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Changing careers can be really scary. Changing careers later in life could be absolutely terrifying.
New Global Sales Enablement Program Manager at Redis, Philip Bokan, shares his experience moving from a 25-year career in sales into enablement with RevOps Therapist and CEO of Greaser Consulting, Jordan Greaser.
From how to level up a team to doing that and working remotely, these two cover a variety of topics on the journey from sales to enablement.
Hello, this is Jordan and the owner and CEO of Greaser Consulting. In today’s episode, we have Philip Bokan with us. He has spent years, I think 25 years he said, carrying a bag in a sales role. And he just recently transitioned over into sales enablement. Now, he’s been saying that he’s been doing that for a few years as an element of his job in sales, but this is the first time that he shed that quota, and is solely focused on just up-leveling the entire team. So we touched on a handful of things in this episode. This is not one of those episodes where we sort of pick a topic and we stay. It’s really interesting; we’re going to talk through things like how do you make that change, after 25 years, to have the confidence to jump into just a whole different side of the game? We’re going to talk about some of the things that he went through early on in his journey in sales, on how to rise to the top, some comments around remote work, and how to just activate the workforce. So in this episode, if you have it on your mind at all about career change, and that hesitation and the courage to just take steps, this would be a fascinating one to listen to, especially with a guy like Philip, who’s just, he’s been around for a little bit. He’s done a great job for quite a long time. And still, he’s in a position where he’s willing to challenge himself and make some changes. So this is one you’re going to want to lean into a little bit. And I know you’ll enjoy it. Dive on in.
Say you want some clarity in sales and marketing and SEP? Well, we have just the remedy: our podcast, RevOps Therapy. Yeah.
Hey, everyone, this is Jordan, owner of Greaser Consulting, and I got with me Mr. Philip Bokan himself. We’re going to talk about the transition out of being in a full-cycle sales role for, or AE, you know, everything in the tech world for basically forever, and then moving over into enablement. So I don’t want to age you there, Mr. Bokan, but why don’t you go ahead, introduce yourself? Let us know who you are, what you’ve been up to. And then we’ll we’ll jump into this.
Yeah, Philip Bokan. I’m now a Sales Enablement Program Manager with Redis Labs. We are the world’s most popular database. It’s true. Anyway, enough plug of that. I’ve been 25 years now…
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Five, nines are table stakes. Man, c’mon. It’s all about the instant experience, you have to understand that. It is… I’ve been carrying a bag for 25 years. And I’ve done everything from run multiple SDR teams to manage people. My last gig was closing, moving into management, and doing enablement and onboarding and all sorts of fun stuff. And I’ll tell you, I had been talking to my current boss about two years ago; we talked about it the last time you’re gonna have to go last time. And my long-term goals are getting into education. And this is one way to continue to right here to kind of transition to that long-term basically. So I’m able to kind of use what I know right now and work with corporate team there. So it’s kind of exciting.
So let’s talk about the… obviously, you go from quota to no quota, right? I remember for me, which I was only SDR, SDR manager, sales world for like, a handful of years. And then I went over to training. But I remember the first month when I made the transition, and like the, the 31st fell on, like a Tuesday, and then the 1st was on a Wednesday. And like that was the first time in years that Tuesday was Tuesday and Wednesday was Wednesday versus like, it’s the end of the month, beginning of the month. So, you know, first things first, walk me through just that feeling of like, quota’s no longer necessarily a part of your life in that same way. Right?
Yeah. I put on 14 pounds in the last few weeks. And I put on like just normal weight in the last few weeks. I’m sleeping really well. I like yeah, it’s a weird transition. It’s a weird transition: emotional at times, you know, just because it’s like, I feel like I’ve crawled through glass, so many different quarters. You know, I know I’ve been responsible for executive bonuses more than once for 11pm plus deals, you know, and it’s like the stress of doing that and then go do it again. You know, if I can make people’s lives a little easier, don’t be me on certain things. I mean, it’s a win. You know?
How long has it been since you transitioned out of you carrying a bag to you’re now in enablement, like, this is fairly fresh, isn’t it?
