When your sales team is small, everyone has to wear multiple hats. The challenge is recognizing when it’s the right time to specialize while balancing a rapidly growing team.

In this panel, Aaron Ross, author of Predictable Revenue and Impossible to Inevitable, chats with Bridget Gleason, VP Corporate Sales at Sumo Logic, and Don Otvos, VP Inside Sales and Sales Operations at Datahug, on why specialization is so important and how to do it correctly.

Bridget and Don offer up their perspectives on implementing a solid leadership structure, determining the optimal ratio of SDRs to AEs, the importance of clean data (spoiler alert: it’s very, very important), seamless handoffs (if the customer complains, it’s because you’re doing something wrong), and more.

Check out the full transcript below! 

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Aaron Ross:  Just before we get started, I’m going to say I actually was first tasked, or appointed, or asked to moderate the prior panel on Outbound. If you don’t know me, Aaron Ross, Predictable Revenue. But I want to do this one. I said, “No, I don’t want to do the Outbound panel. I want to do this one on sales specialization because it’s so important.”

But, I’ve got two asks or one thing to tell you. If you haven’t gotten it yet, Jason bought a bunch of these. He’s the one who funded 1,000 copies of the new book, but they didn’t really tell…They put them in the very, very back of the top floor, in the closet, hidden under the stairs. There’s like a trap door and a secret code.

But if you go up there, there’s a bunch of books, you can go get one for free. Then we’re doing a signing at the carb.io booth, it’s our software company, at 12:30. Free books. Make sure you get one. There’s only 1,000 books and there’s way more than a thousand people here. But they’re hidden. It looks like you’ve got to pay for them, but you don’t. That’s one.

Two is my thirty seconds on Outbound is actually I just did three short videos on how people get so fixated on these damn cadences. “Should it be four email sequences and a LinkedIn?” Oh my God, you’re missing the entire freaking point. I just did three short videos on Predictable Revenue the blog and people love them. Go check those out. That will be my 90 seconds or 30 seconds on Outbound.

Scaling. You can’t scale as your sales roles are specialized. Hopefully not news to people here. A lot of this is also how to specialize the best way, because there’s a lot of questions that come up around, what if you have account management versus customer success. How many are the ratios? What if we do enterprise versus small business?

Let’s kick it off. I’m going to ask each of you just a bit about, let’s start with Bridget. Can you just introduce yourself? Is there another fact, first one, a fun fact about personally? Then I’m going to ask you about the team you’ve run.

Bridget Gleason:  All right. I’m the VP of Corporate Sales at Sumo Logic. Starting with the fun fact, I’m one of seven, which seemed like a lot until I met Aaron. My father was an entrepreneur. I think my father really understood specialization very early on, because he learned that among the seven children, that on the weekends, they had to specialize the tasks. They specialized indoor versus outdoor.

The outdoor was a very early picking weeds the younger kids did. This is a tip for Aaron, if any of you don’t know this. Helping him with this…

Aaron:  I’ve got to work on this. I’m taking notes right now.

Bridget:  The indoor, this was the more specialized. I was really good at ironing. I hated to do the gardening, which I liken to my closing reps that don’t like to do prospecting. We learned specialization very early on in my family.

Aaron:  Just tell us, before we get to Don here, how big is the team and what kinds of roles do you have today?

Bridget:  On the team, we’ve got a lead enrichment team, actually, that we contract out from the Philippines that does all the lead enrichment on the list. There’s a lot of talk about list building. We have that on just lead enrichment. We’ve got BDR team, a closing team…

Aaron:  The BDR is doing prospecting, 100 percent?

Bridget:  Outbound, 100 percent outbound. We’ve got then the closing team and account management team. Then within the closing team, we’ve got SMB midmarket in one segment. We’ve got field and sort of enterprise in another segment. Then we’ve got sales engineers, which is another area of specialization. Then of course, management.

Aaron:  Roughly, how many people overall?

Bridget:  Sumo Logic has 300 and some odd people. The sales team, there’s about eight in account management, roughly 15 in the field, 32 inside midmarket, and about 10 on the BDR team.

Aaron:  OK. We’ll get into that. What you’ll find too is every team, you’ve always got places of tension and friction. We’re getting customer success or account management like who does what, or inside outside. We’ll get to that. Don, what’s maybe a fun fact, secret vice or hobby before telling us a bit about the team you manage.

Don Otvos:  I think people that know me, I think little fun fact about me, I was an SDR for a long time. I think one of the…

Aaron:  We’ve got that in common.

Don:  You probably know this trick too. Every area code in the country, you name an area code, I could tell you where it is. Give an area, I could tell you where the area code is. It’s just from having dialed so many numbers and knowing associated city, and where those were. Having that…

Aaron:  Does it work the reverse, if like Topeka?

Don:  Topeka, I believe, is 316.

Aaron:  I have no idea if that’s true, but it’s impressive, so pretend it is.


Don:  [laughs] That’s my trick.

Aaron:  Size of sales team, rough like people…

Don:  Size sales team?

Aaron:  Yeah.

Don:  Today I’m at Datahug. Today I have a, similar to Bridget, I have a data enrichment person that I have that goes through and finds names, builds out the list according to the…

Aaron:  List building is actually a separate role. Whether it’s inside the company or not, it’s a separate function. List building, list enhancement. What else?

Audience Member:  Then we have an SDR team. Extending two offers today. We’ll have a team of six.

Aaron:  SDR, the prospectors, feed response.

Don:  Prospectors, managing the inbound as well. Because we’re a little bit smaller than Sumo Logic, so I don’t have a ton of people, so a lot of people do multiple things. Then we have a team of three AEs. Specialized between SMB and mid market enterprise.

