SMB vs. Enterprise Selling w/ Alex Buckles

#65: Listen as Alex Buckles, CEO of Forecastable discusses the differences between SMB and enterprise selling. He and Tyler cover the transition into enterprise selling, what effective team selling looks like, and how to navigate the closing process.

Listen to the episode by clicking play below OR search “the sales lift” wherever you get podcasts.

The Sales Lift Podcast
Episode #65
SMB vs. Enterprise Selling w/ Alex Buckles
Hosted by: Tyler Lindley


[00:00:00] Tyler Lindley: Hey Sales Lift Nation it's your host. Tyler Linley. Today I have Alex Buckles on the podcast. Hey Alex, how's it going? It's going, how are you, Tyler? Hey, doing great. Doing great. Alex is the CEO of Forecastable, which is a intuitive and collaborative sales acceleration platform. Today's topic. We're going to talk about the differences between SMB

and enterprise selling Alex. I know you have a lot of experience selling enterprise. I've got, looks from experienced selling S and B. So we're going to have two different perspectives, but I think sometimes we see these companies they're selling us in B and then they might get an enterprise deal. And the next thing you know, they're trying to sell enterprise, but there's a lot of differences between the two.

There's a lot of variation and it's not necessarily an easy transition. Talk to me a little bit about some of those difficulties that a company might have as they start to ease into that enterprise types. Sure.

[00:00:51] Alex Buckles: I like it, as you said, typically starts with an SMB company, typically series a series B, they're closing a lot of SMB deals.

And then all of a sudden they get that enterprise deal that falls in their laps. And again, it could be by happenstance, they just happened to win an enterprise deal. And they're like, I want more of those. It's a great lifetime value, larger deal sizes, but they're also much harder to earn and to earn systematically and intentionally, all these folks will just take an SMB rep and say, okay, we'll go close more of those.

And it's not the same process. And I would say. Biggest change is just the number of stakeholders involved. And I'm sure we've all seen the statistics about the average number of stakeholders and enterprise deal. It's seven people, but it can be many more than that. And it's not just about going, can't just get to the decision maker, handle some objections and then try to seal the deal.

It's a group consensus game. Yeah,

[00:01:39] Tyler Lindley: definitely. And I think for me, that was always intimidating. Cause I used to selling SNB when you had all these people, all these hands in the cookie jar, a lot of people involved in the decision. Wow. I've got a lot of people, a lot of different opinions to consider here, a lot of consensus to build.

And for me, that was intimidating. How did you go about doing that as an enterprise? It

[00:01:57] Alex Buckles: is intimidating for one, if you feel intimidated, it's okay. Everybody feels that at some point, just to state that, but two, it comes down to when you view the entire group, that's where it feels intimidating. All these different people and these different roles.

A lot of them are senior leaders, but at the end of the day, each individual stakeholder has their own unique. Usually self-centered selfish interests as to why they want to purchase one solution over another. And it's your job as the sales rep to go figure out a stakeholder by stakeholder, what is important to each individual and then hone in on that.

How do you deliver that value? And you can't just deliver, you have to let them know that you're delivering this value and say, Hey, if I do this and I can deliver it. Do I have your buy-in that's the type of conversation you want to ultimately end up

[00:02:38] Tyler Lindley: having? Yeah. That makes sense. You recommend doing this on the individual level where you need to go and have these individual conversations with each of these stages.

[00:02:47] Alex Buckles: Correct? Yes. I recommend you have individual conversations with every stakeholder when possible. It's not always achievable to have those one-off conversations, but you need to at least pay attention to each individual stakeholder. If you don't know, what's important to this stakeholder over here, that could be a wrench in your gears.

And the last mile after you spent eight grueling months of your life, trying to work that deal only because you got a little lazy and decided not to take care of that one stakeholder, that's your fault. So it's important to do it.

[00:03:12] Tyler Lindley: You bring up a good point there, hate months, some of these enterprise.

Take a long time. It takes a long time just to do some account mapping, figure out who are those stakeholders. You've got to get all that individual buy-in, it's just a long drawn out process. One thing that I always found is I would lose patients, lose interest. You're playing the long game, which is so different than in a smaller sale where it's a little bit more transactional and immediate might take a few weeks a month or two.

How do you stick through that grind of an enterprise sale, which can take a very long.

[00:03:40] Alex Buckles: It's tough. Sometimes, especially if it bleeds into multiple fiscal years, you have no idea what the comp plan is going to be like next to you. You have no idea what you're going to get paid on that deal. You want to close it and you don't even know if you're going to have that account next year.

