Serial Entrepreneur with a Background in Recruiting

Jeff Ellman, Co-Founder of UrbanBound

Jeff Ellman is the Co-Founder of UrbanBound as well as HomeScout, Humatal, Hireology, and more. One of Jeff’s first companies was a recruiting firm and he has hired thousands of employees, raised millions in VC funding, and lead from the Co-Founder seat in several companies. Learn from his experience on this episode of The Best Team Wins Podcast.

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Connect with Jeff on Linkedin and Twitter.
































Adam Robinson: Welcome to The Best Team Wins podcast where we feature entrepreneurs and business leaders whose exceptional approach to the people side of their business has led to incredible results. My name is Adam Robinson and, for the next 25 minutes, I’ll be your host as we explore how to build your business through better hiring. Today on the program, Jeff Ellman is a founder of several companies, including his current company, UrbanBound, based out of Chicago, as well as companies such as Humatal, HomeScout, Hireology and others. Jeff is a seasoned sales leader and entrepreneur. He’s hired thousands of employees. He’s [inaudible 00:00:48] millions in DC funding, is worldly and has seen it all and, Jeff, we are excited to have you on the program today.


Jeff Ellman: Thanks, Adam, I’m thrilled to be here.


Adam Robinson: We are going to be sharing real live experiences over the course of your business-building career but, before we dive in, let’s set the stage for our listeners. Give us 30 seconds on UrbanBound and what you guys are up to.


Jeff Ellman: Sure. We started UrbanBound about six and a half years ago. What we found was that, in corporate America, there’s a big problem, and the problem is that most companies, when it comes to hiring talent, typically they have to go outside their backyard with the unemployment rate right now being around 4.5%, and they have to relocate employees. The way relocation usually works is, “Adam, here’s $10,000 for your move. Good luck. We’ll see you on your start date or go figure out your move on your own and we’re going to reimburse you for some of the costs along the way.”


  Our goal is to provide a better experience for employees by building software that allows a company to create a policy that really is the guidelines for the entire move through the software that points the employee to the best suppliers to use, tell them more and more about their city, and overall have a proven process to follow to ensure that their relocation goes well, to really factor in on how we improve the best possible onboarding experience at any company in this country and in this world.


Adam Robinson: Wow. All right. If listeners want to learn more, what’s the best way for them to do that?


Jeff Ellman: By visiting


Adam Robinson: All right, so let’s jump right in. Jeff, you’ve done how many companies at this point?


Jeff Ellman: Six companies.


Adam Robinson: Six. You can I, along with Michael Krazman, partnered to launch Hireology going on eight years ago now, which is hard to believe, but let’s talk about UrbanBound and the origin of that business from a people standpoint. You guys have been, I know, working on that for a while under the name ThinkChicago before embarking on scaling that business. Take us to the moment you knew that you needed to staff it differently to add different people to the organization and grow it. Just take us through that thought process and how you approach that.


Jeff Ellman: Yeah, let’s take you back to actually the ThinkChicago days which was, for any entrepreneur who was looking to start a business, really starting with the MVPs, so the Minimal Viable Product and, for us, it was how can we get in front of as many HR leaders as possible, see if there really is a problem out there that people are willing to pay money to solve. The idea of UrbanBound really went back to Think Chicago which was, we realized that most companies, when they were relocating employees, they really weren’t providing a great experience and there was very little support.


  Yet, the City of Chicago was doing everything they can to attract companies to be headquartered here, but those companies that were in Chicago were doing nothing to really get employees to be excited to want to move here. We partnered with the city. This goes back seven and a half years ago with Mayor Daley, and we had CD-ROMS that went out to HR departments and sent to employees, really to focus on workforce attraction and work towards retention.


  Then, we quickly learned there was a big problem that we were solving just in Chicago, and we had to scale this to other markets, so we got rid of the name, Think Chicago, and launched UrbanBound and then really learned that, if we can actually write policies and guidelines for companies and control the expenses on behalf of the employer, we can move those funds in the right direction, to the right suppliers, and report back on performance to ensure that relocations are going well.


