Outbound Isn’t Dead, You’re Just Doing It Wrong with Colin Spector

# The Bridge the Gap Podcast - Colin Spectre Interview

What makes up a company, right? People. People make up a company. And if you invest in people, your people will invest in the company, right?

>> We're going to dig into AI assisted dialing, manager habits that actually move pipeline, and what it takes to scale a coach first culture.

>> Sales is an emotional experience. There's a ton of people try to overcomplicate sales and so much jargon and so many metrics and this and that. Welcome back to another episode of the Bridge the Gap Man, it's Friday Podcast, powered by Revenue Reimagined. Today's guest is Colin Spectre, the SVP of Global Sales at ORM, which is the AI powered calling platform that helps revenue teams have more live conversations with the right buyers. Led sales teams from New York to LA. Was a top 1% producer at Namely and is known for building elite sellers through coaching and clear go-to-market systems. We're going to dig into AI assisted dialing, manager habits that actually move pipeline, and what it takes to scale a coach first culture. I'm super excited for this, Colin. I follow you. I've known you for a long time, but your LinkedIn posts all about coaching and how you actually get your hands dirty and how you actually coach and call with the team—not enough leaders do that. Welcome to the show, man. Thanks for being here.

>> Thanks so much, Adam and Dale. Such a pleasure to be here. Very excited to jam with you guys today and just connect with you and the audience and share any insights I can from my perspective and experience. So happy Friday. Pleasure to be here.

>> Happy Friday, Colin. Thanks for joining the show. Of course. One of the things that you talk a lot about is "coach first, pipeline follows." How did you learn that developing people, not just pipeline, is a key way to consistent growth within your GTM strategy?

Well, you think about what makes up a company, right? People. People make up a company. And if you invest in people, your people will invest in the company, right? You build up your people and your people will build up the company. And the more you take care of your people, the more they're going to take care of your customers. And your customers are what make the company and what is a company about? It's about making money. And how do you get money? From servicing customers. And so you create this cycle, right? This life cycle from focusing on people and developing them and their careers and helping them achieve their goals. And they're going to reciprocate that from my experience into your client base, right? That is a huge part of the ethos and culture within the teams that I've led and built. And I think proof is in the pudding. It definitely helps. Our customers always cite our people as a holistic differentiator in the market. And I think in a time when software development is happening at such a rapid pace, you need to lean on holistic differentiation, right? Because one week your competitors come out with something, one week you come out with something. And the buyers, on the surface when they're buying something one time every year or two, they still need to make decisions on who they like, who they trust, whose values are aligned with them, who's culturally aligned with them. And so yeah, I'm a huge believer that people are the throughput, the consistent throughput no matter what happens in the tech and in the market, etc. So yeah.

>> So people want to buy from people they like. People want to buy from people they trust is what I hear you saying. People want real human connections. They don't want to buy from an AI STR. I have very strong feelings on that. I think all of what you're saying is so true. I often talk about what I call the culture of coaching. I think in fact it's something I say with every client when we're doing our audits: "Tell me what your coaching looks like." And if you don't have a culture of coaching, you're going to have a problem. What is in your mind what does great coaching look like just at a high level? I know it's different depending on the role, but overall what makes a good coach a good leader?

>> Yeah, I mean someone that connects with the people on their team as individuals and understands that each individual is unique in the way that they want to be led and coached and what their personal goals are. And I think the best leaders can flex and flow to the personalities and spectrum of human emotion and desire of each individual and help unlock within that person more than that person could achieve on their own, right? At the end of the day, you are here to develop that person and help them reach heights that without you, they could maybe get there, but it would not be as accelerated the way that they get there or as efficient the way that they get there, right? Like you win as a coach when you really help them achieve those heights and accelerate their learning and their growth in a way that they really could not get to on their own or without a coach like you.

Yeah. Individual coaching—I think too many people try to spread the peanut butter so thin and they're like, okay, we're going to try to do everything for everybody in the same way and that's just not the way it happens. And I think unfortunately today coaching is a thing that gets left off last. Like we talk to leaders all the time. They're like, okay, I got to run the HubSpot report or the Salesforce report. I got to get this board deck together for my CEO. You're doing all this busy work. And it's funny. I talked to a friend of mine that I'm going golfing with tomorrow and he always says, "You're not busy, you have to be productive." If you say you're busy, that's a problem.

