How To Increase Bookings Through Strategic Account Management With Bain's Greg Callahan

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This is a podcast episode titled, How To Increase Bookings Through Strategic Account Management With Bain's Greg Callahan. The summary for this episode is: <p>What if someone told you they could increase your company’s bookings by 20 - 40%? Not a bad hook, right?</p><p><br></p><p>The strategy to support that hook comes from this week’s guest, Greg Callahan. Greg is a Partner at Bain&nbsp;&amp; Company, and the Founder of Coro Account Planning.</p><p><br></p><p>In his work with Bain’s portfolio companies, Greg has developed a blueprint for getting the most yield out of your customers that have the most potential: Strategic Account Management.</p><p><br></p><p>In our conversation, we review the four core components of strategic account management, we offer specific plays you can steal to run within your customer base, and Greg explains why if you’re being strategic on everything, you’re being strategic on nothing.</p><p><br></p><p>Like this episode?&nbsp;<a href="" rel="noopener noreferrer" target="_blank">Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp;review</a>&nbsp;and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts.</p>
The four components to successful strategic account management
03:41 MIN
Why it's important for you and your team to have a common language in place
02:52 MIN
Advice for when expanding into different verticals
01:56 MIN

Sean Lane: Hey, everyone. Welcome to# Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. What if someone told you that they could increase your company's bookings by 20 to 40%? Not a bad hook right? I'd probably listen, I'd open that email. This isn't a hand waving statement that turns out to be just nothing. This is real data straight from our guest this week, Greg Callahan. Greg is a partner at Bain and the founder of Coro Account Planning. In his work with Bain's portfolio companies, Greg kept coming back to the same challenge over and over again. And he created his own blueprint to guide the rest of us through that challenge. Now, his challenge that he kept finding was getting the most yield out of your highest potential customers and his solution to that challenge is what he calls strategic account management. In our conversation, we review the four components of strategic account management. We give you specific plays that you can steal to run within your own customer base today. And Greg explains why if you're being strategic on everything, you're being strategic on nothing. But to start, we can't explore this concept of strategic account management without first defining it. Here is Greg.

Greg Callahan: Strategic account management is clearly something we've been thinking about a long time. And truthfully our perspective has changed over the years. A little bit gone are the days of this idea of you have to write a really long thoughtful tome that sits in your top drawer of your desk and you never use again. I think that was the ways of old and it was pretty brutal. And at the end of every year people got going on that. I think it's probably helpful just to take a broader lens real quick and work our way into strategic account management. So we think about strategic account management as a piece of a stool. And so the stool is made up of three things, territory planning, which I know you've had a ton of podcasts on already of how do you think about the right accounts and the right targets and how do you get the team against the right stuff? Then you go into accounts. So actually, how do you maximize the accounts you're working with and how do you get more out of them? And then ultimately opportunities. And so how do I actually increase my win rate in the opportunities that I'm in? Which again, you've spent a lot of time on how do you actually improve your win rate and drive upsell, cross- sell all that kind of stuff. And so as we think about it, that tow, territories accounts and opportunities are the three big components and strategic account management sits right smack dab in the middle of how do you accelerate and expand the value of those really big accounts. And this is not for your high velocity stuff where you're doing 50 to 100 calls a day. It's not, this is really the top 100 to 200 accounts where you think you can maximize the value, you can really expand that enterprise segment. How do you strategically think about expand and grow those accounts? And so that's the sweet spot of why we think a lot about strategic account management and where it sits.

Sean Lane: And to be clear, when you talk about maximizing those accounts, could that be for both new business accounts as well as accounts that already are in your book or is maximizing those accounts exclusive to existing customers? How do you think about that second leg of the stool?

Greg Callahan: Yeah totally. So it's both new logo and existing business. And just to put some numbers around it. So we've been doing this with clients for a while. Folks who do it well typically see a 20 to 40% increase in bookings when you do this right. And so it's not theoretical opportunity, it's not just 10, it's 20 to 40% new dollars in your pockets within 18 months of pushing against this. And so it's really expanding the thought process. And the reason why we push there is twofold. We spend a ton of our time. There are wonderful set of CRMs out there that are really good and helped us nail down this stage one through five, stage one through seven, closing your deal pipeline. But what we've lost a lot of is the art of going out and saying, what is the full potential of this account and what do I need to do to expand it? And as we get more and more complex sales, even within your own business, the number of frontline people plus solution consultants, plus engineers and architects and specialists, and you bring a whole team together to try and sell to an account, you typically lose the thread of what's the need of the business. And so if you can take that step back and say, these are all the things going inside my enterprise account, here's all the buyers. And here's all the different places where we can expand the value. And so let's build that plan against it. That's what we're really pushing towards when we work with clients and work with teams around strategic account management.

