“Crisis Isn’t Terrible” A ProServe Tale with Deirdre O’Connor

Jordan talks with Deirdre O’Connor, North American Outreach Program Leader at SAP, and they share a story from their Outreach days when things didn’t go as planned.
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Show notes

What do you do when it all goes wrong with your customer?

RevOps Therapist and CEO of Greaser Consulting, Jordan Greaser, and Deirdre O’Connor, North American Outreach Program Leader at SAP, share a story from their Outreach days when things didn’t go as planned.

Pro-tip: Don’t hit the “Clone” button 20 times; it won’t do you any favors when you’re about to meet the Outreach ProServe Team.

But, when you’re on a ProServe team, and you’re looking at a customer who told you they knew what they were doing, but they don’t, where do you go from there?

As it turns out, overcoming these challenges can lead to the best customer relationships down the road. Jordan and Deirdre will have you laughing along the way as they share their stories and tips.

Jordan  00:01

Hi, everyone, this is Jordan, the owner and CEO of Greaser Consulting. On today’s podcast, we have Deirdre, who is the program leader of Outreach at SAP; her and I worked together back in the Outreach days and she… like we were counterpoints in building out the ProServe onboarding motion for Outreach right at the start. And the premise of today’s session is just about what happens when you’re just starting, and it doesn’t go right. Okay, like, what are the outcomes? What are some of the things that you need to think through? And who are the right types of people to help you with that, beginning on the groundwork for building any type of program, whether it’s pro serve and onboarding, or just, you know, some department of the company? I’ll tell you what, there’s, there’s I don’t think, too many other people on the planet that I would trust in building out programs other than Deirdre. We had a blast working together; we still have fun catching up today. I think you’ll feel that throughout today’s podcast. And with that, let’s kick in, dive in. Go ahead and enjoy it.

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Jordan  01:30

Hi, everyone, and welcome to today’s episode; we have with us Deirdre. Deirdre, why don’t you go ahead and introduce yourself?

Deirdre  01:37

Yeah. Great to be here, Jordan; this is so exciting. You’ve definitely come a long way since when we worked together at Outreach. And this is really cool to be here. But introduction. So I have gosh, where do I start? I currently am working at SAP. And I’m running the program for Outreach in North America, which was a really awesome transition from being over at Outreach as a, as the main consultant on the SAP project and had been working at Outreach for gosh, since 65th employee, so five years. And we’re really figuring out what Outreach looks like at SAP and really just building the program, which has been really fun, cool. Live here in Seattle, Washington and excited to be here.

Jordan  02:30

It’s funny, you know, you’re talking about when we first got started, I know like the premise of this thing is just around ProServe and even your transition a little bit. But when we first got started, I was the trainer. And you were the sort of ProServe consultant on how some of these things went. And I don’t think I’ll ever forget, I think it was our first on-site project together. We, we won’t name the company or the individuals involved, but it was somewhere in the south. And it was a very large customer. And we’re like, we’re like, okay, we dotted our i’s; we crossed our t’s. We’re like ready for this first on-site training, beaming with optimism. And then it happens. Could you, could you walk us through? Like just remind us all of that day?

Deirdre  03:21

Yes, I would very, very, very much like to reminisce about that with you. I will though, like just pause for a quick second, though, because you were on the training team when we first started really working together. But I remember you very well, at when you were managing the SDR team and learning a lot from you about how you were using Outreach. So I would just say that there was a lot of Jordan influence in my Outreach career be like before that moment, but yes, going back to that. That day. Yeah. And I had, you know, there there was, there was definitely some rumblings of potential challenges to come in previous, in previous on-sites that I had had, and also previous conversations. But I had gotten a lot of “yes, we’ve done that part. Yes, we’ve done that part. We’re ready to go.” And yeah, you and I show up to actually, like, hit the ground running. So getting users on board, making sure everybody’s got all the tools they need to be able to use Outreach and the things that people had said that they had yes done and checked the box of, as we started uncovering, you know, those things, we started realizing there were big, big gaps I think. I don’t know, like Jordan, how, how well do you think our audience is going to know Outreach? Can I get into the weeds on that, or is it do I just say “go for it”?