Yeah, but I was doing enablement in my last few gigs anyway. So just whether I’m running film review or I’m on an outbound motion or onboarding people and mentoring, whatever it is, I’ve been doing an accumulation of it. So it just made more sense to kind of put that motion now. It’s tiring carrying a bag for all those years. You know?
First off, I’ve never understood this, like you said, for 25 years, right? How do you do that for 25 years?
I don’t know. It’s interesting. There were two or three times, like no joke, I’ll be very vulnerable when I say this, where like two or three times where I mentioned maybe going into a different department and doing something, and I got teased on the sales floor, like real hard about it, you know, and they like, people I liked, respected, called me names and told me to get back to work, basically, and I just kind of put it away. And when I realized…
“Those that can’t sell have to market.” Isn’t that like the saying, “If you can’t…”
I guess; I don’t know. You know, it’s weird… in enablement, there’s, this is no dig on anybody, but there’s not a lot of experience in the field in enablement. It’s a lot of people that, at the end, at the end of it all, they’re making other people’s stories theirs, right? And they through, vicariously, go through it. The weirdest thing out of everything of this whole transition is I’m going to be answering questions, or hypotheses not out of frustration to have them answered, I have to fight through it myself to answer that question of whatever it is, you know, that’s… it’s weird. It’s great. It’s great weird, though.
Explain what explain what you mean by that, though. Go a little deeper on that.
Yeah. So in the past, if I had to build, if I was like, “oh, my pipeline’s light,” like my hypothesis is I need to get on the phone and do that. Or I need to build it in some way, shape, or form myself, if I’m not being supported, let’s just say which every salespeople feels they’re not, right? So I would have to figure it out myself versus now it’s not my frustration to make my number to fight through it to get answers. I’m helping other people with the answers now, you know, hopefully be preventative at the same time.
You talked about, you know, getting teased two or three times when you wanted to switch. Like how, how long ago was it when like that first time that you were serious about switching? Was that like 10 years ago? Was that five years ago? When was that first sort of shift in your mind opening up?
I will say this… when we were at Outreach together, that was the first enablement team I ever saw. All the tech companies have bandwidth; we never had, we never really had enablement; we had some training and they were in sales ops, where they were coming up, right? Or they bring in trainers, usually, at spots I was in.
I remember, I remember outside, like investors would come in or different companies would come in and be like, “wow, like you’re so early to have an enablement department, like, we’ve never seen this.” And even the function was fairly new. And it was like really early. So so you’re what that’s like, what, seven, eight years ago was your first sort of touch with that world? Is that the case?
Yeah, in ther I think: the first time I saw it, and it was always managers were always pegged to do the training. They’re always you know, you got X amount of one-on-ones all week, plus your management meetings, team meetings, whatever is the time to sit and coach individuals. So like the enablement team, I view myself as an assistant coach on The Club. I’m going to work on projects, help people be hands-on, and, like, I think it’s, you know, we are… I’m so lucky to have found an organization that’s investing like this because it’s going to… it’s awesome. Yeah.
What, like, so what was your aha moment? Right? Like you meet this, this enablement team for the first time? What was your aha moment to go “Yeah, like, I think that’s it”? Now you got teased a couple of times in between. But What first got you going “Yeah, okay. This is why.”?
The, the rep I was mentoring last year, Heather, she, she had a breakthrough when we were at a trade show, and turned, just killed on her first deal and turned it into a three-year deal by herself. And that was the highlight of my year last year. And even I crushed it. And it was like, that was the highlight of my year last year. So as I moved into full-time management, I looked at this as a greater opportunity at scale to transfer knowledge than working in this you know, I’m gonna go be a small fish in a really big pond, hopefully, here. You know, I kind of like that: help out.
Well, you were… we talked about this right before we started. You were just like heavy in the tech world doing the San Francisco, West Coast thing for a while. And you went remote a long time ago. Right, like before, before a lot of others did. Just thinking about this whole idea of an enablement in general, you’ve been doing remote much, much longer than anybody else. And now all these companies have to figure out how do you ignite a remote workforce? So you mentioned earlier, oh, there’s not a lot of experience in enablement. Well, what’s a couple of things around remote work and even your like heavy background in sales that you’re like, “Okay, here’s a couple of key things that everybody should be thinking about right now.”?