Possibly. You want to close it this year, if at all possible to make it a little bit more manageable and to keep yourself sane, it's all about having a closed plan or a mutual action plan mutual success plan. At forecastable we call them evaluation plans because 100% of the time a buyer is evaluating the purchase of a product or service.

And this is their plan to conduct the evaluation. And an evaluation plan is nothing more than a project plan. It's identifying everything that you think needs to happen between today's date and the date that you're forecasting to close the deal, which is typically your contract execution. And the enterprise world, there's two very distinct cycles in a deal there's decision process.

That's generating group consensus. That's getting every stakeholder and converting as many as possible into supporters. And then there's paper process, right? And that is procurement. You might have legal red lining. You might have an information security review, and so documenting everything that needs to happen in collaboration with your prospects.

So they're bought into the timeline. Makes the entire cycle more manageable and predictable. Otherwise you're just drifting in the wind, kicking the can down the road might have a conversation every once in a while, but you're not really pushing the

[00:05:00] Tyler Lindley: yep. That makes sense. Are those two processes, the decision process and the paper process, are those typically happening simultaneously in an enterprise deal?

Or do those happen separately? Are they one after the other or has that.

[00:05:11] Alex Buckles: The lion's share, it's separate, but a great enterprise. A we'll try to get that paper process started as early on as possible. You can test the waters without, so for some tactical advice, but you're in a deal, you feel like you're going to be getting vendor of choice.

Maybe you already know you're going to get vendor of choice, but the official decision isn't going to come in for another three weeks for all vendors. So maybe you tell your champion, Hey Mr. Champion, we've got our master subscription agreement or Ms. Ready to rock. Why don't we get that process started now?

Cause I have no idea what the legal redlining process is going to look like any chance you can get that off to legal for review early. And if you can make that happen, you can save two or three weeks on your

[00:05:45] Tyler Lindley: deal. Yeah. Yeah. That makes sense. You mentioned the vendor of choice. Do you feel like a lot of times at an enterprise sale, I feel like an SMB.

We're mostly sometimes selling against the status quo they might just choose to do nothing. Is that the same case in an enterprise up market sale? Is the status quo, the biggest competitor, or does an enterprise made the decision? They're going to go with something. They're looking at these three to five options and they're going to choose one.

Is the status quo always one. Is that the biggest competitor usually, or is it usually you selling competitively with another. The status

[00:06:17] Alex Buckles: quo is usually the competitor. If you're outbounding into the account, there is no defined initiative is no defined pain. So there's no budget set aside for this, but you generate some interest and you uncover some pain.

And at that point, the status quo will always be your number one competitor. Now on the side where there's a defined initiative and the enterprise organization is like, okay, we need a new marketing automation platform. We already have this one platform. We're not going to look at them again. They're done.

We're going to look at these other three and here's our. I love those because you already have the group at the table budget's there. And now you're in the business of generating group consensus and just systematically working

[00:06:51] Tyler Lindley: the deal. Is that typically an RFP they're an enterprise company. Are they usually putting out an RFP or are you finding that they don't or does it depend on the company?

[00:07:00] Alex Buckles: It's a 50 50 shot. If it's an official RFP driven process, RFP, sometimes it makes me cringe. Sometimes it makes me happy. It depends on how well structured the RFP. I can't send RFPs where they don't allow for proper discovery. And I try to build all this efficiency into their evaluation process, but they're really just doing themselves a disservice by not engaging each vendor the way they should be engaged.

And so RFPs are hit or miss

[00:07:24] Tyler Lindley: for me. That makes sense. So it sounds like one thing I've heard is trying to get involved in the RFP before it even goes to RFP. You want to understand when they're going to RFP understand some of those decision criteria is that they're looking at that's ideal, I guess that doesn't always happen.

If you find out about an RFP after the fact after it's already gone public, are you dead in the water at that point? You usually are there already other relationships that are already made at the enterprise level or are you still have a shot?

[00:07:49] Alex Buckles: No. Even if you weren't involved early on in the RFP creation process, you have a very solid shot in the deal, but if you can get in at the RFP creation process, that's awesome.

I've done that so many times. I feel like somebody is about to do something or they're about to put out an evaluation or they send out an RFP that looks a little light. I usually will float a standard RFP. It's obviously all the requirements are in our favor. This is not forecast. Was your prior companies I'll say, Hey, you know what?

Check out this document. Most RFPs for let's say marketing automation again. Let's say most of the marketing automation, RFPs look like this, and these are the five categories that we typically see. Now I took a look at your RFP and you've got two of the five categories. Why is it that you left out the other three?

