HOW THIS REP WENT FROM GOOD TO GREAT IN B2B SALES
17 Mar 2025 · 38 min
Conor Gilbride, an Irish sales rep now in New York, spent 15 years moving from HR recruiting to construction-tech software. He explains why consultative selling beats transactional deals, how to hire for collaboration over likability, and why staying even-keeled matters when coaching teams.
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Absolutely. How's it going, Brian? So, I live in New York, originally from Ireland. So, obviously, it's an important time of year for me with St. Patrick's Day around the corner. moved across to New York 7 years ago, born and bred in Dublin, Ireland. I have been in sales for just over 15 years, software sales, and worked across HR technology, construction technology, most recently in a couple of small startups. And yeah, I live with my wife and 2 young kids in a tiny apartment in Brooklyn. So, there you go.
And what was that transition like? I've never been to Ireland, so I don't know what It's like?
A big transition. So, working for— I worked for a large recruitment organization in Ireland, the Stepstone Group. So, very— they know their stuff. And I was there for 8 years, very kind of like plug and play. And I moved to a very scrappy Irish construction technology startup. So, I was moving out from the HR world where you'd go to meetings with your suit and tie into the construction world, which I'd know familiarity with whatsoever. And I always remember my first client meeting, go to the site. I wore a suit. Thankfully, I didn't wear a tie. They saw me walk through the door and they straightaway, this guy knows nothing about what we do, who we are. So it was a very fast learning curve, but it was fantastic. I learned a lot. I learned a lot about construction. It's not just putting bricks together, particularly construction in New York City. So It was a big adjustment, a big adjustment professionally and a big adjustment personally. But I think in sales, you got to be nimble. You got to be able to adjust on the go. And, you know, it all worked out. I'm still here. I met my wife, 2 young kids. So, it was certainly a success story. I miss home all the time. My family and friends are back there, but my life is very much here at the moment.
And I'm getting a sense that you have like an adventure gene that you like a little change, a little—
Yeah, I went to— I did a year in Australia when I finished college. And I always liked the idea. Ireland is very, very small. Everyone knows each other. The people you went to school with, you know them your whole life. Everyone knows everyone and everyone's connected. I like the idea of sort of going outside of that. But when the opportunity arose to move to New York, I'd actually kind of sort of settled with, no, my career is here and this is where my life is. And it kind of had— it was no longer a drive for me. But the opportunity came up and the circumstances were right and I just went for it and I haven't looked back. You certainly miss— you miss things. You miss your family, you miss your friends. As you get older, it's harder to build that sort of social circle. But it's been a really positive experience and I think it's sort of shaped me for the person I am today, I hope anyway. Yeah.
And why sales for you?
Good question. Um, sales again was— it was never something that I had an urge to get into.
You didn't aspire to be a rep?
I think— no, I just— you know what, I always— and the thought of picking up a phone and calling somebody was like, I could think of nothing worse. And I kind of fell into it. I was— I finished, um, I finished, I graduated out of college and I had the education, but I had no real work experience work experience in the real world. So I went into this organization that I ended up working for, and they did resume skills, interview skills, that kind of stuff. So I spent a few hours with them, and they said, hey, we've got an intern role on one of our sales teams. Would you like to come in and work for us for free? You get that experience, that real work experience. And that's how I started. And I was with the company for 8 years. I went from intern to a junior account manager, senior account manager, up to sales manager. And it was just something I don't know if I just, if it was luck or if it was timing. But yeah, that's how I landed in the industry.
For 8 years, it's more than luck, right? There's got to be some pattern of a match for what you like to do and what they needed.
I think it's speaking to people. I think it's meeting people. It's learning from people around you as well. I think the work environment has changed so much. I remember I was on a sales floor with all the other sellers. And you would listen, you would listen to what that person said, how that person handled objections, and you would sort of take pieces from everybody and try and make it your own. And I always found that was a really good way of sort of honing your skills. Now it's different. Everyone's at home, they're sort of remote. You're maybe listening to Gong or Clari calls to upskill yourself. It's different. So I think it's the ability to working in that environment, there's a lot of energy.