Oh. Man, that’s so tough. You know, I think the biggest obstacle that everyone faces is in remote is how do you maintain that human touch? Right, and that is not web meeting to death? Zoom Fatigue is real. I love people with Zoom. They’re my people from WebEx like, absolutely. But it’s it’s real, you know, we spend time in it repetitively. And if you’re not, if you haven’t been conditioned to do it, yet, it’s an eye opener. I am who I am, an advocate now of seeing how much we can get back into the office: two, three days a week, please! The team or you know, the camaraderie when it happens in like, I think the majority of the staff, if they can get back into the office needs to, because there’s so much you miss out if you don’t have that. I mean, I was able to do that years into my career after I had my blocking and tackling down. You know, that’s the thing: fundamentals I think carry the most when it comes to being remote because you have to get up in the morning and you got to do your reps, you got to do you know, you have to do your work. And you have to communicate with management constantly so they know you’re working too. I think that’s a big thing in terms of earning the trust. And I was always good about constantly communicating with my management. I think that’s really important.
Our remote folks like even, I’m thinking about even in your case, right? You’re in what Texarkana. You’re down in Texas. I’m in central Pennsylvania. So I think somehow, you know, we get it, right? Is it is it better when like everybody’s remote, like if you’re a remote person and everyone’s remote? Does that culturally make it easier? Or to your point, if everyone if there’s an office somewhere that people are going to two to three times a week, and you’re in Texarkana and you’re not in that office? Does that somehow actually help even you be brought into the culture? Or does that hurt?
I, you know, I’m going to regularly go in to Austin, once a month, if not more is what my charge will be with the team. I remember when I started with Marketo was running Sales and Marketing for firm basically, and they were like, if you want to start here, you got to… on Wednesday, they offered me the job, and then you have to be in the office on Friday. So I had to like… it was really painful. And it was not good. I felt kind of the exit on that from where I was, but I committed, jumped in, went, was in the office; I was there early, I left late. And that’s the sort of thing as I was saying, earning it. That’s how I felt I earned it. I had the discipline to work all day in front of people like hustle. They know they can trust me. And then you’re there. Again, I think that for remote workers, that’s the whole issue is there’s kind of an opaqueness of it there. I mean, you look at a web meeting you’re on, let’s say your grander web meeting, I think from a culture perspective, everyone should have their camera on. Right? So you see everybody’s engaged. And they’re not like doing whatever, you know. And it’s like, I think that’s one of the aspects of remote culture that needs to happen. Everybody has to have their cameras on all the time, because you have to be engaging your coworkers as if you’re there.
Well, I know, at many of the video conferencing companies like that’s a policy, I know, BlueJeans, for example. It’s a team we’ve done some work with, I mean, if you’re on a meeting, the video’s on, and that was a requirement, you know, back back in, like 2018, when I first got to know that crew. This is before everyone’s remote; if you’re on video, even if you’re in the office, and you’re in a conference room, the video’s still on right? Just to try to make some type of connection. But I want to go back to you talking about how you sort of earned it. You went in, but I might be mixing stories, so you can tell me that I’m just way off. But isn’t there a story related to this, though, that while you were doing that, you had to come in, you had to stay in like a hotel every night, and it was like some of the loneliest times you had? Or am I, am I, like, making a story up?
Cinco de Mayo, 2000, mid-2000s, I was homeless for a period of time like no joke, no joke. I had moved to Marketo, moved through to Marketo. And I was, I had to move out of the place I was at. I had to move out; it was just a divorce was going on. It was really unfortunate. And I ended up on the El Camino Real near San Carlos at a stoplight on Cinco de Mayo with nobody there. And it was like dead because it’s the Bay Area’s partying on that day.
Yeah, everyone’s having a good time.