Then we have a customer success team, which also functions as our account managers. They’re responsible for renewals and upsells as well.

Aaron:  There’s got to be somebody in here at some company that doesn’t have specialized sales teams or specialized as far as they should go. I say generally more roles are better. The more roles you have are the better. More people doing different things, but each person does fewer things better.

But in case someone’s still, “Hey, do we specialize? We’ve got salespeople that are prospecting and doing a lot of prospecting, more than 20 percent of their time, and closing. I don’t know, my CEO’s not really bought in,” why specialize? Or why take it to an extreme?

Bridget:  It’s interesting. I’ve been at Sumo Logic now about eight months. Many of you are starting companies or in companies that are smaller and maybe early on, and Sumo Logic definitely had this issue early on, or not issue, but situation early on, where they weren’t specialized.

You could have a small team of salespeople that actually could pretty effectively do a number of roles. Just before I came on, a few months before, the closing reps were also essentially prospecting, they were closing, and they were also handling what we would now consider account management.quote1-gleason

When you’re small you can get away with it. The prevailing thinking at the time was, “Hey, if it works for four, it’ll work for forty.” I’ll tell you, what works for four does not work for forty. Because what happens is that the lead flow also needs to be distributed among a larger group, and so there is more of a need for outbound.

For us, as we’ve gotten bigger, it’s definitely been imperative that we do more and more specialization along the way. My encouragement would be, even at the beginning, even if you don’t specialize roles and have a big team, to have an eye towards specialization and know that that’s what you’re building towards…

Aaron:  Actually, that’s such an important point. This might be the number one thing to take away with you today, is look back. When you created a new role, from the time that you wanted to create it until you felt like, “OK, basically we’ve figured it out,” if you had to just guess, how many months…?

Bridget:  At least six.

Aaron:  When you’re growing and you’re like, “OK, we’re going to do outbound or enterprise or something,” it’s going to take probably way longer than you think from starting to, “OK, we’re doing it” to, “It’s not working.” It’s at least six months, probably, for a lot of these roles.

Bridget:  Aaron, you asked the question teeing this up around other people in the organization not understanding why to specialize. I’ve definitely encountered that at Sumo Logic, where oftentimes the BDR or some of these roles are seen just as cost. “Why should I add a BDR or an SDR role when I can hire a closer that I can associate revenue with?”

Part of it is also is an education process around the dividing up of the role and how that actually contributes to the overall quota attainment of a team.

Don:  I think when I joined Datahug one of the things I found too, is the BDR team that was there was doing a lot of the research themselves. When you have a BDR team…

Aaron:  The prospectors, right?

Don:  Yeah, the prospectors, but then they default to the easier thing. If you want to turn up the number of calls or you want to turn up the number of meetings, but they default at doing the research.

It’s like, “OK, I want to take the research off their plate so I can get them focused on the things that I want them to do so that as you’re doing the specialization you know, ‘OK, my BDRs are doing this and it’s going to create enough meetings for my AEs.'”

Having a specialization allows them to focus and know that, “This is my job, this is what I need to do,” rather than maybe defaulting on something that is easier or not as hard to do.

Aaron:  Actually, Don, again, maybe you took off the research, when you made that kind of split and defined new roles, did you feel like, six months? What do you feel like is that sort of time frame before starting it and how long is it going to take to get it nailed down?

Don:  The BDRs that were there before I joined were probably there about four or five months. I can tell you, it was a little bit of to their system too. It’s like, when I joined, I said, “Wow, I think you guys should be doing at least a meeting a day,” and they were doing maybe a meeting a week. They were like, “There’s no way we can do a meeting a day.” I’m like, “Yeah, there is. Let me help you get there.”

All this research you’re doing, I’m going to take that off your plate now. Now you can focus on making calls. Now they’re doing a meeting a day. They were able to see that by offloading this piece that was burdening them with a lot of time, they were then able to focus on doing the things they could do, which is going to make them money because they get money for the meetings that they book.

When I up the quota, took off the responsibility of doing that data research, they were then able to focus on making those calls and then making themselves successful.

Aaron:  We’ll say, it’s for sure not painless to further specialize to add roles because it involves change but it’s better to bite the bullet. Sometimes it’s easier to layer on a new role, sometimes you got to restructure.

What do you think has so far been, for example, the…? You mentioned, the main way you change roles that help make an increase. Was it this, I’ll just call it outsourcing, separating research from the prospectors or was there another one that really helped make the lives of someone on the team much better? Or be a second one.

Don:  It’s like creating the problems at the different levels. It forces us to specialize. it’s like having someone who’s a researcher who’s generating a lot of names to give to a BDR, BDR then creates a lot of meetings. You have enough meetings for an AE, then you know you got to hire more AEs.

You have enough AEs, you’re closing enough business, then you know you got to hire new customer success folks. You have customer success folks, things are coming up on your renewal, you know you got to hire AMs.

It’s like trying to break things at each level to know, “Now I got to do this, now I got to do this,” as you’re going through and creating enough strain on the system to create that role and have those folks be specialized.

Aaron:  Great point so far. First, which is start thinking about the roles, you’ll need to create early, because it’s going to take longer than you think. Just look for, people are doing any of these roles, what’s the low value tasks for them that someone else should handle?

Actually, Bridget, what’s one of the changes you’ve made that you saw…I don’t know if you’d say proud of, but we did X, we changed these roles, and that really made a great difference, really helped.

Bridget:  I think the biggest thing is introducing. We didn’t have actually BDRs for the corporate team. That’s a brand new role that we’re introducing and layering on.