Yeah.
So I really enjoyed that and just learning the craft, and I'm still here today, you know. Yeah.
So it sounds like you're an extrovert, somebody who likes being around people. You get energy from others. Is that true, or?
Yeah, I think that is true. I think I've struggled. I would struggle is the wrong word. I think the past couple of roles I've been in have been more, more sort of leadership roles where I'm supporting a team, and part of how I try and sort of have success with my teams is like by building that relationship, establishing that rapport, establishing that trust. That's easier to do in person. That's easier to do when you're, um, when you're able to go for lunch with someone, go for a beer after— on a Friday after work and get to, get to know them, look them in the eye, shake their hand. Um, so, and I also, I missed that. I missed that energy from sort of being around people. I think you can— it sort of breeds creativity.
Yeah.
Uh, it helps with with problem solving. I know the past couple of organizations I've worked for, um, you would have a once or twice a year offsite where the whole company would come together. And the amount of, um, I guess energy created from that problem solving, you walk away feeling really good about the company you work for. Um, that used to be all year round, used to be in that environment all year round. And it's kind of, it's shifted. And look, it's, it's, it's, I think it's a, it's, it's a beneficial shift for, for a lot of people. I have again, 2 young kids. Working remotely allows me to, um, it's a good daycare. Yeah, there's, there's pros and cons. I do like the hybrid, the hybrid approach. I think does work. And I, but I think the, the remote aspect does allow companies to hire people from everywhere, um, and you can hire the best candidates. It doesn't matter their, their geography, their location. So there's, there's pros and cons. I don't think, I don't think the industry has sort of mastered the best mix yet, and it's kind of back and forth, but it's interesting to see how it, uh, how it plays out.
And when you moved into leadership, did your view on sales change?
Because I think how I moved into leadership, um, I think is, is a, a result of the leaders that I'd had in, in, in the past. Um, I think sometimes the, the best salespeople are very individualistic. They're very driven by the commission dollars, and that leads to somebody being very, very good at their role. Me personally, I think I get more satisfaction out of seeing somebody on my team bring in a big sale or develop themselves. We had, when I was starting out in my career, we brought in consultants to one of the sales organizations I worked in, and they sort of introduced the idea of coaching and consultative selling and actually how they delivered that training, how they helped upskill us, that kind of opened my eyes. So I would love to be able to work with a team and provide that kind of sort of training to them. So it was a kind of a— it was sort of a natural evolution as well. And yeah, I think that's sort of where I'm at today. It's interesting, people will ask me, what do you do? What's your role? Now, say I'm sales, I'm in software sales, but I haven't actually done a lot of selling over the last couple of years. When you sort of move into maybe a more managerial role, you kind of, you sometimes lose that technique, that ability, that skill. And it's an interesting dynamic because you're there to upskill your team, support your team. If you're not an expert at that, then maybe you're missing something. So it's something that I think is You often listen to the best salespeople and they make it sound so easy. The best salespeople make it sound so easy. I could do that. Like, they're just having a conversation. But then when you're put in that spot and maybe one of your team members is out or they're on leave and you're taking over a renewal or a sale and you're put in that spot, it's not that easy. So, it's an interesting sort of dynamic how things shift, but it's probably a story for a different episode.
Well, it certainly is a profession that looks infinitely easier than it is.
Absolutely. It's a— you go back to sort of the best leaders that you've had in the past. When sales is easy, it's the best job to be in. You come in and everything is great and you're hitting your numbers. It's just fantastic. It's not always easy. And I think it's the leaders that you're able to foster a connection with They're the ones that when things get difficult, they're able to pull that extra bit of juice out of you in terms of being able to say, okay, we're at the end of quarter, I really need you to do this. And so it's those leaders that you sort of have built that connection with, you have that respect for, they're the ones that are going to be able to get you across the line. So they're the people I kind of really, I look up to when I think about sort of leaders in the past and kind of what's shaped me in terms of the type of leader I want to be now and in the future.
And what do you look for in a rep when you're hiring them?