Sean Lane: Like I said at the beginning, 20 to 40% increase in bookings sounds lovely. I'm sure it does to all of you as well. But how did Greg even get here? How did he go from being a partner at Bain defining himself needing to solve this particular problem? It turns out it's a pretty common trajectory he's seen a lot of companies go through.

Greg Callahan: There are a few things that I have come across. I think first and foremost, there are a few different life stages of businesses and maybe I'll start there. So there's kind of I think the core of the core audience here which is the somewhere in the 50 to 200 million revenue business, you're growing like a weed and you're exploding. And somewhere in that range, in that 70 to 100 million, you've been knocking out this like really effective mid- market commercial growth target. And you say, okay we got to go into enterprise and we've seen pretty easy success today, we're going to just see this same thing fly through this wheel over and over again as we go into enterprise. And all of a sudden people start going into enterprise and they're like, whoa, this feels a little different. This is a longer life cycle, longer selling motion, it's more complex. So we see it there a lot. We also see it in bigger businesses where they have really big enterprise teams and someone probably in our operations team has taken some back of the envelope math and said like, if we can just take a few net new logos and expand our share of wallet by 10%, we're going to nail our number every year. And the back of the envelope math is easy, the execution of that is quite hard. And so why has it come to us? I think really it's people who have come to the realization that there's a massive amount of value sitting in that enterprise segment and they don't have a consistent way to drive their team to go get that value. And so it's just like you build in a forecasting methodology or an opportunity management methodology or you guys recently had a QBR methodology approach. Being really clear and purpose driven around how do you drive into that enterprise segment, that is really where it's come front and center for us many times over now.

Sean Lane: Got it. Okay. So let's talk about what that methodology actually looks like. So let's assume you decide, you know what, this is a good idea. This 20 to 40% lift in bookings that you're describing. If I'm listening to that like, of course I want to go after that, where do I start? What is the actual methodology to go from the back of napkin math that you're describing to this actual executing with all those different teams you described too? Because the other thing I would imagine is probably a little bit of a challenge here that you have and that you see with your customers and also companies in the portfolio is if we do have all these roles, working post sale on these accounts, it's one thing to even have the strategy it's another thing to align all these different folks and the customer around where we're trying to go. Is that fair?