Aaron:  Do you buy them Predictable Revenue when you hire a new BDR?

Bridget: Aaron, we have Predictable Revenue everywhere.

Don:  [laughs] It’s all over the office.

Bridget:  It’s all over the office. In fact, I was going to give a bit of a spoiler alert because I’ve already read From Impossible to Inevitable about another challenge that we’ve had is that…We have a team of 30 to 40, depending on any given point in time in the quarter of closing reps.

When I first went to introduce this notion of needing BDRs for the team, one of the thoughts that came from management was, “Why didn’t you just re-purpose some of the existing closers and make them BDRs?”

Aaron:  Ow.

Bridget:  Thank you for understanding.

Aaron:  It does not work.quote2-gleason

Bridget:  Ow, and ow on so many levels. Ow on taking somebody and saying, “Here, you’ve graduated to this role. Hey, we’ll still pay you the same, but we want you to do this other role for a period of time,” which is not good for an individual’s development. That wasn’t going to work.

You have finance pushing back, saying, “Why am I going to pay a more experienced person to do something in SDR role and still pay them at that higher salary when I don’t need to?” There’s a lot of friction all over the place. Needless to say, this would’ve been what our CEO also cares about is, what’s going to come out on Glassdoor about Sumo Logic and how we’re restructuring the team?

That’s why I say, it is really important to have an eye on specialization at the beginning. What we needed to do is then just keep layering in, as opposed to re-purposing some of the people there. It’s amazing what ideas…

Aaron:  You’re always evolving it.

Bridget:  Yeah, always evolving. I think the other thing is, this isn’t a “set and forget” type of situation. With particularly cloud computing, these new disruptive technologies and companies are being introduced all the time, which can help in terms of work and products and services for sales people but it also disrupts markets.

You never know what your competition is going to be doing, so you need to always be re-looking and re-jiggering the ratios of BDRs to closers, when do you add account management, SCs, those ratios are going to continue to change as things change within the company and the landscape.

Aaron:  It’s good. Do you have some current ratios you use between different roles, Don? I’m going to ask to…

Don:  Today, what we tried to strive for is two SDRs to one AE and then we managed the customer success team around number of customers. We try to keep it…

Aaron:  Do you have a number in your head for number of customer success people per number of customers?

Don:  Yeah, 40 to 50 is what we’re trying to track to. It’s what I tracked to in the past.

Aaron:  By the way, that number will vary a lot based on if you’re enterprise, small business. Don’t just write down, “1 customer success person for 50 customers.” No.

Don:  [laughs] It depends on your ACV and a lot of things.

Aaron:  In the book, there’s actually a case study on a company called Guild. They have three tiers. There’s enterprise, mid market, small business, and their ratios. About some ratios that you use, Bridget, for your…

Bridget:  Don, you have two SDRs per account rep.

Don:  Yup.

Bridget:  Ours is really the opposite. We’ve got one SDR per three sales people, per three closers.

Aaron:  Average deal size though?

Don:  I was going to say deal size got to be higher.

Bridget:  What is your deal size? It doesn’t necessarily have to be higher.

Don:  20, 25K.

Bridget:  It starts low but the average deal size for my team can go up to 300K ARR. However, the reason… I’d love to get to that, that’s my goal… is to reverse it to have more of the prospectors feeding the sales team, because I also believe, as per the last session, outbound is really important. You can be very targeted.

Aaron:  Hallelujah!

Bridget:  I know. Let’s all…

Aaron:  Inbound is fantastic, people. Peanut butter and chocolate, they taste great together.

Bridget:  They do taste great together.

Aaron:  None of this, “Outbound bad, inbound great.”

Bridget:  No. They both have to work well together but what I’m also dealing…because I’m starting with a one to three, so one…

Aaron:  Prospector to closers?quote3-gleason

Bridget:  Correct. I’m hoping to shift it. This is where it’s important to have metrics and data and have clean data and to be monitoring that all along the way. Again, this isn’t a set and forget. One other thing that I would strongly recommend, particularly as you’re setting up your sales team and your organization, is pay really close attention to data and hire a sales operations person…

Aaron:  Collin, are you listening?

Bridget:  …very early on because you can’t…all of these metrics, you’ve got to be monitoring over time. Again, I’ll use what’s happened at…Sumo Logic is a great example. Fantastic growth and success. The company is doing well and growing quickly. Those are all great problems to have.

What got left behind was really paying attention to clean data, how we’re tracking data, what are the important things to measure, because the thinking was, “We’ll get to it later. We’ll get to it later. We’ll get to it later.”

It makes it super hard to unravel and then to determine what is the right ratio of prospectors to closers, when is the right time for us to introduce an account management team and how many accounts should they be managing. Again, it’s going to change also. It’s not going to stay the same. Having good systems in place to continually monitor it is also important.

Don:  I think one of the great things, for me just personally, coming out of Yammer…I joined Yammer really early. I was the first sales operations guy on the ground. I got there and it was like, “OK, just please listen to me. Let me help build this right so that we can make this a great company.” To David Sack’s credit, he was like, “Just listen to what Don says.”

I went in there. I was like, “OK. You guys just bought Salesforce. I didn’t have a mess to clean up.” I was like, “This is the way we do data. This is how we’re going to import stuff. This is what needs to be there. Here are the required fields.” Having all that stuff laid out really early, having everyone on board really early, it’s really, really critical.

Aaron:  Plus, I got to say I really like your color palette.

Don:  Thank you.