  As we were scaling the company, getting back to your question on hiring the right people, it was all early on. In the early days, it was about specialization of job functions. We knew we wanted to scale, and we wanted to scale quickly, and we felt the best way to that was, specifically, we had to get customers. Out of the gate, we wanted to bring on the Lighthouse accounts. If you think about the TWCs or the C.H. Robinsons, the PepsiCo’s, the Fortune 500 companies of the world, we wanted them as customers, so we targeted them.


  We had different pricing, if you want to call it free or very low price, to get them in the door, knowing that we could have case studies to help us scale. Then, we hired people for specific roles so, whether it was a BDM which was a Business Development Manager who was responsible for having meetings or an AE who is responsible for closing those meetings and, of course, account managers who are responsible for their renew and upsell of those accounts at that point in time, so very specialized hiring.


Adam Robinson: What did that early team look like?


Jeff Ellman: It was a team of people who really had no experience in relocation because I, myself, had no experience in relocation, but it was a team of people that were all wanting to solve this problem, that everyone could relate to, which was moving is not a great experience, and there could be a better way and software should really be the way to do that, but these are people that were really eager to learn and excited to teach and wanted to offer something new to a market and had never seen relocation software before.


Adam Robinson: You approach to finding those individuals comprised of what when you were getting started?


Jeff Ellman: Luckily for me, and I told my investors when we first started the company is that my prior life, I was a recruiter. I started a recruiting company and had a very large database of talented salespeople in the Chicago area, so I was able to go through a list and identify the top 20 people who I call social kingpins who were very successful in their selling career, and I asked each one of them to make three introductions for me. I gave them the template and, from there, word really spread that there was a high-growth company in the relocation space in Chicago and HR tech that was looking to scale their sales team, and we had a plethora of candidates that were great.


Adam Robinson: Let’s talk about that recruiting company, Humatal. You had the benefit, not only of having hired lots of people for your own businesses, but having done it on behalf of lots of other companies. What have you observed in your time doing this that is the number one or two reasons why companies aren’t very good at the hiring part?


Jeff Ellman: I was always surprised when I sent over candidates who I felt were phenomenal for the job, and the employer would reject him or her for reasons that I would never have been able to predict, and it really went back to that they didn’t have a hiring process that was asking them to ask the right questions. Even when they asked the right questions, they didn’t even know what answers to look for that would predict success.


  I found that most of my clients, the people who were making hiring decisions back in the day, weren’t even trained on how to run a hiring process, weren’t trained on the right questions to ask, and really were hiring with their gut almost 100% of the time, so it came down to heads or tails. It was a coin flip to see who they would hire and, the majority of the time, they were making bad hiring decisions, which was costing their company a tremendous amount of time and money and resources.


Adam Robinson: What’s the first thing you would typically do with an organization that was going from no process to some kind of structured hiring process?


Jeff Ellman: One of the things that I’ve done is, I’ve done exercise with the job function, so people who are in that role, really understanding who do you want to be in this role? What words would best describe a sales person at your company? We want them to be curious, we want them to be aggressive, we want them to be persistent and then, what are the things that we need to do to try to find those people and really identify what are the questions to ask that would [inaudible 00:07:50]?


  Does that characteristic exist in this employee or candidate? If we’re not asking the right questions, really factoring in what are the top 10 or 15 things that we want to get out of an interview and, also, what are the things that we can look for in an interview that ties back to our core values as an employer because, at the end of the day, if they don’t align with your core values and they say all the right things to every single question, they’re still not going to be a fit.


Adam Robinson: Is there a particular interview question you find most valuable as you try to figure this out?


Jeff Ellman: There’s not one specific question, but one of my favorite questions that I typically ask is, “Adam, if you could share with me your previous place of employment, what was your boss’s name? How do you spell his or her name? When I call your boss and I ask about your performance on a scale of 1-10, what is he or she going to tell me? What are they going to say that you need to improve upon?”, etc., and you can really dive deep just in that one question, and I think that question is like truth serum because they really do start to visualize in their mind that, “You are going to call my boss. You are going to learn these things,” and they really tell you everything that you need to know in that one question.


Adam Robinson: What’s the range of responses you typically get when you ask? That’s a pretty full frontal question in an interview.


