Building Your 1st Outbound Team: How To Get It Right the First Time

Ladies and gentlemen, please welcome back to the stage, Aaron Ross.

Wow, we have a full house. Look at this. We got people sitting in the aisles, jammed on the sides. Thank you. We have a great panel for you today. I'm going to introduce three of my cohorts here. Let's start with Alicia Anderson. Come on up, Alicia. Yeah. Woo hoo. Alicia actually has worked, worked with me before. Right now running an SDR team at a company called Captivate. Of how many people?

There's about 10 of them.

10 of them. Okay, great. Has built multiple teams. And we've got Ryan. Ryan, come on up. Ryan. Ryan, I've known you for years. For some reason I'm totally blanking on your last name this moment. Donahue. That's right. Thank you very much. What are you, Are you running a team at Venminder right now? Again, multiple teams help build multiple teams. Excellent. How big is that team right now?

Currently right now we're at eight reps.

Eight. Okay. And last but not least, we got Andrew Burger from Square. Come on up. Hey, Andrew, thanks for joining us.

Absolutely. Thanks for having me.

Like what, you came like a block or two away?

Just a block away.

Alicia from New York. We are based in Colorado and I'm up from LA yesterday morning. Okay. So we're talking about building outbound teams. Your first time. I know, I have my notes here. Here we go. But before we get to that, I want to actually start with a quick fun fact. Sastra cash doesn't really help me here, so maybe Andrew, I know you said you have a new fun fact just about yourself, something personal here, a couple things.

So one, probably the only person in this building, probably San Francisco, that swallowed a toothbrush at 18 months old and still here to live the tale gave my mother and my father a heart attack. But we're here and in a former life, used to play professional sports. I'm sure a lot of you know that sales translates to or sports translates to sales. And so. And here it is. I played baseball. I was with the Diamondbacks and the Giants in the minor leagues. If you ever want to know what it's like to be a professional, professional or minor league baseball player, it's just like being an sdr. You're grinding every single day. There is no glory. You're taking 10 hour bus rides from Augusta, Georgia to Kentucky, up to Pennsylvania, back down in the middle of the summer. It's a grind, but it's the glory's at the top.

Yeah, cool.

Yeah, cool. Mr. Ryan. Ryan Donahue.

Yeah. Donahue.

Interesting.

Fun fact.

I mean, it doesn't have to be interesting.

Kind of morbid, I guess. But I collect skulls. Not human skulls, but.

Pokemon skulls. Yeah.

Like, I just got a gift from my folks right in the mail, and my mom texts me and said, hey, check your front door. And then my dad texts me, hey, did you check your front door? I'm like, what is going on? All right, I'll check my front door. So I checked the front door, and there's a cup from an Amazon coffee cup that has a skull in the bottom, like an actual formed skull. It was pretty cool. Like I said, kind of morbid, but still like you.

Thanks.

Okay, Alicia, so I'm known spontaneously to break out into my favorite print song after any presentation that I get. So if you're lucky.

Yes, in 20 minutes. All right, so, okay, quick question. Start off. If you're starting from. If you don't have a team today or you're just starting at the very early stages, how long does it take to get a team built where you have something working? Because I feel like that's a huge misunderstanding for time. Alicia, what would you think to get.

Something as working as an optimized pipeline.

Or just, we've got some traction.

We've got something working here usually much longer than expected, because I think most people bump up against.

Is it 30 days? Okay, 12 days.

It could be two or three months.

Honestly, that'd be fast, too.

Well, so the way I would look at that is, you know, when can you actually start tracking some actual data that you can start to see some trends in? And for me, I think you're looking at, you know, four, five, six months before you can really start getting some data that you can use to help you understand where you're going, where's the market? What can you expect as far as quotas? So for me, it's normally four or five, six months. You can bring people in right away and start churning results if you set up a pretty decent process. But to really have it be predictable.

See how it's working.

Right, right, exactly.

Because unless you can see the funnel, you don't really know.

Right, right, exactly. Yeah.