Is that unintentional or is there a reason for that? And you just start poking at that thing and try to poke holes in it. And if you've done your job well, you've hopefully taught them something in that process. Yeah.

[00:08:38] Tyler Lindley: One thing that's interesting is we think about this idea of team selling, selling with multiple people inside your organization.

Smaller SMB sale usually might just be one person, maybe two or three are involved, but it seems like the further go up market and enterprise deal. You need more than one stakeholder. Not only there's more than one stakeholder externally, but you need more than one stakeholder internally helping to sell that deal.

What does good look like there in terms of team selling in an enterprise? There's

[00:09:05] Alex Buckles: a whole lot. So team selling is a lot of fun. So that's the name of the game though? Team selling is a, you can't lone ranger. It use your team. An executive at a prior company wants tell me, she's like, if you're going to lose, never lose alone.

That kind of really stuck with me. And so when it comes to team selling, let's say upfront, you're doing your outbound and you're hunting. You should be working with your SDR or BDR on that account plan. What messaging are you using? Don't just spray. There's a little bit of teamwork there in that regard.

Then as you get into the cycle itself, your team starts expanding. Once an opportunity is on the table, your STR probably not so much involved anymore. They're often to the next thing, but now I might involve my manager. I might involve subject matter experts. I might get solutions, consultants, technical architects at times.

Let's say I've got a stakeholder that I know is struggling a little bit and they're on the fence and I haven't converted them to a supporter yet. Let's say they're a VP of marketing. I may grab our VP of marketing and say, Hey, would you mind having a conversation with a stakeholder? I think she's struggling in this one area and just get a little bit of executive alignment.

You as the rep use your team, you're quarterbacking. This deal, you need to spot where there's issues in the deal all over, and you need to bring in the right people to go solve for those challenges and convert as many of those stakeholders into supporters as possible,

[00:10:20] Tyler Lindley: right? The enterprise rep there's a lot going on that they have to manage.

There's a lot of moving parts here. If I'm a company and I want to go and find. Yeah, good enterprise rep. What skills am I looking for? What are those intangibles? And I guess what backgrounds are successful in quarterbacking? These large enterprise deals. In terms

[00:10:42] Alex Buckles: of skill hiring is always hard. So I hesitate on that question because hiring is just, it's a crap shoot, but you try your best.

And at the end of the day, sometimes it's just

[00:10:50] Tyler Lindley: possible that very different hiring an SMB rep, which is a little bit more straight forward versus this enterprise, but it's very different. So I just wonder what would you even look. I'll

[00:10:59] Alex Buckles: just walk you through maybe a little bit of my own process. So when I'm looking at an enterprise rep, the first thing I start with is I want to talk about how do you build up your territory?

What have you done in the past to do this, to get a feel for what they've done in the past, and are they creative? Have they held their own events before they used to doing stuff like that? Are they reliant upon. Marketing 100% of the time, or can they do their own outbounding? I'm a fan of separating. I don't think they should.

Outbound. I think it's a very separate function. I may ask some questions around that. I'll then get into process. I'll look heavily at sales process and focus on group consensus. I'll ask them specifically, how do you generate group consensus? What do you do? Just dig around that to see what they've done in the past.

And I might have them walk me through a really hairy deal where they were, where they either succeeded or failed. It doesn't matter as the experience and seeing that they understand. How to navigate the complexities of a large enterprise deal is really important. Another thing is probably self-sufficiency a little bit, be surprised how many reps can't build a PowerPoint deck.

If a rep is going to sit around and wait for marketing to produce something for a presentation he's doing to a prospect, that rep is probably going to waste a lot of time. And I have been burned hard a couple of times with reps, not being able to build basic PowerPoint, slides, little things like that are important to pay attention to.

Yeah. Prioritization is a really big thing too. So managing priorities it's like, is this the best use of my time at this very moment? And is the rep good at that? Or are they just chasing the next shiny thing and stuff like that? So I'll probably dig around priority management and stuff like that. As part of my interview.


[00:12:30] Tyler Lindley: Back to our original question where we started the conversation. Is it possible for an SMB rep to make that transition to enterprise drift? Have you seen that? How do you make that transition? Or they might have some of these things, some creativity group consistent self-sufficiency prioritization.

They might have some good things in those areas, but they've never quarterback that big deal. So how do you know if that SMB rep is right or not? And what does that maybe training look like to get them to that? I

[00:12:56] Alex Buckles: don't know if I would take a pure SMB rep it's never worked large deal and just throw them into an enterprise role.