I mean, I think the coaching also comes down to career development, which I think is a big part that a lot of people miss when they're hiring, when they're coaching, and how long people stay. I mean, you've been at ORM six years, which in startup world is unheard of. Most VPs of Sales last what, twelve months, maybe eighteen if we're really lucky. But I think, you know, number one, that certainly probably has to do with the revenue that you've helped drive for the company, but that also has to do with the type of leader and the type of coach you are, the type of people that you hire, whether they stay, whether they go, if they go, how they leave. Like, I don't believe we own anyone, right? Like, as a leader, my job is to get you where you want to go. And if that means I have you for eighteen months and you're amazing and I need to ship you off with a great reference to somewhere else because that's best for your career, that's my job as a leader. But I think when people are developing career development plans, a lot of people do it, Dale, like you said, spread the peanut butter, right? I spoke to a BDR yesterday and everyone says, "Oh, BDRs, they all want to be AEs. They don't ever want to be a BDR." This guy's like, "I have no desire to ever be an AE." He wants to stay in go-to-market, but he's using BDRs as a stepping stone to, in his words, do the hard work first, know the customers, etc., etc. It's like, I don't want to be an AE. I actually want to go to marketing, but I want to cut my teeth getting to know the customers and getting to know how to sell the product. Like, I love that. But as leaders, I think we often make this assumption of, well, we know what everyone wants and we're going to coach everyone the same. Every person's going to get coached the cold call the same. So I love how you talk about individualizing it. How do you do that at scale?

>> Yeah, it's a great question. So I think you do teach some of the fundamentals. I think a lot of fundamentals are the same from the perspective of like, here's our company messaging, here are our competitors, here are the battle cards against these competitors and with these personas, here are the questions and messaging that resonates, here's the product suite, right? Like there are blanket lessons just like if you go to school, right, and you're sitting in a classroom, there are blanket lessons that you'll be taught. Now, the coaching, the individual coaching is like the after-class tutoring, right? Like that's the individualized one-on-one. So like a sales coaching operating rhythm, right? Like you think about the rhythm of your business and your team, you need to establish individual one-on-ones in addition to the team meetings. Now, ideally, you have individual one-on-ones on a weekly basis.

>> Ideally, no. And some companies meet on bi-weekly or quarterly or monthly. And it's a lot of that what we have seen is happening because the rep to manager ratio is starting to get stretched very thin.

I was just going to ask you that question. Like, what's ideal to you? Because I hear it all over the place and I hear people managing fifteen people and I'm like, you're not coaching anybody.

That point without some serious help, it's really your one-on-ones become more performative, meaning it's like you're just kind of showing up and going through the motions. It's very difficult to have a really true individualized focus on that specific person. In my experience, because of all the other things you mentioned before, the leader is not only a coach typically—you're also your peer with marketing and RevOps and finance and you're in all these other internal meetings. And so from my experience, like I like five to seven is great. It's beautiful.

I totally agree. Now if, thanks to technology—and for example, we drink our own champagne at Oram. We're an AI coaching and calling platform as Adam so eloquently introduced at the beginning—you can get AI insights that synthesize and summarize a lot of the unstructured information that you normally would manually need to prep for ahead of those one-on-ones to really have a thoughtful one-on-one. If you think about it, an SDR leader or a sales leader, really any people leader, if you're really doing a thoughtful, data-driven one-on-one, it's going to take you maybe 15 minutes of prep for each one-on-one. And that might not sound like a lot, but at like 15 reps, 20 reps, that time compounds, right? And you really start to lose your calendar because if you think about what the utopia or ideal state of a one-on-one is, you're doing call review and tape review. How do you go and find the best call to review? Well, what most managers default to is like, I don't have time to go dig through call history in Gong or Chorus or Vulma. I'm going to ask the rep to bring their call. Which call are they bringing?

They're bringing their best call.

