Life / Work Balance with Jacob Turner

Jordan  00:00

Hi all, this is Jordan, the owner and CEO of Greaser Consulting. In this episode, we talk to Jacob Turner who’s from Xebra Consulting. He was Outreach’s second employee, just a fantastic resource on all things Outreach systems, ecosystem. Real really, I don’t think there’s anybody on the planet, at this point, that has seen more, like, various implementations, ways that Outreach comes together, all of that. But the sort of focus of this conversation was just how do you put balance in your life? The two of us were really early in what is now a unicorn startup. And, you know, he sort of became this expert. But what did he have to give along the way? And then how did he establish boundaries to have some more work/life balance? And then even into today: how is some of the things that he’s learned about, like life and work and culture and balance, how has that sort of spurred him into starting his own consulting company all around this Outreach ecosystem? Just a fascinating call today with a really great guy; he’s really mindful of people, conversations, relationships. So I encourage you to just lean in and enjoy listening today.

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Jordan  01:39

Hi, everyone, this is Jordan. I got with me today, Jacob. Jacob, why don’t you go ahead and introduce yourself?

Jacob  01:47

Yeah, hey everyone, Jacob Turner here, owner, operator of Xebra Consulting, second employee of Outreach.io. And what we do at Xebra is help companies implement, optimize, train, and enable their teams using Outreach. That’s what we do.

Jordan  02:07

Yeah, I think every, you know, every company talks about, right, the OGs, like, the people that were there at the beginning. And the thing that’s just kind of funny about this is I was employee 36 at Outreach. Like, two weeks before I was there, there was, like, 15 people at Outreach. Like they just got a funding round; they hired a bunch of people. And there’s not too often that I can say, “Oh no, like, that person’s the OG, not me.” And when I talked to Jacob, every time, like, he’s literally the second person ever hired at what is essentially a unicorn today on the path to going public. And I mean, at those times, were you hired as like, you know, I always remember you as the Solutions Consultant, but were you a CSM at that time? Or like, what was the actual title that you came in with?

Jacob  03:00

Yeah, the title was CSM. Yep. And from what, at that point in time in 2015, I don’t know how… I didn’t even know what a CSM was, other than the job description at Outreach. But now I realize that job was not a CSM at all. If I was a CSM, I probably would be in a totally different place right now. But I’m excited. I’m happy where it turned out.

Jordan  03:28

Yeah, so walk us through, walk us through just some of those early days of like, you know, you’re early in a startup that doesn’t know its path. And you’re a CSM, like, what were you doing every day? Because again, I just remember, like, there was no greater library of information on what Outreach was than like, go talk to Jacob. So like, what did you do?

Jacob  03:52

I mean, I think you just nailed it; I talked to people all day long about their problems without reach. I was like an Outreach therapist, doctor, construction worker, whatever service you can think of, that’s what I did. But no, I mean, we would, we bring in customers, and myself and David Lewis as well, who was, who was another CSM at the time; he was the first employee. We would basically handhold them through the implementation, training, deployment, growth, all of it. We basically were the post sales, you know, everything. We also did a lot of webinars and started to… once we started to realize we couldn’t do one-to-one training for all the new customers we were bringing on we, me and David actually developed a way to do one-to-many trainings. So that ended up being a big part of our lives. But I would say most of my days in the first few months was spent in Zendesk answering tickets, planning and jumping on calls, fixing people’s issues, and making sure they didn’t run up millions of API calls because of some glitch in the system.

