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Head of Sales @Comtrade 360 | Host of the Struggle Bubble podcast | Entrepreneur | Advisor & Investor
You know you’ve arrived as a sales professional when you have repeatable business as an enterprise seller. Large deal sizes and a 7-figure W2…you’ve arrived.
So, how can you start to climb that sales career ladder today to become a successful enterprise seller? Is enterprise sales or sales leadership your end goal?
In this episode of Closing Time, Craig Surgey shares his insights and the ways the sales career path has changed over time…and remained the same. If you’ve got enterprise dreams, this is the episode for you.
In the fast-paced world of sales, reaching the top of the enterprise sales ladder is often viewed as the pinnacle of success. But what does it take to get there, and how can new sales professionals navigate the path from entry-level roles to the big leagues of enterprise sales?
Craig explains most sales professionals begin at the BDR (Business Development Representative) or SDR (Sales Development Representative) level. These early roles are critical stepping stones, building the foundation for larger and more complex deals down the road.
According to Craig, the skills honed in the BDR/SDR role are invaluable—not just for sales but for life in general. Picking up the phone to cold-call someone you’ve never met can be intimidating, yet it’s a vital skill. Building rapport with prospects who initially don’t want to talk to you requires resilience, patience, and tenacity. Craig reflects on his own experience, where some of his closest professional relationships started with prospects who said “no” countless times before eventually opening the door to a deal.
He draws an interesting comparison between the BDR role and childhood experiences, where we were introduced to new people through teachers or friends. In sales, the process is similar: building connections and fostering relationships, even if it takes multiple attempts.
LinkedIn is an essential tool for any sales professional. Craig recalls how LinkedIn evolved from a simple resume builder to a crucial part of his sales strategy. As a BDR, he used LinkedIn to research potential clients, map out industries, and make connections. The platform allowed him to initiate conversations based on shared interests, like a mutual love for sports, which helped break the ice and forge stronger relationships.
LinkedIn has grown into more than just a networking tool—it’s now a platform where salespeople can showcase their personal brand and even create inbound opportunities. Craig praises the introduction of video on LinkedIn, which has enabled him to pitch himself and his company directly to prospects, adding a personal touch that email or cold calls can’t replicate.
One of the most impactful strategies Craig shares is the importance of channel sales. In his view, channels are an extension of both the sales and marketing teams. When Craig isn’t in the room, channel partners represent him and the solutions his company offers. This partnership model creates more opportunities, as Craig’s contacts help introduce him to new prospects and sell on his behalf.
Craig breaks down his approach to channel sales into three key buckets:
His advice for anyone in sales is to master the art of channel relationships as quickly as possible. Partnering with the right distributors and regional managers can be the difference between breaking into a new market and missing out.
When it comes to enterprise sales, nothing beats the value of a referral. Craig is a firm believer that referrals carry more weight than any cold email or call ever could. In fact, he likens referrals to “executive connections”—they come with built-in trust, which can make or break a deal.
Craig’s approach to maintaining referrals is rooted in building genuine relationships. He’s all about giving back to those who send referrals his way, whether it’s a steak dinner or an introduction to someone who can help them in their own career. Additionally, he hosts regular get-togethers—often casual social events—to keep his network engaged and ensure those relationships stay strong over time.
Not every sales professional chooses to move into leadership, but for those who do, the transition from individual contributor to leader requires a mindset shift. Craig sees sales leadership as akin to coaching. It’s no longer about closing deals alone but about helping a team succeed. Sales leaders must cultivate an environment where the team thrives, recognizing that sales success is rarely achieved solo—it’s a team effort.
For many, the decision to move into leadership is also influenced by life outside of work. Craig notes that factors like family, travel, and personal goals often push salespeople to leave behind their individual sales quotas and take on more nurturing roles within an organization.
As Craig wraps up the conversation, he emphasizes that a career in enterprise sales is all about relationships—whether with clients, channel partners, or colleagues. Cultivating these relationships, staying adaptable, and learning from each stage of the sales journey are critical to long-term success.