I mean, that's a great question. I initially thought, yeah, three to six months, we're going to see some results. And we saw incremental results, but we really didn't have an understanding of what was working until about 12 months later, to be completely honest. I mean, about a year. Aaron says in his book, we use it as the Bible at square. I give every new hire of the book, nine to 18 months. And I was like, oh, no way. We're going to get this thing rocking and rolling much sooner. But it's completely true. I mean, still to this day, we're about to 18 to 24 months into it by now, and we're still now tweaking. We know what to expect, but we want everything to go up into the right and we really don't know what the levers to pull to make things go up and to the right till about 9 to 12 months from putting someone in seat and saying, here's a list call that doesn't really work. You need to optimize. Get with marketing, get with hr, go with finance, Pay these people. You ever want to deal with payroll and your commissions and checks not working, that's always fun to deal with, too.

Yep. Okay, great. Okay. So, Ryan, what's a mistake? You know you've built three or four teams now, Something like that. A bunch. How many? So what's a mistake that you've made at least once or twice or you still see people, probably most of the people in this room might be making as they're getting their first team off the ground?

Well, I'll give the people in the room a break because I don't know you.

Or their last name.

There's a couple things. Some of the mistakes I personally made is going out and purchasing the wrong tool. Okay. A lot of people out there. I get calls all the time, hey, what tools should we use to kind of help our SDRs and make them awesome? And I'm like, well, it kind of depends what's your process? Because there are tools that are built specifically for certain processes. And really what the tool's supposed to help you do is, is help your reps become more efficient and then also help you with tracking data. So getting the wrong tool that doesn't fit your process can be a real setback.

Why did you buy the wrong tool? Was it because someone told you best and you just bought it? Was because you didn't? Sort of. What did you miss when you were evaluating them or looking at them?

I'll be honest, I'm kind of a demo junkie, so I love sitting through demos of the latest and greatest stuff out there.

I just.

I dig it.

But That's Ryan Donahue.

200 emails.

I didn't even think about that.

Oh, you're so screwed. Shouldn't be your last name again.

I'm a sales guy at heart too, so I'm an easy sell.

But again, Ryan.

No, I didn't ask the right questions. Okay. Like for instance, is there a limit on how many emails my reps can send per day?

Some of the tactical day to day.

Like, I mean, just functionality.

So how long do you think you should be running a team? And let's say it's two weeks, A month? Two months before you feel like you might have a better sense of knowing how to evaluate the right tool if you haven't done it before.

Well, so if you haven't done it before, the first thing I would recommend is get your process down. Okay, so how do you want your SDRs to function?

So process first and then before tools, Right?

Exactly. I know there's a lot of talk out there about people process tools. Okay. First off, I think you need to, number one, make sure you have the right person running the team. Building out the sales development team, business development team. Because if you don't, you're going to run into a lot of mistakes that are going to be made that are going to set you back. You're not going to be tracking the right data that's going to help help you be actionable. I mean, that is the biggest mistake, quite honestly, that I see out there.

With wrong leader of the team.

Yeah, you got the wrong person running. And it's typically the first SDR you hire who really kicked ass. You're like, oh my God, they were amazing and you should be the manager. And they don't have a clue what they should be tracking or how to coach somebody.

Actually, I'm going to take that. It's a great point. I want to get to and use that Alicia here, which is if you're starting out and you either don't have someone who's dedicated SDR or you can't get a dedicated manager or dedicated sdr, you sort of have to work with part people or part time. What do you think are some ways to get going when you can't put as many people or as much focus as you want on it, but you're ready? Have you run into that much?

Definitely. Where I'm working now at Captivate, not.

Everyone can get a manager up front.

Not everyone, no.

Right. It helps, but so generally you would start with specializing your time. So you're not necessarily going to have a specialized team, but you will be.

Able to one person, have one person.

Divvy up their time and designate call blocks and email blocks where they can just devote their time specifically to prospecting because that's when you're going to going to get the best results. When you can actually focus because it's really difficult to switch gears to go from I'm a hunter to now closing to account management.

Or it could be the founder. Right, Set aside like a day. Like Tuesdays.

Exactly. Yeah. It could be whether it's hours within the day or it could be entire days where you're just focused on one particular piece of the funnel and that's when you'll get the best results.