So I think this is going to sound like dating advice almost, but I think you can look at somebody's resume on paper and they're a really good fit. They've got the experience, they've done it in similar roles before. I place a lot of emphasis in that conversation I have with them. Is this somebody I can see myself working with on a day-to-day basis? Is this somebody I can see myself having a conversation with on Monday Monday morning when we're tired after the weekend and it's the last place we want to be. I place a lot of stock in that connection and that personal connection because I believe if you have that personal connection with someone, you're going to be able to, um, import your ideas on them and you're going to be able to get the most out of them. So that's something that I really look for. I get off a call and it works both ways. If I get off a role that I'm interviewing for or somebody I'm interviewing, can I see myself working with this person? Um, Do we connect on that level? And then there's also, I place a lot of stock in collaboration as well. I do like to bring other people into the process, people that I trust in terms of the interview process. I think it's important to get more than one opinion. Sometimes too many opinions can clog everything up and you'll never hire anyone. And you have like 5 people and one person says, oh, I don't know, I didn't like their hair. Okay, let's move on to the next one because there's so many candidates out there. Too many opinions, too many cooks can be too many. But I do believe in bringing other people into the mix to sort of validate your thoughts on the person you're looking to bring in.
And how would you characterize that? Likability or rapport building or ability to connect?
I think likability is one that we want to kind of avoid. I think in terms of a manager role, do you want your team to like you? Yes, that's good. You want them to like you. But more so, you want them to respect you and listen to listen to what you're asking them to do. So I think it's, it's more personality. I think, I think you can tell that very quickly. Does the conversation flow? I think sometimes the, the best interviews are the ones that, hey, we've reached the 30-minute mark, we've reached the 45-minute mark, can we keep going? Is it just, is it a natural conversation almost? You'll also have your list of questions for them and they'll have a list of questions for you, but do you sort of spin off into other areas? Things like that are a good sign for me that this person is going to be somebody that I can connect with, but more broadly, somebody else, somebody that the rest of the team can connect with. I think it's important we sort of, we talk about sales teams, but really everyone's an individual. You're an individual contributor, you're focused on your own numbers, your own quotas. But if you can foster that team environment where you have individuals that are going to mentor other people on your team, then it's a recipe for success. So is this somebody that I can work with? but is this somebody else who's going to add to the culture of the organization? And more importantly, is this somebody who can work with the rest of the people on my team as well?
Yeah. And what do you see as kind of the key differentiator between the best reps that you've noticed in your career and the rest? What do they do differently?
So I think it— I think this— I think the answer varies, um, from job to job, from industry to industry, from segment to segment. Are you enterprise? Are you mid-market? Are you SMB? I'm not— I'm going to give a very boring answer here, but I think hard work. I think it comes down to hard work. I think sales, there's a formula, there's math behind it. We can coach, we can upskill, but if we know the formula, it's putting— it's the hard work, and it can be a grind. It's a grind where you're— it's repetition day day over day, week over week. And you need to remain even keel. I think the best salespeople are even keel. Don't get too high, don't get too low. And things can change very quickly. You come in the next day, there's an email waiting for you. Even keel and hard work. I think hard work is something that maybe we— it's not a fashionable answer, but, um, I think it's important.
It means different things to different people, right? Because being busy is hard work to some people. where, you know, really studying sales is hard work to other people.
Yeah. And I think to your— I think to that point, somebody who is open to new ideas, somebody who is— I always want the people I bring onto my team to— they'll have to learn about us as an organization, what we do, what we value, our unique selling points. But I want them to bring themselves. What has made you successful in the past? Bring yourself, bring that. But also be open to new ideas, new processes. Because you've done something one way in the past does not necessarily mean it's going to carry through for the rest of your career. Somebody who's coachable, is open to new ideas, and candidly will also share that. I like the best performers. I want them to sort of share what makes them good with the rest of the team. And sometimes best performers just want to focus on themselves. The more time they have on themselves, the more numbers, the higher the numbers they can hit, the more calls, the more meetings. But if you think about the broader picture of the company and the team, somebody like that being able to, for them to be able to share what makes them good at their role with somebody who's less experienced, I think that is a fantastic trait to have in somebody.