Their best call. I'm not going to bring a bad call. So thanks to AI though, AI can now surface up in the last week: "Hey, these are the five calls that could use coaching because we've seen the theme of this rep is running into these objections where others are running into that objection and seeing success." So AI can score calls, can look for trends in calls and then compare those trends against peers on the same team calling the same market, right? And so this is where AI can help you start to scale that rep-to-manager ratio and really make the manager and the rep—for that matter, the rep also be empowered with this data—but the manager can show up to a call with the specific call and moments in the calls that they should review on that one-on-one this week because of the information that happened last week. So every one-on-one you're going to have a set of calls to review. You're going to have, of course, the weekly activity numbers. We call them WAN, right? Weekly activity numbers. And where is the rep stacking up against those weekly activity numbers for themselves on their own individual path? How are they trending week over week and against their peers and against the team goal that expectation that we have set for those reps? And so at minimum, to really be a data-driven coach and help hold to account your people against the plan that we all agreed to when we signed up to go on this mission together up the mountain—like, we agreed these are the steps we're going to take every day. These are the base camps we're going to hit in order to summit this mountain, the gear we're going to have, how we're going to check our gear every day, right? We are climbing this mountain together each quarter. We agreed to that upfront at the start of this arrangement. So each week we're checking in: "Hey, are we on track on the plan that we agreed to at the beginning?" You have the information, right? So number one, you have to set expectation up front. Number two, you need to have instrumentation to be able to measure that you are staying on path, you're staying on track to the flight plan, the climbing plan that you agreed to in the beginning. And you need to be coaching to actual conversations, right? Tape review is a must-have ingredient requirement. And just recognize that most teams, by the way—this is most teams—they're cherry-picking calls. They're asking the rep to bring their call and it makes it hard to know what actually needs to be developed or helped. These days, thanks to technology, you can get much more insightful and smart about how you approach coaching and that can help you scale the ratio essentially.

Yeah, I totally agree. I think tape review is an art of coaching that not enough people do. And I think you laid out great reasons, but all the excuses why people don't do it. The best leaders—the ones that do it and do it the right way—are intimately involved in the business. I want to piggyback on something. So you talked about how AI could help surface the best calls, worst calls, etc. Let's talk about AI-powered calling but in the real world, right? So there's all this fluff around AI SDRs and whether parallel dialers are good or bad and where to use AI and not use AI. Talk to me—as a sales leader at an AI-powered calling solution—where does AI genuinely really remove friction in outbound today? And where do you think it really still falls short that people are like, "Hey, yeah, like don't do that, dude"?

Yeah, so AI can help. Go ahead or feel free.

Sure. So from a calling perspective, AI can help before the call is even executed, right? And so when you start your day, AI can help clean through the list of people that you're going to call that day and help you prioritize based upon—again, looking at what AI is really good at or is getting better at. I'd say still leaving more to be desired, but like today, what is working really well to answer that question: AI can look at history and patterns and start to provide insights and summary. So I'll give you an example. AI can look at millions upon millions upon millions of answer behavior and ideal call times and ideal call from numbers and caller ID patterns and connection rates and then smartly sort the contact list that you're going to call. Even if you're going to dial them with a keypad, it's like, "Hey, these are the people you should call in your call block right now. I don't care how you call them. Call them."

I can help you do that. So that's one very upfront way before the call is even made—so kind of automating the prioritization and task list to place calls. People buy from people. That's why companies who invest in meaningful connections win. The best part: gifting doesn't have to be expensive to drive results, just thoughtful. Sendoso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Sendoso competitor and I can tell you no one does gifting better than Sendoso. If you're looking for a proven way to win and retain more customers, visit sendoso.com. Okay, then AI can actually help you place the calls themselves. So you know, because even though it's the best time to call these people, maybe they all still won't answer. Maybe you're increasing your likelihood. But AI will also say, "Hey, this is the way we recommend you should call them. Choose this caller ID," and in fact, the AI will choose the caller ID for you and which number for that contact is the best number to call. And the AI will actually click the button for you and then it's ringing and you talk to the person when they answer the phone. If they don't answer the phone, the AI can take care of all the manual work there. Meaning historically you'd have to log—

Oh, brutal.

