Bill Whitebone: Ditching The Comfort Zone, Drupal, EdTech & Racing Cars

I drive cars on racetracks for fun. It's a stressful activity, right? So while you're doing it, it's super intense. But after you're done with it, you feel such gratification in doing it well. 

Piyush  0:13  
Hello. I'm Piyush Poddar, and you're listening to the Humans Behind DX podcast, where I talk to leaders from digital agencies and organizations delivering awesome digital experiences. Today I'm going to talk to Bill Whitebone, Principal at Advance Velocity. Welcome, Bill.

Bill  0:33  
Glad to be here Piyush, thanks for inviting me. 

Piyush Poddar  0:36  
Awesome. Tell us who you are. 

Bill  0:39  
Who am I? I am a technology professional living in Boston, Massachusetts or outside of Boston, Massachusetts. My career has been 20 years in professional services, customer success. I have two children, 10 year old and 11 year old; I’m married. And I live in a small town that's just west of Boston called Sunbury.

Piyush  1:08  
A beautiful city. I've been there in, you know, a couple of times, so totally love it.

Bill  1:14  
Yeah, a lot of history. It's great. The zip code’s actually 01776. So we get the 1776 going for us. A lot of historical connections. 

Piyush  1:26  
Absolutely. Right from the Boston Tea Party days. 

Bill  1:28  
Yes, exactly. Exactly.

Piyush  1:31  
All right. Cool. And, I mean, yeah, you definitely have a great career spanning more than two decades, as you mentioned. Talk us through your story a bit, you know, the journey and how you reached here.

Bill  1:48  
It's really interesting to me when I think about how I ended up doing what I do, and it really stemmed from an early interest in engineering and also in design. So I studied environmental design in mechanical engineering. And I was really interested in becoming an architect, and not a technical architect, but an architect who designs houses and buildings, and actually had gotten an award in high school for a design I had done of a house, and was really passionate about it. So I started studying that in college. And one day, my boss at the time—so I was working for housing services to make a little bit of extra money. And the boss came into the room—it was about 10 of us in the room. We were all fixing computers. We used to drive around to different locations on campus to to fix computers, which most people wouldn't even recognize those computers today. There were 386s and 486s. So quite a long time ago. But our boss came into the room and said, hey, there's a new thing out there called the World Wide Web. Does anybody want to look into it? So I of course raised my hand. I was looking for a new challenge and to really dig into something new. And little did I know that that would be the beginning of my career. So I didn't really think about it at the time as I started to work with the web. I really found it interesting. And it seemed to align very well with the things that I like to do. And now looking back on it, I think about why it was such a good fit. And I think about architecture and what architecture is, and architecture is design on the outside. And then it's the engineering behind it, right? So that's the web, the web is the same thing. So it was a really easy transition for me to get interested in that and my career went from there. 

So I started out as an engineer and was doing web development in college—really basic web development. I think people would be amazed at what it would look like back in those days. And from there, I became a webmaster at a company in Maine, in Bar Harbor, Maine, which is a beautiful place. And I ended up doing some tech support there, and then I was the webmaster. So I actually had the title of webmaster. So that was the beginning, which was a really interesting beginning for me. And you know, from there, continued through my career progressing through from engineering over to project management.

Piyush  4:35  
Gosh, I can see so many similarities, you know. Really late 1990s, when even I started my career and started by selling computers, my first machine was 486 DX4, which was way better than a DX2. Or at least I thought so. But it was like just a very marginal difference. Yeah. Those days right, I mean, you know, I started selling CD drives and it was like, wow, you can have a CD drive in your PC! Yeah, what does it do? Well, you can use it to listen to music, first of all, and then you can always, you know, there are some PC, CD ROMs and all that stuff. So, yeah, love it. Interesting, very interesting. 

And now, you know, now that you are here, anything you feel you would have done differently, given a chance to maybe you know, teleport back to those days?

Bill  6:03  
Let me think. Okay. Well, it's, there was an interesting inflection point for me. So I was an engineer for several years. And I ended up taking a job at Digitas, which was a great experience for me: a large agency, got to work with some really large brands. To be the age that I was at the time, which is probably my mid 20s, and to be working with companies like FedEx, and American Express, was great and such a great exposure and really helped me understand how enterprise works. But when I took that job, I was offered a job that was going to be a split between a project manager and an engineer. So that was my pivot point where I moved from being an engineer over to doing some project management—at least that was the plan. When I took the job and started working the job, I did no engineering. So It was really, really interesting to me that my plan was to be splitting 50/50. I was kind of tired of sitting behind the computer all the time, and I wanted to start to work with clients, but it was pure client work. So I wouldn't have minded working as an engineer a little bit longer. I really did enjoy it. I can't complain because of how my career has progressed since then, and the opportunity that Digitas offered me. But yeah, being an engineer for a little longer would have would have been something interesting for me.