Aaron:  The orange…


Don:  …I was told to wear bright colors because we’re going to have a dark screen. [laughs]

Bridget:  I didn’t listen to that.


Aaron:  But in all seriousness, here’s something about data because…I called out Collin and he’ll laugh at this. Collin is CEO of Predictable Revenue but also our software company called Carb.io. For a year, I tell him and the team, “OK, yeah. There’s this cadence, blah blah blah, like email, blah blah blah.”

Really, all this is about, you can’t have an outbound team that is successful in scales past three weeks unless it’s all about data management because if you don’t keep your data clean…and this is true about not just outbound but the teams…

If you don’t keep it organized to some level…because you can’t keep it perfect. If you don’t keep it organized or clean to some point, you’re going to hit a wall. It will be successful for three weeks or three months but not three years. It’s that data.

Bridget:  The wall, Aaron, that is a painful crash landing when you hit that wall.


Bridget:  This is not a bump. This is a [makes noise] .

Don:  This is like when you bring in that sales ops person there like, “Oh, I got to clean this mess.” [laughs]

Aaron:  It’s going to take at least four months, if not longer, because now so much of these great apps about more calling, more emailing, more social. Generally, what that means, whether it’s for prospectors or sales people, is that the more activity they’re doing, the faster the database gets screwed up.

It’s tough. We’re taking a different approach to it but I’m glad you brought that up because it’s really another major key alert, cloth talk. [laughs]

Don:  Another point I want to go talking about doing ratios, one of the things I try to stay away from is doing one to one because I think when you have a one to one ratio between a prospector and a closer, you may have bad habits to develop between those people that are…

Aaron:  They come too close?

Don:  Maybe. Maybe a closer will treat their prospector like their secretary.

Aaron:  Have you ever had a prospector team that was pooled, where they weren’t assigned to specific closers?

Don:  Yeah, that’s typically how I try to do it.

Aaron:  You pool them?

Don:  Yeah. There’ll be a group of the prospectors. They’ll have whatever opportunity they happen to get for a meeting. It just goes off to whatever the correct closer is. It’s not a one to one ratio.

Aaron:  I’m a very evangelical believer that let’s say a prospector has to be assigned to a specific…some number from half to maybe four or five specific closers because of that relationship. Specialization is really about the relationships.

When a prospector and a closer work well together, when an account manager works well with an AE, because that can help trump all…if the data is bad, if the process is bad, if there’s miscommunication.

It’s not to get lost in the shuffle, but the relationships between the teams are so important, any role to role, because that really can tie it all together.

Bridget:  I think, Aaron, that’s really important also for our customers. One thing that you talk about in the book is this hand off, and is this hand off…

Aaron:  The new book or old book? [laughs]

Bridget:  They all blend together…


Don:  …yeah. I think both have that. [laughs]

Aaron:  There’s a question, “Doesn’t having people get passed off from one to another makes service worse?” If that’s what you’re…

Bridget:  I’m saying no. It shouldn’t make service worse but the service can be disrupted if there isn’t a good relationship between the people behind the scenes. I don’t think it needs to make it worse.

Aaron:  It should make it better.

Bridget:  I think in most cases, it should make it better but if it’s disrupted behind the scenes, trust me. It will get disrupted for the customer also. It’s really important to have, I agree with you, good tight relationships behind the scenes because that will only help the customer experience.quote4-ross

Aaron:  I will tell you if you’ve ever either been in place or had someone complain that, “Well, the customers hate being passed off from the prospector to the closer to account manager,” well, because you’re not doing it right. That’s the problem. Either it’s the relationship or the process. There’s something there. It’s not the specialization, it’s how you do it that is the problem. We’ve seen it done well many, many times.

There’s one tricky area I want to dig into here. That is this area of, OK, someone signs up. They become a customer. It’s called account management, which to me implies there’s someone who has a sales quota selling to current customers versus customer success.

The two ideas, when do you combine them into one person, when do you have to separate them so you reduce the inherent conflicts between, “I want you to be successful but I also need to make money”? How do you balance those? What works and what doesn’t? Maybe Don…

Don:  The way that I’ve seen it done that worked really well is making sure that the customer success person is tied to KPIs, paid on KPIs that have nothing to do with how much the customer is bringing in as revenue. Normally, those things get tied to how well are they engaged? How many users do they have meeting goals or different things that aren’t revenue related.

Aaron:  Yeah. It’s hard to do that. There’s no perfect way but you got to do something.

Don:  You have to find something. The account manager, of course, is going to be the person that’s tied to making sure the renewal happens, making sure there’s some level of upsell within the account.

Then of course, the customer success and the account management person have to work together so that the account manager can be successful with that renewal. Now when you’re small, it’s hard to break that off but you have to…


Aaron:  …you got to start early.

Don:  You got to start early.

Aaron:  You got to start early when you’re small, earlier than you think.

Don:  Yeah, earlier than you think but if you’re really small, it’s going to be the same person. That’s going to be one of the first places you want to look to specialize, is to break those two people off.

Aaron:  Jason says, and I believe Jason, most companies, by the time they get 10 or 15…most tech companies, 10 or 15 people. One of them is generally a dedicated, someone to customer success, whether they’re an executive, they’re…but there’s someone who is focused on that full time earlier than you think. Bridget, do you want to add anything?

Bridget:  We have…

Aaron:  Or when you’ve seen it fail?quote5-gleason

Bridget:  We have an added layer of complexity. If this isn’t already evident, newsflash here, the distance between the idea of specialization and execution can be quite long and bumpy. It’s not that easy. It may sound easy, “Let’s just specialize.” It’s not that easy.