Yeah. And now the even-keeled part, how do you keep that in check? That's not easy.
I think it's, it's, I think it's an experience thing. I think, um, like, I've been, I feel like I've been in sales long enough to know that it's peaks and troughs. It's peaks and troughs. It's how we, it's how you react, particularly to the troughs, that is important. Everyone is going to have down months, up months, and that's just the, that's the nature of it. You hope it balances out across your team. 2 people are having a very good month, one person is having a bad month, it'll balance itself out. And then something similar might happen the next month. I think it's just reframing to your team, to the individuals that, yes, it's a bad month, we need things to pick up, but you've done it before, you've demonstrated before, you know what you need to do to be successful. But just sometimes, you know, that contract doesn't sign on the last day of the month, maybe it signs next month, and it has a huge impact on the outcome of your quarter or of your month. There is a luck element, there is a timing element to all these things.
Yeah.
the right things and you've demonstrated in the past you can have success, you will have success again. But if you're down here and you bring that negative mindset into sort of what you're doing, um, that will have an impact on the conversations you're having, on your outlook, on the people around you, on the prospects you're speaking to. So it's important to try and park that and realize, you know what, this is the moment in time. I will get back up here. Just don't carry that negative mindset with you.
And that's hard to do. And most leaders don't do it. They ride the quarterly roller coaster. First month, there's a bunch of meetings. Second month, people start to hunker down. Third month, everyone panics. How do you avoid that? Because I'm sure you get pressure. You're in the sandwich, right? You've got pressure from the bottom and the top.
Yeah, I think it's about thinking about the big picture. And again, it's going to depend on the the type of business you're in. Is it a small startup where every month, every quarter is the most important quarter of the company's existence? And you know what, the next quarter is gonna be the most important. So it's about, look, it's about sort of, I think it's about keeping that positive mindset and trusting that you're doing the right things. For me, is there, can I bring in my leader? to look at, hey, are we missing something here? Is there something that we could be doing differently? Trusting my leaders, my managers to identify areas. Hey, you know what, you're missing something there. Let's try this. But it's keeping that positive mindset. It is difficult, but if you've been in sales long enough, you do know, again, to the previous point, that it is peaks and troughs and things will turn around. They won't turn around themselves. You've got to put in the hard work. You've got to put in the effort. But they will turn around as long as the product is strong enough to sort of garner that market demand.
And when you were going through sales, did you notice kind of particular stages of skill or ability or success?
I think when I was going through sales, and this has become a very sort of, you talk about consultative selling. When I sort of started in sales, I don't remember that being— it wasn't something that was sort of thrust upon me as this is a technique that you should use, being conversational. It was very much, you have a prospect who's interested, get them on the phone and tell them every single thing your company does great. Tell them about why they should choose you above everyone else, all these amazing features, make sure you get every single one of them into the call. And I remember we brought consultants in, and part of the exercise was to listen to those calls. And I thought, you know, I'm doing quite well. I'm a good seller. I'm confident enough to put one of my calls out there for everyone to listen to. And the actual process of listening to that call was like me going 100 miles an hour and making sure every single feature was listed off. The person on the other end of the phone barely said 2 words. And I think that was a real eye-opening moment for me in terms of like how it can be done, um, turning it into a, turning it into a conversation. And Bill, like we, we, we speak about having rapport with people that you want to work with. I think the same exists in terms of the people that you want to sell to, is that can you build a bit of rapport? Can you, uh, identify something about that person outside of the whole sort of sales conversation that you might be able to weave into the conversation? Is there a poster of The Who in their office? And you can talk about, you know, I saw The Who 10 years ago, they're a great band. Things like that can really break the ice. So it's that consultative, conversation-based value selling that was a real eye-opener for me in terms of like how I approached my conversations. And I've tried to sort of keep that sort of throughout my career in terms of like how I We'll try and upskill my team and how myself I'll try and have conversations with people.
Yeah, and it's a critical skill because if you don't have it, you're only talking about the transaction.
Yeah, yeah.
