Faces of Marketing podcast: Jill Nelson, founder of Ruby Receptionists

Jill Nelson, founder/CEO of Ruby Receptionists — one of the fastest-growing Portland companies for 11 consecutive years, Forbes Best Places to Work company. Jill was recently recognized as Oregon’s top Tech Executive.

Jill was highly influenced by her Mom who was an artist + forbid Jill and her brothers to play by the rules and her Dad was an engineer and creator of systems. Jill herself is this beautiful melding of Accountant / Creative / Rule-breaker / Entrepreneur.

Tune into this podcast interview between Jill and me on the Soundcloud audio file above or on Apple Podcast, Stitcher, Google Play, or most other podcast players.

Ryan: Hey there, welcome to the Faces of Marketing podcast where we talk about the human stories and lives of different people and perspectives in the marketing profession and entrepreneurs and movement makers. This is your host, Ryan Buchanan, and I’m here with my good friend Jill Nelson, who’s one of the top entrepreneurs in Oregon and beyond, and she started an incredible company called Ruby Receptionists, a tech-enabled service business here in Portland. Welcome to the show, Jill!

Jill: Ryan, thanks so much for having me here. It’s really a pleasure and just a really fun time to reflect on a journey that the two of us have had somewhat together.

Ryan: Yeah. You and I hung out five or six years ago in Panama City when we were both on the Board of this entrepreneur organization (EO Portland) here and had just a late night bonding session — all kinds of stuff going on in our lives and that’s really when the friendship kind of took off for me. I don’t know about you.

Jill: That’s right. I felt the same way except for, that’s not how I first met you.

Ryan: Oh, tell me.

Jill: Remember. So it’s part of the origin story of Ruby Receptionists, which is way way back when, when we were an anything virtual assistant, an email company called CoolerEmail convinced us to be the tech support for their email marketing company and one of their clients was this small up-and-coming company called eROI. And I remember you calling me for email tech support and me helping you, which is so ironic.

Ryan: Since that was over the phone — that was you — wow! Oh my gosh. That’s awesome. And that’s one of the things I love the most about this podcast is I learned stuff about my good friends every time I do this interview. And so thanks for reminding me on that origin story. Okay. Got It. Um, cool. So, um, just to dig in here. We always start off kind of at the very beginning — what you were like as a, as a kid, a little girl. I know you grew up in Lake Oswego, right? You’ve got two brothers sandwiched in between age wise, right? And, Mom and dad. And like, what was it like as a kid?

Jill: Yeah. So I think growing up, it was a little bit of the wild, wild west kind of childhood, being the daughter of, you know, two brothers, um, you kind of had to, you know, tag along. Right and keep up. So that was, that was always fun but challenging. And then I would say my big influence was my mother who was a very, very creative, and somewhat eclectic artist and she really, really was against us essentially playing by the rules. And so I remember her sort of confiscating any coloring books I would get my hands on because she was appalled at the idea of her child having to color between the lines.

Jill: So we were, we were given every possible art supply and easels and paints and, but anything that had to do with rules, was really just, you know, against everything she stood for. So otherwise, we still were pretty traditional. I got the girly things, my brothers got the Legos and the erector set construction sets. But, of course my mom would take out the rules sheet on how to build the Lego things, the instructions — those were removed before my brothers were allowed to try to play with them.

Ryan: That’s a trip because I see these two sides of you — this creative, wild abandon, entrepreneur, and non-rule follower, yet you also have this background of “I’m an accountant”, not that all accountants are robots and rule-followers. But, there’s an element of both in you — rule following and breaking the rules. Fascinating!

Jill: That’s right. And in fact, my dad was a civil engineer and he was very much a science-based, math-based and he absolutely encouraged me to follow those left-brain sciences. In fact, and yes, I do have a degree in accounting and much to both of my parents’ chagrin because again, my mom just was appalled that I would do something so boring and uncreative as study business. And then my dad, who was a builder, civil engineer, he worked for public works and built bridges and roads and, and he always felt like business people were, you know, they just were paper-pushers, just moving stuff around and weren’t actually creating real things of value. I always say that being an accounting major was an act of rebellion, but, you know, being an entrepreneur, if you think about it, it really is both of those things.

Jill: It’s using your creativity to come up with something truly of value that hasn’t been out out there that you know, that someone really does need and has a use for. So I kinda think being an entrepreneur is a mix of those things that my parents instilled in me.

Ryan: Cool. Cool. So going back to: you’re a kid, you’ve got two brothers, Lake Oswego — suburbs of Portland. Did you play sports? Were you into dance? Like did you play in the dirt? What kind of like — the 10 year old Jill? Like what were you into?