Yeah, like "I have to log no answer" or "went to voicemail" or "if I want to leave voicemail," etc., right? So the AI can take those actions for you as optional, you know, just to keep me rolling through. And so as the human in the loop, what I want to focus on are live conversations. Like, I know my account list. I know my contacts. I want the AI just to help me focus on what I'm best at, which is connecting with people. And so it's cleaning the list. It's removing the manual tasks between each live conversation and then plugging all that data back into your CRM so I can see what tasks I've executed today. And when I have someone on the phone, when I actually get someone on the phone, the AI, of course—this has been around for a while thanks to Gong and Chorus—can listen to the call and Oram can listen to the call, transcribe the call and these days even give live assistance on the call. So you can get help if you need, right? Or to bring up maybe past experience with that specific person in that specific account. So you have a lot of reference point. So AI can bring in research about the person, about the account, any past interactions your company has had with an account. And so you're really armed with all the context. By the way, typically, you know, as the account owner, if you inherit a book of business, think about this: you have to go back into Salesforce or HubSpot. You got to look at all the past AEs or AMs that had that book. I need to go and synthesize the data of like, "Okay..."

# Transcript

What are my past interactions with this account or what's their usage in the account? Now AI can take that unstructured data and create a beautiful little summary for you. And I would say someone that started out doing this really well is Actively AI. This is kind of where they got their start.

Yeah, Actively AI. I'm pulling it up to look at later, but then Dell will tell me I have to minimize it because I'll start going on this tangent and looking at it.

Yeah, no, all good. Giving a plug to them. They're great people over there as well, partner of ours. So they'll bring in all your unstructured historical CRM experiences with an account and then create a nice little script you can plug in, and you know, reps use that when they're calling on accounts, for example, right? So research on the contacts thanks to AI makes that really easy. And just keeping you more organized and consistent in the way the information shows up too. Because the AE or AM might have a very specific way that they research an account, but that might be on chicken scratch on a notepad, and when you connect, it's missing from the CRM. Whereas now we can get more consistent. Because, to your point before, Adam, sales people and sales leaders they turn over every 18 months or so, or two years. AEs typically stay two years after they invest a couple years, hit their commissions, and move on. A lot of people are inheriting these accounts, right? You have to think about that. How do you keep the flow and information continuing? So those are some of the ways.

And then after the call, after the call you get all the insights. You get your call scored, right? AI can score the calls. And at ORUM, you know, we have our own call coaching frameworks that we provide off the shelf. So you can score leveraging ORUM's call framework, or if you have your own methodology, right? If you're subscribing to the Adam and Dale methodology, you can customize your scorecard.

You're assuming Dale has a methodology.

Yeah. Don't subscribe to the Adam methodology.

Yeah, or we both said the same damn thing at the same time.

Why not? Hey, license out your methodology. A little side hustle income here. So the bridge the gap methodology, right? And so people come to us, maybe they bought or invested in Challenger Sale or Sandler Sale, or they have very specific methodologies. So you can bring in those methodologies, or you can leverage our own. So batteries are included, and then you can add sections as well. So let's say I launched a new product. You know, if I'm in a very large company and I've launched a new product, how do I know if my people are actually sticking to the narrative, right? So it helps with narrative control and scoring. Is the narrative working? You know, these days a lot of companies are launching AI narratives, but they don't know if it's working. Like, how do I know if it's actually resonating and leading to higher win rates? Well, thanks to AI and scoring calls, you have that information.

So before the call with the list cleaning, on the call actually placing the call, on the call, after the call, and then getting all that into a nice little performance scorecard on each of your people and your teams. Are my scores up?

So are they down? There you go. So let's take a little turn here. From STR to SVP. So what did you carry forward from your time as an SDR and AE that still guide you as an SVP? Like, as you've grown through your career, what did you take to guide you through that? Urgency, follow up, follow through. I think you want to set yourself apart, especially today. I think it's rare to see someone that consistently drives urgency and follows up and follows through. I think like you will stand above and beyond the crowd if you just do those three things: follow up and follow through. If you want to pull one thing from this, if you're a sales professional listening out there, follow up and follow through. You will be known as somebody that's dependable, that is somebody that gets stuff done, that is persevering, that is resilient. And just by simply following up and following through, right? So like when a lead comes to me, I'm like a boa constrictor. I grab that lead and I won't let it go. I won't let it go. Like if you're qualified and you're in my view, we're together. Like, this is not going away. We're not ending until you've already signed someone else, and then I'm following up with you at your renewal or until you've completely shut me out.