Yeah. It's just too much deep end. Yes. I'm sure there are some exceptional SMB reps and vice versa. An enterprise rep could not go into an SMB role and succeed right out of the gate. They would spend way too much time on an account and work it it's about volume and velocity and enterprise is not all about that.

So I would probably get them into larger deals. But maybe like mid-market deal say, Hey, let's get into a little bit of a larger deal. You're used to closing 10 to $15,000 deals. I want you in the 40 to 50 K range with a few more stakeholders. And then once they've done that successfully then graduate to the larger, more complex deals.

[00:13:33] Tyler Lindley: Yep. That makes a lot of sense. And a lot of the companies that you see a lot of sales orgs, do they bifurcate based on, are they splitting up, get SMB mid-market enterprise that usually those three buckets or. Two buckets, usually it's smaller, larger. What do you typically see in terms of how companies are grouping their AEs?

[00:13:52] Alex Buckles: There's a wide range, but I would say the majority have commercial. They call it commercial for SMB, commercial and enterprise. And then you sometimes see I'm starting to see a lot of growth, a growth role. So I see commercial enterprise and in growth, which means typically an accountable. And you've got some footprint there's room for expansion.

It's not SMB because it's usually very little room for growth in an SMB account. And you want to have a team that's specifically there for upsell cross sell. And then the last category above enterprise, you might have some folks that will specifically call out major accounts or strategic. And that would be the highest level.

[00:14:26] Tyler Lindley: Yeah. You bring up up so cross sell, which I think is it happens in SMB, but not as much. Usually they ended up buying the majority of what that SMB product offering. They buy most of what they need on the front end. So there may not be that upsell cross sell potential as much in an enterprise sale. Is that a huge part of the game and enterprise?


[00:14:47] Alex Buckles: think it is absolutely. Again, it depends on the organization you're in a lot, has to do with the comp plans. There's a lot that goes into whether or not it's worth upselling or cross selling, but I've had great success in my career selling into the install base. In my opinion, there is no better customer than your current customer, and that's where your loyalty should be focused on them, serve them well.

And they will be there for you. They will continue buying from you, but it is an essential part. And that happens. I think if you have installed base and your goal is to upsell, cross sell, build that close relationship with your customer success manager. Getting into the account, serving your customer, being there when they need you.

Don't just show up when there's an opportunity to support. Shoot them text messages. I used to try to break that text barrier as early on as possible and the relationship for whatever reason, any excuse to get that first text message out the door. And then once you have that, you've got to use it carefully once every month or so I would text the customer and say, Hey, Sally, anything that I can be doing to add value to your life right now, anything at all?

And just random. And a lot of times they just say, no, I'm good. Sometimes it's like, yeah, actually you're not having a problem with support right now, which I wasn't even aware of yesterday. And now they view me as having helped them. And it's just a really good situation.

[00:15:51] Tyler Lindley: Yeah. I think that's an important point that you bring up.

Not just when there's opportunity. It's not just when, oh, there's a clear opportunity for us to upsell them now because of this trigger event. So I think it's trying to build and maintain that relationship. Do you feel like in enterprise selling there's a lot of that account management aspect where you typically the one that sold that net new deal and then that became your install base?

Or did you just inherit that instance? How long of a relationship was this typically a few months or this years and years and years of you working with the same?

[00:16:21] Alex Buckles: For me, it was a couple of years at one company. It was there for a few years and I service the same customers for a few years. They knew me.

They knew me. Well, I was always there for them just top to bottom. And that did really well for me. They were loyal to the company. They were loyal to me. They wanted me to make money. They're like, Hey Alex, I've got a deal for you. We might be able to buy more of this. And I'm like, awesome. That's the relationship you want with an enterprise?

[00:16:43] Tyler Lindley: Yeah. Yeah. That makes sense. What haven't we discussed yet, in terms of what advice would you have for these companies that are starting to go up market? Getting into enterprise selling? They've got a team of SMB reps and I've sold a few big ones, but they don't really know how to take that next step.

What advice do you have for companies at that inflection? Yeah.

[00:16:59] Alex Buckles: I would say, stop, just take a break, think about it. Don't just rush into it and take a break, take a breather and focus on what are we doing? What will it take to close? And what does it take to close an enterprise deal? And then test the waters you take your best rep or somebody that you know is exceptionally suited for enterprise role, and just say, Hey, let's go work this deal.

Let's build that process. Figure out what process works. And then scale it instead of just saying, okay, we're going up the enterprise now, new segment, go for it. That's how I do it. Pause.


[00:17:31] Tyler Lindley: Be intentional. The intentional that's great advice, Alex. How can my listeners find you online? If they want to learn more about you?