Jordan  05:06

So I remember your, like, your one-to-many system because I actually, anybody that got onboarded at a certain point, we watched like the Outreach University videos. And like Andrew Kinzer was recording some of them; you were recording some of them. And I distinctly remember, and this was like public-facing for everybody, like on some of the videos, like, you’d hear someone just closed a deal. And in the background, you can hear like clapping and people going AHHHH, you know, screaming; it was like right in the middle of like, “click your initials to go to your…” AHHH. That was about as bootstrap as bootstrap could come. But I mean, over time, and I know we’re going to talk about like starting companies and this whole thing, but like over time, you morph from this like churn and burn CSM role to like a really sophisticated Solutions Consultant, solving really difficult problems. And so, you know, as I think about like, that evolution, like is there any part along the way, when you like first started and you’re doing CSM work to like, now you’re doing like the huge, like massive scopes of how we’re going to implement this thing into this system and get reporting that like, at some point, like, when was the point where you realize like you are that library of information? Like, did you know that one month after you started in the gig? Or is that like two years into the role? You’re like, “Okay, I know this better than anybody else,” right? Like, what was that moment when you realize, “I’m kind of I’m kind of the guy that knows this stuff.” And I’m not trying to be weird about this. It’s just, it’s the reality, right?

Jacob  06:43

Yeah, I would say it was a much shorter timeframe for me to realize that. I’d say probably like, six months into the role is when I realized, like, I was actually the go-to person. And it wasn’t even like a desirable place to be for me at that point, because I was, it was a lot of pressure; you know, if everyone knew that I was the go-to person and was willing to offer my time to support them, like, people just took me up on that. And I tell this to new folks who are getting into the industry nowadays, and I’m like, set good boundaries up front with your job, because I did not; I was working 12-13 hour days; I didn’t really have much of a life outside of Outreach. And that was because of my own doing. I didn’t set those boundaries. But yeah, I’d say six months in, is when I really started to feel my expertise and that was, you know, all of the lessons learned and sitting in a Massage Studio with the founders right next to, you know, Andrew Kinzer, who basically taught me everything about the platform that I needed to know until I become, you know, until the student became the teacher.

Jordan  08:00

Right. What are you doing sitting in a massage parlor? Like, what? What is this? You’re sitting in a massage parlor? I gotta know, like, you can’t just glance over that like that’s no big deal. Like what’s going on?

Jacob  08:12

Oh, yeah. I mean, there was there was no massages happening in the studio. We just rented… that was our first office that I worked in Outreach was a Massage Studio. It was very distinct green walls if you ask anyone. And yeah, that was the first place that we had an office. And I remember when we moved from that office, I was sitting on the floor with a box, my laptop sitting on a box, taking an implementation call with zero furniture. All we had was a router and a box for me to actually take calls. After I got off that call, I took the router and the box to the new office down the street. That’s how small, small we were. 

Jordan  08:56

Yeah. That’s just that’s like, that’s just a crazy, this makes me think about you know what Google’s starting out of their garage or something ridiculous. Like, I was, I was there with the router and the box. But you, you bring up a good point, though, about those boundaries early on. And like you became the guy, and it’s also served you well. But you also, you know, you’re giving like a huge part of your life to this thing that probably wasn’t healthy. So like, how long did it take you, in your journey here, to like, get to that place where you’re like, “look like I got to slow down”? Because I mean, I feel like I was in that place for for like 18 months or two years where like, I just I couldn’t turn it off. I was on Saturdays, on Sunday night, and I just like… it’s the path to burnout, but you don’t really see it, and you feel like you can’t say no. Right? Because you kind of are that guy. Like what, like what was the moment for you and like, how did you navigate through that? 

Jacob  09:58

Yeah, well, it didn’t really shift until I left, honestly. I was emotionally involved with Outreach; it was like a long-term relationship. You know, I compare it to a relationship with like a partner. And that, like, you know, there’s dynamics that don’t work; there’s dynamics that do work. But by the end of our relationship, I had already set a precedent of not having those boundaries. And so it was really, really hard for me to reintroduce myself, and not have it impact the way I was seen internally and externally. And that made me feel really uncomfortable, because I’m like, “Okay, I’m setting these boundaries, and they’re not being accepted. They’re not being welcomed.” And now, you know, doing more work on myself and understanding what those boundaries mean, in the long run is like, yeah, boundaries aren’t meant to be comfortable for anybody, you know. So, I probably didn’t need to leave, necessarily, but it felt like I did at that time. And that’s when I actually left and went to DocuSign. And had like, what I would call a regular job. Because I wasn’t, I wasn’t…

Jordan  11:10

yeah, I know exactly what you’re talking about. 