I literally felt like Tom Hanks in that movie where he’s stranded at the end. He’s at the stoplight and like, I don’t know which way I go, you know, left to right, drove all the way down to Santa Clara, and no rooms were available. It was like, I drove for like two plus hours this night. Okay, so I ended up back near the airport, and it was the most… it was a travelers hotel, for lack of a better, better way to put it. A lot of interesting characters would be there. And I, I literally had to live in this hotel for three months.
There’s a different word, there’s a different, different word for that hotel in Texarkana than what you’re saying?
There is, but I was, I would say that the highlight of me living it up there was I dressed up like Steve Martin in The Jerk, and full on bathrobe and slippers and went down to the bodega like that as a joke. So I made it back alive.
You survived. Yeah. Like, listen, you’re on the one hand, now you’re like, you’re telling me people like you kind of earn it, you get you’re blocking and tackling, then you go remote, you know, whatever. But you know, at the same time, you’re telling me like those were some of the hardest years of your life; you’re going through some difficult things. One point you said you’re, you’re sort of homeless in between. I mean, like, like, I don’t know, I don’t know, Bokan, I don’t I don’t know if I want to get blocking and tackling if that’s what it costs. Right? Like…
Oh, you know, what, I think through that I was very mercenarial in my younger days, to say the least, like absolutely go to good ops and move on to the next. And I was willing to do what it took to, what I needed to do always. And I think that, but that also transferred through my selling style, to like, I hustled, drag things across the finish line. You know, I mean, that’s kind of transfered. I’ve definitely dialed back men in the last few weeks, feels really good. You know?
Did you, did you, did you dial back because you just wanted to take a break, or you gained 14 pounds, and you’re moving a little slower? Like what?
No, I needed to gain 14 pounds. I’m feeling more healthy. Now. This is great. I’m like, you know, geez.
Yeah, well, some of that stress is removed, and you can relax a little. But listen, you talk about hopping jobs every opportunity you get. That’s the job market today, though. I mean, like, what I’m saying I mean, like a guy will come in off the… listen, he just finished college. He’s an SDR for six months. And then the next thing you know, he’s getting offered $150,000 at some other company to be an AE. And he’s like, “Well, why wouldn’t I take it? Right?” So like, there’s a lot, a lot of job hopping today. But you know, it’s a little bit of a, there’s like two sides of this too; there’s the other side of like, some, like probably in your case, you have to hop jobs because they’ll never promote you. Like you could have, you may have killed that manager role. There’s a director role that opens up, but you know, in our high-growth environment, instead of giving the manager, the director role, let’s go out and hire somebody from the outside who’s done it three times before? Right? Which makes some sense. Listen, I don’t even, I don’t even know where I’m going. But what are you about to say?
No, I think some of it in the workplace… I always looked at it like you have a tolerance for pain and a tolerance for BS, other people’s BS, right? And if that threshold gets reached or passed, you know, life’s too short. It’s kind of the way I looked at it. I would say what changed for the most in terms of growth in like the workplace, and when I stopped going into interviews being like, why would you why would I want to work for you? And I was more like, I want to sell for you. And the reasons I’d want to work for the companies I went for made life a lot easier. You know, it really did.
You’re just immediately with the program. When you act like that. I’ll tell you one thing that I’ve noticed over the years can’t have any negativity and anything that’s going on right now. I’ve tried to avoid that as much as I can. You see, it ruins things always.
I just talked to somebody earlier today about that. And they were talking about the concept of poisoning the well. Right of like, for so long, if somebody was a top performer, go ahead and poison the well: you’re a top performer. But I was chatting with this person. They’re like listen, like that’s not… I don’t know if that’s ever gonna go away, like that’s one of the benefits of being the top performer: you can be whoever you want: you still get, but I think there’s a little bit of a crack happening in that and some people are starting to say look like, like, especially with everything remote. We have to find a way to foster a positive culture like above all in order for people to stay because paychecks matter, but like, seems like the culture somehow matters more right now. I don’t know. It’s just, it’s just strange how some things have shifted recently.