If they're not interested.
Yeah, and it, it, it really goes back to like you are trying to solve a problem for them, and if you don't really know what, what that problem is, and if you can't get under that problem, there might be a surface problem, but there's probably something under that That service problem that is a business problem that really needs solving. If you can't tease that out, and if you can't bring that to the center of the conversation, it's going to make your life a lot a lot more difficult. And I think the same goes for if you talk about pre-sale and and then post-sale. You're talking about continually solving the customer's problems and continually to understand what's going on with their business more broadly so that you can tap into that and that you can align their solution. You can align your your solution to what more broadly is going on in their organization. And that's going to sort of set you up for success, I believe, not just pre-sale but throughout the journey, the customer journey.
And I bet that was very helpful when you transitioned into construction.
Absolutely. And I think one of the things I needed to learn a lot of things, I still need to learn a lot of things for sure, but when I moved into construction, it was Like, again, you've got software, and the construction industry is kind of software. We don't know about that.
They're not up on the digital transformation.
And they've been sort of taken a sledgehammer when brought into the 21st century. But these construction projects are so technical, the people who work on them are so— they're brilliant. But the environment is just like, it's a construction site. So technology and construction sites just do not mesh well. So it's really So important to understand what's going on in their world. Like, we worked for a company called Go Contractor Safety. It was a safety program. So when you're speaking to a safety manager, it's not about selling them on ROI, on dollars saved, on hours saved. It's actually speaking to them about, hey, this is going to have an impact on the safety, the health and safety of your team. Conversely, you might be speaking to a project manager. Of course, they care about the health and safety of their workers, but they care about delivering the project on time, on budget. So you constantly have to understand the language of a construction site. All these are all things that I had to sort of learn on the go. But it's a very traditional industry. So going to site, shaking hands, building that relationship is something that still really exists. And that's how the industry works. Your relationship with your subcontractors, your vendors is Really, really important to how a building gets off the ground. So that piece of like solving their problems, understanding their world because everyone's trying to sell them something is is critical.
Yeah, and I think that relationship exists in every industry. We just ignore it, and somebody gets it.
Yeah, the best, the best, the best, the best, the best sellers will get it because you're speaking to somebody. and they're interested in your solution, you can guarantee they're gonna be speaking to 2, 3, 4, 5, 10 other vendors because their procurement team will mandate it. You gotta speak to multiple vendors. So you have really, you have one shot really to elevate yourself above the rest. And if you're just talking about yourself, you're just talking about your product, how great it is, you know what, that mightn't come off as if you actually care about solving the problem that this person has. So those first impressions, They're really important to sort of give you that opportunity to progress things along.
Now, did you learn this from trial and error going on site, or did somebody say, hey, drop the tie and relax a bit?
Well, I never wore a suit again to a construction site. I can tell you that much. I think how I learned was listening, was listening to them on site. Listening to them interact with their vendors, they will talk you. When you go onto a construction site, they're very proud of what they're putting together. And like some of these are one of the projects we did was the J.P. Morgan headquarters on Trina on Park Avenue. It's like a seventy-foot skyscraper demolished and rebuilt in this tiny space. It's incredible. And they're really proud of the of the work that they're doing. So they'll take you on a take you on a tour of the site. You'll wear the the hard hat and the goggles, and they'll sort of show you things. So just being able to just understand their world, and when you're talking about how your solution can help them, weaving that into the conversation. You tell me about this. Well, this is how we can help with that, because it makes it seem more real rather than just, hey, it's another piece of software that our manager thinks we should bring in because corporate think it's a good idea for us to move into the 21st century. So Yeah, there's luck that goes into it.
And is that the thing that you learned or wish you had known earlier in your career? Was this connecting with other people, talking around the transaction instead of only about the transaction?
There's lots I wish I had learned earlier in my career. But I think if I spoke to 20-year-old Conor coming out of college, I think probably he probably wouldn't listen. But I think the one thing that I would, when I think back early in my career, when I started my career, I was very focused on the progress in terms of promotions, in terms of titles. I'm this age, I'm this title, in a year's time I should be this title, I should be, and it should just be that sort of linear journey.