Let me add one more thing to that too. What I said about hiring the right manager, that's really hard to do. All right. There are not a lot of people who are still a newish proficient in this, so it's not an easy task.

Besides you, that is once again, Ryan.

No, just kidding.

Yeah, no, it's tough. It's not like the current form of that role hasn't been around for that long. So it's still relatively new.

I mean, to jump in there. It's a great point. Because the manager, the way that I see it, also has to be a builder. You have to continually to tweak and build the infrastructure and build the processes. Some of the best people that I've worked with and that run our teams are builders. First. They want to aspire to see greatness from the team and from our production. Yes, they have to mentor and be in the trenches, but they also understand the metrics, they understand the processes, they understand how activity tracking works in Salesforce to take a step back and see everything from bird's eye view, but also can dig in and tweak when necessary. You know, you hear the builder versus manager a lot. And where I've seen success or I like to jump in, is I like to build things too. And the people that are successful at square, specifically in these type of roles, in these manager roles are people that want to build as well and tweak and continually to push and pull what will yield the most success and not just be this high level like okay, go make 30 calls, go make 200 emails. But they want to dig in and build as well.

Yeah, actually. So Andrew, now it's been in about this for a couple years. What would you say everyone wants to know about the fucking email template? What do I write in my email? My email. Ok, but in the scheme of things, would you rank the email templates that they write, the specific ones and separate that from the ability to write? Is like there are certain templates. Was that in the top 10%, most important things? How would you rate one out of 10? How would you rate it as importance? Because People obsess about them.

So I hate when people obsess about writing emails. I just want them to throw shit at the wall and see what sticks and iterate off of that. Sometimes I see people spending literally hours trying to tweak their language, misspell words on purpose for it to be the prospect thinks that they're actual human. You're not spelling 100% purposely not a template. It's absurd. I don't think email templates are the most important thing. I care about the action after the email. Whether that person responded to you. Great. Or did they open the email? Every tool out here can tell you what they open, what not. Did they call you? What did you do after that email? Did you follow up one day, four days, five days, seven days? I care about the action afterwards. That's what I want to see. And so the email templates, yes, it's important. But I mean, I'm sure everyone here, everyone here gets 20, 40, 50 emails a day selling the next best thing. And there is basic templates to fit in a cadence, a sequence, a template, or whatever happens afterwards. But I care about the next step afterwards, what action is yielded from that. So going back to your question about the template.

Five don't care. Five out of ten.

I tell my friends who are running their own companies, their founders are digging in because they don't have sales. They have like 10 people, and they're just trying to get their feet off the ground. I was like, just go. Stop spending time looking at the computer, trying to tweak the best language. Just like throw stuff at the wall, see what sticks. Okay, you get 10%. Okay, what did you do for those 10 emails out of 100 that work? Okay, now tweak them a little bit and do it again and again and again.

Great.

Okay, so we got about 10 minutes and a really important topic now, Lisa mentioned before is I think a lot of people, again, doing their first teams don't realize the potential differences between different types of companies and different verticals, different industries you target. Now, you have been at companies and even at Captivate, you guys have multiple different. You have two lines of business, different verticals. What has it been like and how similar or different can be the different types of verticals that you're targeting?

It's interesting because you can be within one organization and it can be like night and day from one side of the business to the other. And even within the ad sales side of our business, we are going after multiple verticals, and each one of those is completely Different. So the only thing that I would say would be consistent is our value proposition on that particular side of the business, but how we're positioning our conversation and who we're going after. They may be heads of marketing, but our conversation is completely different. And so it takes a lot of time to figure out all those nuances when you go into a new vertical. And so it takes more time than what usually people expect and anticipate. So you just have to build that into your process long term.

So what's one of the. We actually call it Nailing a Niche, which is the first part of the From Impossible book. And again, that section, if you don't know. So From Impossible to Inevitable is the book I did with Jason Lemkin. The whole first section, Nailing a Niche, came because for years, when people struggle with outbound, it's because they hadn't nailed a niche that's like number one. So what's a niche that you've nailed with Captivate? And then how long. I know you're working on multiple niches. How long did it take to nail that first niche? Or how long are you expecting to take to sort of nail the second niche because you've nailed financial services or.