Culture, every…” Culture this, culture that. We have the best culture.” No… culture is who you want to, you’re gonna hang out with the people you work with. Right? So can you? Can you hang out with them for long periods of time? Are they good people? You know, what I’ve always looked for in hiring is, are people willing to pick up a shovel? And are they nice? You know, I mean, that’s the two things I look for and qualities in hiring always. Because if they’re willing to work hard, you can’t teach that.
Are you part of that now? Like going over to the enablement side? Are you, like, are you part of the hiring process for that? Like the org you’re in now?
Well, I don’t know. I don’t even know my full. I mean, I understand my role, my marching orders, but I mean, I’m just getting started there. I don’t want to interview anybody yet. I don’t know.
You’re fresh. So how far into this thing are you?
This is week two. Right now, this is week two. So we did a little pre-work. We were there all last week in Austin and started at the same time with my, one of my partners in onboarding. So we’re a good cohort.
Alright, so your week two, and this is, is this you’re…? You mentioned you were doing enablement in your last roles. But is this your first, like, this is your full-time role enablement only? Or were you, was that like that in the last ones?
No, this is my first full enablement role. Yeah, like I’ve joined that enablement society. So the enablement society, like going on three years ago and just kind of paid attention to things from the sideline and picked up good habits.
Is onboarding, does it feel different this time coming in an enablement only versus like a salesperson? Does it feel fundamentally different?
You know, I’m going through all the sales roles, enablement, actually, to see how it’s presented and the like, so strategically to take a look at what we have on the floor already. Yeah, that’s been interesting coming in as a new employee and looking at different views and how people were brought on. It’s fascinating.
Are you, are you like dreading that situation a little bit where, like, you talk about in the past, you’re the sales rep, you never really had a whole lot of help. You got to figure it out yourself. Now you’re gonna go and you’re going to tell the sales rep that’s been doing it for a while “Well, here’s how you might want to do your job.” Right? Like, is that, is that a little concerning to you?
It’ll never be like that. I’m not telling anybody how to do anything, man, at all. I, I’m coming into this very, the whole few weeks, first few weeks, you’re gonna be discovery and then go from there. I need to understand so much more. Yeah. The one thing that I’m curious about, you know, I always thought about with sales, you know, you close a deal. You can talk, right? Where is that inflection point where you can talk, right? I’m just gonna be quiet and try not to solution. In the beginning, when I get all excited about things I need to take my time. And you make sure…
You’re asking like when, when can you walk in with a little bit of clout, like, “Hey, do you see those three decks I put together for you like, yeah?”
No, no, nobody, you know what I’m talking about, like, as a salesperson, whenever I’ve been at a gig, I don’t… I’m more observational and analytical until I have actually put something on the board otherwise, you know, do it first. You know?
I’d imagine it. You know, you’re working with I think, Jerry, right? So Jerry’ll give you a couple projects; you’ll run a couple, and then you’ll measure, you know, you’ll measure the success there. But I remember Jerry, his big thing was, he always talked about this: He wasn’t a good salesperson; he was just a good hack, which is what made him a good trainer. So in your case, I got Jerry’s pitch on why he’s, he’s a great trainer in that regard. What’s your pitch that, you know, this is your first time coming into it? You were teased in the past about maybe trying this. What’s that thing in your mind? It’s like “no, like, here’s, here’s why I know, I’m, like, I am good at this.”
I’ve crawled through glass numerous times to make my number. So I can hopefully impart some wisdom on the good and bad and that I think I can, you know, that’s what really draws this to me, as I said… Well, go ahead.
No, you go ahead. You go ahead. You’re fine.
Yeah, to see, as I said, it was just the biggest aha moments in Heather blow up on her deal and feeling so proud of her. You know, and if I can do that at scale here, man feels good.
What else in life do you want, but to help, help some other folks? That’s what, when I first got into training, there’s like one thing about you’re talking about you walk through glass, and you do it. But then there’s another thing when you like, you help five other people do that same thing, right, or whatever their goal is, like, it’s just a different, different emotion. But why like, for a lot of folks as they’re maturing, right, you said you’ve been in sales 25 years, you’re now in enablement. Most folks, like the epitome of where they want to go, is they want to be a VP, right? Because that’s their version of “I’m going to help everybody.” Why is yours education?