[00:17:38] Alex Buckles: Just follow me on LinkedIn. That's how most people communicate with me. So just feel free to follow me on LinkedIn. I post all the time. I respond to the most messages, so it shouldn't be out there.

[00:17:46] Tyler Lindley: Perfect. Awesome. We'll link to your LinkedIn profile in the show notes, Alex really appreciate you coming on and sharing your thoughts on enterprise.

Alright. Thanks Tyler. Thanks Alex. See ya.

Thank you so much for listening to today's show, you can find all the links discussed and the show That's the T H E sales S a L E S. Lift L I F have questions for me. Email We look forward to seeing you back here next week, and we hope today's show brings you the sales lift.

Your business needs. Remember ideas. Plus action equals. You've got new ideas. Now it's time to take action and the results will fall. See you next time. .

Don’t feel like listening? Read the Episode Cliff Notes instead below:

Difficulties When Starting (28)

Typically, the transition starts with an SMB company, typically a series B, closing many SMB deals, and then they get an enterprise deal that falls in their laps.

The biggest change is the number of stakeholders involved.

SMB can be intimidating because you have many people involved in the decision-making in a lot of different roles, and some of them are senior leaders.

Each stakeholder has unique, usually self-centered interests as to why they want to purchase one solution over another. 

It’s your job as the sales rep to figure out, stakeholder by stakeholder, what is important to each individual, and then hone in on that.

Have individual conversations with every stakeholder when possible and pay attention to each stakeholder. If you don’t know what’s important to this stakeholder over here, that could be a wrench in your gears.

If at all possible, you want to close it this year to make it a little bit more manageable and keep yourself sane. But remember, you’re playing the long game. 

The Process Behind the Deal (4:16)

There are two very distinct cycles in a deal’s decision process in the enterprise world: generating group consensus and the procurement paper process. 

The lion’s share of the two processes happens separately. You try to get the paper process going as early as possible.

If you’re outbounding into the account, there is no defined initiative and no defined pain. So there’s no budget set aside for this, but you generate some interest and uncover some pain.

The status quo you’re selling against is always your biggest competitor.

RFP do themselves a disservice by not engaging each vendor the way they should be engaged. So they’re generally hit or miss.

Even if you weren’t involved early in the RFP creation process, you have a very solid shot in the deal. But if you can get in at the RFP creation process- that’s awesome.

Smaller SMB sales might involve one person, maybe two or three, but it seems like the further you go upmarket and enterprise deals, the more stakeholders you’ll need.

Team Selling (9:01)

You can’t be a lone-ranger when teams are selling; if you’re going to lose, don’t lose alone.  

You should be working with your SDR or BDR on that account plan. Then as you get into the cycle itself, your team starts expanding, and your STR probably won’t be so much involved anymore.

You, as the rep, need to spot the issues in the deal and bring in the right people to solve those challenges and convert stakeholders into supporters.

When looking at hiring an enterprise rep, the first thing to start with is talking about how they build up your territory. What have they done that similarly in the past, and are they creative?

Self-sufficiency is also something to look for because the last thing you want is a rep who sits around waiting for someone to give them direction. 

It’s probably not a good idea to take a pure SMB rep that has never worked a large deal and throw them into an enterprise role. 

It’s better to start them with Mid-Market deals and work their way up. 

Driving Sales (13:47)

There’s usually very little room for growth in an SMB account, and you want to have a team specifically there for upselling and cross-selling.

The organization has to do with the comp plans. There’s a lot that goes into whether or not it’s worth upselling or cross-selling.

There is no better customer than your current customer, and that’s where your loyalty should be: focused on them. Of course, then, they will continue buying from you. 

Don’t just show up when there’s a problem. Instead, try to break that text barrier as early as possible and use any excuse to get that first text message out the door. 

It’s not just about upselling. It’s about building and maintaining relationships. 

For businesses looking to break into enterprise selling, Alex suggests taking a break every so often to look at what you’re doing. Then, ask yourself what it will take to close an enterprise deal and test the waters first. 

Build the process, figure out what works, and then scale it rather than jumping right in.

Alex’s Bio:

Alex Buckles is the CEO at Forecastable, where he focuses on delivering scalable sales certainty to chief revenue officers by empowering frontline sales managers to drive individual sales rep success. After serving in The Marines, he spent the next 16 years in enterprise revenue roles from startup to large enterprise. He’s a proud father of three, an active Autism advocate, and a strong supporter of paying it forward.

Important Links:

Alex Buckles LinkedIn Profile