Jill: Okay, so 10 years old. I always have loved dancing. And growing up as a 10 year old, I got really, really into my Scottish heritage and my Mom did encourage that and um, got me into Scottish highland dancing and she sent away to Scotland to have my kilt sewn in the Macintyre Tartan [as a side note: Buchanan is also very Scottish and check out the Buchanan Tartan here as well].

Jill: Mcintyre was my maiden name, which is great. And I did that until I did this competitive highland dancing, even compete in the Highland Games. I come to find out as an adult, nd I did the ancestry.com report, there’s not one Scottish person in my heritage. It is Irish.

Ryan: No way! I’m Scottish, too. And my whole family — like my dad, my granddad was tracing it back to everyone. But I see a lot of that might be a little bit of a myth, too. Now, I really need to find this out.

Jill: So that was kind of a funny discovery. But I have always been social. It’s interesting that I started Ruby Receptionists as really, I thought it was about productivity and getting, you know, the work off of somebody else’s plate. But what I really figured out was that our true value is the connection we make with other people on the phone and we help small businesses win business through that.

Jill: And whether I was dancing or, you know, in, in high school, I will admit I was not the “A” student. I was the very social, social person — you know — friends, parties, you know, whatever it was. That was fun. That was me. And so I think I brought that into entrepreneurialism as well. We will probably talk about our workplace culture, but I don’t like doing anything that’s boring and you know, that I’m not driven to do or inspired to do. And I think that kind of informs the workplace too.

Ryan: So when an adult would come to you 10 year old Jill and say, what do you want to be? Or what do you want to do when you grow up? Like, what was your immediate answer?

Jill: I really don’t remember. I remember wanting to be a Go Go dancer when I was really young because I really liked the white shiny boots, um, and I just wanted a pair of those white shiny boots. And I also remember actually playing, instead of playing house, um, I played receptionist and I would set up my office. Dr. Bill Meyer was our doctor, I can’t remember his secretary’s name, but whatever her name was, I made a little nameplate and I was her and I received people answered the phone. But I actually don’t remember what I want to be when I was 10. When I was a junior in high high school, it was all interior architect is what I wanted.

Ryan: Interior architect and accounting. That’s fascinating. All the interviews I’ve done, usually people are in one camp or another, but you are eclectic, which is great. It’s probably helped you create such a connecting employee base and all that stuff. So that’s killer. I think we were talking before we got on this interview about: I was talking about this trip to North Carolina that I did with my wife and two daughters in looking at colleges and things like that. And so kind of wanted to get a sense of in high school you went to Lake Oswego High School, which is a really good school, public school. Did your parents have an expectation that you’d go to college and then did, did you only look at University of Oregon or did you look all over the place? What was your decision criteria of which college you’d go to and then also your son, like how did you help mentor and navigate with him of what college he decided to go to?

Jill: Okay, great. So first of all, I grew up believing there were 16 years of school. So I never even imagined it was an option not to go to college. It just never occurred to me. And it never occurred to me that there was anything other than state schools. So it’s either you have UO or OSU and that decision came based on, I’m gonna just say it was really where my friends were going. They were all going to UO. I just, I really, I think, you know, there are many other entrepreneurs where they follow that academic path. I was always intrigued by business. I found a paper that I wrote in college class “Writing 121” around why every small business should own a personal computer. And this was in 1983 and that was odd. So growing up, you know, it’s interesting.

Jill: I think there was that, that expectation. Everybody went to school. I should clarify. I grew up in Mountain Park, which is a little more modest area. And then, my high school years were pretty challenging. When I turned 16, in fact on my 16th birthday, my mother suffered a nervous breakdown and she was committed to a mental institution and my dad was pretty absent by then. And so the last two years of my high school was kind of a free -for-all, there was no adult supervision. And so as a high school student at first that was, you know, that was pretty wild. But then, you know, as school started ending, it really was my own sense of what do I want to do and what do I want to be.

Jill: And I had to make those decisions for myself. So I don’t really feel like either one of my parents were really pushing me when school came. It really was truly my own decision. Now when it comes to my son, it like the age of eight when I was like, “Gosh, you know, you really have this sort of creative creative thing in you.” hey, it sounds just like my mom, um, but of course he didn’t ever listen to me. So anything I thought, oh, you would really like this. He’s like, “oh mom!” And then in fact, he went to Northwest Academy, downtown Portland, which is a creative and academics focus high school, really great experience for him. And I had encouraged him to look at this one college of which he just refused to look at, until he came home from school one day and he was like, “Mom, I know exactly the school I want to go to — it’s this amazing school, blah, blah, blah, blah, blah.”

Jill: And of course that was the school that I had been encouraging him to take a look. It was California College of the Arts, which is where he had just decided this is this cool for him.

Ryan: And did you bite your tongue or did he acknowledge it?