You know, I’ve, I’ve kind of been my own drummer. I want to just raise my family, and I’ve been lucky enough to do that. I, I’m not done, you know, I don’t want to, like, retire. And although it does sound kind of nice to be the school bus driver, I think that’d be like an ideal thing to do, you know? Send kids off, make sure they’re happy.
I tell my wife, when I make enough money, I’m gonna go into landscaping. I’m just gonna, gonna get a shovel. Just shovel all day. Right?
Sounds good to me. Oh, no, you know? Yeah, it just seems like the logical next step for me. And the reason, the reason I really driving me want to go to school is we have a lot of children here, who have never been more than 10 miles out of town. And not seeing the world. I’ve seen the world; I’ve traveled the world seen, you know, all sorts of things. You know, been involved in business in Silicon Valley, SaaS native, you know, I still I’ve worked for a really cool company right now, there’s, there’s not a lot out here like that. And I think that if I can transfer a little bit of that hope, I don’t use hope in my business life at all. But I’ll use hope in my personal life all day.
That’s what I hear. I’ve worked with someone who tells me all day, I can’t help myself, I’ll say, “Oh, I hope this happens or I hope whatever.” And she’ll beat on me a little bit. I think rightfully so; she’ll say “hope’s not a strategy. So stop talking about hope.” And you’re like, you’re right. Like, you’re right. You’re beating me. But I think to your point, there is a little part of you that like you have to hope for things right? Like you have to hope Texarkana, maybe you can, you can have a tech renaissance in Texarkana, right, like something?
I’m not thinking about that, you know, more of just like if I can inspire some kids to go do something, you know? A lot of fatherless children for sure. Yeah. Living in the South, there was a whole different ball game, you know?
Well, hey, there’s a whole other, there’s a second episode right there of being the tech guy down south, right?
It’s had its moments, I love it here. You know?
Alright, man. Well, hey, is there anything, we’re like getting right up on time here. I think, I think we sort of covered a wide range. Originally, this was just transitioning from sales to enablement. And then we talked about, oh, man, some, some interesting times in between. But is there anything if anybody’s thinking about transitioning to enablement, or anybody is like, to your point, living it out of a suitcase, in San Francisco, anything you just want to say to people here before we hang this thing up?
I know, it’s interesting, as we’ve both seen, people go through the ranks and, you know, either falter, excel at that role, or whatever. I think people get into blinders, not realizing that they can really do whatever they… the only person that’s stopping you from doing it is you, right at the end of the day, and taking that chance. But we get set in our ways. And you know, for me to be able to make… I was talking to my best friend yesterday, after work, and we were chatting a little bit, and it’s like, I made it. I’m 48 years old, and I made a career change. That’s not normal, always, you know, to completely kind of change your paradigm, what you’re doing. So I just think it’s fascinating at this point.
It’s not normal if it’s not forced.
Yeah, right, it’s not forced; it wasn’t forced. Yeah. Right. So I made the decision myself, which is not… Yeah, right.
Yeah, especially. I think yeah, like, we’re gonna we’re gonna, we had this great conversation, and we end on like, “wow, yeah, forced change. Oh, my goodness.” But we talked about this, though, right, before we actually started recording is that Gen, Gen Z seems to you know, they’re still figuring things out. But that seems to be one area, they’re pretty strong on if, like, if they have an idea in their head that they want to do something good luck telling them no, you know what I mean? Like, that has its positive attribute.
That’s true. I mean, I, what I find interesting is, is now having spanned some time, it’s you have to be able to communicate to different types of people to survive, right at the end of the day, at the end of it all, you have to be able to be relatable and be able to communicate. It, it remains to be seen how we’ll have to keep communicating with everybody. I don’t do TikTok, so I don’t know.
Yeah, well, neither do I. So we’ll see. We’ll see; you and I ought to get on one and dance, dance around together, shake it a little bit. Thanks for. Thanks for coming on with me today. For everybody who’s listening, thanks for listening in. I appreciate all of you, and we’ll see you later. Bye.
Thanks, Jordan. Pleasure.
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.