Jordan  04:48

Hey, go for it. Right? If you don’t, if you don’t get it, close your ears; it’s fine. So go ahead and go for it.

Deirdre  04:53

Okay, perfect. So I think the first moment of, like, fear that I had that morning was, I had asked that there was, I think it was five sequences ready for each of the trainings. So five sequences that these reps could actually go use once we got done with the training. And we looked at the first sequence, and it wasn’t my favorite, but it was fine. But then we looked at the second sequence, and it had a different title. But it was exactly the same content from the first sequence. And then it was just repeated all the way through for all of the sequences that they’d said they’d done uniquely. And it just was a unique title. It wasn’t a unique sequence.

Jordan  05:37

So I remember that you call me up, you’re like, “Jordan, like you need to get over and work.” I think her name may have been Sandy or something, like “go work with her. And like, you got to make sequences fast.” I’m like, “What are you talking about?” So I go sit down with her, and she’s walking me through. It’s the same exact content for like, what’s supposed to be 20 different products? And I’m like, “Well, what, what were you thinking here, just trying to understand?” And she’s like, “well, to be honest with you, I didn’t know what anyone was talking about. So I found this clone button and just clicked it 20 times.” And I’m like, “wow.” Like, we’re going like, we’re sending people emails today. What are you doing?

Deirdre  06:14

Oh, my gosh, so you must have done that discovery, as in and then you brought me in. And I think at some point that morning, we got Sandy crying too, which that was not very fun, because like, we’re about to launch, and I’ve got like our quote unquote, admin, like in tears in the corner, because she was a sweet lady. Um, but yeah, and then we were like, “well, we gotta go.” So we we went. I mean, gosh, and it was just spiraling all day long. I don’t know, like, all the various different parts and pieces of that day that we thought were in place and were not. I felt like just accumulated throughout the day.

Jordan  07:00

It all, it all hit its apex, right. Like, I come in; I find you after this meeting that I was in a training while you were in like a backdoor leadership meeting. And you come out of that meeting with like, your face is red; you’re like, “you will not believe what just happened.” Anyway, we don’t we don’t need to like, rehash old wounds, right? But the long story short is like, there was a berating that wasn’t necessarily justified. There was just, if you would have said like for a first like live on site, let’s go like, like, what’s the worst possible scenario that could have occurred? Like, I don’t think, I don’t think it could have gone worse? 

Deirdre  07:42

I think, you know, the other thing that I remember about that day super vividly is that you and I walked into the building together and then I think we probably exchanged maybe five words. And it was just you and me. And I had to like, be like, “Jordan, go run this,” and you had no idea any background any anything because and thank God it was you because I can only imagine if I had somebody supporting me that wasn’t, didn’t have like, the background and knowledge that you did. But we literally didn’t say like two words to each other until that point, you’re talking about the end of the day. When I came out of that meeting, I was just like, “oh my gosh,” so anyways, back to your question. I mean, the… I think that the problem really stemmed from a lack of, a lack of clear understanding of what I, as the main consultant on that project, needed to double check on and needed to not just take a “yes, we checked the box” but actually go uncover and dig into stuff. And so I think that was my big lesson learned after that was that I just can’t; you cannot trust that your clients have done what they’ve told you they’ve done. Like, it’s just not, like it’s not okay; you can’t go down a path like that because you end up in a situation like we were in; although I would, I will say is that if you are into that, make sure you’ve got somebody really awesome as your right-hand man to go into the mess with you because like, like I said, I think that it was a nightmare of a day, but I think somehow we still made it through with some success coming out of it.