Jill: I laughed. It’s just so, so typical either. So typical teenager or so typical “Al” [my son] — it’s got to be his idea. But I was really happy for him because I did agree that it was a good place for him and he ended up, you know, it’s just so funny because he’s a freelance graphic designer now and he gets his work through his own peer network. So all of his friends that have graduated that have gone in, you know, in work, on the client side or whatever. And he’s getting work from his friends, which is really wonderful to see.

Ryan: Creative and an entrepreneur. It’s the family lineage. Crazy. So I do want to go back to when you were a junior in high school and so you have a younger brother too. And I’m not sure if at that time your older brother was in college, but did you kind of have to parent your younger brother and then still have parties at your house on the weekend but then kind of be a Mom in a way to your younger brother? I mean, how did that work?

Jill: It was tough. And so my Mom, from the time I was about 16, she really had a really tough time getting back into. She never fully recovered from that time. And then, when I was 18, my Dad died of a heart attack just out of nowhere. So if my younger brother who was 13 or 14 at the time, you know, I talk about him being raised by wolves. So I do feel like I am the mother figure to him, although I still was a very young, um, you know, let’s just call it party girl and, but I did have a sense of, of taking care of him and making sure he was taken care of. But it was just a teenager’s view of what that is. But I think if you asked him he would, he would probably say that I was a parent figure to him during that time.

Ryan: And so you’ve already answered kind of one of the big questions in the first half of the interview that we always do and which I think is the answer is what is your biggest obstacle that you had to overcome as kind of a kid through kind of through your college years, but if you expanded on maybe looking forward, do you think that that gave you the resilience and some of the fortitude and other positive qualities that through all that crappy, really challenging scenario that you had to figure it out on your own to navigate through that as an entrepreneur?

Jill: Yeah, totally. One hundred percent. 100%. Tenfold, and in so many different ways. And I actually feel so fortunate. I mean the things that I have to work with today directly correlate with this experience of having to really kind of figure it out as a teenager. But, there’s a couple of things I think as a teenager — going to Lake Oswego and of course there’s many affluent people there — and not experiencing that myself and having an unstable family, you know, at first it was like, it’s not fair, you know, why do these other people have it so good and I have it so tough and that, that was a very early lesson. And I think with entrepreneurship, fairness doesn’t really enter into it. It’s like you’re either driven and, and you either, you know, it either works for you or it doesn’t really work with everyone, doesn’t get this equal opportunity to solve the equal number of things.

Jill: And, putting that aside for what I’m entitled to or are not entitled to — that of has nothing to do with it. And I think that was an early lesson that I had to learn. Um, certainly. And then I became my mother’s legal guardian. So navigating chaos was another thing that I think I’m really comfortable with. Like my brother, how it shows up today for him — he really enjoys going down to The Mission and serving meals or going to the homeless camps and you know, and helping them and it doesn’t bother him — the chaos or you know, things that maybe we all might be uncomfortable with. I think having that chaos in our lives, we, we have a little bit more stamina for that. We did not have a safety net.

Jill: There was no safety net, there was nothing to fall back on. And so I think that helps us with the risk profile. Then finally is that, you know, there are things that you can absolutely get through really tough stuff. And I think knowing that you can get through that, um, gives you a sense of confidence and then also that the little things really aren’t that important. And I’m so I think that has shown up in many ways. Everything about, you know, taking those risks as an entrepreneur and being willing to try step or just grow really rapidly and habit. Everything seems super chaotic. And that feels very normal.

Ryan: So I’m gonna push back a little bit on this. Again, coming back to this fascinating dichotomy that you have that, that worked so well. I totally hear you with a context of the little things aren’t that important as far as like not having the stress overwhelm you and derail your path and all that. But you were on a panel at my company — with Kim Malek and Sadie Lincoln on Hospitality. You raised the bar big-time from a hospitality standpoint on little things being super important to…

Jill: I guess we just have to agree on what the definition of little things are and I maybe could have substituted the word “petty” things so I think that’s what it is. I don’t enjoy getting caught up in petty drama or things like I don’t like to waste emotional energy on things that in the big picture aren’t important. So maybe that’s what I mean, because the little things in my view, the littlest things that are intentional can absolutely be the biggest things there are.

Ryan: I learned something from you a while ago and it stuck with me. Yeah.

Ryan: So, we talked about what you studied in college and so that I find, you know, I work with a lot of folks in college and coming right out of college into looking to get a job and I always find like that first job being so stressful and you usually don’t get it in like the ideal company that you want and things like that. But your path seemed (from Linkedin) seemed kind of linear.

Jill: Really? I started Ruby when I was 37.

Ryan: Well, I’m talking about right out of college. There was a sales job and then you became a business broker or that you use your accounting degree in there somewhere. Yeah. Talk about how you got that first job.

Jill: Yeah. So my first job out of school was a computer resale company and it was just one of those like where you go in your interview at college and they come and they recruit and that this college recruit program and it was back in the day where you had to, uh, you needed a full time salesperson just to sell a personal computer …

Ryan: Did you have a suitcase with a computer?