Right. We've gone after finance. We actually had some issues because of that exact conversation and nailing Aneesh. And so that we actually learned a lot in what we didn't know. And we only had three months in terms of how we're going to go after that vertical and actually conquer it. So it's not enough time. So we're actually planning to circle back to it. But we've launched into a couple new verticals which are travel and automotive, focusing on our niche there. And we're seeing tremendous success. Within one month, we've achieved the same conversion rates that we were achieving after three months in finance.

So even though a working team, sometimes you have to re. You know, almost like not start from scratch, but it doesn't mean you can have automatic success in the next market as well. Sometimes you will, sometimes you won't.

Yeah, it varies. Tremendous.

Just one point. What about, for example, calling versus financial services and Versus. I know you mentioned before, we were getting ready one vertical, people don't pick up the phone at all, but in another one, people pick it up like crazy.

Exactly.

Which were they?

So in finance, we're having. We didn't get basically anybody on the phone. We were generally getting voicemails, or we're just getting automated systems where you actually couldn't even get a live Human on the phone. But in terms of travel that vertical, they're willing and want you to speak with them. So they pick up the phone all the time. Our conversion rates are incredible and we're getting referrals left and right, so it's completely different. So obviously you tweak the tools that you're using in outreach based on those sort of variables within each vertical.

Yeah. Part of the lesson is don't stay behind your computer just emailing all the time. Also pick up the phone and realize what works in one kind of target market might vary to the next. Actually, how do you guys look at the phone? Slash. When you look at email versus phone versus other, like social, how do you. What are the priorities? Are they all equal? Is one dominant?

We talked about this. You go ahead.

Look. I think the phone is probably the number one tool an SDR has, in my opinion.

Phone's number one.

Phone's number one. Good.

Okay, good to know.

That is the number.

I wouldn't disagree.

Yeah, well, I appreciate that.

Thank you.

But, you know, email's important and we use email as a tactic to kind of make that cold call, not so much a cold call, so that they've seen an email from the SDR and they kind of, you know, they see the name and they might not have paid attention. They might not even open the email. And probably 70% of the time they don't. But when you call and that name kind of triggers something within the prospect's mind, like, oh, wait, that sounds familiar. So to me, calling is vastly important. My SDRs book 75% of their meetings through the phone versus email.

Now, are these generally cold calls or they're calling them direct? Is it five follow up calls if they have emailing? Because you can have multiple types of calls. There's mapping calls.

Right, right, right. So it's typically within the workflow cadence, whatever you want to call it. So it's the series of touches that you make at a prospect. Okay, so our first touch is always an email. Second touch is a phone call. Third touch is another phone call. But we don't leave a voicemail. So so they call it a ghost dial. So it depends. I mean, we've done a lot of data gathering, data mining on when is the best touch that we actually get the most appointments booked. But really what I try. Which is, which is step one. I'm sorry, step two. So the first phone call, ironically. But what I really try to look at is, okay, so when my reps, we track when they connect with somebody, all Right. So when they connect with the prospect that we're trying to speak with, I want to know how many of those converted to a meeting. Because you could have a rep who sets up 30 meetings and you're like, man, that reps a rock star. Right on. But that rep also talked to 100 people. But you got another rep who set up 25 meetings and talked to 35 people. I want to know what that rep's doing. Okay. And I want to emulate that. Okay. So I saw an article on LinkedIn a few weeks ago and they call it, I think it was Steve, Steve Richards. They call it the batting your batting average. What's your reps batting average? And that is one of the most important metrics that I try to track and help coach my reps on. So the phone is vastly important.