Piyush  7:35  
So, you know, after that, has that had a significant impact on what you're doing today?

Bill  7:47  
That pivot point definitely did and the further engineering wasn't something I needed. I was an engineer long enough that I can actually understand what engineers do and really what the challenges are. And that's been key. It's absolutely key to understand if you're leading engineers, what they're doing day to day and some of the challenges that they face and those sorts of things. I don't think I could have been nearly as good a leader, as I have been, or people have told me I am, if I hadn't had that experience as an engineer. So I think that the pivot point was important for me to get into project management because that's really what set the basis for what I've done since. So the progression from that point has been different levels of management throughout project management and then into larger leadership, also getting involved in customer success. So that is a key change of the direction I was going. But it was an important change for me to be doing what I do today.

Piyush  8:50  
Right. So an engineer converted, transitioned to a project manager, further transitioning to customer success. But end of the day, it's customer success and customer experience that, you know, really all these three roles are ultimately delivering. And yeah, that's, that's amazing. That's really inspiring. 

Now, let's shift gears a bit and talk a bit about the present, right? 2020, a year that no one's gonna forget. How are you keeping up this year? You know, any big goals you're working towards?

Bill  9:33  
Yeah, so it's definitely a different year for all of us than we anticipated. And being early on with my company still, it's certainly not an optimal situation to be in, but things are going well. So last year was a very good year. Good to establish some really good presence with several important and key clients and really been able to continue to develop those relationships throughout 2020 and also leverage some of the peer consulting I did last year to continue to work with those clients and also to get some new opportunities with your consulting. So it's been an interesting mix this year. And it's been... considering the situation that we're in, it's been a better year than anticipated, based off of my experience with with what's going on with COVID. But not nearly the year that I had anticipated if it weren't for that situation to happen. But I'm definitely happy with where the company is at considering the situation that we're in. It's been a year where it's been harder to get people's attention, it's been harder to get commitment, but it's happening, and a really good part of 2020 is built on what we did together last year too. So having worked on the Staples project and built Staples a very nice platform for them to manage their their marketing on—that's something that has been key for this year, to continue to do development for them and the maintenance for them. So certainly the work we did together and the success of it has been a key thing for 2020 for me.

Piyush  11:12  
Awesome, awesome. Staples is a pretty big name in their respective space. Have you seen a lot of uptick in terms of, you know, their digital projects or transformation initiatives or you feel it has gone on hold? Like where are things in the in the industry at this point of time?

Bill  11:34  
I think a lot of things are on hold. So I think the initiatives that are under way are continuing, but a lot of things have been put on hold. If you look at Staples, in particular, they definitely have had some financial challenges. I think they're doing better now and they saw quite a bit of demand from the home office angle. So there was a good amount of business they got when people were building out their home offices. But my impression is that there are a good number of initiatives that are paused. But if I think about the things that are most important to them and what I'm seeing with what are their clients, certainly still seeing a drive and have consistently seen a drive for many years towards personalization, right? So personalization is still very key. So seeing that, really being able to manage marketing and personalization, certainly part of marketing but being able to understand where marketing spend should go, understanding the performance of the marketing that that's being done—that's certainly a key part of the initiative at Staples that we did, is them being able to allow their their partners to go ahead and book marketing in different across different platforms, be it online, offline, and then be able to track that. So that that's certainly an initiative that speaks to it. Another thing that's no surprise to anyone who's currently in this situation, but video... video is seeing a huge drive towards that. Another area, which I've recently become involved with is EdTech. And I've been in EdTech before because I was at Better Lesson for almost a year, really building out some of their capabilities. And... but right now I have an EdTech opportunity, which is really focused on the challenges of children not being in actual schools right now. So I think that that space has quite a bit of opportunity. And it's a space where you're doing good, right? So really helping kids to have a connection to schools and to their teachers, I think, is something that's very important. We don't know what's going to happen in the fall still. Here we are in August and it's not entirely clear how my children are going back to school. And I think many people are in the same situation, that they're going to be educated from home. Is it going to be a mix? Are they going to be in school? And I think for the most part, no school is going to have all their children back in the school. So I'm working on an initiative which will help to bridge some of the gap that's formed by students only being in school part-time or not being in school at all.