Greg Callahan: You've nailed it. There's a really important word there you put at the end which is, and the customer. And at the end of the day it really is it starts with what are the customer needs and so how do you do that? And we can talk specifically about the plan and the approach but I think the methodology is simple in essence which is there are four core components to really successful strategic account management. The first one is having really clear articulation of which accounts. So it's not a hundred accounts per rep. It is what are the accounts that I can drive the biggest absolute dollar change over the next 18 months. And I use the absolute dollar change as an important clarification because typically people run to your biggest accounts. And in your biggest accounts, that's great. But the reality is is that they may not have a lot of change and the absolute dollars there's accounts that have real risk in them. And so that absolute dollar change can go up and down. And it may be a mid- market account that you've massive expansion opportunity for that you want to go after. And so really defining what are the accounts. The other thing I'll throw out there in the account status is if you are doing more than four strategic account plans per rep, it's no longer strategic. It is really time consuming and thoughtful process to put it down on paper. And so you may have 8 accounts or 10 accounts or 20 account or 25 accounts. But that strategic account planning process, if you're being strategic on everything, you're being strategic on nothing. So that upper bound is four and it's typically kind of two to three is a good number of things that you think are going to have differential value over the next 18 months. Part one is accounts. Part two is around cadence. This is where it gets different from the way even our parents did account planning is that account planning is two parts. Part one is actually getting the team together and building a plan. It doesn't need to be a massive exercise like putting people in a room for two hours and saying, what are the customer's needs? What is their ambition? What does the competition look like? What does our product set look like? What is the plan and sets of plays we want to go run against them? And getting really clear articulation of what you want to go run. And the second part of the cadence is okay, now that we've got that and we've documented it, how do we come back to that every 30 days? And we drive that mutual accountability across the team to go deliver against that. What we find time and time again and why strategic account planning fails is people do the heavy lift at the beginning of the year. And they probably spend way more than two hours but they spend the time up front, write down a plan and never do any action against it. And so that 30 day coming back and that touch stone own of making sure you create that accountability, that cadence is really important. And I want to be clear, coming back to our opening conversation that come back to is different than opportunity management. And so this is not your forecast call. This is not dealing with deals. This is not like closing conversations or legals. This is exclusively talking about things that out in the pipeline that you want to go do. And so carving out that time's really important. Third, and we'll jump to the fourth real quick but the third one is plays. And so this is a concept that now lots and lots and lots of people are talking about. A bunch of the enablement friends in the space are talking about, but this idea of creating simple, easy to use plays for your team that they can run consistently. It's a new buyer play. It's a new product play. It's a new customer play. It's a whole bunch of stuff, but the idea is how do you crystallize and put together a series of actions that make it really easy for your sales team to go do? We do an awesome job with this when we have new product launches. We have our marketing package, we have our selling collateral. But if you think about all of your other products that sit in the portfolio that you haven't refreshed or done anything around in the last few years and the team does, we should just have really clear plays and product marketing as a cross- functional team is actually building out consistency into these plays. And then last but not least is tooling, simple, simple, simple, simple, simple. Two things, simple and digital. It needs to be simple, it needs to be able to fit on a page. There are a series of questions we've actually maybe to a fault have been pretty dogmatic that we don't allow people to add stuff to an account plan. We have a pretty simple, easy to use account plan. If you want it, add a question in but you have to take one out. This is not the wonderful place where everyone gets to ask their series of questions. And the second thing that really drove us nuts, personally over the years was for a long time we did them in PowerPoint and Word documents. And at the end of the day, that was just not a great document for mutual accountability. And so putting it into your CRM and finding a way to create that digital accountability and that touchpoint and that 30 days you come back and say, hey, we committed to do the following things with the following due dates. And we assign these owners to go get them done. I don't care how you do it but get that singular surface where you are committing to those sets of actions together.

Sean Lane: Okay. Let's review, Greg's four components of strategic account management are one, which accounts. Isolating those with the biggest potential dollar change. Two, pick your cadence to align and document the plan. Three, simple plays your team can run. And four, simple and digital tooling. It's also worth pointing out how Greg started his explanation with the customer itself. Don't forget that understanding your customer's problems and needs is the prerequisite to any sort of value that you're going to be able to bring them. All right, I had a bunch of follow up questions for Greg about each of these categories. Starting with his recommendation that a rep has a maximum of four strategic accounts. If I'm an operations person designing a book of business, does that mean someone's entire book is just those four accounts? Is there a specific percentage of someone's book that should explicitly be strategic? I needed his help to fill in those gaps for me.

Greg Callahan: I think about average book size depending on enterprises, is somewhere between 5 and 15 let's throw it out there like that. In general, in any given year depending on your sell cycle, that kind of stuff, three to four deals are going to probably drive all of your business. With a smattering of longer tail stuff, that's kind of either tag alongs from deals in prior years or maybe warming up deals in future years. But conceptually, I think about it as those three to four that you're spending your time on is probably 50% of your time in a given year. Then there's a bunch of longer stuff that you need to keep warm and work it and do all that kind of stuff. But that's probably where that number is. I'm curious Sean, from your perspective, kind of how do you think about that book planning?

Sean Lane: So I think about it in two ways. I think depending on which way your company wants to go, either a pure number of accounts or a dollar amount for your book of business. And I think depending on the model that your company has, the answer to that could be slightly different. I think the thing that's most important about your answer is having the discipline to say, regardless of whether you have 4 or 15 accounts, those 4 need to account for about 50% of your time right. Because if you're actually trying to, and I think sales people are really good at this, they spend their time on the that's going to be the highest value to them. And to hitting their quota and getting that. So I think that's kind of built in. But I do think whether you're an ops or if you're a frontline manager, having some sort of benchmark like that 50% and then tracking and measuring whether or not that is actually coming true in terms of meeting time, activity, those cadences you're describing, how often we're meeting with the customer itself. If you've got 15 accounts and you're spending exactly proportionally two thirds of your time on the lower two thirds of value, that's not a good use of your time. And so I think that to me is probably the most important answer that you gave as opposed, like who cares how many accounts you have. Spend 50% of your time on the ones that you're going to get at least 50% of your number from which I think is really important.