Jill: We had brochures and ended up, um, I only did that job for some time. I was technical and I certainly liked to people but you know, that really challenging, um, the rejection and calling on people that can be so stressful as far as that was not my thing for, for sale. So No. Then I ended up leaving the workforce, having my son became an apartment manager because it was the only way I could have my son. And then I was um, and then I stay-at-home Mom and then,

Ryan: For the record, I was way off on your path being linear. My bad.

Jill: And then the piece that you may not have seen is to get back into the workforce — my neighbor was like, oh, this person I know is looking for a receptionist and because their receptionist is going on maternity leave. And I was like, well, I’m not a receptionist. I have a college degree, blah, blah, blah, blah, blah. And she was like, oh, well, you should just talk to them anyways. And then I found out it was for business broker and that actually I was quite interested in that.

Jill: I went in for the interview and I, it wasn’t really an interview. He was just like, Oh, you’re taking this job, you have no choice. And I was like, I ended up staying there for five years as a receptionist on an office manager. And during that time it was just a, it was the funniest job experience and relationship with a boss that to this day, uh, you know, I cannot believe I did well. The relationship was like, well, I’m not taking this job because you actually don’t even use a computer yet. And I am not taking this job unless you have a computer. Sees like, oh, buy a computer. And then there’s like this old fashion filing system. And I’m like, this is crazy, but then I would go home and write a paradox database program for his filing system.

Jill: And so he thought that was great. And then he used this big blue book to do his amortization tables and I thought that was crazy. So I wrote this excel sort of Amortization, you know, template. And so he loved that, but then he could never get me to show up at work on time and I would take hour and a half lunch breaks and he would get so frustrated and I just would refuse to show up on time. And then he wanted me to wear nylons and I was like, “I’m not wearing nylons because your desk has little, you know, things that make my nylon snag.” It was just this really funny relationship. But we both, I think really appreciate each other and what we brought to the table. And then maybe I became a business broker for a little while.

Ryan: Okay. That is fascinating. I didn’t know any of that. So what was the origin story of how Ruby started?

Jill: Ruby. Yeah. And so, as a receptionist for a business broker and I think that was the thing I did absolutely care about — their customers and helping them win business. I understood that was my job there. Um, but then, you know, I did become a business broker for a little bit and then the .com boom and year 2000 bust. So I was out of work for some time and then was in my son’s school quite a bit. He was in grade school and middle school and I was like, I gotta get a life. So when I was at that business brokerage office, I got to see every possible kind of business come in through the door and I got to see what was attractive and what was not.

Jill: And while they had one sense of what sold and what was in demand, I just was like, service business, service business AND this subscription idea. I was just like, if I ever have a business, I’m going to have some sort of subscription service. And at the time I was, I was looking at dial-up Internet Service Providers, so I was like, that’s just a brilliant idea. You get a check.

Ryan: AOL?

Jill: Yeah, only it was a smaller local Portland version and, and I was just like, that’s the only kind of business I would ever want because I’d been a salesperson and I didn’t like selling. And I was like, well, if I could have a subscription business then customers, if I could just keep them happy, then they would stay and they would tell other people and I wouldn’t have to sell. So this was like, if that was the sort of the parameters of the type of business.

Jill: The original idea, I thought of doing an executive suites — kinda like the way WeWork today, but the old fashion Regis where you have a Class “A” office space and you rent out smaller offices and you have the shared receptionists and shared secretarial back then and basically everything administrative that, that small businesses could have those shared resources wanted to do that in the Pearl district at the time that was up and coming. But I had no money and I had no business experience so I couldn’t find a landlord willing to build that Class “A” office space. So I just started thinking about, well, what could I do with the resources I had? And essentially took away the real estate and went, well, I could do this, all of this virtually, but how could I do the phone piece?

Jill: And the phones were the most interesting to me. At the time, you know, people had answering services that said they were receptionists services, but nobody was actually using technology to answer and be able to represent that you’re a part of that office and then get the calls actually to the people that needed the calls, like as if you were at the front desk seamlessly. And just got really interested in that. But as far as I mentioned at the very beginning of our time together here, we originally offered everything administrative. [For our client CoolerEmail], Leif was the most persuasive person I’ve ever met. So the fact that he got us to do tech support for his email company was um, was, was really a testament to his skills as a persuader. But we mostly did receptionist work and the receptionist took off and everything was really hard to scale and hard to do efficiently.

Jill: And so we let that go pretty quickly. And then became Ruby!

Ryan: And you had, as all of us entrepreneurs do, especially through growth, some times of almost running out of the cash. Right? And you got an investor at one point, early on?