Whether you’re just starting out in a BDR role or aiming for a sales leadership position, Craig’s insights provide a roadmap for navigating the enterprise sales ladder with strategy, resilience, and a personal touch.
Get everybody in the room and it’s a social event of everybody Winning in enterprise sales is the epitome of success for many sales professionals. Let’s track that career path on this episode of Closing Time. Thanks for tuning in to Closing Time, the show for Go to Market Leaders. I’m Sal Riley,. VP of Marketing at Unbounce and Insightly. Today I’m joined by Craig Surgey. He is head of sales at Comtrade 360 and co-host of the Struggle Bubble podcast. Craig, welcome to the show.. Hi, Val. Great to be here.. Okay, so you already win the prize for the most memorable headset of any closing time guest. Good job. But let’s get down to business and the business of enterprise sales. Why do a lot of sales professionals see success in the enterprise as the pinnacle of a sales career? Yeah, it’s a great question. And I think, a lot of it comes down to, career goals. Right. And mixed with the career goals is that race to the finish line or that constant race to the finish line,. I should say where I may, most people start as a BDR/SDR inside sales, and there’s a path chosen, the sales industry to get to that point. And when you start hitting that enterprise ground and you start talking about the clients, the numbers, and kind of the strategic structure that not just impacts the sales process, but also the business outcome. I think that’s part of the reason people really strive to get into that, that role in the sales, industry. Yeah, you mentioned that BDR/SDR role and I would venture to say today that’s probably where about 90% of new sales people are starting from. What can a new sales professional take away from that role to use to build towards an enterprise sales career? Well I actually say that role, and. I advise this all the time is a life role. It’s not just in the sales world. Being able to – It’s a difficult skill set and sometimes unnatural for people to pick up the phone to someone they do not know, try and find some medium ground that they can start discussing, be that family, friends, etc. build that relationship. And you know, from personal experience, those relationships came from nobody wants to talk to me 10, 15, 20 times to break in into that account. And those people now are friends, right? I can call them about advice, etc.. So it’s a great learning model from, again, kind of holistic approach to life of trying to meet somebody new. And if you think about it, we do this at school when we’re kids, we teachers help us introduced to new people, new students, etc. it’s the same process as we get in that sales world, right? So starting that SDR blag of the real learning curve of the sales process. If you are going to get 15 no’s before you get one, yes. And then cultivating and using that, going forward. So enterprise sales and LinkedIn really go hand in hand today. Can you talk about how you started using LinkedIn early on in your career, and then how you use it, continue to use it today. Yeah great question Val. You have your CRM or Insightly and you are using all these different tool sets and maybe ten years ago was a primary point of LinkedIn there where you could see people. Number one, this started to become a resume builder. It started to be a real professional social media aspect to the game. So when you in the kind of BDR role or SDR role, it was great to see, hey, this person has been at this company, this company, this company, and now we can start mapping it of, okay, this is their industry, this is their people, this is how to connect. And what I did was I use that and I started to use inbound and also, LinkedIn requests of, hey, this may be interesting to you and I want to connect with you, but it goes back to that original question of when we were at school. You meet new people. Well, LinkedIn was that across the globe. I can go in and my, you know, my background in sports was able for me to go in and say, hey, I see you coach soccer at blah, blah, blah, blah, blah, but you’re also in the tech industry. We have a natural connection now and then from that point we can then, you know, move forward with it. The next part with LinkedIn. And I think it’s evolved after, you know, the acquisition was made, was being able to use video. I thought that was genius by LinkedIn of me now being able to pitch myself the company I represent, the products we’re selling into, you know, the global footprint, basically. And stop basically being my own, kind of lead gen as a side of marketing that I can do personally, my own brand again, pitch who I’m working with, but I can get the voice out there. So now you have marketing and sales. You have marketing personnel, and you have sales personnel all bundled into one entity. It’s fantastic. Now it’s a little social media format. It’s not as much business, but again, it’s a great