there, you helped them,

[00:33:09] and you had to earn out and all that type stuff?

[00:33:12] We did.

[00:33:13] So we stayed there for a couple of years.

[00:33:14] Non-Competes came up.

[00:33:16] So I had two co-founders with me with Rent Sentinel.

[00:33:19] We left after a couple of years and Non-Competes came up and we got the band back together.

[00:33:24] We had been in the apartment industry now for a good seven plus years.

[00:33:29] And we saw this new emerging marketing opportunity for apartment owners and it was around short-term rentals.

[00:33:36] And we said, how do we enable sites like Airbnb and Expedia, Vrbo, Booking, so that owners could participate in short-term renting their vacant units?

[00:33:48] Because vacancy is always a problem in the apartment industry.

[00:33:50] And plus, those same owners and operators were really ticked off that their renters were all putting their listings onto those sites and profiting in from it, but they were unable to.

[00:34:00] So we built a company called Apartment Jet.

[00:34:02] And it was a tool for owners and operators to take the vacant units.

[00:34:05] We helped them through the process of furnishing it.

[00:34:08] And then we listed those units on the short-term rental sites.

[00:34:13] But then we also managed it with a centralized concierge team.

[00:34:17] Because you think about some of these big companies like Graystar and others, they're not equipped and their leasing teams on site are not equipped to do short-term rentals.

[00:34:26] It's a very new concept to them.

[00:34:28] So we would manage it all from here in Chicago.

[00:34:31] And it would be crazy.

[00:34:33] We'd be dealing with people getting locked out at 2 in the morning on a Saturday night.

[00:34:37] And we would be getting the phone calls and handling it.

[00:34:40] Expedia scooped us up after 18 months into the business.

[00:34:44] Wow.

[00:34:45] Did you stay on with Expedia?

[00:34:47] Stayed on with Expedia for almost two years.

[00:34:51] Loved it.

[00:34:52] So we were down in, based out of the Vrbo office in Austin, which is great.

[00:34:59] Like so many smart people love the Expedia team.

[00:35:03] And everything was going great.

[00:35:04] We were building a new division to compete against Airbnb.

[00:35:07] And then this pandemic happened.

[00:35:09] Wow.

[00:35:10] And that, you know, obviously hit the entire world hard.

[00:35:14] But for travel and hospitality, we didn't last out of that.

[00:35:17] So they ended up closing our division.

[00:35:19] Which is how I segued into, hey, the off-boarding process sucks.

[00:35:26] I'm following the path here.

[00:35:27] So you, with ApartmentJet, you exited out at the right time.

[00:35:32] We did.

[00:35:32] Yeah.

[00:35:33] You exited out at the right time.

[00:35:34] We would have been goners.

[00:35:35] Yeah.

[00:35:36] If we didn't exit.

[00:35:37] Right.

[00:35:37] So question.

[00:35:39] I want to go back.

[00:35:39] Just one quick step.

[00:35:41] As you're in your earn out period, in your original exit, were you already formulating

[00:35:48] the next, were you hatching the next plan with the original co-founders?

[00:35:52] Or was this just something you guys left, you guys were done, you're like, what are we going

[00:35:57] to do?

[00:35:57] Get together for beers.

[00:35:58] Yeah.

[00:35:59] All right.

[00:35:59] All right.

[00:36:00] So while we were at RealPage, we were not hatching the next plan.

[00:36:05] But I can tell you, taking an entrepreneur and locking me and my two buddies up in a very

[00:36:12] corporate world where it moves like a battleship.

[00:36:15] Yeah.

[00:36:16] Like we're clawing to get out and do something different.

[00:36:19] I do remember we got together after we had been out and we sat in my buddy Kevin's apartment

[00:36:25] with a big whiteboard and just started writing ideas up on the board.

[00:36:29] That's how.

[00:36:30] Yeah.

[00:36:30] And looking at all different types of solutions and the one we kept coming back to was, man,

[00:36:34] this Airbnb thing is getting big and there's got to be a way for owners to be able to get

[00:36:39] their listings on there.

[00:36:40] But yeah, it was like, we weren't sitting on that knowing we're going to jump into it.

[00:36:45] It was purposeful sitting down.

[00:36:47] Okay.

[00:36:47] Where do we go next?

[00:36:48] We know this industry well.

[00:36:50] We knew the pain points around vacancy.

[00:36:52] And then we saw the opportunity with new ways to list your apartment.

[00:36:56] What's it like to have three co-founders?

[00:37:01] It's a good question.

[00:37:02] I think it's actually, in some ways it can be good.

[00:37:05] In some ways it can be great because you're not alone.

[00:37:09] You also, we are fortunate in our situation and that we each brought different aspects.

[00:37:14] So, you know, our CEO was Eric Broughton, who is a great sales leader and a good figurehead,

[00:37:23] a natural CEO.

[00:37:25] And then my other co-founder was Kevin Kapersky, who is a brilliant designer, creative, author

[00:37:32] of books.

[00:37:34] Brought in a whole different thing that we didn't have.

[00:37:36] And then there was me who was very operational, very in the weeds with how you run everything

[00:37:41] and put together teams and organize a business.

[00:37:43] So we fed off each other really well.

[00:37:46] That said, like we've been doing this for a number of years together.

[00:37:49] Yeah, you worked out the chemistry.

[00:37:50] And you start to have challenges with personalities.

[00:37:52] Oh, yeah.

[00:37:53] Because people want to grow, but they want to grow in different ways that aren't as useful

[00:37:57] or in competition with.

[00:37:59] I've seen that before with three co-founders or more, that at some point it's hard because

[00:38:05] you're great at one thing or, you know, a couple of things, but you might not want to

[00:38:09] be great at that.

[00:38:10] You might be bored.