Jeff Ellman: Before the response ever comes out of the candidate’s mouth, you start to see the non-verbals. You see the wiggling in the chair, being uncomfortable, the red blotches on the neck because they’re going to have to give me some information they know I’m going to verify versus the rest of the interview. Some candidates can say things that you probably can’t fact-check, so it’s just a fantastic way, early on, to get to the root of the candidate.


Adam Robinson: Let’s get back to UrbanBound. How many employees are in the business today, just to give our listeners some ideas to the scale?


Jeff Ellman: We have 35 employees as of today.


Adam Robinson: What is the leadership team that you have in place that are required to operate the business at that level?


Jeff Ellman: Leadership team. I always say that a leadership team should never be able to, if you’re having a meeting, a large pizza should be able to service your entire leadership team. If a large pizza is not going to be enough, then there’s a problem. We’ve got six people on our team, potentially maybe a seventh as we grow, but you have a Director of Finance, you have your head of engineering, your head of your product, your COO, and then two co-founders and your head of sales, as well.


Adam Robinson: As you evolve the business, what is the biggest challenge, or obstacle, you’re facing as it pertains to the leadership team communication in growing the business? What’s that one thing on your plate you’re working through?


Jeff Ellman: It always come back to, as a software company, we win or we lose with our product, so any kind of conversation around the product direction and the roadmap would probably be the answer to that.


Adam Robinson: Has your approach as a team to diagnosing product-related questions changed as you’ve gained experience?


Jeff Ellman: It has because, the more and more customers we bring on, the more promise we can hear in the market and the more, call it advisors that we’re able to reach out to before we actually built something. Over time, our product market fit is just spot-on versus the early days of the company. We had a hypothesis, we built something, and test it, and we always said we were far off but, right now, we are absolutely in the right direction, which is why we’re going to be raising more money and adding more fuel to the fire so we can scale this company at a faster pace.


Adam Robinson: Congratulations on that. As you look forward then, to be a leader in your organization, what do you think is the most important quality to have in the way you do business?


Jeff Ellman: For me, personally, I feel like my passion for the business has to be contagious. I have to have empathy. I have to understand each employee’s challenges in their role and be the person who can help remove the roadblocks. I always prided myself on being approachable, and I also think a great leader has to be very curious to understand the ways that they can impact the business and help. Even by curious, I mean reading blogs, reading books, attending seminars and gaining that knowledge, then sharing that knowledge with your coworkers.


Adam Robinson: How are you digging that stuff in interviews? What tips do you have for folks listening, based on your experience?


Jeff Ellman: We have specific questions about that, so I do want to know in the interview process, tell me things that you’re passionate about because, if they don’t have a passion in their personal life, then they’re certainly not going to be excited and passionate about my business. Trying to figure out if someone’s curious or not, Adam, I’m going to ask them again at the end of the interview, what questions do you have for me?


  A great candidate, 100 out of 100 times, is going to have 5, 10, 15, 20 questions. These are not questions about what’s your vacation policy like or what are the benefits like. These are questions like, “Tell me more about the biggest challenge you have in your business” and “How long is your sales [inaudible 00:12:50] goal?” and “What’s the average retention rate of your customers?” Really, it’s thoughtful questions that shows me this is a curious person, and they’re intelligent, as well.


Adam Robinson: You mentioned some things that are important to you personally. How does that translate into the core value system of UrbanBound? Do you have core values and, if so, what are some things that you can share with us about the role of values in the interviewing process?


Jeff Ellman: For any of the companies I started, if I think back to the very first days of starting a company and coming up with a blueprint for what would, hopefully, be a successful business, it went back to the core values. It seems that the businesses I started, the core values have been different at some of them. Some of them carried through but, here, we always talk about being eager to learn and excited to teach because there’s no blueprint out there for how to build relocation management software. No one’s ever done it before.


  As a startup, we talk about doing more faster. That’s one of our core values is, can we do more faster in a short period of time? Can we accomplish goals that we set out for the whole year maybe interest first six months of the year? We always talk about [inaudible 00:13:52] as a core value so, once again, when I give someone a problem, I want them to come back to me with a potential solution and try to figure it out on their own before relying on me to give the answer.