For us, the closing reps, our product really lends itself to land and expand. Oftentimes, the initial deal is small but then it grows over time. The first question you have to answer is, “When do I make the hand off to account management or customer success? Do I do it right at the point of close?”

For us right now, we settled on six months. We’re looking at the data there because there’s still a lot that they can do to realize more the potential of that particular account. From there, it goes to an account manager that is very proactive, that looks at their usage, that looks at how are they doing based on a similar, let’s say, cohort. Are they having any issues? They’re very proactive.

Customer success for us is much more reactive. They work really closely together. In fact, all three groups have to work closely together but as soon as the selling motion starts to tip from less selling and more maintenance, that’s when we wanted to go to account management.

We’re looking at that data, again, right now to see when does the selling motion tip to be more account management versus more selling or upselling. It may go to nine months. It may go to three months. Again, it’s back to data.

Don:  Similar situation I’ve seen it where…because when you have a land and expand situation, you have a closer who just wants to get the foot in the door, but then they have to have some level of time to be able to do that upgrade and get compensated for that upgrade.

You got to have that clock so that they know, “OK, I got to do this within the certain time frame or else, I’m not going to get compensated, and it’s going to get handed off to my customer success person or the account manager. They’re the person who’s going to get the upgrade.”

You got to figure out what is that for you at six months. I’ve seen it. We’ve done it in 90 days because we want to keep our closers focused on closing but again, like smaller ACV, it’s a little bit more transactional.

You got to have that point in time. It’s got to be in comp plans. Everyone is going to know this is the date that it happens. It has to be exceptions that occur. Everyone knows what the rule is.

Aaron:  Here’s the trick. I like that. I think everyone struggles with that AE to AM account closer to account manager hand off. At what point generally does the AE or closers introduce either the idea or the person of the account manager?

Because it’s not going to be like…let’s say there’s a six month hand off. That’s not when they do it. They should do it earlier. Is it 30 days earlier? Is it actually when they buy? How early do you start introducing that, “There’s going to be a hand off. Here’s the process. Here’s the person.”?

Bridget:  Go ahead, Don.

Don:  For us, typically, as you know that there’s a contract out to be signed, we’ll get the customer success person involved. Normally, our customer success person is typically involved in the trial. The person is already introduced into the account. People know who that person is…

Aaron:  Earlier is better, yeah.

Don:  Earlier, the better. Then once this is transitioned off of the closer, it’s the customer success person that’s managing the account. As they identify, “OK. Hey, there’s going to be an upgrade potential,” or it’s getting closer to renewal like within a 90 day renewal, that’s when we make sure that the account manager is introduced into the account.

Bridget:  I would agree. In an ideal world, in which we don’t live, the earlier better, like right away.

You want them introduced, at least the concept that this account is going to move to an account manager that’s going to be able to be proactive and take better care of them, like to your point, that they’ll get better care with specialization and handing off than if they’d stayed with a salesperson.

The reality of it for us is a little bit different. There is this tension of a salesperson trying to optimize the amount of, let’s say, upgrade or revenue potential that they could get from this account within the first six months.

It’s important to me that nobody on the team is doing unnatural acts to try to pull in additional revenue. That’s not good for the customer.

Having just a healthy balance between trying to optimize around the revenue but always bearing in mind the customer has to be first and has to be what fits their buying schedule as opposed to what we need to do because the account’s going to cross the line and go to an account manager.

Aaron:  That’s true, and ultimately you have to keep that principle in mind which is customer success is not just the role, it’s the teams together working together even if the rule…Sometimes you have to break the rule. It just doesn’t make sense. Let’s make the customer successful for XYZ reason.

Bridget:  That goes back to your point, Aaron, about just having good relationships between individuals…

Aaron:  Yeah, where there’s trust.

Bridget:  …and where there needs to be a lot of trust. Really in any SaaS business it’s so important that all the different functions – product and engineering, and marketing, and customer success, and account management, and sales, and finance – all of it has to work so seamlessly together.

Having one single agenda, which is the customer, and at all touchpoints that everybody’s thinking about really how to optimize that experience. If we optimize to that experience, everyone is going to do better. But it’s in reality…again, it’s hard.

People do have their own different things that they’re optimizing towards, and so to get everybody rowing in the same direction takes continual diligence and effort.

Aaron:  I’m going to open this up for questions pretty soon so if you have one…but I’m going to ask one last question here.

In terms of executives, there’s sales development, there’s customer success. What’s the basic leadership structure for the team’s that are touching customers in either sales cycle or prospecting sales cycle after? Is it all to you? Is there a couple other…? How does that work?

Bridget:  For us customer success reports it directly into the CEO, which is great. I think that’s where it belongs. I think sales operations, my opinion, right now it reports into the SVP of sales, but I also believe that should report in to the CEO. It’s very cross functional.

The SDR team reports in to me. What else did you ask? And the account executives report up into me.

Aaron:  There’s a customer success team and executive who’s a peer to you.

Don:  Yes, the SDR team reports into sales ops. They report in to me. AE team reports in to our VP of sales. Customer success reports in to the CEO today. We’re small. As you grow that splits out into more of a…

Aaron:  It’s all relative because to a two person business here you’re huge.

Don:  [laughs] Yeah.

Aaron:  Let’s see, any questions so far? We’ve got some hands. Who’s got the mic? Actually, we’ve got a bunch of questions so let’s…maybe we’ll use the rest of the time for questions.

Audience Member:  I don’t know if you guys have this, but can you talk a bit about the boundary between…

Aaron:  Sorry, where are you? OK. Why don’t you stand up for a second?