Greg Callahan: I'm going to build on you real quick.

Sean Lane: Yeah.

Greg Callahan: The other thing that's built into that is I haven't spoken to an ops person yet who's experienced this or particularly salespeople are like, man, I have so many resources. I just, whenever I ask for them, like I always get what I need. Everyone's always available. They carve out their time.

Sean Lane: Who are you talking to?

Greg Callahan: That has not been a conversation I've ever had. And that's a little bit of where that prioritization comes from. So even if you think through these are your bigger accounts, particularly those folks that have ecosystem partners or GSIs or SIs or a bunch of different consulting partner arrangements where they've set up. There are a number of finite resources that you're pulling on through this process. And so the more actually you focus as a team on the priority accounts, makes it a lot easier for the finite resource that you have, the specialists, the ecosystem partners and such. You can focus their time a lot better so you're getting the right amount of energy on those accounts. And so it's as much a time allocation for the rep as it is a prioritization exercise internally from an ops perspective.

Sean Lane: So something I think within that, I think we should probably be more specific about is when we say they should be spending 50% of their time, or the rep should be doing this, who do you actually have in mind or who do you typically see as the audience for strategic account management? Because as we said, there can be a lot of roles. You might have an account manager, you might have a CSM, you might have the original rep who sold the deal. Like again, every company's model is a little bit different. But I know for me, one of the places where I have made mistakes in the past is I've been so focused on naming like a quarterback for who owns the account. And that gets me into trouble every time because everybody wants to be the quarterback kind of. And so I'm curious, when you think about the strategic account management function, is it specific to account managers or is that cadence that you described really involving a true team of people?

Greg Callahan: Yeah. I'm going to use your word, but in a slightly different way but that quarterback concept. And for the non- Americans, American football quarterback, I've run into that before, is a really important concept because the quarterback doesn't move the ball down the field, they use the team. And so you can use wide receivers and running backs and you can, as a New Englander here, you can use all, you can use tight ends and everything. But the concept here is that you need one person that is orchestrating the offense and how you're going about it. And that quarterback can change to your point. Typically, because we're talking about absolute dollar change, there is probably an account executive sitting on that and there's a CSM who's sitting there as well if it's an existing account playing a really material role. But if the CSM is really managing the day to day and making sure the client is successful but there's an absolute dollar change you're seeing, you're going to need that account lead to be that quarterback with very tight connection points typically with your solution consultant and your CSM. That is the trilogy if we're looking for the groups. If it's an non- existing customer, it's just the account rep and the CSM but it's those three. And the expectation typically is the account executive is going to be the quarterback, the true quarterback of the exercise.

Sean Lane: Can I just say that I have struggled with this quarterback metaphor for years. Every time I've used it, I've gotten myself into trouble but Greg just gave me a new and better way to think about it. Naming a quarterback is not about the concentration of power, but rather the conductor of an orchestra. The conductor knows which instrument to call on at each moment. And that that instrument brings its own unique sound and skill to the audience. And a good conductor leverages the skills of a violinist. She doesn't try to play the violin herself. Let's move on to Greg's second and third core components, cadences and plays. I was curious if these two related to one another. If Greg recommends that a standard cadence should be to meet every 30 days to align on a strategic account plan, does every single one of those recurring cadences result in a play? How should our teams think about whether those routine meetings that they're holding are being productive or not?