Jill: Very early on. It was really, it was one of those almost like cosmic things because we had, we were a year into the business and lose losing money. I never ever put myself like today in the startup world, I didn’t even know what an angel investor was. I didn’t know that startup capital existed. I actually did get an SBA loan, um, off of literally the business plan uncollateralized other than the assets of the business, which I thought was a vote of confidence for the plan. But I learned — a year into the business — that our phone system, I thought it would Max out at 2000 customers, but in fact turned out it Maxed out at 200 customers and we were at like 180 and there was no upgrade path.

Jill: And you know, it takes a while to get to economies of scale. So we were not profitable and I was like paycheck to paycheck for all of our employees and actually I didn’t pay myself. And anyways, this guy comes out of almost nowhere and says, “Hey, I’m gonna start a competitor, but don’t worry, it’s in Arizona, can I come up and visit you?” And it’s a longer story, but I really, to this day, I’m so confident in our culture that you can come and look and see, but you can’t copy us because it’s just, it’s “un-copyable”. And so he comes up and he likes and he’s like, you’re onto something. And, but, you know, he felt like, oh, it’s super technical and that’s not me. And, “Are you interested in investors?” And so just like that, uh, we got on the streetcar. I went down to the law firm and filled out a nondisclosure form. And like, I think it was a few weeks later, he had given us a big loan for his equity stake, you know, that we were able to get that big new phone system. I got a reasonable salary and was able to sleep at night. And the rest is history.

Ryan: And was that the point that you considered, that you started moving more towards tech, would you say? Because I think the rest of the world might look at your company at least early on and go, “Oh, it’s a service business.”

Jill: Totally. Yeah. No, actually I would say we thought of ourselves as a service business all the way up until when we did in 2008 when we followed the Rockefeller Habits system [great book, too] and created this five year plan and we were like, at the time I think we were doing like a million in revenue and we’re like, wouldn’t it be cool if at year 10, we were doing $10 million in sales and so we created this 10 at 10. At year 10 we, you know, we want to do 10 million in sales and that would have been 2013. And we did the Rockefeller Habits and we’re like, okay, well what are the big initiatives that are in our way in our way from doing it? And we realized in order to scale and serve that many customers, we absolutely had to get on to our own software platform. It just, we were on our second platform, we had used somebody else’s stuff and we hadn’t had them kind of, you know, modify it to fit our needs, but it just wasn’t going to be able to work. And we really understood by that time we had taken millions of phone calls and we knew what we needed to build to be able to scale the service for that no matter who is taking that phone call, whether it was a receptionist and their first day or they’re, you know, 400th day that they could completely take care of the caller speak, as if they were right in our customer’s office and be helpful and design that from the ground up.

Jill: And so that was when we launched that in 2011, we realized how integral our own technology was for our success. And that’s when we were like, “Hey, we’re a tech company.” And then the mobile app, the customer facing the first iteration of the customer- facing mobile app took place. But it was really more of an accessory piece. So I would say 2011 is when we first identified ourselves as, you know, we really are a technology company and in order to scale, and then when we repainted the vision, when our main investor Updata came in, which is a few years later — the vision became more crystal clear and, and the shift of value to our customers where, where the receptionist, the live receptionist services, the, you know, the leading actor in the play and, and the mobile app is the supporting character more and more today, the features and functionality that come along with a receptionist service and also enable our customers to free up their day. They’re more on equal footing. We’ve put more and more power in our customer’s hands, more functionality, telephony service, you know, and we continue to add new features every day. Not every day, every month.

Ryan: Yeah. So a couple things that I wanted to have our listeners learn from you is: you have this saying of WOWism and I think that’s more customer-facing. But what I think is fascinating, and I kind of said it in my last episode with Kim Malek, is that most people think Salt and Straw is an ice cream company, but it’s really an employee training company and I feel like at Ruby — above all else, you prioritize employees, number one and then out of that comes customer WOWism and like surprise and delight with customers and stuff like that. A lot of people can say that, like how do you do it? What are some examples and just walking through the office with your photo booth and you just have been recognized for three or five years as Forbes one of the best companies to work for. And People magazine. Just like again, again, again, but like what are some of those little things we were talking about earlier that you basically when shit hits the fan, you support employees over maybe like a tough customer. I mean that seems so intuitive but it’s so hard for most of us to do in the moment. Like give some of those examples of the employee culture, like how you built that cult-like following among employees and everyone knows that Ruby is the place to work for.

Jill: Aww. It’s not the place to work for everybody because I would contend that what’s truly, truly special about Ruby is not really any of the things that we do for our employees, but it’s how people treat each other. And, and so I will give you some really fun examples because we do some great things and we’re always trying to practice WOWism across the board. But our, our company’s mission is to keep alive and perpetuate that human connection that’s increasingly lost in today’s virtual focused world. And, and I would add to, you know, kindness and humanity even even take out the technology, you know, it can, it’s increasingly hard to find whether it’s customer service. So we employ people who think that’s a noble mission of that. The human connection is really was truly valuable. You know about one of the things that’s really valuable about life.