Jordan  09:24

And like, this, like tickles me to this day that like that was our sort of first client, first scenario, first situation. And yet even as you and I were rolling out of Outreach at our own different times, like one of the last clients we were still doing projects with was that same company, and they like loved us; they would welcome us with open arms when we showed up, and the like, the lesson for me, not that day… the lesson for me sort of at the end of the journey, because we were still doing stuff with them. It’s like when you get into those like crappy situations, and it all hits the fan, and you think it couldn’t go any worse, like you think your relationship is lost with people, but like two things happen there: one, that was the beginning of us, like, learning how to work with each other. And at the end of the day, you and I would go into meetings, and we would, like, fight through meetings together, like through the rest of Outreach, but it wasn’t from a stand of animosity; it was like, we’re on the same team, let’s go figure this out. And there was trust. And the second thing is because we responded so well with that client to like, make things right. Like that ended up being one of our best relationships long term. So like, crisis isn’t terrible, like if you rally the right way, right?

Deirdre  10:44

100% agree. And I think that there’s also when you started even brought, it brought it up, like there’s a sense of, of, like you said, like, we’ve been in the battle together. And I think that built our relationship, and like you said, built a relationship with a client, as long as you’re able to turn it around. If you just left it there, it definitely wouldn’t be funny for anybody. But I know that day, I talked about that day with the client; you know, a bunch of the stakeholders in like, you know, with, a year or so behind us, and we all felt the same way. Like we all were laughing at our like, just kind of disaster of a day and had a sense of camaraderie around it. But it did take us like really showing up and being there for them all the way through it, and then all the way through for a year plus, and I think that was a good call out that you said; I totally agree.

Jordan  11:41

So I know that one of the premises of this conversation today is just that whole idea of like, when you’re in the early phase of building out this whole ProServe motion, right? And you touched on it a little bit, but but talk more about it of like being ready, like when you’re in those early days, and you don’t know what you don’t know. Right? Like, like, how, how do you be ready for this kind of stuff?

Deirdre  12:09

Yeah, I mean, there’s a, there’s a bit of planning, not a bit, there’s a good amount of planning; there’s a good amount of conversations. And, you know, it’s it’s funny, I’m a very outgoing people-person, and I really enjoy work where I’m in front of people. But when I first started in the, in the role that I was in, we were… I was the first person to build out what onboarding and what, cuz like, what services looked like, at Outreach. I did a lot of project plan building and a lot of thinking through, like, what could this look like? And a lot of it was just me at my desk and me trying to figure out like, what platforms I could use to support me and, and to be really frank, I loved it. And I remember for a couple of weeks, like when I was doing that, I remember being surprised, leaving work after like eight hours with just sitting there pretty much by myself, like trying to figure out what to do. And being like, “This is really exciting and inspiring.” And I think it’s because you know, it’s going to come. But I mean, I think that the reality of the situation for anybody is that there’s no way your first project is going to be perfect. And you have to really learn from everything that comes your way. I think the other thing that’s really important too, in that early, early stage, is making sure that you’ve got a group of people around you, you know, as you’re building more people into that program, as you’re building, bringing in more consultants or trainers or whoever else you’re bringing in, that those people have this spirit of that same excitement for what you’re building, and also a spirit of ownership, like really being totally fine being the trainer that has to then consult on, like you did content because the content’s wrong, right? Or, you know, be the person that you know, you thought you were walking into the situation to be, you know, the project manager, but all of a sudden, you’re having to consult on something completely different and being okay with that and excited to learn with the client. I think that’s really the most important part. So I guess what I’m trying to say is, I don’t think that there’s anything you can do that isn’t going to make for just a little bit of a shaky start. But I do think that making sure that you’ve got as much as you can planned out and have the right people around you, you can you can build pretty fast.

Jordan  14:29

Well talk about things you don’t expect, like being willing to consult on things that isn’t even your world, right is like the calendaring function in Outreach, like I had to learn in Zoom where you could get an individual link. And then I would do Zoom trainings so that people know where to find their link to put it in the Outreach calendar. Or you go on-site and this like, oh my goodness, how often do we run into this one: this is how you turn your com add-ins off in Outlook so that you can actually find our app and put it in? Or the phones! Like, “do you have headsets?” “Oh, we didn’t realize we needed headsets to call.” Like, what are you talking about? Right? And so how do you, how do you know that upfront except for experience?