Jacob  11:12

You come in, you clock in, you clock out, you do good work. And that’s it. And I set the expectation upfront, like this is, I’m in this role. And this is how much I’m going to show up; everything was already established. It wasn’t me creating things; it was me following and adhering to a process. And that was me stepping back and being thrust into a boundary space, which was way more comfortable than me having to set new boundaries. You know, which, in hindsight, I’m like, it probably would have been more healthy for me to stay and set boundaries and then leave than to just cut ties and be and never have set those boundaries internally. Because I had to learn the hard way, even beyond my job at DocuSign, where and how to set boundaries in an appropriate way.

Jordan  12:03

So it’s just so interesting you talk about this, because for me, I was on, I was on the SDR side, and that was kind of like my vein. And then actually, you were part of the interview process. Do you remember this of like me transitioning to the training team? Do you remember this? Like, I came into the interview with you. And it’s like, like, I know, you you’re like what? Yeah, so like, what are we talking about here? But for me, you talked about you had to leave the company, whether you did or you didn’t, you know, you’re saying you’re not sure, my sort of reestablishment of boundaries was when I went to the training team. And it was like, “Oh, I almost got this, like second lease on life.” And so that’s where I sort of set some of those boundaries. Now at the time, what was interesting about it is, is I felt kind of guilty, though, of like, “Oh, I’m just not as busy as I used to be, or should I be doing more?” Like, man, it took me months to like, kind of work through this, but the only thing that got me through it was my was literally my wife and my two kids. It’s like, my wife’s like, like, “I don’t care if you feel like you should be doing more like you need to spend more time at the house.” And I’m like, “okay, like, like, I’m gonna listen to you before I listen over here, like, I’m with you.” But it was still hard for me. And I and I also remember, I had a lot of good support over here. So I don’t want to like just bash on the place because I had some great support. But I remember, one of the like, leaders at the time I was talking to said, “you know, you could be great in this role, but you’re not giving yourself to it. Like you’re you’re you’re you’re not really like pressed in like you used to be,” and I remember thinking like, “you’re right, I’m not… that like I can’t do that long term.” So anyway, I’m just interested to get your take here. Like you’re saying, like, maybe it would have been smarter to stay, but you didn’t, you know, all these different things. Like, like, when you come to the job site now or you come to work, right, you’re a couple companies removed; like, do you feel like you’re still able to give that like high value impact, even though that those boundaries are set up? Is it better? Is it worse, like, because that’s one thing I’ve thought about over the years: like how do I not go all into this? Like how do I still keep a boundary but also do good work? And, you know, sort of mesh this all?

Jacob  14:21

Yeah. Honestly, now that I understand, or at least, you know, have a better understanding. I wouldn’t say I understand boundaries completely. That seems like a lifelong journey. But now that I have a better understanding about boundaries, I feel like I’m more able to show up for people, companies, projects than I was before. I was a chronic procrastinator, and then the overwhelm made me do things in the last minute and even though I would be available to people to answer questions, I wasn’t actually fully available with all that I could offer. You know, even giving 75% of myself to any of those moments, any of those interactions was valuable to people because they were getting me whenever they needed me. But they weren’t getting 100%. And nobody was. My partner wasn’t; my family wasn’t; I wasn’t giving myself 100% of myself. So I was just like a fragment, I was just walking through the world as a fragmented version of myself everywhere. And when I started to set boundaries, I realized like, I was able to be 100% in less spaces, but I was able to have bigger impact, because all of me was there. So all my relationships changed; the projects changed, people started to do, expect things more clearly, because I was more… I had more clarity around what my boundaries were. And so they were like, “hey, Jacob’s not working on Fridays anymore.” So we’re not going to book meetings on Fridays; that made me way more available on Monday. And I was, you know, anyway, that’s, that’s kind of that my journey of of setting those boundaries was realizing that I actually wasn’t doing my best work, even though I was working my ass off.