Jill: And so if you have that and we do have our set of core values, it doesn’t say, oh, we’re going to keep alive the human connection for our customers or it doesn’t say we’re going to practice, but you know, values, our values are the things that you live no matter what to everybody. So to us, yes, we prioritize employees and reprioritize customers, but we just really prioritize our values and our, and our mission above everything else. So if we have to walk our talk, then it should show up in the workplace and it should show up in our service. I think that’s the big picture idea. Um, so when we, so practicing rouse them, it really is. I’m practicing. WOWism is essentially getting a wow. But how we talk about it, how we train to it is really about the human connection because we are training people to listen and to anticipate somebody unexpressed needs, which I think that’s a Ritz Carlton phrase of unexpressed needs and, and then to respond to that.

Jill: And so whether it’s one of our wow station gifts — and this is customer facing — but it is, I’m a get well mug with some tea and tissues and some chapstick. So when we hear somebody sneezing on the phone or calling in sick for the day, you know, a little ‘get well’ gift shows up in the mail. Just to say “hey, we’re sorry to hear you’re sick, hope you’re feeling better.” So that was a little bit of practicing WOWism. But we got that because we’re paying attention to, to our customers. So, um, how that shows up at, at Ruby, again just hiring people who say, “that’s what I want to do every day is a big part of that.” I think that’s why people like coming to work and then we just try to empower them and get out of their way.

Jill: So we talk about a people-powered culture. So, um, how that shows up in parties or photo booths or whatever it is. We have sabbaticals. But one of my favorite ways to use funds for the employees, just general happiness and community is we have culture funds and it’s a crowd sourcing thing, um, where every employee, it’s a modest amount. They get $100 per year. They can spend it any way they would like as long as it builds community at Ruby. It could be a party, it could be, you know, a Vitamix for the kitchen or whatever. But obviously you can’t buy a Vitamix for $100. So that’s where crowd-sourcing comes in. So if someone has an idea of like, hey, let’s do a wine and paint party, um, which my mom would have never allowed me to go to because it would have been following the rules or if someone wants, hey, let’s get some equipment for the fitness room, who’s with me?

Jill: And what’s interesting is that the most popular ideas actually get funded and you know, and, and things that maybe people have less interest in, you know, don’t, don’t actually happen. So rather than me trying to figure out what do 500 employees want to make them feel like they’re supported or that they can have fun at work, it’s like just put it in the hands of the employees. So that’s one really fun thing and it’s turned into something — like there’s this annual space kitten pizza party that I still don’t even know what that is exactly, but it’s a thing and our Ruby’s love it and it involves pizza and dressing like a space cadet in and it’s once a year. People use their culture funds for it. But um, but yeah, we also, I think what we’ve done in the last few years has really elevated. There’s the fun stuff and the supportive stuff, and then there’s the things that really support our employees as they go through their life and some of them have grown up with us and as they go through challenges.

Jill: And so things like workplace flexibility: we offered paid parental leave very, very early on, back in 2008. I think we doubled that in the last couple of years. We try to support people with really being flexible with people’s work day I think is the number one most valued, um, thing we can do for our employees here. And it’s not easy because we have to answer 50,000 phone calls daily — all within four rings live every single day. And that’s not easy to do when if you just say, “Hey, come on to work whenever you’d like”, but we really try to innovate around that. But at the end of the day and we try to have fun and most of the really cool things, in fact, all of that, they’re really cool things we do. It’s somebody else’s idea and we just didn’t say no. We just said yes. At the end of the day, I just have to go back to the core values and trying to from top to bottom, live them to our customers, live them to our employees. And at the end of the day, we all feel super proud about the work we do, which makes us want to continue along our growth path and want to protect the culture that we’ve built.

Ryan: And kind of going back to your experience with your Mom and and things, your Mom when you were 16 and Dad at 18 years old. Is there a sense that you are giving like you’re, that maternal instinct is kinda kicking in and that you’re, you’re just giving back like you’re saying “yes” to things that if you were looking at the budget line item all the time and following the rules, you’d probably say “no” to a lot of that stuff. Like do you think that there’s an element of that?

Jill: I definitely don’t like being average or normal. I think that’s something that I would run from. There probably is something there to propel to be something unique and different. But I just think that the thing that’s most important to me in my life is the relationships that I have with the people in my life. And so to come to work everyday and, we have experienced tremendous success and I’m so, so fortunate. So the idea that anyone of these wonderful people that have helped us get where we are today is not feeling supported or you know, like, that just doesn’t sit with me. I think of course, where were we all spend our time together, why not make it the best possible place for everybody.