Audience Member:  Can you talk about the boundary between an SMB team and an enterprise or mid-market team? How do you draw the line and then the relationship…?

Aaron:  How you segment those…?

Audience Member:  Right. How do you figure out where the segment is, and what kind of relationship is there between the two teams?quote6-otvos

Don:  Today the way that we do it is we look at the number of people that are on LinkedIn. Because, again, this goes to data sources and data cleanliness.

You have to figure out what your one true source is, otherwise you’ll have someone going, “Oh, Mattermark says this, and LinkedIn says that, but then I look at this press release, they say this.” You always have to look at what your one true source of truth is.

Aaron:  Even if it’s wrong, it’s better to have one source.

Don:  Exactly. Even if it’s wrong. But usually looking at the number of people on LinkedIn if someone says they’re working at the company that’s usually a good judge of knowing how large a company’s going to be.

That’s what we rely on. Then you just figure out what the demarcation point is between SMB and enterprise and…

Aaron:  What is it for you guys?

Don:  We do 0 to 200 is SMB…

Aaron:  Employees.

Don:  Yeah, employees. 200 to 1,000 is midmarket, and then over 1,000 is enterprise for us.

Bridget:  I could almost just say ditto, ditto, ditto, ditto. We also use LinkedIn as our source of truth, and I agree it actually doesn’t matter. Just pick one and then stick with that one.

Aaron:  It’s the consistency.

Don:  The important thing about LinkedIn, too, isn’t what they say the company range is, but the actual number of those people that are…

Bridget:  That have profiles.

Don:  Yes. [laughs]

Bridget:  The only issue that we’re running into with that is that around lead routing it’s hard to do automatic lead routing, because LinkedIn doesn’t have an API that tells you what that number is.

Don:  Exactly. Exactly.

Bridget:  But we now have SMB and midmarket right now is together, and that’s less than 1,000 employees as measured by LinkedIn, and then 1,000 and above is field. But, again, it’s going to vary by company, and industry, and really the sales motion.

When do the sales motions look different? For Sumo Logic…you may have the same at Datahug. We can have very big deals because all of our pricing is just around the amount of data that you’re ingesting. You can have a small company that can have a huge deal. You can have a very large company that does very…they’re not as likely to, but has smaller deals.

You just have to look at the complexity of the solution, the complexity of navigating your way through the sales process. Those are two factors to determine where the line is.

Aaron:  Basically, in other words like most of the answers you have to use your damn brain to fit it to your business.

Bridget:  Damn.

Aaron:  I know. Sucks, doesn’t it?

Bridget:  I know. You can’t just read it in a book, unfortunately.

Aaron:  Only this book.

Bridget:  That one.

Don:  The other important thing, too, is once you stick with a team, if someone happens to find that it changes you can’t change the team. I think that’s another good point. You don’t want to shift teams just because oh, LinkedIn now says this. So now you’re going to get a new sales rep?

If a team is working with a customer you want to stick with that team regardless of what ends up happening. If they end up having explosive growth, and they crossover some point where they’re now enterprise instead of SMB, you want to stick with the team they started with.

Bridget:  Just so you know, even that point is highly debatable. Companies will do a different way. You just have to decide how to do it.

Do you make the decision that no matter how big or small the company gets it stays with that particular segment or person who’s selling, or is there some rule that when it crosses a threshold for X amount of time either higher and lower that you make a change?

I think you just…there’s not a right or wrong. You just have to have some way, otherwise you’re going to get all kinds of territory disputes. It’s highly distracting.

Don:  Have the rule and make sure everyone knows what the rule is.

Aaron:  That’s really important so I hope you heard that. You pick your rule, and it’s never going to be perfect, perfect, but you have to stick to it. It’s the consistency which is super important, not…

It doesn’t matter if it’s 200 employees to 250, whether if companies grow they change. Pick something and stick to it.

Then, of course, you’ll change it. When you change it you change the whole thing because everyone knows, because you’re always changing it. It’s a paradox. You pick one thing and don’t change it, but then you change it all the time, unfortunately.

Bridget:  Exactly. That’s exactly what you do.

Aaron:  See? There’s your answer.

Bridget:  That’s what I’m saying. This isn’t…this is messy.

Aaron:  It’s easy. OK, another question. We’ve got a bunch of hands. Who’s got the mic? Bit slow here. This guy first. One, two.

Audience Member:  What do you have to say about micromanaging cold calling scripts down to the word, and even demo scripts?

Aaron:  Good lord.

Don:  I hate that.quote7-ross

Aaron:  First of all, in the outbound session I don’t know what they talked about around that. But I will say scripts are very handy in training. In training. As soon as someone’s trained they should go away, basically. They might have cheat sheets, but…

Be as micromanaging, as anal as you want, in the training. Once that’s done, let them do their thing.

Don:  Trust you hired the right people to do the right things, because you don’t want to come off as scripted on a call. That’s the worst.

Aaron:  It’s the kiss of death.

Bridget:  I think the way also just to think about it is think about how you respond to a scripted message, whether it’s a phone call or an email. But I agree that to learn it, super important.

Aaron:  Hello. You have won a free trip to the Bahamas. OK, question, next one.

Audience Member:  I had a quick question. My team originally so take SDR and then to sales rep, and my original ratio for my sales reps was they were booking 50 percent of their meetings.

Drove that down to 25, now drove it down to 20. Have it probably at 15 percent next quarter. Do you recommend taking that all the way to zero? Are you saying that a sales rep doesn’t need to prospect at all?