Piyush  14:21  
Right. Yeah, makes sense. And, you know, EdTech, of course, I mean, you're based out of Boston, you've been there for so many years—you know, Harvard, and so many great institutions out there... Talk a bit more about EdTech. Because I've also been curious about, you know, the, the maturity stage in which this industry is. I mean, all of a sudden, you know, COVID has created a lot more need and urgency for innovations and improvement in products and experiences. The velocity of this, the, you know, digital growth in this industry has, you know, pretty much changed, I feel. I mean, do you agree? And are there any experiences or specific instances that you'd like to share with the audience here?

Bill  15:10  
Yeah, I can speak to EdTech in general: why I became interested in it, why I ended up with Better Lesson. Really, it's a combination of things personally, but purely from a career perspective, it's a space that has a ton of opportunities still. So I think it's really early in, what the capabilities are of that tech, and we can see it through over the last few months, just some of the shortcomings of some of the tools that are out there. So I think it's a space that really has a lot of openings for people to come in and fill gaps, especially gaps that are being formed by the fact that we're not doing traditional education right now. And if I look across the types of EdTech offerings that even in the Boston area there are, there's online online learning tools that were originally intended for remote learning for example. Harvard and MIT have done a lot of work in really being able to offer remote education even long before COVID. But those tools need to be refined. So they’re still very early in their lifecycle. And I think many of them are still pretty rough. So there's a lot of work that can be done to really make these tools easier to use, make them integrate better. And there's no standards across EdTech either. I'd love to see some thought around standards and some standards on how systems are integrated, and some standards on how things function in general. So it feels very disparate. I mean, many technology spaces are that way. But education I feel is collaborative, and if really, there could be more collaboration happening and more standards, it'd be of huge benefit.

Piyush  16:59  
Right. I mean, you know, even I have come across a lot more interest and uptick in terms of opportunities, even if they are like, okay, let's get on a call and understand, you know, what, what technical capabilities do you have, or what can we do? There’s definitely a lot more that people need and that can be done, specifically in EdTech.

All right, cool. Now, let's do a bit of a soul searching here. You know, based on your career, your experience, it will be a shame if I don't get some solid advice from you, in terms of, you know, where you are, and you know, how others can have similar growth… starting from more internal aspects, right? I mean, do you want to talk a bit about your philosophy of success, you know, maybe in life or work?

Bill  17:56  
Sure, yeah. So if I look at really what my... things that that make me do what I do, one of them is, is really pushing myself. So I spend a lot of time in areas that are uncomfortable. And I’m okay with that. So it is uncomfortable and I know it's uncomfortable and I can feel it when I'm doing certain things. But I really feel like that's when I stretch myself and I learn, and in the end, at least 80 percent of the time, I feel like it was a great thing to do. So even in my personal life, I drive cars on racetracks for fun. It's a stressful activity, right? So it's while you're doing it, it's super intense, and you need to keep 100 percent focus and there's just a level of stress that happens while you're doing it. But after you're done with it, you feel such gratification in doing it well, and learning so much. I mean every time on a track, I feel like I'm learning a ton. So throughout my life, throughout my career, really pushing the edge of what I feel comfortable with has allowed me to do to do things that I didn't necessarily know I could do. So if I look at the transition from being a developer to a project manager, that was super stressful. If I look at working with large enterprise companies, walking in, 25 years old, looking like I was 18, into a boardroom at American Express, you know, that's, that's uncomfortable. And I had people regularly asking me how old I was. And, you know, and I knew that I looked young, and I knew I didn't have credibility. But I continued to push myself and be in those situations and learn from those situations. And throughout my career and job changes that I've made, I think that it's easy to become complacent. You can become complacent in many ways. You can stay in the same job, you can stay in the same technology, you can stay in the same role that you've been in forever, and that's fine for some people, but it's not for me and I really have to look at what is the goal in life. My goal in life is to continue to challenge myself and go as far as I can, right? It's not about money to me. Money certainly is a nice outcome of the effort that I put in and the stress that may be related to it. But really, I'm looking for new challenges, to know more. It's funny, I get a lot of feedback from people who I know that I know a lot about a lot. And I don't necessarily feel that, but I find people coming to me asking about random things. “I have a problem with my sink, and here's the problem. What do you think it is?” “I have a problem with my car—here are the issues.” “Thinking about buying this or that. What do you recommend?” I think that people know my personality is one that just finds out as much as I possibly can. And really, it really just stretches to understand as much as I possibly can. So I think that that's an important thing is to really push. It's not being fearless. The fear’s there, right? Like anybody that says, “be fearless”—maybe there's personalities that can do that. That's not my personality. I feel the fear. But I push myself in it and I feel great in what the outcome is. I'd say that probably the most extreme example for me of really taking a leap is my own company, right? So I worked for a lot of very successful companies. I really had enjoyed working at those companies, enjoyed the growth and moving into my own company and certainly there's there's all kinds of stresses, yet I feel such gratification on a daily basis around looking at what I've accomplished and looking at the the partnerships that I've formed, the friendships that formed. the clients that I've gained. It's a great feeling, and that's really what I thrive on. So I think it takes a certain personality to feel comfortable with that. I have people on a regular basis, friends that have known me for a long time, who have been saying I'm crazy in taking that kind of leap. But that's what I like and that's what drives me.