Linear, yeah.
That's not the reality. And I think if you can get out of that mindset and sort of be open to, hey, your career is going to go in a direction or different directions that you don't expect it to go, that's okay. I think when you're younger, you're very much set on, I need to be this, I need to be this, I need to be getting here by the age of whatever. And that's going to impact you. It's going to impact your decisions in terms of career decisions you make, life decisions you make. So I think if I could sort of transport back to when I was starting my career, Don't be too hung up on that. Be open to conversations, be open to new ideas, and the direction your career goes in, it will go in, and, um, and that's okay.
Great. Hey, Conor, I appreciate your time today. Where can people go to connect and follow you?
LinkedIn is probably the best place, uh, Conor Gilbride. Um, it's been a, been a pleasure speaking with you, and, uh, yeah.
There seem to be some patterns there with the great salespeople. The willingness to take feedback, to accept that it's about somebody else, to be able to understand what they're going through, talk about what they care about, not just the transaction. Because what I'm learning more and more is that Sales is the intersection between really great sales process, understanding the flow, um, the ingredients of a great sales process, great questions, and authenticity, meaning going with what feels organic and natural to you. Now, probably for the first 5 years of sales, those things don't have much Overlap in the Venn diagram. Why? Because you're following your instincts, which typically have nothing to do with a good sales process. It's probably very reactive, and it's not your fault. It's natural. I went through it. Everybody goes through it. So how do you speed that up? Experience. And this is one of the things that you get with brevity, is that repetition You see, you think it's the knowledge, knowing what to say. That's 5% of it. The 95% that nobody cares about or thinks about is how well you say it, how you feel when you say it. Does it sound like you, the real, organic, authentic you, or does it sound like the sales rep you? See where I'm going? That distinction, you think, is minor, but it is huge. This stuff that we talk about with rapport, what we want is them— them being the client— to want to speak with us. Not just about the transaction, not just when they need us, not when they have a question or they want something. But there's something else that they get. They enjoy talking with you. You bring information, ideas. I hate using the word insight. It's so overused today. But you bring a vantage point, which— if you take a look at yourself, if you're talking to people like them all day long, you probably know a lot about what's going on. That's what they want to talk about. I know we want to talk about the transaction, but to talk about the transaction, we've got to talk to them and with them and get them live, and that's their choice. So developing that skill is critical, and like everything, it's repetitions. We don't want to believe that. We want to think in our mind, if we believe we can do it, or we tell ourselves that we're good at it, we'll be good at it. That'll give you the confidence and may improve your performance, but you know what works best. Ask yourself if you were coaching, you know, the person who was 2 years behind you. What would you tell them? Oh, just think about it. Just read a book. Just memorize it and visualize it. No, you'd say practice it. And now you can. And that's the, the use of AI to be able to make us better at sales. No other product does this. Everything else is about spamming people more. And that's a diminishing return. The more people do it, the less effective it is. And I think we're getting near the end of it. I hope, because it's kind of not very effective to begin with. You know, it was certainly effective 20 years ago, but it's gone down dramatically. But you know what does work?
What?
Starting conversations and getting meetings with people. People think it might take too long. No. Well, you're already at no, so you don't have to do anything to get there. What you have to do is build to a yes, and spam doesn't do it. The other course I have is Closing the Complex Sale, and we had a great office hours yesterday where we were talking about exactly what has to happen internally at your client's site to get a purchase of a particular dollar amount approved. I walked people through it, and a lot of people— if you sit on LinkedIn, people think it's the CFO. It's not. CFO has near zero to do with 99% of the purchases. Certainly 99% of the ones that happen outside of the finance department. And if you believe that, you're walking into an assumptive trap. Now, what I'm most excited about with brevity is getting you guys up and running with it and getting your feedback. Because I'm thinking of, you know, what are the things that are going to make it very engaging? We've got lots of ideas, but we want to prioritize them that will have the most impact. So stay tuned on the podcast. Go to brevitypitch.com. Get on the waiting list. We'll see you next time. Thanks for listening.