It's so funny that you say follow up and follow through. So I had a parent-teacher conference with my 14-year-old this morning. I'm proud of him. He stood up for himself with a teacher. It's his freshman year in high school, and my general rule now in high school is like I really don't want to be involved with your teachers. You have to. I did that in middle school. You have to do your own stuff. But he stood up for himself. He felt that he was wronged by a teacher, and he asked for help and said that he would set up the conference. Everything we would want the kid to do, right? And the key takeaway from that conference call, going back to ninth grade from where we all are now and we'll be nice and say our forties and fifties, is dude, you got to follow up and you got to follow through. No one's going to hold your hand. No one's going to babysit you. No one's going to give you rewards for just saying that you're going to do something and not doing it and not following up. So very timely that it's coming full circle from 14 to when you were in SDR to when you were in AE to all the way as you've moved up. Because the amount of people that don't—and listen, we're all on the receiving end of sales pitches all day long, right? Many of which are really bad, but some of which are good. The amount of reps, the amount of VPs, hell, the amount of CEOs that don't follow up and follow through, I think far outnumbers the ones that do. So I love that that is where you started because it's so important and it starts super early in your career and should progress through your entire career.

Yeah, no, I appreciate that. And hats off to your son obviously, leading and teaching a great example and modeling great behavior. And that's going to set you yourself apart. I know a lot of young professionals are nervous and scared, and I'd say like just in this market we're in, right? I hear it from parents. I hear it from other leaders. And I think, you know, especially people graduating college, et cetera, I think again, getting to the people connection and being someone that is dependable and being someone that does follow up and does see the job through to the end, right? Like you took the garbage out, put the new bag in the can, you know, just as a home tour example. And the other side of this, right? It's not just about the activity of taking the action of following up and following through, but it's also your attitude and the throughput is a positive attitude. I have said this from day one: attitude and activity. And in the activity, the sub-bucket is following up and following through, right?

Yeah.

But your attitude is really, sales is an emotional experience. There's a ton of people trying to overcomplicate sales with so much jargon and so many metrics and this and that. Sales is an emotional experience. I'm a subscriber to Zig Ziglar, very classic sales trainer. And you know he says sales is a transference of emotion, right? You're transferring your excitement for what you have conviction for to someone else. And yes, there are many tactics and tips and strategies to do it, and following up and following through are part of those tactics and tips and tricks to do it. And so just keep that in mind. And so the energy that you put out, when that resonates with a buyer, they want to have that spark with you, and that gives them the emotional spark to even think about becoming a champion for you, right? If we're talking about more B2B complex selling, you still have to get the individual spark with the individual through an emotional connection.

So piggy-backing on that, you're 100% right. Piggy-backing on that, there's all of these posts, all of these people saying outbound is dead, right? Cold outbound is dead. Your email goes to spam. Your call isn't getting answered because Apple's new call intelligence has it going to this. You know, you have to say who you are. LinkedIn DMs don't work. You can't go show up at someone's door. Outbound's dead. The only way you can sell is through your network. I don't agree as a whole. I agree with part of it, but as we...

Look at the next two to four years of outbound, Colin. What's going to define the best outbound teams? How is outbound going to win? Stay human.

So let me talk about the iOS screener since you brought it up. We are actually seeing higher connect rates and higher conversation and meeting rates thanks to the iOS screener. And let me explain why.

People, what happened was people were getting so inundated with crap calls from robo dialers, right? Robo dialer meaning like a machine that just randomly calls numbers, blasting out all the car warranty stuff or free cruises or what have you. Timeshares. All kinds of scammers, right? So many scammers. And there's a real thing there, right? There's real people pretending to be like Amazon and stuff. So the cell phone companies came up with a screener. But the beautiful part of the screener is the buyer has a chance to see: Is this a human?