Piyush  22:11  
Right. Yeah, end of the day, you know, the feeling that you have built something, you've made something which is adding value to someone else or, you know, a company or person or whoever—I think that's a big thing. I totally agree. Right? I mean, money is a byproduct of efforts, but at the same time, not the only goal or not the key North Star. If you do the right things, it'll come by default.

Right. Okay, cool. Forward thinking out, given this assumption that, you know, we will be over this pandemic in a couple of months, you know, hopefully, not long—things will be back to normal. Looking into the future and especially based on the different industries that you have really worked in, what trends kind of excite you? You did talk about EdTech. Any other space or aspects that you'd like to share? Like personalization, I remember you did mention personalization and in one of our earlier conversations you brought it up as well. So really, yeah, you know, what trends do you think kind of excite you going forward?

Bill  23:31  
Yeah, for me, one of the areas that I really am looking into more is where the CMS space is headed, right? So... and that's an important one for me, because a lot of my career has been based in CMS and particularly in Drupal. But really looking at where is that headed, and I definitely feel some evolution and it's not entirely entirely clear to me where that evolution is headed, but it's an area that I'm keeping a close eye on. And if we look back in the day when I was at at Acquia, there was a huge transition happening to open source and open source was super hot. And I think the open source space continues to be a very strong space. But I am seeing some movement towards licensed software, again, in particular in the CMS space. And it's interesting for me to watch looking at the cost of some of these pieces of software—it's quite large, but they also offer a lot of capabilities. But I do watch Drupal in particular. The evolution of Drupal has kept up pretty well. But it's not clear to me, in general, the open source... where the open source space is headed. And it's something that I'm trying to do some research on, trying to get some different opinions on. But it's an area that I'm very passionate about. Certainly, I want to know where people think it's going,

Piyush  24:57  
Right, yeah, I mean, open source is definitely one thing that is exciting and interesting, but at the same time, you know, you cannot say that open source wins in each use case, right? There could be a need of moving faster, you know, the time to market, time to value. There are multiple aspects, right? I mean, you know, Drupal is definitely an amazing, open source project, I believe the biggest open source product, or the community is the biggest at this point of time, which is, you know, but definitely I myself have been in this industry for almost 10 years, seen Drupal from where it was to where it's heading. It's definitely become bigger, better. But that's a lot of time, right? Things change, needs change. And you know, other players out there, the market keep evolving, including their messaging, their positioning and probably the value that they deliver.

I guess this is also, you know, depending on whether content management systems are more being adopted in enterprise versus small and medium industries, which is where, you know, the question of whether you should go for an open source solution or proprietary kind of matters.

Bill  26:22  
Right. Yeah. And there you go. The smaller side, it's a no brainer, right? So, products like Drupal and WordPress are for a company that doesn't have a lot of money to spend. They're great solutions. And then I think WordPress, starts to drop off a little bit as you get more towards an enterprise solution. And I see Drupal really being the leader there, right? Yeah.

Piyush  26:43  
Yeah, yeah. Okay. We're up the hour. Talk a bit about you know, some resources, share some resources, you know, maybe books you love, you know, authors you follow. Any of those that have had, you know, significant impact on the way you work or live or think? 