Jordan  16:10

Just makes me think about, I was like, four or five months into the training thing. And I was actually feeling kind of bad about it. Because we would travel all week and just be home on the weekends. I thought, “Man, this is worse, like, like, I wanted to be around my family more, and now I’m gone more,” but I, I can still remember is one of the Saturdays I was home. And I was hanging out with my wife and kids. And she’s like, “you know, the weirdest thing about this.” This is after setting some of those boundaries and whatever. She said, “You’re, you’re not here more, like you’re, you’re here less than you were before. But you’re more present now than you’ve ever been.” And so she was talking about like, like, when you’re home, you’re actually home. And I think there’s a lot of value in what you’re saying here of like, you have this temptation just to pour everything you have into something. But then it starts to take from other areas, like there’s only so much you can give before other things start to suffer. And, you know, that was like a, it was just like a profound moment in my life of like, “I don’t ever want to be in a situation again, where my wife’s telling me like you haven’t been present for a long time.” You know?

Jacob  17:18

I mean, fast forward, after I left Doc, I left DocuSign to move to Hawaii to actually be more present. And, like, I tried to keep my job, you know, just for the record. I tried to keep my job at DocuSign and work remote. This is pre-pandemic. But we decided to move for that exact reason. Like we wanted to be more present with each other, and living in Seattle didn’t feel like it gave us the space to actually sink into our brand new marriage, sink into our relationship, sink into what it meant to be authentic living authentically ourselves. So yeah, moving to Hawaii was was like I don’t know… what do you what do you? What’s the word that people use? Just like a not a midlife crisis, but something to that nature, which is like, all right, what do you do? Yeah, I ended up getting a non-tech job. I started working for the county of Hawaii in the, in the County Clerk’s Office.

Jordan  18:25

Yeah, but don’t… shoot, don’t you remember, this was years later? Well, this was like years later, right? When I called you up, like, “hey, I need you to do Outreach implementations.” Like “I work at the county.” Like what, like, “What are you talking about work at the county?” You know? Oh my goodness.

Jacob  18:42

I mean, I loved that job, too. And it was, it was very structured, you know, if, if anyone out there listening is working a government job or has worked a government job, you know, like, once you leave, you leave. There’s no, unless you’re like a politician, you know, which I would not claim myself to be, like, I left my job at the office. Which now in our world, everyone working from home, that is a very seldom experience for folks. So it was like, I go to where I go, this is my routine, and I’m gonna gonna share some personal information about my life right now. My routine was to wake up at six o’clock in the morning. This is all also pre-kids, right? This is not how my life is now now that I have a child. But when I didn’t have a job yeah, I get ready pretty quick. Go drive into town. Go to the yoga studio, do yoga for an hour. Then I would go into the office and they had a shower there, so I’d shower at the office and then be in my chair every morning. 8:30 every morning. Like I didn’t, I didn’t miss a beat because it was really easy for me to be in that routine. After, on Tuesdays: Mondays, Tuesdays and Thursdays after work, I would go to paddling. I was going to outrigger canoe racing club called Kamehameha canoe clubs in Big Island, Hawaii. And I would go practice in the canoe, and then I would shower at the beach and then go home. And then every now and then I’d stop at the store and get groceries for dinner. But then go home, prepare dinner, cook, eat, you know, enjoy some downtime with my partner, and go to sleep. And that was like, Monday through Friday, what I did. And it was so nice to have that routine. It was weird.