[00:38:11] You're tired of finance.

[00:38:12] You want to do something different.

[00:38:14] You want to open up offices.

[00:38:15] You want to do international expansion.

[00:38:17] Somebody else owns that.

[00:38:19] So I'm always curious because solopreneurs, I get that.

[00:38:24] Partners with two, I get that.

[00:38:27] Three, four, five, eight, ten.

[00:38:29] Like I struggle with the politic of how work gets done.

[00:38:35] There's a lot.

[00:38:35] Yeah.

[00:38:36] There's a lot.

[00:38:37] There's a lot there.

[00:38:38] And now with WEN, I have a co-founder.

[00:38:41] Right.

[00:38:43] And so it's dealing with, you know, just the two of us.

[00:38:46] In some ways it can be easier, but, you know, I think three, like you do bring different

[00:38:50] perspectives.

[00:38:52] Yeah.

[00:38:52] In some ways it can help that creative process.

[00:38:55] And certainly like when you go through, you know, the rough patches, having two folks

[00:39:00] in the room can be helpful as long as you respect each other and you can work through wishes.

[00:39:07] Right.

[00:39:07] Like I would, like anybody that's asked me like about starting a business and doing it

[00:39:12] on your own, I encourage them not to.

[00:39:14] I think like by yourself, you are in a vacuum and it's going to be really hard to get through.

[00:39:19] That's right.

[00:39:20] And you don't have anybody to bounce the ideas off of or to check you.

[00:39:25] To check you.

[00:39:26] Or worse, you're bouncing it off your wife or your spouse, your partner, et cetera.

[00:39:30] Yeah.

[00:39:30] Grounds with the force there.

[00:39:32] Right.

[00:39:32] Now you're bringing, you're pulling all that.

[00:39:35] I'm just saying.

[00:39:36] You're pulling all that stuff into the marriage or the partnership.

[00:39:38] My wife can give two, like she does not care.

[00:39:42] She doesn't even know what, she still thinks I'm a recruiter, Andy, from like the year 2000.

[00:39:47] She has no clue.

[00:39:48] It's better that way.

[00:39:49] It's better that way.

[00:39:51] It's like, you got a good sort of separation between the two.

[00:39:54] I like that.

[00:39:55] Yeah.

[00:39:56] Question around teams.

[00:39:57] You brought this up a couple of times.

[00:39:59] And I think people struggle here, especially as they're starting.

[00:40:02] So, you know, scenario, you're talking to a young entrepreneur, someone who started a

[00:40:08] couple of partners and they're looking to grow their team.

[00:40:11] What makes a good team?

[00:40:12] How do you put together a really solid team?

[00:40:16] Yeah, it's, it's, I think the hardest thing to get your company from that founder state to actually evolving into like a real company.

[00:40:24] Where do you make those initial hires?

[00:40:26] I can't say for all companies, but me personally, like we've been building technology solutions and it's starting with bringing in really smart engineers.

[00:40:34] Put a focus on the product.

[00:40:37] Make sure you get the product right.

[00:40:39] Your founder, your co-founders, like you guys are responsible for the sales and marketing, running the finances.

[00:40:44] Surround yourself with good engineers right off the bat so that what you're trying to sell actually works.

[00:40:50] And I think like in some ways, I think they're the easiest hires because they're just true to who they are.

[00:40:57] Like a lot of engineers are pretty rigid and like they're not selling you.

[00:41:02] Like I'm a nerd and I'm here to write code and that's what I want to do.

[00:41:07] Don't ask me to do other stuff.

[00:41:08] Yeah.

[00:41:08] I've always found they're easier to hire and like there's less turnover on the engineering side.

[00:41:13] So if you're building a technology solution, I start with getting good young engineers.

[00:41:18] Do not hire that manager right away.

[00:41:20] Hire the doers, the programmers, and then you help guide them.

[00:41:25] I love that.

[00:41:26] Last question for me is the people at this stage in your career that thrive around you.

[00:41:31] What do you need, either personality or otherwise, what do you need around you for you to be successful?

[00:41:37] For me personally or the individuals around me?

[00:41:40] The individuals.

[00:41:41] I mean, they have to stay challenged, but they also like this is I think a hard part for me is like this is my first time being a CEO with one of my startups is making sure you keep them in the loop with the business.

[00:41:56] Like you forget like anybody that joins you early on, they're entrepreneurs in training.

[00:42:01] Like they have that same drive.

[00:42:04] They've given like you a lot of risk to join your organization.

[00:42:10] If you don't give them visibility in the trajectory of how things are going, whether it's good or bad, you're going to lose them and they're not going to be as supportive and they probably won't stick around.

[00:42:19] So you just have to constantly talk to them.

[00:42:22] And like you have to be an open book, which we've learned over the years.

[00:42:26] Like I did certainly a lesson learned with our first two companies, making sure people stay in the loop.

[00:42:30] And now me as a CEO, making sure that like we continue those conversations.

[00:42:35] And I can tell you like later today, I have like a one on one with a couple of our member service team player like employees.

[00:42:41] So like I want to make sure I continue to talk to all the individuals on my team so that like they know they're part of something with me.

[00:42:49] Oh, I love that.

[00:42:50] Such a great answer.

[00:42:52] Drops mic, walks off stage, Ryan?

[00:42:54] I believe so.

[00:42:57] As long as you don't break it, we're good.

[00:42:59] All right.

[00:43:00] Andy, this was wonderful.

[00:43:02] Thank you so much for being on the show and sharing your wisdom and your experiences.

[00:43:06] My pleasure.

[00:43:07] Thank you guys for having me, Roy.

[00:43:09] And thanks for the audience.

[00:43:10] Until next time.

[00:43:11] She's horrible.

[00:43:11] One of the past.

[00:43:12] And I did it here.