Bill  27:12  
Yeah, so I would I would say, somebody who I follow regularly is Robert Glazer. He has a weekly email that he sends that I've been reading for a couple of years at least. And I just find him to be a pretty inspiring person, somebody who's really thinking about lots of different things in life and primarily around business. But especially recently, there's been some more personal postings that he's put out there. I read his book Elevate recently, too, and I just find him to be a pretty inspiring person who... he's very successful, and yet, I think fairly down to earth and really has a broad perspective. So I found a lot of things that he's put out there to be inspiring and then also some things out there that I've just like... yeah, that's how I feel too. And I think that there's a lot of common challenges out there. And he touches on a lot of a lot of those common challenges. So just to see somebody’s having the same challenge or thinking the same way is really helpful on a day to day or week to week basis with his weekly emails. Especially through this whole pandemic stretch, there's been some postings that I just find to be spot on. So I think for several years, he's been somebody who I've looked to for some guidance and inspiration. If I look in general there's... I think about the largest evolution in in my management, I look back to my time at Vistaprint. Vistaprint had a management training and here's a management training—you've grown, but it actually was amazing. And really what it did is it pulled together many, many publications, many authors and some of their their best work and I really feel like there's just so much. There's so much out there. But there's so much good information out there, it's hard to find. I felt like that what that whole curriculum was based on was trying to take some of the best teaching out there and the best writing out there and pull it together. And there're things like dealing with difficult conversations, right? There's a book out there, Difficult Conversations, and I should remember the author but I don't. But I remember reading pieces of that during that training. And I thought about some of the situations I had been in, be it with clients or with employees and just... it's so easy to to walk around the point of a conversation or walk around the thing you're trying to get to because it feels more comfortable. And really reading something like Difficult Conversations or parts of it and understanding that value of being direct is huge, and there were so many things throughout that training that there were like that. I felt like it... I feel like even now I look back to it to reread some of the things that I found were quite valuable because there’s just so much out there. You can never read even all the best of what's out there. But I felt like this pulled together a lot of those key things.

Piyush  30:22  
Yeah, absolutely. And, you know, I have personally found that sometimes, you know, instead of doing that exercise of, you know, reading and then figuring out hey, this was probably not fit for me or something like that, you know, go by people's recommendations, you know? Ask questions, get into those conversations. It's really helpful. Also saves time and you know, gets you some initial ideas. One resource that I am a regular reader of is this thing called Rands Leadership channel. I don't know if you’ve heard about it.

Bill 30:59  
Yeah, I have.

Piyush  31:00  
Rands Leadership Slack, you know, they have this interesting Slack channel with 600 public channels and more than 12,000 participants. And, you know, one of the channels is actually, you know, these difficult conversations and it's amazing the amount of insights you can capture from, you know, just browsing through that channel. And you know, sometimes you can ask questions and people can respond. So yeah, you know, what I'm saying is, you know, mix of books, and these can really help, especially at this time when you need a lot more wisdom to keep you on the track, both mentally and physically.

Bill  31:41  
Definitely, definitely. I feel like especially for me, the last two years have been challenging and starting the company as I've been so focused on the day to day and the functioning of the company and the sales and the delivery, it's... some of the resources that I've relied on in the past, I just haven't had the time to even tap into them. So certainly resources that are easy access and quick to read are really valuable.

Piyush  32:06  
So, so moving on, this is, you know, my favorite part. Last question, which is post COVID-19 when the world is back to normal, Bill, where would you like to travel or do anything exciting that you'd like to share with us? 

Bill  32:23  
That's a great question. It's hard to even think about leaving my city at this point. But yeah, thinking about travel... I spent a lot of time in Europe when I was at Digitas. So I was there for several months and travelled consistently and I was living in London. But on the weekends, I was traveling everywhere. So I really miss Europe and haven't been there in a very long time. And I have a 10 year old and 11 year old child, and I have never brought them there. So really the other day I was thinking about what a great experience it would be when we can travel again to show them some of those really old places. The thing that was most striking for me living in Europe was really that the age of some of the buildings, and it's just... coming from the US it's mind blowing to think about things that were built in the, you know, 1200, 1300, you know, that's... it's really something that's a spectacular experience. So, I'd love to put a European vacation together and do a tour with my children so they can see some of the things that I saw.

Piyush  33:25  
Awesome, awesome. Well, we hope and we wish that you get the opportunity to travel to Europe, you know, soon along with the family, and all the best for that. Because when that happens, you know, even I'm looking forward to get on a flight. I don't know where, but at least that's something I'm definitely missing. 

Bill  33:46  
Yeah. The plane will be a novel experience again.

Piyush  33:51  
Absolutely. All right. Bill, thank you. I think that was great. Thank you for your time and sharing your story with us.We will add the links you mentioned in the call notes of this episode and hope to get you back in one of the future episodes.

Bill  34:10  
It sounds great. It was great talking to you, Piyush, and I appreciate the opportunity.