Yeah, couldn't agree more. I think understanding what process is, you first have to understand how does your business make money? What are the economics or the unit economics? Our business is probably different than a lot of people's businesses out there where we have to close a ton of velocity and we're selling to. Everyone in this room would say SMB, but for us they're like large businesses, local businesses that actually process money, that use point of sale technologies. And with that, who we target, they are usually by a phone, whether it's any vertical or any segment. Our board of directors and our board meetings, we go out to the market and we say there's4.48 million businesses in the United States that could potentially use square. It's like, how do we find your niche? And then focus on there and per vertical and then per segment of those verticals, they have different propensities to what they respond to. I always instruct our team, our managers instruct their teams have an email first and then use it as leverage for the phone call. Right. I'm always about what's the action after the email. And so you reference that, whether it's saying an update, whether it's like, of course we hate the check ins and follow ups and you know, hey, I'm just here to check in, you got my email. But you use it as leverage because maybe they've read your email, they've seen your name and then you say your name, you explain why you're calling. I couldn't agree more. Like there's nothing that emulates the human touch. We love chats and chatbots and this and that. Everything's trying to be faster. But at the end of the day, I only see success by the people that are not afraid to pick up the phone and not afraid of rejection.

Yeah, we see it usually doubles your results when you take the phone seriously.

Yep.

All right, so we're almost out of time, so quick question first. And by the way, I know there's a lot of people here. Maybe if you have questions, you want to mob them, maybe go hang out at the. I have another panel after this. But if you hang out, the predictable revenue booth in the hallway might be easier for people. People to manage. But in terms of a last tip to leave people with, let's start at this end.

The last tip. Don't underestimate the infrastructure that it requires to build a sales team. An outbound sales team, especially from my experience of being a product driven organization, high organic growth, building sales on top of that and building an outbound sales team is. It's vastly different. Infrastructure, technology, hr, finance. You gotta know what you're getting into. You have to work cross functionally. You can't be a maverick on the sales side.

I think earlier you said it took three quarters just to get your tools.

And I mean it took us. I mean we couldn't even put a comp plan in for six months for internal reasons. And you have to make your relationships and leverage people internally to understand what your shared goal is.

Yeah, actually I will emphasize I usually tell teams not to put a comp plan in too early until wait a few months until they have some data before. Otherwise you're only going to fail because either it'll be too aggressive and they'll miss it and be upset or it'll be too easy and they blow it away. Then they get upset because then you chop it.

That's such a, such a good point. I mean there's so many people that put really high goals and you get people discouraged and then you get churned. Or you put goals down here when you're first getting started and you get ever excited and then you come back and then they're all angry at you because guess what? Your goal is here. But now it's here.

Yeah, quota's up. Quota. So building an SDR team, let alone is hard. But imagine for the SDR and if you don't have a process built out for them, that number one, helps them be efficient and number two helps them be successful. Okay, so if you've never built a team, when I first got into this, insidesales.com was a big deal back then and they were an inbound engine. And so I reached out to ken Krogh on LinkedIn. Never met the guy. Said, hey, I'm just building out this, this business development, sales development team. I know you guys are a madhouse over there. I'd love to, if you could spare a couple hours, you tell me when and where and I'll be there. I'd love to pick your brain. So he actually got back to me and said, come out to Utah, spend the day with us. So I went out to Utah and spent the day@insightsales.com and they have a massive insight, you know, SDR team, inbound team, sales team. And it was awesome. It was great. And I learned a ton. So if you're just building a team, reach out to people out there who have done this before. Get ideas from them. Because quite frankly, if they've done it before you and done it successfully, why recreate the wheel?

Yeah, a lot will be helpful.

And my recommendation would be to create a solid product process for hiring those builders. I think the biggest mistakes you can make early on is hiring growers instead of builders. And it's very expensive and ends up there's a huge impact on the team ultimately and you want to avoid that long term. So if you can get the right people right out of the gate who are actually hunters and are going to build your program and bring in those new leads and that's the most important thing.

Yep. Last thing I forgot. Can you switch the slide? So I haven't put it up yet. I forgot to put it up before they ran out of time. On my Twitter, we have a couple tools. If you hear the last session, we have a couple things from Ralph Barcy and Mark Roberge. I just put up here. There it is. There's a but I will put up too in about either five minutes or like an hour. It's called the Deep Dive 25 exercise. It's sort of my favorite project based learning exercise for new STRs. It's the basis of our predictable university group training. But I'll put it up here soon again, like after this or an hour. But it's Moto CEO on Twitter. All right. Hey, I want to thank you all for coming up and doing the panel.

Thank you.

It was fun.

Thank you.

If you're sticking around, Alicia.