So first of all, salespeople, if you're running to a screener, absolutely you should say who you are, why you're calling, where you're calling from, and ideally, if you've also been reaching out on LinkedIn or email or other places, mention those other channels so the person can reduce even more uncertainty. Like, "Hey Adam, calling in from Orum. We just became friends on LinkedIn." And then you're going to look at your screener. It's a push notification to your phone. You're going to see my name, my company. So there's an impression. By the way, it takes like nine to ten impressions to be persuasive. There's an impression right there. I've just advertised to you on the device that you have all the time.

So even if you don't accept my screener call, you know it's me and why I'm calling. And then maybe you reply to me on email. Maybe you reply to me on LinkedIn if that's where you like to reply. Or you're like, you know what, it's a human. This guy's been reaching out and maybe you feel this need to reciprocate my effort, right? For whatever reason, people are answering those calls more. I think a lot of it is due to that psychology of reciprocity and the fact that it's a pattern interrupt that a human is calling you and you know it's not a scammer. It's like, oh, this is a real person. I've seen their picture on LinkedIn. I've seen their emails. I've seen the case studies. I've seen them liking my content.

So it's in the holistic outbound approach. So under the question you asked, is outbound dead? I think you need to be on the channel. I think you need to keep it human. I think that you should respond to screeners. You should leave voicemails. Any opportunity you can to humanize yourself, which is through your voice, and you can use LinkedIn notes, you can use video. So yeah, I think outbound is very much thriving and alive for the people that are putting in the effort and trying. I think those that are trying to completely automate their way, you can pick up on the AI emails, you can pick up on robocalls, right? But I think if it's you and you're actually putting in the effort, now some of your steps might be automated, some of your steps might be a templated email, et cetera, and that's okay. But you need to sprinkle in some of your authentic approach. In my opinion, that's what's still working today.

Yeah, I love that. I totally agree.

Okay, Colin, as we wrap this up, let's do a little bit of rapid fire. See if we can get a couple of questions in really quickly. One outbound method you wish would die forever.

One outbound method that I think wish would die forever? Gosh, I think just the LinkedIn AI bot connectors. I'm so sick of them. It's getting harder and harder to tell: Is it an AI profile or is it a human profile on LinkedIn? I love LinkedIn, right? So it's like, gosh, don't kill this platform for me. And there's just a lot of pitch slapping connections on LinkedIn that I can just tell it's AI slop.

Absolutely. That's the one I would pick.

Colin, what's your favorite question to ask in a call review?

Nicole, I always put it back on the rep. Like, how do you think you did? Any areas that you'd improve? How do you think that went overall? I start with them: "Hey, before I share, how do you think it went overall? Any areas that you'd try again or improve?" The more self-reflecting the rep is, the more self-aware they are, the better they get. The best reps, they know the answer right away. They know their own answers.

What's a deal-saving habit every rep should learn early?

Following up and following through.

I knew that one was coming.

What's the clearest signal? I was going to say the clearest signal of a top performer in an interview, but you're going to say—I'm going to guess you're going to go with following up and following through.

Well, I'll plug in champion. No champion, no deal, right? That would be the other answer to the other question. It's like, look, you can follow up and follow through, but you need to follow with the right people. That's the thing. You need to follow up and follow through for the right people because you might have an amazing coach, an amazing coach with high influence, and you might feel like you've really got something there. But you need to follow up and follow through for the right person, that's going to be your champion, the person with authority.

All right, Dale.

Dream vacation destination, Colin.

Dream vacation destination? I feel like I've been everywhere. But my wife and I have been talking about so we're expecting our third and fourth babies.

Congratulations.

Yeah. And so we've been talking about doing like a wellness retreat for like a month in Bali, like after we go through this journey. Never been, but just do like a whole holistic healing wellness retreat there. So that would be awesome. I've never been, but yeah, I love to surf and love, you know, just meditation and yoga and all those things. So if I just like dedicate like a monthlong healing journey, that would be incredible.

That sounds awesome. Colin Spectre, thank you so much for joining the show, for sharing your insights about all things outbound and how to stay relevant in today's day of overused AI. Thank you both, Adam and Dale. Such a pleasure. Thank you to the audience and connect with me on LinkedIn, everyone. Have a great rest of your day. Talk soon.