Greg Callahan: Plays are typically longer data, they take a little bit of time to evolve. They're probably typically a series of action. So those 30 days is really for every, you should be running three to four plays and they can be around products. Or a lot of times people come back and they're like, we need a relationship play. We have no access to this buyer. And so we want to figure out a way and it's not just take them out to a bar anymore in COVID. But how are the ways we can get to that person and create a relationship and an enduring relationship? And so there's probably a series of actions. To make it incredibly tangible here for a second, the team we work with was launching a new product and that new product they had a specialist salesperson sitting over top of. And so the core team wasn't as capable at the time to sell the product because brand new and so you brought in overlays and specialists to help them go sell it. The challenge was is that the core AE didn't know enough about the product and they didn't have access to that buyer. And so it was still within, for lack of it, let's call it the IT department. They were selling to a different buyer inside the IT stack and they needed to get access to a new person. They have great relationships with their buyers. And so the play was pretty simple. The first one was, hey, can you go talk to your friends and here's 10 questions. We called it the Q& A scout. And the Q& A scout, talk to your friend and ask them these 10 questions. And that gave us a really good insight into what this person we didn't know what was going on in their portfolio. Once you asked that person, got those 10 questions, you bring it back internally and you sit down with the specialist. The specialist would say, hey, based on these answers, they're all set, they don't need our help. Or based on these answers, wow we can really deliver a lot of value. The step one was go to the Q&A. Step two was sit down with our internal specialists and consultants and overlays to evaluate what the feedback from that Q& A was. Step three was if we like them and we thought it was a good one, immediately put them on an ABM drip campaign and start to drip feed this new buyer on all the stuff we can do. And step four was set up the meeting with that new buyer, with a warm intro from our friend. And that took about 90 days to unfold. We sat there with that team. We said, okay, there are a hundred accounts we could go run this play at. And we recommended it to those 90 of them. Of the 90, 60 executed. 30 of them didn't do it for a whole host of reasons. They were in live deals or whatever. Of those 60, 40 translated into meetings and 30 closed. Their close rate was like 70% versus an average close rate of 30. That play, even though it took 90 days, you could see that pipe build. And so as an operations leader, I'm walking into a year, I've got a forecast. I know what I need to do in my high velocity end of the segment, I've got to add new people. It's productivity per rep or number of reps. In my upper end of the segment. I've actually got a drive growth. And so starting to use these plays to say, I know this play yields X. And so I need to get this number of plays in the field with this number of follow through. And I need a system to drive that through. And so this whole idea of play based selling is incredibly powerful for this upper end of enterprise.

Sean Lane: So I'm so glad you brought up the relationship component about that because even if you let's say you come up with the best plays in the world. You write them all down, you've documented them perfectly, everybody knows what the play is. If you don't know who the right people are within the company that you're trying to run this play with, you're done, you're toast. And so I'm curious, especially in these enterprise level examples that you're giving where you might be selling into a pretty big company, how are you recommending to your customers that they go about that process of identifying the right person? And then also, how do you think about categorizing them? So we think about kind of like the roles within different companies. And one of the things that we've tried really hard at Drift to do is think about, I don't necessarily want to think about them in terms of our terms. Or in terms of like selling terms. Nobody in the history of being a customer wants to be known as like the economic buyer. What is their role in terms of how they relate to Drift? Is this the admin that's going to actually run Drift? Is this the person that's going to teach the sales team how to use Drift? Is this the person actually is responsible for the pipeline number? And so we try to think about it in those terms but I'm curious like what you preach to your customers about how to do that and then how you actually operationalize that.

Greg Callahan: Yeah, really good question. Clearly I'm going to give a few flavors of the answer here. But I think first and foremost, particularly as you go into enterprise, what you find is there are many buyers and many buy points of the same product and offer. And so you've picked your favorite company and they have multiple divisions with multiple buy points. Even if you are a really horizontal SaaS player and you can sell everywhere, the number of websites that you can embed. I'll pick on you guys for a second. There are many different components to JPMorgan Chase. You can sell to multiple places. And so the first is that landscaping exercise of just saying, where are all of the buying centers? And then based on that, who are all the buyers? And then using all these amazing tools that are out there that give you a perspective of who the potential buyers could be, doing that landscaping, getting clear on that. I think the second piece to your point is maybe I'll answer it in a different way. I don't care what religion you believe in, as long as you believe in religion, as long as you have a religion. And so whether you use a rapid approach or a racey approach, or I've seen A, B, C, D, E approach or just simple buyer, influencer, or other. Just being able to have everyone in the company speak consistently so that you say, okay, you know what Sean, Sean is a true influencer in this buying process. And everyone's like, okay, I know exactly what that is. And being able to use that and communicate that with your customers. And that's the interesting unlock is when you're close enough to those customers and you can turn around your account plan and say, hey, we started our account plan with what is your ambition and needs, and what are your personal metrics you're driving towards this year and how do we fit within that? And then how do we support you through that? And once you flip that conversation from what I need to what you need and how we're going to support you, the unlock is unbelievable. And say, oh, actually it's not Sean, it's Joe or it's Sandy, or it's Philip. These are the people you need to be talking to, would you like a warm intro? And so it doesn't always work that way. But when we think about actually setting up that strategic account plan, and I'm digressing here for a second but it starts with what is the customer ambition and what are the financial and operational metrics and objectives for that individual this year? And if you can't answer that, you can't actually get going on the plan. And so who are those key people and what matters to them? The second step which you may capture elsewhere is just getting really clear about insights. What is the competitive intensity in the account? So who are all the competitors, what's their level of penetration and then what's our level of penetration? And so we all try to get really cute in operations. We're like we're actually 33% share wallet or 35% share wallet. I really don't care. Either you're 0, 50 or 100 and your team should be able to answer that question. Because if you're a hundred, there's nothing left and so let's go find a new product or a new buyer. If it's 50, great there's a whole lot more to go. And 0, wait, we got a lot of work to do. But if you can get clear on how much headroom there is for you to go get, that's a really clear indication of what to do. The third piece is that landscaping. And so being able to just draw out a hierarchy of what's the account, what's the buy centers, how's that going? It is such a powerful tool as you build it out as a team. And then the fourth and fifth are simple, we say you spend the first little bit thinking about those first three sections, ambition, the insights and the hierarchy. But you spend all of your time on those plays. Sales plays and relationship plays you should be running three to four at a time. And that's the momentum. And so if you can create the plays and create them as an operations lead, standardize them, make them super easy, put them into your sales enablement platforms so you can click to here's the new customer play. Here's why you do it. Here's the collateral. Here's the information that you need. Here's the key people internally that you should talk to. Here's the ROI story. Making that really easy is going to be all the gold you need.