  Also, another important core value for us is being able to see the big picture and understanding the why behind what we do every single day because, at the end of the day, what really is exciting about our business is how many people we actually helped relocate. When you can see … We have a flat screen TV in our office where you can see, today, we moved Jennie Smith, and Jennie Smith is working for PepsiCo, and she’s moving to New York with her two kids and a dog. That’s really rewarding to see the impact we’re making on this employee who’s going through a difficult life transition and the fact that we made it easier, and a successful process is very rewarding to everyone.


Adam Robinson: Jeff, let’s transition to more of the tactics of pay and rewards. What’s your philosophy around compensation at your company, and how do you approach what you pay employees?


Jeff Ellman: When it comes to our compensation philosophy, first of all, we always want to make sure we’re offering a competitive base because we know that we need to attract and retain the best possible talent. With any position at any of my companies, there always has to be tremendous upside, whether that’s ownership in the company, whether that’s really aggressive bonuses or commissions. When the company wins, I want to make sure that all of our employees are winning at the same time.


Adam Robinson: What do the [inaudible 00:15:21] look like there? I know, from our experience, Chicago is a give-me based salary, not necessarily a lot of equity town. If I’m on the West Coast, base is somewhat important, but equity’s the most important thing. How does that sit with UrbanBound’s model?


Jeff Ellman: Very rarely, even when we make an offer to someone in Chicago when they’re negotiating salary, do they negotiate anything around options in the company. It’s typically around base pay, but we do feel strongly that, as the company grows, we know that the options are worth more, and we want our employees to be tied into the future success of the company. We train people. We do Options 101 right out of the gate to make sure everyone understands what it means to be an owner because we do find that, in many companies, the reason why employees don’t value options is they don’t know what it means, so having that as part of the hiring process has been helpful.


Adam Robinson: That’s great. What things do you do that’s non-comp, non-monetary comp-wise to help people feel like they’re getting more of a total reward for being with UrbanBound?


Jeff Ellman: A lot of the things that we do are around career growth. Yes, it’s about measuring their paycheck, but there are so many opportunities here, whether it’s to be on different committees where we have our Culture Club, helping plan events. We’re constantly doing things with nonprofits or for charities or giving back to the community. These are all the things that really make people feel like it’s part of this family environment that makes us have a high retention rate of our employees.


  Also, really challenging employees to even create some of their own career paths here because the career path at a company that goes from 10 employees to 30 employees to 100 employees is typically not well defined so, when people see the opportunity to be promoted and go into different roles, it really creates a lot of excitement and buzz in the company.


Adam Robinson: Let’s take the flip side of the coin, then. How do you approach feedback? If things aren’t going as well as they should with an individual, or someone’s struggling for whatever reason, how do you approach that, individually and philosophically?


Jeff Ellman: My approach to feedback … First of all, there’s two different ways that we approach it. Number one is, we do anonymous surveys, leveraging software called TINYpulse, where we can collect on a scale of 1-10 on how happy are you at work, for example. We can actually quantify the types of employees that are here and are they happy? Are they not? Are they being challenged, etc.? I, personally, want to give to someone straight between the eyes as to how they’re performing, so you always know where you stand with me.


  If you’re not meeting your goals and if you’re [inaudible 00:17:58] effort-related goals, you’re very likely to be put on the performance improvement plan and given a timeframe or warning to turn things around. If that doesn’t happen, that person’s dismissed from the company. Either they fire themselves or we fire them because, at the end of the day, what I promise to every employee that works at any of my companies is that, when you look to your left and you look to your right, you’re only surrounded by A players and, if there’s not an A player next to you, there’s a good chance that person won’t be there for too long. That’s my promise to them.


Adam Robinson: What does that conversation look like with someone? Just give our listeners a sense for how that sounds or is delivered. Let’s say you and I have had a verbal conversation about my particular, let’s say, sales numbers, and you need me to be at a higher level. We’ve operated for another couple of weeks. You just haven’t seen it. What does that conversation sound like?


Jeff Ellman: Those fierce conversations always start off the same way. I will bring you to my room privately, and I let you know we’re about to have a difficult conversation. I would start off by asking you three or four questions. Before I ask you those questions, my philosophy, and my employees know this, is that I truly believe that success is a choice. Every day when you come to work, you have a choice to be successful or not be successful, so I will ask some open-ended questions. Do you feel like you’re putting your best foot forward when you come in to work every day? Can you give me examples of that? If you were in my shoes, how do you think I should feel about your performance and why?