Ryan: I had a conversation with our mutual friend Su Embree who has been on the show, and I think there’s just a larger observation that it’s consistent in your life, not just with your employees but also in your family and all of that, of like this kind of nurturing, give back mentality.

Jill: Yeah. And so she listened to you say one thing that I do talk about at Ruby. As we get bigger and there’s more at stake and especially whether it’s customer service or even employee engagement, there is that temptation that you start making more rules and you start making more processes and things get less customer-focused. Like if one customer stiffs you and all of a sudden you change your terms and conditions so that you know, it looks very onerous to do business with you. And so I always talk about not letting the one percent or the point one percent or the one hundredth of one percent ruin it for the 99.99% of people who absolutely have good intention. So we have really liberal policies around trusting employees with 24 / 7 access because we have really cool spaces.

Jill: So why not open it up and let them have their theater practice or you know, we have dance teachers here and they teach dance out of our fitness room. I was like, why not let them do that? And if occasionally at some time in it’s never happened, but if somebody in 15 years, you know, took advantage of that and it didn’t work, what I would hate to ruin it for everyone else. Just you. Except that occasionally someone’s not going to play by the rules and that’s okay. That’s humanity and not let that ruin your optimism or sort of belief in, in others.

Ryan: Yeah. And so, a couple of questions left. One is that I have noticed this about you: 1. you are a person that really lives into having once in a lifetime experiences often like different ones and so because, you know, we talked about how you empower that with your employees and they like every five years they can go on some amazing trips and all that stuff. But I do want to kind of go back to you and share with us. I’m about to go to Ireland for two weeks. So I’m in that head-space — what are some one or two things that you’ve done, like I know the Vancouver BC trip when you were kind of celebrating a big life moment or your trip to South Africa or maybe it’s something you did right after college …

Jill: I did spend a term in Sydney, Australia. I took a break from and I went with my friend and we, um, she had, her family had an apple orchard, so I went and picked apples to earn a plane ticket to Sydney, Australia and then spend a few months there and I’m really that, you know, I have not been back, but Wow — what an experience and say then youth hostels, I met kids from all over the world and just experience, you know, a different country entirely. And that was probably my most memorable big experience of life.

Ryan: And then the last question is, and it may be the same answer, but maybe it’s a twist on it or something else, but when you reflect on maybe one thing the audience may not know about you that happened kind of in your teens and early twenties or some time in there that either gave you the resilience or maybe the independence to where it makes sense that you are an entrepreneur at a pretty high level of success. But just a successful entrepreneur or just a whole. It seems like your whole life. Like you look at the whole picture and not just business success but like you, you’re in a good place in a lot of areas in your whole life. And so like when I look back, I look at when I read it from my freshman year in college, I drove by myself a 2,500 miles to Glacier National Park — talking to myself the whole time — and didn’t know a soul there and then I just massively fell in love with the Pacific Northwest and I went on like eight backpacking trips and it indirectly led me to be in Portland and I’m such a huge fan of Portland and it gave me the confidence to do anything from there.

Ryan: So I don’t know if that was the Sydney trip. I don’t know if the experience with what happened with your Mom and how you had to adapt to that scenario. And I’m sure it’s a little bit of a lot of experiences, but I was wondering what, like, as you reflect on that.

Jill: Yeah. And certainly I think we covered that earlier where I think my Mom really affected my ability to sort of navigate chaos and you know, no safety net, but it’s interesting because regarding that question people have asked me like, what gave you the ability to like go fearlessly and start a business or you know, did you ever think you’d be there this successful or. And I was like, I think it’s not any of those things because I think I didn’t think about being successful. And I think I also didn’t think about failing. I just became obsessed with the idea and I just wanted to see it work. I just, it was really more just that creativity and building something of value that I became obsessed with doing and just seeing it come to fruition.

Jill: And I don’t think it really ever occurred to me actually until I was almost out of money. Then I became frightened, but I don’t think I was afraid at all. I just wanted to do what I wanted to do and I just needed to figure out how to get it off the ground. So maybe that’s, I don’t know if it’s a good thing or a bad thing, I just and it, I didn’t think, I didn’t think about the content. I didn’t think about success or failure.

Ryan: The way I described my similar experience as an entrepreneur is I feel like being naive is a bonus going into it because it can be super hard sometimes. I mean the rollercoaster ride is amazing. One thing, and I didn’t ask this question before, but I haven’t met a single entrepreneur except you who has predictably grown 40 percent a year and like you have the whole KPI Dashboard and the whole machine to do that and it’s like how do you be that predictable? Like how you create the culture, you focus on that, but then you also have the business side to pull the levers to be precise about it. That’s so hard to do. How do you, do you just reverse engineer it?