Deirdre  15:14

Yeah. I actually… one thing really quick before you go, I, the other day, when somebody had like a, they hit a PC. And when they opened Outreach Everywhere, it like resized all of their, all of their browsers. And I thought of you, Jordan, I was like, “Dude, I gotta reach out to Jordan and ask him how to how to like do that on a PC.” I remember him helping out to teach them how to do that. And like you were still the person I think of when like, there’s random stuff that pops up that I like, I’m like, “Oh, wait, Jordan knows how to do that.” And I think I found a different workaround. But it’s funny how you start leaning on each other for those pieces of knowledge that you build over time.

Jordan  15:51

And you talk about part of the relationship, like, your job was to project manage things, but you know, over time, because we worked so much time and time together, like if if we were out on the fly, and things need to happen, you would let me project manage a couple of things if it had to happen. On the flip side, you’d always listen to the first training, and you’d pull me aside and “hey, for these guys, like don’t train this way, this time, like, like, do these three things differently,” right, like, that’s gonna be. And so that sort of humility, back and forth, was important. But I wanted to touch on something that I think is really important, you talked about at the beginning of building something like this out, like you need a lot of folks that are just invested and own it. But what I’m also hearing is like, like, be careful just to go out and hire the specialist right away, right? Like the person who all they do is train or the person that all they can do is project manage. I think there’s some reality that you don’t necessarily want a SME to be your trainer for a lot of reasons. But when you’re first getting started, like you just don’t know what’s gonna go wrong. So you need folks with this sort of wide range of knowledge that’s even outside of the scope of what the position should be. But over time, like that, that shifts right, like as you start to lock in the way things work. There’s a natural evolution from generalists to specialists.

Deirdre  17:20

100% agree. Yeah. And I think you were critical in that role because you did, you came from managing a team of SDRs, like, you’d already been teaching and training SDRs at Outreach, how to use Outreach and how to sell and so you already had that background. And I didn’t, like so I think, to your point of, like, you know, being able to lean on each other was, and here’s the other thing, too, is, I think that we the role that you came in is is a training role, like an enablement role. And I think that those folks are undervalued, especially in the early days of SaaS businesses and, and maybe services businesses as well, like, over time, you’re right, you can, you can hire somebody who is a SME and is like, you know, “I come in. I do my thing, and I leave, and that’s kind of my, my job.” But in the beginning, enablement is so much more than just, this is how it works. Like you really have to have a, like a skill set that’s just way larger than I think what a typical trainer we expect them to have. And so I guess that’s actually and maybe it’s not just you, maybe it’s maybe you can have a SME enablement person, a trainer, but you still do need a few other people that have that more wider skill set. And I think the enablement person was so critical, or such a great role to have somebody with that wider skill set, because you’re on-site with me; you’re traveling; you’re face to face with these people. And it’s not somebody who just sits back in the office and is like, you know, doing it, like, you know, maybe my boss at the time, right? Like, he really couldn’t have done what you were able to do. And you were on site with me. So it was like an extra bonus. So I guess I like what you said, but I would also say that like maybe in the beginning, you also need to think about making sure that the people that you’re you have in training are, are so much more broad than then than what you maybe typically hire in the future.

Jordan  19:29

Well, that’s part of that evolution, right? Like once you nail, once you nail down the like, “Okay, here’s the 10 questions that we get.” You learn that right? Like, there’s always going to be… you can do this for 10 years, and you’re gonna get some oddball questions. That’s always gonna happen. But in general, like, here’s the 10 questions we get every time and then you start to solve, what can we train ahead of time or what can we build into the project that’s going to answer that first, or are we always just going to get this question and you need to be able to answer quickly adjust quickly all those kinds of things. But over time, once you know the answers, it’s a lot easier to like roll it into the facilitator guide, put it as part of the project plan. And then folks don’t need to have that, like, knowledge. But then you can go out and you can, you can hire someone who’s, doesn’t maybe have that same breadth for the project management because you can plug them in, okay, or they don’t have that same breadth for training, but you can plug them in. But the reality is, they might actually be a better trainer, because that’s their, like, specific, great skill set; they might be better project manager, because that’s their specific, great skill set. But there’s no way up front to take, you know, put the infrastructure together to even get it started.