  Having the conversation by asking questions first and really going into what my expectations are to make sure that we’re aligned and giving that person an opportunity to quickly turn it around. The majority of the the time, you’ll see employees cannot turn it around, but those that do, they usually take off and really do great in their career here.


Adam Robinson: How often would you say, in percentage terms, do people, in fact, turn it around?


Jeff Ellman: When I think about people who I’ve put on performance plans, I’d probably say about 20-25% will actually turn it around and get the kick in the butt and get motivated, and the other 75% just don’t have the right skills. They could’ve been a mis-hire or they have the things that I can’t teach. I can’t teach someone to be driven to be curious, to be really well spoken, so that would be an example of a mis-hire that somehow kind of slipped through the cracks. To prevent that from happening in an early-stage company, I highly recommend, and I know, Adam, you do this at Hireology, that me, as the co-founder, I interview every single person that we hire to make sure that those mis-hires don’t happen consistently.


Adam Robinson: Absolutely. That pays big dividends and, in fact, paid big dividends again today not an hour ago, I have to tell you. I absolutely concur with that. Is there a particular book or source of content that has been influential in your approach to hiring?


Jeff Ellman: Specifically around hiring, I can’t say there’s been one book that really influenced me. I mean, there’s the book Who by Jeff Smart which, in the early days, really helped me understand what a scorecard was and how a scorecard should be in existence for every job function. I think that is a good book. As far as scaling a company, Aaron Ross has written some great books, Predictable Revenue, or Impossible to Inevitable is the one I’m reading right now. It really gives you the blueprint for how to scale a company at a rapid pace. I guess a final book would be Traction by Gino Wickman has had a big impact on my companies.


Adam Robinson: Yeah, you and many of our guests have reported that book to be profoundly impactful to them, and I’m certainly counted among them. Let’s talk, as we close out here, a couple of big picture questions for you. What do you think is the greatest lesson you’ve learned about doing this in the people side of the business?


Jeff Ellman: The greatest lesson I’ve learned, first of all, is that I don’t think there’s such thing as work-life balance. There’s work-life integration. Once I understood that, that was important for me personally as an entrepreneur because your success at home carries over to your success at work and vice versa. With my employees, on the people side, it is really understanding what makes them tick.


  When I look out and they’re 65 years old and they’re retiring, what would success have looked like in their career and how can the job at my company been the best job for them to have success? I want them to really own the job and not rent the job. We have a lot of millennials who probably, most companies would rent the job, they’d work there for two or three years, then move on to the next opportunity. Here, I will encourage my employees to own the job and, hopefully, be here for as long as possible.


Adam Robinson: As you sit in the seat today looking out, what do you think is something that you could or should improve upon as it pertains to talent management at UrbanBound?


Jeff Ellman: Probably our performance reviews. I think we do a really good job getting people in the door, and we give constant feedback. That’s one of the processes I constantly look at because we do them manually, and I do think employees need feedback probably monthly or quarterly, and that’s something that I would like to change in the very near future.


Adam Robinson: Closing question here, Mr. Ellman. If you were to come back on this show a year from now and report to us on whether or not you were able to successfully tackle the single biggest people-related issue or opportunity that you have in front of you, what will you be telling us happened?


Jeff Ellman: The biggest opportunity for me on the people side is helping people be promoted, helping them stretch and try new things within the framework of our business, and that is something that we are constantly striving to do, and that’s something we can definitely measure success by.


Adam Robinson: Ladies and gentlemen, that’s the final word. You’ve been learning from Jeff Ellman, Co-Founder of UrbanBound and many other companies, including Hireology. Jeff, thank you so much for being with us on the program today.


  That’s a wrap for today’s episode of The Best Team Wins podcast, where we feature entrepreneurs and business leaders whose exceptional approach to the people side of their business has led to incredible results. My name is Adam Robinson, author of the book The Best Team Wins, which you can find online at Thanks for tuning in, and we will see you next week.