Sean Lane: And I would imagine all of those kind of exercises like the landscaping or the hierarchy mapping all kind of ties into that fourth tenet of tooling. I know the goal is to keep it as simple as possible but am I right? Are those parts of the exercise inside of like the tooling that you guys offer or what you recommend to folks?

Greg Callahan: Bingo. Yep, exactly right. We even do it internally. But there's nothing more painful than sitting down and breaking out a PowerPoint slide and copying names from your CRM system into a Word document or PowerPoint and knowing that they should sync and link together and update all the time and directly sync from LinkedIn, all kind of stuff. Yes, it should all be simple and tooled and really easy. And you can even imagine that that plays library, you've a library of plays. And so people can say like what I want to do is a new buyer play for the financial services space. And click two drop downs and it says here's the two or three things you should consider. You can do a little bit of reading here and this is how you can get going. And so what we're talking about isn't all that complicated but it is massive save on time for the team.

Sean Lane: Other than Greg's great line about having a religion, I think my biggest takeaway here is the common language you need to arrive at with your teams. Once that common language is in place then you can start to run these plays and execute on them consistently. One play that Greg kept mentioning a couple times is the idea of expanding into different verticals. For those of you at companies that are scaling into enterprise, chances are you've had a conversation internally about which verticals you might want to target or experiment with next. I asked Greg if there's a tactical play all the rest of us can deal from him when we're facing such a situation.

Greg Callahan: Yeah. So I think there are a few things that jump out as you go through this process. The first and foremost is that you typically see the most innovation happening on your products and tools in your biggest customers. They're the most embedded, they're the most use cases. They have the most things. And so from a product innovation perspective, the insight you're getting from those, and so making sure product is getting the feedback and seeing what's going on. That's typically where a lot of the innovation can come for where do you go and what are you going to do? The second piece is, as you get deeper into this, you're going to start to sub segment these plays. And so our product is terrific as a standalone tool in the mid- market for any segment or industry. But once I get into like really big enterprise for financial services, the amount of regulations and stuff that has going on in there, it requires me to change my product. And so I actually need to sub segment and think about those customers differently. And the strategic account plan is going to illuminate all this stuff. So if you go through all the major financial institutions and you do those account plans you're going to quickly realize what you need. Jump over to healthcare and HIPAA regulations and pharma and all that kind of stuff. And then you go into you pick your favorite industries. Each one of those is going to quickly isolate what you need to be successful. And so I think for companies in that rapid expansion part of the funnel, so they're in kind of that $50 to 200 million revenue range and they're going in enterprise. I think a next step we typically see is that they think they can take the same product and the same sales motion and be successful in enterprise. And typically the feedback is actually it's a longer sales cycle with a similar product but tweaked with a very different message that you're walking in with and driving way more consistency around that message. And so that's when you have one enterprise sales rep, you should not have segmentation. But as you're expanding rapidly and you're seeing these things, that constant slicing of saying, now it's time for a geo segment or a vertical segment or whatever, you're going to start to see those fault lines form very quickly as you go through this process.