way to, see prospects, develop relationships and then grow your own brand. And, the company you represent. Yeah. Isn’t it amazing that today’s folks starting out in sales will have a whole career in LinkedIn? It’s not going to be a new thing for them. It’s just going to be natively. How they begin a sales career. Oh absolutely. It’s unbelievable. I mean, we again, I’m a heavy sales channel partnership business guy. And so it was always going out to you know, meetings and then doing the happy hours and then and it was building your Rolodex up basically for your own phone book. Right. And getting it. And now it’s again, you’ve got this global presence that you can tap into to then grow. And yeah, these these it’s going to be it’s tough. So don’t get me wrong, the new the new guys coming through. It’s not I would say. LinkedIn is now ignored a little bit more than it used to be. So you got to do a bit more around. I would say you got to be a bit more direct in what you’re trying to preach. And then I think that was 12 touch points to try and break into an account is now led to probably 24, because you’ve got to be, you know, the squeaky wheel, to get somewhere. Yeah. I think, like all technologies, eventually the pendulum swings. And so we’ll have to figure out what the next new thing is. You mentioned channel sales as a key part of your sales career. Can you talk a little bit about that? And, and how does one step into a channel role? How does channel help you really build up to the next step? Again, Val, great question and I love talking about this one as well as LinkedIn. And for me channel is your second arm of marketing. And second arm of sales. When I’m not in the room there’s people representing me and what I can provide for that client without me being there and with that comes mass opportunities. There’s I look at it in three buckets.. There’s clients I want to try and break into the. I have no relationships with. That’s where I can use the channel. There’s me not being in the room when they’re doing an open, you know, this is who we partner with. I’m not in the room.. They’re doing the selling for me. And then there’s the actual one on one relationships. They know me. They know what I sell.. They know what we do. They’re going to call Craig immediately when they hear certain key words that relate to either myself or the product. So the channel for me is fantastic. And one of my biggest advice to people is learn the channel as fast as possible. Your distis, your partners who to work with, what their skill sets are. Biggest thing is what they’re missing. And does your product fit one of those lines that you can then help grow their business, which obviously then internally build your own brand and business. So for me to get in there, so sit with your cams, sit with the regional managers, start working out a plan of how to sponsor a happy hour, how to sponsor a golf event, all these different variations to get your face into the industry. Then from there accelerate, again, who you aligned with. What makes sense? Yeah. And that leads into my next question because, you know the holy grail of any sales career is referrals. Right. If you’re, if you’re getting referrals, you’re, you know, you’re treating people well and they’re coming back to you or they’re sending folks to you. Is that especially true in enterprise sales? And what can sellers be doing every day to cultivate those referrals? 100%. Those referrals go further than any cold email, call you can. I actually put referral based into executive Connect. So when you do an exec connect, it’s all referral based. Who can I trust, why can I trust, etc.. And those referrals to to keep them close to home is massive. Number one, you don’t know where somebody is going to go and what next. So that tracing that and following that and having that friendship is ginormous referral again of the products that you represent and the person you hire. But the biggest point for me on the referral side of this is how does that all come together? Because again, when I’m not in the room, who is speaking on my behalf and who’s got my back in these certain scenarios, and that referral base will just go, is that six degrees of separation that is just going to keep passing forwards and forwards and forwards unto you. How to cultivate and keep them? Multiple ways. I’m a huge believer on as those referrals come in, whoever give me that referral,. I make sure we go for steak dinner, right? We’re looking after them financially, we’re looking after them, going out, whatever that is. Also from a from a business standpoint, what can I do now to help them? Can I introduce them to the next person? Can I introduce them to somebody that I know, either help them in their career path or whatever project they’re on today? How can I do that? And then the third, I love doing this once a quarter get togethers. I try and do a happy hour once a month somewhere with a reseller, a disti, and, potential clients, and then once