Jordan  20:45

Yeah, it just had to be so different. Like, right, like all the sudden you’re just just off, right? I dealt with that. Like, we just had our fourth child. And what I found for me is like, it took me like a week to get work off my mind. And then all of a sudden, it was like, just super fun to play with the kids and hang out and be around the house that first week. Like transitioning to get my mind to turn off just wasn’t happening. Right? But you know what happens? I just want to ask you like, during that season of life, where like, you were just unplugged in a lot of ways. Like I still I laugh at this, I still remember calling you the one day you’re like, “Listen, I’ll call you back. I have to go plugin, like somebody’s router for them in this office because they can’t figure out how to get their internet to work.” Right? Like I just I remember laughing about that. But like, that had to be so good for you. Right? Like just having this whole season of time where like, like, almost like life hit pause. But then life also turned on, if that makes any sense, right?

Jacob  21:50

Yeah, I mean, honestly, it felt like a return to a feeling I felt in the past. Before I even worked at Outreach, I was working at a Parks and Rec Department in Somerton, Arizona which is right on the border of Mexico. And like that was that was probably the funnest job I’ve ever had working for a government entity. Just planning play, basically planning playdates for kids: soccer tournaments, baseball, Tee-ball basketball, swimming events, outdoor, just anything, really was our job in that department. And you know, same same scenario, I had a very structured routine, because it was a government job. And man, those were some of the happiest days of my life. And I was making little to nothing; I wasn’t able to actually afford my student loan debt. I wasn’t able to, you know, save at all. But I was in such a zone of like, feeling peace, that it didn’t even matter. I didn’t I didn’t even care about my debt or my income or any of that, because it was just like, I felt alive every day that work.

Jordan  23:05

Well, that kind of brings us to today, right? Like you’re, you’re starting, or you have started your own consulting company: Xebra, which, you know, I always joke about this when I talk to Jacob like, I’m not sure if we’re competitors, frenemies or what we are, but you know, he’s, he’s a fantastic guy, does fantastic work. If you need Outreach help, like, by all means, get a hold of them. But you’re at this place now, where you’re, you’re starting your own company. And I suppose the first question is like, is that coming from a place of you have this, and it could be all, it could be something totally different. But like, you have this huge passion to do this work? Is it from a place of like, I want to find a way to to do really good work, but then just be able to unplug and work on my terms like what’s, like, what’s the underlying impetus for you to say, like, here’s why I feel really excited about starting this thing?

Jacob  24:01

I did… a few different reasons. One is I realized that I am not going to find well, I don’t know if I can say I’m not going to, but I felt like I was not going to find a company that I could work for that was aligned perfectly for me, culturally, you know, time-wise, structurally, like I wanted to, I wanted to be the culture of my company. And everywhere that I’ve gone, so…

Jordan  24:32

There’s the quote of the day.

Jacob  24:35

Yeah, so I need to create the culture. Yeah, I wanted to be the culture. And I’ve had influence on the culture of Outreach and on the culture of Sapper and Docusign. But, you know, for the most part, you know, I often felt like it was just missing something. And I realized, like, the only way I’m actually going to get that is by doing my own thing, because the energy of any company is going to be the precedent of who started that company or the founders of that company, right? And I was just sick of, sick of waiting to find that culture of sick of waiting to find the belonging in a company. I was like, I realized, like I belong; I can create my own belong. I belong to myself, you know? And that was, that was one of the main…

Jordan  25:29

So what are those? What are those values? What are those values? Like, what’s the culture you’re trying to build?