Sean Lane: And I would imagine too doing those exercises will tell you just as much about places you shouldn't go as the ones that you should. There's going to be those verticals, to your point HIPAA, you might not be ready. And those fault lines appear very quickly. It's like, okay, well cross this off the list as the next vertical to go after. So I would imagine there's learnings on both sides there where yes, you want to get that 20 to 40% lift that you're describing as like the holy grail but you also don't want to invest a ton of time, money and resources into a vertical for a long time that's not going to yield anything.

Greg Callahan: Yes, you've nailed it. As we look at people who've done it well, Salesforce has done an awesome job. They go and they look at their coverage capacity every 18 to 24 months. And for all of us who are buyers of their products, it's sometimes painful that we get a new person every few years. But what they're doing fundamentally from an ops perspective is saying, we are now seizing the size and scale that it's worth it to split this thing down because we can drive differential value for this customer segment because we can now specialize in business services or in X, Y, Z tech or X, Y, Z healthcare. And so that's being really, it's hard to make those shifts because you always believe it's the relationship that matters. And there's no question that does matter, but people, whenever we ask customers time and time again, surveys on like what do you value particularly in enterprise? It is typically you understand my industry and what our needs are. And so being able to be industry focused is really powerful in the enterprise.

Sean Lane: Before we go, at the end of each episode we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?

Greg Callahan: Ready Player One.

Sean Lane: Ooh.

Greg Callahan: I'm going to go way out there. Ready Player One, the whole metaverse stuff. Man, that one gets interesting.

Sean Lane: I've seen the movie but I've never read the book. It's been on like the next one that I want to buy list for a while. So you might have just pushed me over the edge. So I typically ask people favorite part about working in ops. And so I'll let you either say in ops or with ops since you seem to be a little bit of both.

Greg Callahan: I'm a people person as you can probably tell. I think just being at the hub and being able to see these people and see what people are doing. And I think the most exciting thing is like there is so much innovation happening on the front line and being in ops you get to see it. And a lot of people, a lot of peers just sitting in one territory over don't get to see that. And so I think one of the things that makes me so excited is the people but also it's also the burden that you bring is that you need to take all those best practices and figure out a way to communicate them in an easy to understand and digest way back out. And that's your quid pro quo with the field is that if you have the honor and pleasure to work in that role, you better be giving back constantly, back to the field.

Sean Lane: Flip side, least favorite part about working in ops?

Greg Callahan: Time zones.

Sean Lane: That one's easy, time zones.

Greg Callahan: That's a good one. That's a new one. I don't think anyone said that one before. That's a good one though. Someone who impacted you getting the job you have today,

Sean Lane: Dude you want me to name the name? I can fucking name names. A gentleman named Graham Rose who didn't give up on me. He took this little twerp and said, I think there's potential in you. He is a special guy who stuck with me even when I wasn't thinking it was the right decision. So he really brought me along. That's awesome. All right last one, one piece of advice for people who want to have your job someday?

Greg Callahan: Be curious and focus on execution. At the end of the day we can all really, our problem in ops is that we can sit in an ivory tower and think about really cool things. But if you are not execution focused and don't sweat the small stuff, you will fail. You got to have that tenacious curiosity but also deep, deep, deep focus on execution.

Sean Lane: Thank you so much to Greg Callahan for being our guest on this week's episode of operations. And a special shout out to my friend, Elizabeth Ducoff for introducing me to Greg and setting up this interview in the first place. If you like what you heard, make sure you are subscribed to our show. We have a new episode that comes out every other Friday. And if you felt like you learned something from Greg or from our show today, make sure you leave us a review. Let us know, leave us a review on Apple Podcast or wherever you get your podcasts. Six star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.


What if someone told you they could increase your company’s bookings by 20 - 40%? Not a bad hook, right?

The strategy to support that hook comes from this week’s guest, Greg Callahan. Greg is a Partner at Bain & Company, and the Founder of Coro Account Planning.

In his work with Bain’s portfolio companies, Greg has developed a blueprint for getting the most yield out of your customers that have the most potential: Strategic Account Management.

In our conversation, we review the four core components of strategic account management, we offer specific plays you can steal to run within your customer base, and Greg explains why if you’re being strategic on everything, you’re being strategic on nothing.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts.

Today's Host

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Sean Lane

|VP Field Operations, Drift

Today's Guests

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Greg Callahan

|Partner, Boston office of Bain & Company