Deirdre  20:43

I actually have a question for you, because I think that, you know, enticing somebody like you with that broader skill set into that a role like that, like, what got you excited about taking that role? Like how do you get somebody excited with a broader skill set to go take a role that can sometimes feel a little bit linear, or maybe a little bit more like, you know, clock in/ clock out kind of job?

Jordan  21:06

Well, the first thing is, if you’ve ever been on an SDR floor for a few years, you start trying to find a way off of the SDR floor; I’m gonna be upfront with you. Like, like, I just can’t do this for the rest of my life. The second thing is, I had spent like years in the company sort of giving, like heart and soul to it. And it’s not like I didn’t care as much, so don’t hear it that way. But I had two kids, even though I was traveling all the time, my wife sort of famously said this, like, “you’re gone the whole week. But when you’re here, you’re actually here.” And that’s why I wanted that role. Because I knew like, it was a very, like, simple thing at the… I mean, it was hard, we talked about that. Yeah, we thought it’d be simple. But it was like, at the end of the day, you’re done. And then you’re home with your family. Whereas being on the other side, it wasn’t that way. So I think for me, it just hit this like perfect intersection of like, you know, I’m gonna be honest about it, like I’m a little tired. A little worn out of some of some of this stuff; I’d like to change. And I was a teacher before I entered tech. So it was like a way for me to discover could this work? And I also knew this took faith. Okay. And I don’t think like everybody at first was even aligned this way. But certainly, as I started to work with you, like, I wasn’t coming over just to like, regurgitate information; that was certainly part of it. But it was an opportunity to build, right, and I like to build. So at the end of the day, that’s what made it a lot of fun for me. I guess the reverse question is, you know, how are you, or why are you able to, like let somebody sort of enter your space that wasn’t supposed to be there? Right? I mean, that’s, that’s the other side of the equation.

Deirdre  23:06

How do you mean by that, like, like?

Jordan  23:09

So what I mean by that is like, the initial scope is trainer shows up and regurgitates; you know, the ProServe person just figures, like they figure out the nuts and bolts of how we do, why we do, and all this. And you know, before long, you’re allowing me to sit with you to talk through how do we actually do this thing?

Deirdre  23:29

Yeah, I wouldn’t say “allowing you;” I was like, so super stoked to have you. I think. I don’t know. I, from my perspective, I think that anytime I find and I and I would say that anybody who’s, well, I guess I can’t say that, I can’t; it’s too broad of a term. But anybody that’s excited about building something and find somebody else who’s excited about building it, and has some background and knowledge, like, it’s thrilling to have somebody else to be a partner in crime with. I found that a lot of other people that were building things were thinking, maybe not in the big picture, like a lot of other folks that we were, we were working with, like, you know, were I mean, and it’s not really their fault. I think they were just getting thrown project at for project of a project and they were they were trying to build out how do we make this scale? Like how can we take all these tiny little accounts that we’re getting, and spit out a successful Outreach program? Whereas we had the luxury of, “hey, here’s a really big client that we think we can expand into; we need to really nurture this relationship. You do whatever you got to do to do that.” And so it gave us the space to be able to to be able to spend time and think about it in the more bigger terms and bigger picture, and you know, like I said earlier, like, I’m a people person, and so for me, like doing that on your own is fun. But doing it with somebody else that also can like add a lot of value to it is is way more fun. And we, and also creates a better product. So yeah, I mean, I think that’s yeah, I wouldn’t say I allowed it; I think it was more like thank goodness I work with.