a quarter, I try and get everybody together in the same room and it’s non business talk. It is you can talk about your what you’ve done in your career, but it’s, it’s a get together of kind of,. I call it meetings of the minds. Get everybody in the room and it’s a social event of everybody now expanding your Rolodex with each other. That’s a really great tip. You know, we all love the convenience of remote meetings. And we all love being able to hop on a call with anyone, anywhere in the world at any time. But truthfully, those relationships are formed in person. And so if you can cultivate that by having even quarterly, like you mentioned, it’s not terribly frequent, but it really does make a difference when it comes to getting referrals. Absolutely. Yeah, I’ve got a friend of mine who is a mentor and when he took a certain role, he said, he called everybody in the same role because it was a fairly new title. And they all got around the table and they went, does anybody know what we do? Because the egos that we all have in this world, of like, we do it this way and this is how we crush it and blah, blah, blah. When everybody kind of took that hat off and they all sat around a dinner table again with, this is personal, this is not business. You can talk about what you’ve done in your career, but not what we’re doing today. And everyone goes, I’m so glad you asked that question, because we are all. And it goes back to kind of the struggle bubble, right? Everybody’s trying to do the right thing at the right time. And sometimes when you just take a step back and everyone goes, hey, hats off, do you do it this way or or should we – I think that was one of the best pieces of advice I’ve ever had from a mentor. So kind of, we’re talking about career progression for sellers. And what do you think motivates a seller to leave their bag behind and jump into a sales leadership role? Yeah, great question. I think there’s a few things, and I think there’s an inflection point in that as well. It depends what they did last year. I depends if they’re a W-2 or 1099 and what that number looked like. And so part of that, but then also I think generally with, with most AEs and SEs, when there’s been a successful sale, you hear them say, hey, I appreciate, you know, the thank you’s and we did a great job. But it’s not just me sitting right,. I can’t code. I’m not an engineer.. I don’t run marketing. You know, if you really then dissect a sale of where the lead came from, it came from X marketing or on inside sales, whatever that is. The product was built by someone.. There’s a customer spot. So I think that inflection point, a lot of the time comes with then the top comes down, management. C-level goes okay, It seems like, you know, we’re cultivating a great, you know, environment here. We’re cultivating a great sales leadership team. We want you to work with now that sales group and build that team up as a leadership model. So I think I always relate this to coaching. Right. Again, successful sale means is a team around it, a successful sales group means there’s a leader that has that coaching aspect and ability of bringing everybody else around them up. And then also there’s an interpersonal point of where everybody wants to go in their career. Why do you want to be a sales leader? Do you want to just carry a bag? Do you want to be a CRO at some point? So I think there’s a lot of coaching inside of there as well. That makes people really question, do I want to keep carrying this bag and doing these, you know, having a list of sales or 15 clients, whatever that is? Or do I want to bring my team together and grow the whole business, not just from the sales wise, but obviously sales leads to a larger business in general. And then bring the whole company up and, you know, keep the growth going. So I really think that inflection point hits, when you’ve been in for a few years, ten plus years, honestly, and you realize, hey,. I want to help others around me as much as the team that makes the sales that I’m doing today. I think you make a good point because. Right. It’s. It’s lone wolf versus pack leader. And and like you said, maybe there’s it’s what’s going on in your life outside of work that helps make that decision for you. Yeah. Exactly that. Yeah. Again kind of talking to the struggle bubble. You get to a point of, you know, if you go through marriage and kids and stuff like that, do I want to be on the road, you know, thirty-five weeks of the year, or do. I need a little bit more time at home? The external aspects definitely kick in at the same time. Yeah. Well, Craig, thank you so much for sharing your insights and a little bit about your career path. Absolutely, Val. Again, thanks for having me. I appreciate it, and I love listening. Awesome. Well, thanks to all of you for tuning in to Closing Time. Remember you want to like the video, subscribe to the channel, hit that bell for notifications so you don’t miss an episode, and we’ll catch you next week.