Aaron:  No. Let me answer this. What he’s basically saying is sales reps used to do half of their own meetings and went by…Having prospectors, they’ve been able to reduce the amount of meetings the sales reps has to do for themselves from 50 percent to 15 percent.

Should it go to zero? No, it shouldn’t go to zero. It’s more important the dedicated prospectors should do all the high volume prospecting. The sales people or people who sell should do their own prospecting, but just do a smaller list of targets, like key accounts, like one or five or maybe 10 or 20.

It could be strategic partners that are going to generate recurring relationships. It could be big accounts. But a small number of important ones. All right, question back here?

Audience Member:  Right here.

Aaron:  There we go. Do we want to swing back here?

Bridget:  I think there’s one here.

Audience Member:  Can you comment how this would all work in an organization that was largely remote?

Aaron:  That’s larger…

Audience Member:  That’s largely remote.

Aaron:  Largely remote. Do you guys have any…?

Don:  I haven’t really run into that. One of the things I think that I’ve always tried to do is it’s good having everybody, at least on the prospect side…

Aaron:  It’s the same principles.

Don:  Having people all in the same room and being able to feed off of each other’s energy and hear what’s working, what’s not, is always a good thing. I’ve not run into it as much for a remote team.

Aaron:  It’s just more communication?

Bridget:  I wouldn’t do anything differently if everyone is distributing remote in terms of specialization than I would if everybody’s together. I still think it’s just as important.

Don:  Yes, specialization’s still the same.

Bridget:  I think the communication is what is going to…that’s where you’re going to get challenged. You have to really spend more time on that.

Aaron:  Again, the relationship building between teams, between people is really, really, really, really…this is what my three year old would say, because she’d be like, “Really, really really,” and she’ll just keep saying it. Really important. Really important.

Collin:  Hey, Aaron.

Aaron:  Who’s got the mic?

Collin:  I just jumped in back here.

Aaron:  Collin. Here’s the carb.io guy, my partner.

Collin:  We deal a lot with remote prospectors and our entire account executive team is remote. We’ll actually have our guys when they’re new to the company…

Aaron:  Can you hold the mic a little closer?

Collin:  We’ll have them jump on demos. We’ll have them on weekly calls and on check in calls on the customer success all the way through the pipeline just so they get to know the account executive, they get to know the customers.

You guys are right. The more that you can actually get them to maybe not face to face, but on FaceTime, on Hangouts, on whatever it is, just to build that relationship, so that they’re not just an email address that pops up in your Gmail when you see those, it really helps build that relationship.

Aaron:  Making real people behind the email and phone.

Audience Member:  Firstly, thank you guys. Great discussion. Really appreciate all the knowledge. For some context, six months ago my company we were all inbound AEs fielding everything. We started piloting outbound late Q3, saw some success there, and are scaling that currently. We’re now at a stage where we’re ready to further specialize and do inbound SDRs.

Curious to hear your experiences with inbound SDRs. What attributes do you look for among inbound SDRs as opposed to outbound, and any best practices for taking that leap of faith? We don’t want to squander those opportunities with more junior level employees.

Don:  It’s a great place to hire entry level folks. I think having and inbound SDR usually…I know you say squander opportunities, but normally those inbound leads are usually the best ones to put people on in case…

Aaron:  The easiest, yeah.quote8-otvos

Don:  …in case it does get squandered. That’s where you want them to really cut their teeth, to understand what do people say when they’re coming inbound. When I talk to them they can hear the things, hear the keyboard.

Aaron:  Follow those white paper leads that they mentioned.

Don:  All those white paper leads, yeah. [laughs] If you can have the ability to have specialization down to that point it’s a great place to have those entry level people to be able to…

If you have enough specialization you can then move them into an outbound role, have an outbound role move into an AE role so that you have some sort of a nice career path for someone to be in.

Audience Member:  Do you guys have a sense for how many leads a month that they have to review or touch can one now inbound SDR or market response rep handle? I used to say 400.

Don:  I’ve been at both ends of the spectrum. I came from Yammer where it’s like every sign-up was essentially an inbound lead.

We had all these inbound leads, hundreds, thousands of inbound leads to a situation where we don’t necessarily have a freemium product so we get maybe five. I’ve been at both ends of the spectrum.

Aaron:  In terms of if you’re thinking if we have 2,000 inbound leads that need to be checked by a human, how many people do we hire to handle those?

Bridget:  I think that’s also a hard one to answer, Aaron, because it depends on how easy it is or difficult to qualify or disqualify and disposition them.

Some things depending on the market or the segment that you’re in it may be very easy to determine whether, “Yeah, this looks like a good lead or not?” and who it should go to. If that’s the case they can go through a higher number more quickly.

I know for us there’s a lot of research that someone needs to do to determine is this actually a good lead for what we’re doing and size? They can go through a much smaller number. I don’t have a good answer.

Aaron:  I’m going to stick to my original and one benchmark of one dedicated inbound SDR or market response reps could handle 400 leads a month.

Bridget:  400 a month.

Aaron:  That a human needs to touch.

Don:  That’s 20 a day.

Aaron:  20 a day. It’s like deleting Santa Claus’s… That can vary. If you get 2,000 leads, and they’re are all webinars you may need one person. If you get 2,000 leads and they’re all contact leads you may need 10. But 1 to 400 for inbound is still…

Bridget:  It’s not a bad number.

Aaron:  I’ll say that’s it, because why not.

Bridget:  Until you change. Until you…


Don:  [laughs]

Aaron:  That’s the rule I started at Salesforce so I have some experience with that. 20 a day. They pile up. It doesn’t sound like a lot, but they pile up. Another question. Here we go.