Jacob  25:39

I am trying to… I am building a culture of balance, being the first one, a culture of rest. Meaning that I want to build in for whoever ends up working for this company, months of time off every year. And I was thinking about this the other day; I was like, anybody who works here is going to have a sabbatical at least once every two years at the very least, paid sabbaticals. You know, six months, you don’t work here, you come back fresh, and it’s a new job, a new day for you, right? I want to build a culture of generative conflict, where people can really be honest about how they feel, and it can be handled and not feel like a risk to their future, financial security, or a risk to their employment. I feel like there’s always a place for conflict as long as that can be generative. And not, you know, something that is dangerous or harmful. I want to create an environment where people feel like they can communicate with each other around their personal lives and be friends. And if not families. It makes me think of my my, my godfather; he worked at Sears for, I want to say he worked there for maybe 40 years. He retired from Sears 40 years, right and the same company with the same people for 40 years, and I’m sure they had attrition, just like any other company. But, you know, they had pensions, you know, they had retirements, and now he doesn’t work; he travels the world, and comes and visits Hawaii every now and then. And like, lives this life that just seems so outside of the norm of today. But he worked there for 40 years. And he felt like all those people he used to work with are his friends and family. He goes to barbecues with them, and he, you know, enjoys traveling with them. And, you know, now I feel like it’s kind of like the, I mean, for any sports fans out there. It’s hard for me to even be, you know, a fan of any one team because players just move so often it’s like, I don’t even know, like, is this the same? It’s not even the same team season by season. It’s a whole new team. So who am I? Who is my loyalty to, the brand? You know, like the Sonics don’t even exist anymore, but I’ll use the Lakers like, Is my loyalty to Shaquille O’Neal? Like, you know, is my loyalty to Lebron James? If that’s the case that I have no, I have no care for the team itself or the brand. I have a care for the players, right? And it kind of resembles, to me, the tech industry. Now. It’s like, if you’ve worked at a company for two years, you’re like old at that company.

Jordan  28:44

Yeah, we always used to joke about, right? Like, you’re the dinosaur.

Jacob  28:48

Yeah, exactly, exactly. But I think that companies can be built in a way where there are no dinosaurs, like, your goal is to be there for 40 years. And these companies just aren’t making it sustainable. I think for people to be long-term employees. They’re not offering you know, six months off every two years; they’re not offering the things that people need, in order to feel like they can stay, right? They’re offering more money to new people instead of promoting the people within. I mean, there’s just a lot of little things that I think companies can do to retain the people who have been loyal to them throughout the, the, the creation of that company, or since they’ve been a part of it.

Jordan  29:29

Yeah, well, hey, man, I appreciate you hopping on today and talking through like a little bit of company vision, a little bit of, you know, just walking through the process of, you know, like you… and I mean, this, like you were the guy for so many years, and just processing through boundaries. And you know, you said maybe you didn’t have to leave Outreach, but you maybe you could have did a different like we all have warts and things that we look back on, and we say, or maybe it could have been this, maybe it could have been that, but at the end of the day, you know, highly regarded individual, lots of respect from a lot of people. So I don’t think you have much to be concerned about there. And, you know, it sounds like, you know, this is all part of that process and journey, right, that we all walk, that we might look back on some things that were like, I’m not sure. I’m not sure I handled that one right. But like, you know, next time that comes up, like, here’s how I’m going to do it. And again, that’s not even to say how things were handled wasn’t right. You know, it’s, we live our lives, we learn, and we kind of move to the next thing, right? And we, we hope along the way, that is we give grace to others, grace is given to us, right? So I know like we before we started this, like we were gonna talk about sales engagement, and we were gonna go down this whole road of, of starting a company and what that looks like, but, you know, I appreciate just some of the ways you were candid today of processing through just change in boundaries and whatever else. So is there anything, Jacob, here before we round out that you want to, you want to say? Any final thoughts as we as we close this thing up today? 

Jacob  31:16

I think the main thing that I want to impart on folks listening is to be very intentional with the decisions that you make. Discernment has been something that I’ve been learning is, has a bigger impact than any amount of money, any amount of time. Making the right decision in a proper amount of time, I feel like, has a much bigger impact than any other resource that you can throw at something that you’re looking to solve or something that you’re looking to, to embark on. So yeah, discernment is the, is the word for me today.

Jordan  31:56

Alright, Jacob, thanks for coming today. And thank you, everybody, for listening. I hope you go ahead and join the next time. See you, Jacob. See you, crew.

32:07

Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at www.greaserconsulting.com. Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.