Jill: Yeah, it’s the engineer again too. And that is the, it’s the ying and the Yang. It’s all this. I’m really, it’s people stuff, but there’s a lot of technology and data that goes behind because at the end of the day we have to answer all those 50,000 phone calls within four rings and also we have to have employees that are happy and so you just cannot do that without the data analytics to be able to predict when those calls are going to come in and predict how many people might call in sick that day and know exactly where you need them when and be able to model that. And, and really in fact the first time we ever measured data, um, the reason we measure data was that our receptionist actually, and this is one of those learning lessons, really felt super overworked and I had not at all kept up with our growth. I hadn’t ever looked at our numbers and come to find out when I looked at their numbers, they were literally answering, you know, double the calls that they had been answering per person, you know, like a year ago.

Jill: And, and it was the realization that we, because we grow so fast, if we’re not looking at the data we have, we could easily, you know, ended up hurting our employees and our customers experience. So the data analysts and I, I would say everybody here knows to the data really aligned really well with both the customer experience of course, but also the culture, we always, we have a receptionist dashboard and, and there’s some controversy about trying to measure, you know, culture related things, but if bed, it’s a balanced scorecard. So if we can also measure the things that we say are the most important, all we’re left with is attendance and productivity and we certainly don’t want to reinforce those things as the most important thing. So, data is a really, really important piece. In terms of productivity and work, it really is a balanced approach. So we’re not trying to squeeze every last piece of productivity out. We’re also measuring to make sure our employees feel well-balanced in the day, too.

Ryan: I love it. It’s WOWism, it’s humanizing things, but there is definitely a strong business and data component that makes it all work and really frees you up to be more human. Right?

Jill: That’s right. Exactly. As long as we’re giving it the space also.

Ryan: Well, thanks so much for being on the show.

Jill: You’re not going to ask me the marketing question?

Ryan: Oh my gosh. Well, I was just worried about protecting your time and all this stuff, but yes, but I’m learning this stuff and I’m like, oh my gosh. Mental note, mental note. This is great. And yes, it’s called the faces of marketing plan. The marketing question is you’ve built this cult-like following. You’ve grown 40 percent a year for 15 years. It’s incredible. How did you do it? What were the marketing strategies that played into that?

Jill: Okay. The number one, best marketing strategy we have is ANSWER YOUR PHONE. The data shows and Google even says it. In fact, we can show it. So your phone, the phone is not dead. Phone calls are on the rise and it’s click to call. It’s actually the me-generation, it’s actually talking to Siri and it’s dialing a phone number and so especially for small businesses, 40 percent of all inbound phone calls are buyers ready to buy and they pick up the phone at the moment of trust and your 30 percent likely to close a sale over the phone and only 2 percent likely to close a sale through the web form. The phone call has won us business and it’s won our customer’s business. So treat your colleagues well and don’t ever let them get voicemail during the day. That’s my tip. Honestly, it’s still the king.

Ryan: It’s so true. I crave that. I craved that human interaction on the phone. So much more valuable. So, but to be clear, your best marketing strategy at Ruby is to educate small businesses on the value of the phone. And I mean, do you do workshops?

Jill: Yeah, yeah. Okay. So today we have grown like, like you said, on average over 15 years. An average of 35 percent every single year, you know, 11 consecutive years on the fastest growing list. Even though we have quite a generous marketing budget, word of mouth referral from our customers is still our top source of new customers. So it really is just, again, treat this back to the original thing which is treat the customer as you have. They’re the most important thing and really deliver something of value. And I think at the end of the day, that’s what we do and that’s where the technology has continued to help bring value to our customers. And as we get bigger, we are looking at the small business and how small businesses need help. They don’t have, you know, marketing geniuses like you, you know, on staff. They are looking for their partners to not just deliver a service but to be a coach or a team member or you know, a, a source of, of thought leadership. And so we try to engage our customers — how to be great on the phone, which is really, really important, but you know, in, in other ways, how can we support the small businesses.

Ryan: I’m going to have you come to all my other podcast interviews so that you can remind me of my own questions. The ONE question and the whole thing that’s relevant to the title of this podcast, but I really, really appreciate you being on the show and it was awesome.

Jill: It was so great talking to you and, and, uh, it’s really an honor for you to ask me to do this. That was a lot of fun, so thank you. I hope you all enjoyed it out there!

The author, Ryan Buchanan, is a social and for-profit entrepreneur with starting a racially diverse pathway to leadership program called Emerging Leaders as well as founder + CEO of a data-driven, digital marketing agency, eROI.



Producer of the Cause An Affect podcast. Digital Marketing Agency founder + CEO, Thesis. Co-founder of non-profit, Emerging Leaders. Portland, Oregon lover.

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Ryan Buchanan

Producer of the Cause An Affect podcast. Digital Marketing Agency founder + CEO, Thesis. Co-founder of non-profit, Emerging Leaders. Portland, Oregon lover.