Audience Member:  You were mentioning, Don, that when you were starting out you got your Salesforce set up, blank slate.

If you guys were going back and deciding to track data that you wanted to track that you find the most relevant, and especially things that you would recommend people to be tracking early, what are some items that maybe aren’t the most obvious, like obviously, revenue opportunities all that that everybody’s going to be tracking?

What are some non obvious things that you’d definitely recommend setting up in early Salesforce?

Don:  If you have the ability to do it, if you can have some way to tie in your usage data back to Salesforce, either…

Aaron:  Like product usage.

Don:  For your own…because a lot of times what happens is you have all this back end data from your own product that doesn’t associate itself with Salesforce, but that’s really good data if you can marry it.

If you have a way to either use an API to sync it into Salesforce or create a data warehouse so that you can then say, “Oh, hey, for all of our users I now know all this demographic information.”

Aaron:  People still use the term data warehouse? I’ve lost track. That’s a good question and good answer.

Don:  If you could do that early on, it ends up being such valuable information for your product team. You have a lot more…Yammer is the example I’m thinking of.

When people signed up for Yammer they would use an email, and that’s all we would have. Then my team was responsible for going, “OK, if someone came up from this domain tell me information about this domain.”

We got InsideView and we said, “OK, I have this domain. Now I know revenue. I have location. I have number of employees. I know what industry they’re in.” But none of that existed on our back end system. All we had were these emails.

What we did was created this data warehouse to say, OK, now for all of these people that I know are users that are most frequent users of our product, they’re in this city. Why don’t we have a roadshow here? You’re able to start doing that kind of analysis.

Aaron:  You get many AOL emails?

Don:  [laughs] No, not for Yammer because you’ve got to have a corporate email to sign up for Yammer.

Bridget:  I totally plus one that. I would say usage data, that’s probably the most significant that you can incorporate to give an idea of what a sales rep should do with regards to a prospect, or a customer, whatever.

Don:  Then you can also start measuring your CSMs that way, too.

Aaron:  We have time for a couple more questions. We’re going to end a couple minutes early, partly because I’m doing a book signing at the Carburetor, The Carb.io Predictable Revenue booth at 12:30.

Either we’ve got books, or if you get your free one upstairs in the swag shop. It’s way at the top in the back hidden under blankets.

Don:  Behind the stairs.

Aaron:  Yeah. It’s 12:30. But last couple questions. How about this gentleman here? This one. You first.

Audience Member:  I know the topic of scripting a sales process is obviously controversial, so I was interested to hear that the three of you agree post training to not script it. I’m curious. How do you recommended evaluating what is and isn’t working if you’re not scripting it after training?

Aaron:  You look at the final metrics plus you just do one on one coaching, typically. The metrics are useful but they can also lie. If someone’s struggling…

Audience Member:  But if you don’t know what they’re saying on the call, how do you know what to recommend as best practice?

Aaron:  First you find out is someone struggling and then you would listen to the call. If they’re doing well then, great. If they’re doing super well then you’d listen, too. What are they doing so well?

Don:  A lot of what we do, I know Kyle was on before, but we do use SalesLoft. One of the wonderful things about that is it has a click to dial where it records the call. Every call is attached to the Salesforce record.

It’s really easy for us to go back and go, “Wow, you had a great call,” or if someone is struggling be able to go through their calls and help them, do some coaching around, “Hey, maybe you want to try this, try that.”

Because, yeah, it falls back to metrics. Are they booking the meetings that we say that they’re supposed to be booking?

Aaron:  Are the meetings turning into real deals or is it just being…?

Don:  Are the meetings with the right people? Are they quality meetings?

Audience Member:  When the metrics are down you steer them back to what you see as the best practice.

Don:  Yeah.

Aaron:  That’s why it’s so important, because it’s sort of like clean data and consistent rules, can lead to useful metrics. If you have irregular data, and you have people doing different things, the metrics are worthless.

Audience Member:  Thank you.

Aaron:  Yes, sir.

Audience Member:  I guess we talked about deciding when to introduce and adjust specialization. Would you look at any particular revenue cost or growth metric in order to make or adjust a decision?

The decision to introduce specialization, ideologically, you have to work on management concerns and challenges about, “Hey, you know, we’re going to introduce what used to cost us just the closer to bring the deal in, and now it’s going to cost us the closer, the BDR, the list builder, all these extra costs at least initially.”

Aaron:  Extra investments.

Audience Member:  Extra investments. What metrics, if any, would you look at or other factors to make and adjust that decision?

Don:  Employee happiness is one of them. Because I think one of the important pieces of specialization we haven’t really talked about, is being able to give somebody something different to do. Doing these, especially like the prospector’s job, the SDR job, it’s hard.quote9-otvos

People can get stale, they get burned out really quick, but if you have specialization, you can move them into something different, maybe they start as a prospector and then they start inbound then they do outbound. They shift from outbound and then they do…

Aaron:  They’re all good farm teams.

Don:  Then they do target accounts and they can start closing SMB deals. As long as they have something different to do at each stage they’re going to be happier employees. They’re going to stay with you longer. You’ll retain them. It’s hard to quantify.

Aaron:  Yeah. First you have to do it.


Aaron:  The way you do it could be a bit different. You can start small and get some data if you feel like you need, but you have to do it. It’s not an option. No you don’t have to do it the same way as sell, one call consumer, one phone call and you close it and you’re done.

Don:  Yeah, it is transactional.

Aaron:  Very transactional. We’re going to wrap up. I’m going to be here. I’ll say hi to you. Hey thanks very much.

Announcer:  Aaron, Don, Bridget, thank you very much.

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