Jordan  25:16

Well, I think that that speaks to the attitude you have to have, though. Like, often when, when you’re in some of these situations where you get the opportunity to build something, like, as humans, we can become far too territorial. And like, well, I want my name to be behind what’s being built, right? So like, let’s go do it. But the fun people to work with are the folks that are like, like, I don’t care who finds the idea, but like, let’s solve this, like, really complicated problem and go chase it. And I mean, my whole career, those are the people that, like, I just want to gravitate toward and spend time with, because it’s like, it’s less about who gets the glory and more about like, let’s like actually solving the problem, right?

Deirdre  26:03

Yeah, yeah. And there’s a satisfaction too of a job that you like maybe botched the first time around. Like that, like the first day that you brought up. And then you know, like we had some other days where I was like, “holy cow, it’s like clockwork around here.” So that was pretty cool, too.

Jordan  26:19

That’s what became, that became fun for a while, of like, when we finally figured it out. And we started showing up on-site, and it was, it was almost like, like, you can anticipate that the other move the dancer is going to go with you or something, right. So you’re just like flowing through this whole thing. But for me, and that’s why I’m curious for you, like did you get tired toward the end, like we’d spent a year just like flying everywhere, going everywhere doing this like week in, week out, week, in week out. And for me, and this is part of like, my problem is like, once I feel like I’ve solved something, it’s like fun to run in that for a while. But after like a quarter or two of that, it’s like, “Okay, I’m ready for the next thing.” Like now that we’ve built it. There’s always room for more iteration. It wasn’t perfect when we left. But my point is like, as soon as it started to feel automatic, is when I started to lose my interest.

Deirdre  27:15

Yeah, no, I hear you. And I think yes, 100%, same, same, same. The thing I think that kept me at Outreach for a bit longer than you know, you lasted was actually moving into well, yeah, that’s, that helps. Yeah, but hopefully it helps. Let’s see this IPO. Um, but was that no, actually, I think it was moving into the SAP project. Because like, we were solving, sure, they were the biggest customers that we had at the time. But we were solving kind of small potatoes, to be honest. When I got into SAP and I looked at the project that we had to do at SAP and I went, “Holy cow, this needs a whole lot more. Like we need it. It’s not just iteration. This is like, how do we start again, and think through this again, and build out, like, build out a company the size of SAP successful Outreach program?” And that was really exciting for me because it did that same thing. It kind of got me back into how do we go build again? Which was and then and then yeah, I mean, there’s a, there’s an end of that story, which is now I want to go do it at SAP. But yeah, I think that’s, that’s kind of what, what kept me.

Jordan  28:40

So we’re getting close to time. And I know we’ve, we had a lot we wanted to cover; we only scratched the surface. So will you come back in X number of months, and let’s, let’s talk about if you’re willing, just that concept of when you were on the ProServe team at Outreach, and you were like, “Let’s build a program at SAP.” To your point, like, you had a real small window into what it actually took. And now you show up at this just massive organization. And now you see the same problem but from the other side. Like I think that’d be a fascinating discussion. Are you, you’re willing to come back?

Deirdre  29:20

I’d be happy to Jordan; we, I guess we could we could shoot the shit for ages Hopefully. Hopefully we can. Yeah, I can. I’m sure we can come up with things to talk about, and that one, and probably many more if, if we decided we wanted to. So yes, happy to.

Jordan  29:36

Alright, perfect. So hey, with that, I think we’re gonna go ahead and round out today. Thanks for being willing to hop in with me and for the listeners, thanks for listening in. If you have any comments or questions, let us know. And Deirdre if anybody wants to get a hold of you, what’s the best way?

Deirdre  29:53

Well, LinkedIn, I’m actually really really good at LinkedIn. So Deirdre O’Connor, and I can Jordan, I can pass over the URL if you want. That’s probably the best way.

Jordan  30:04

Perfect. All right, see you later. Thanks for coming.


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.

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