00:00:00 Conor Hyland: The idea of a collection of yeses versus the collective yes. I've identified a pain, but I don't necessarily know how to indicate that pain or implicate that pain. If the contract's not out, it's never going to be closed. The earlier that we can get that in front and uncover objections, uncover issues or challenges that might come up, the better. Your champion can have power and influence in many departments, but that one department that you need them to have power and influence in — they may not. 00:00:36 Pim Roelofsen: If you could go all the way back and advise Conor from ten years ago, what would that advice be? 00:00:42 Conor Hyland: I think one would probably be kind to yourself. Salespeople probably put the most pressure on themselves more than most. As the saying goes, we're really living for the 20%, or the 30%, or whatever that win rate is — you're 70% of the time losing. So you need to have thick skin and be ready to get up every day and go again. 00:01:14 Pim Roelofsen: Hey everyone. My name is Pim. I'm here with MEDDICC. This is our podcast show, Elite Dealers, where we talk about the best deals that some of the elite dealers in our industry have been bringing into their companies. Today we are with an elite dealer from, customer success week at the park and with GoCardless. And this person has actually transitioned into a sales leader role right now. However, the deal that we'll be talking about is one they did not so long ago. So I'm pleased to introduce Conor. Good morning, Pim. Thank you so much for having me on your podcast today. I'm really looking forward to chatting about some of the deals, how we use MEDDICC, and sharing some wins along the way. 00:02:00 Pim Roelofsen: Yeah, absolutely. So Conor, you've had a bit of a journey within GoCardless over the last year or so — is that fair to say? Could you tell us a little bit about that? 00:02:08 Conor Hyland: Yeah. If I go back a little bit — I'm originally from Ireland. I moved out to the Middle East; I was out there for seven years with the Irish government originally, and finished up with LinkedIn. Came back to Ireland, did my MBA, and decided I wanted to move into fintech. There were a number of companies I was looking at and GoCardless was one of them. I decided to move over to London. 00:02:37 Conor Hyland: So I've been with GoCardless now for about a year and a half. I started off as an AE selling into our corporate and enterprise accounts, and now I've just moved into an emerging sales manager role for UK and Ireland, focusing on scaling startups with revenue between 0 and 30 million. 00:03:02 Pim Roelofsen: Awesome. And how has that transition been going for you — from IC to leadership? 00:03:05 Conor Hyland: Really good, to be honest. I think there have been a lot of roles and a lot of different things that I've done in my life where you are a leader without a title — you have to show up and that manifests itself in different ways. So I guess this time around it's just having six other people that I have to be mindful of and make sure that I'm showing up for every day. It's not just me anymore — it's the other six people in the room. So that comes with an added responsibility. 00:03:43 Pim Roelofsen: Hey, so Conor — I see a lot of books on your shelves there. Anything you're reading right now that you'd recommend to our listeners? 00:03:50 Conor Hyland: Yeah. I've been on a reading frenzy for the past two years. One book that I'm currently nearly finished is Shoe Dog, by Phil Knight — fantastic read. He's a really good writer, more than anything else. But if I was to give a recommendation of a book that's probably changed me the most, it's probably The 5 AM Club. 00:04:19 Conor Hyland: I joined the 5 AM Club for myself back in January and I've been up every morning since. It's probably transformed my life in terms of getting up and seizing the day. So I'd probably recommend The 5 AM Club, but Shoe Dog is a great read as well. 00:04:28 Pim Roelofsen: That puts a little question mark in my mind — do you get up at 5 AM every morning still? 00:04:33 Conor Hyland: Yeah, still. So this morning — bright and early — went and did my CrossFit session, and then yeah, back home. Usually got a bit of a routine: probably an hour and a half of reading in the morning and coffee before anybody gets online and starts. So it's a bit of my safe haven, the morning time. I think I might have listened to a summary of that book — isn't it that you do it together with a few other people as well, so that you hold each other accountable? 00:05:00 Conor Hyland: Well yeah. I'm lucky that my significant other is also getting up at that time, so if she wasn't, she'd probably be pretty annoyed at me waking up every morning at 5 AM. So it definitely helps having somebody to hold you accountable. And also in the CrossFit community there are a lot of the same faces — you might get a little message if you weren't there that morning to encourage you to get in the next day. 00:05:23 Conor Hyland: So yeah, having that support system is always important. 00:05:28 Pim Roelofsen: Very nice. Okay, thanks for sharing that. So we're going to talk about one of the deals you did before you turned sales leader, Conor. What I'd want to know is: what is this customer about? How did you find them? How did you first engage with them and get the initial ball rolling? 00:05:43 Conor Hyland: Yeah. So the customer I'm going to speak about today is one of the biggest credit consolidation companies in the UK. It was one of my top accounts for the year — a priority one account — and something I was keeping a close eye on and trying to strategize around. How I found them: we're lucky enough at GoCardless to have a big sales stack. We have Sales Navigator, we have ZoomInfo, we have Quanticopy, we have Salesloft. So it's really about trying to maximize all of those tools. 00:06:37 Conor Hyland: One great thing you can do on LinkedIn Sales Navigator is look at people that have been in your CRM who have changed roles in the past 90 days — which is always a leading indicator that they've come into a business to drive some change. One of those signals for me at the time was that the finance director in one of my top accounts had just newly come in, but also had been a GoCardless customer in the past. So they knew our business, they knew the value. And it was really about that initial conversation — seeing if they were coming in to drive change and whether GoCardless was going to be top of the agenda. 00:07:18 Pim Roelofsen: So that stakeholder that you found — what's the story there? 00:07:21 Conor Hyland: I always think about outbounding strategies, and I speak to the AEs on my team today about: what is the best message, how do we tailor the message? In my experience, you can have the best message to the right person, but timing is a huge influence. It's really about when is the right time for that customer to drive change. Sometimes you can be very early in the process where they're just doing their own self-discovery; other times you're coming in where they've already decided this is a project that needs to happen and they're just figuring out what type of vendor to work with. 00:07:41 Conor Hyland: So getting in front of that customer at the right time was really important. And then once you get in there, it's about driving the value drivers — communicating how we can support a customer like theirs. 00:08:04 Pim Roelofsen: Yeah. So if we think about that — how you can support them — you're essentially thinking about what their current state is and what you can make better. The pain that you can solve for. So how did that work in the beginning of this sales cycle? 00:08:12 Conor Hyland: Yeah. I think at MEDDICC, you guys talk about emotions and metrics as proof points. Robert Cialdini talks about that a lot — we view the behavior of others as proof of correct behavior, and people persuade other people to do things. So it's about getting in and demonstrating where we've helped customers similar to theirs in the past, and what kind of business outcomes they've had. A huge part of that is how you command the message. What is the research that you do before that call that puts you in the right position to articulate that? 00:08:46 Conor Hyland: And I think that's a huge part of sales that people forget about — preparation. That preparation manifests itself in the early stage when I'm going to outbound or prospect, but it also manifests itself in the early discovery stage where, at a high level, I understand what's going on in the industry, what the value drivers of that business are, what challenges they may be facing, what the implications of those challenges might be, how we can help them, where we've done it before — proof points — and how we're uniquely positioned to do so. If I have all of that when I go in, I'm already in a very good position to drive value from day one. 00:09:43 Pim Roelofsen: Nice. It's almost like I'm listening to one of our own method masterclasses there. But if you think about that stage of the deal — that period in the sales cycle — what about stakeholders? There's an initial person that you found via the approach you just described. Would you say they were your potential champion? 00:10:06 Conor Hyland: Yeah. So they were the finance director — just come into the business, had worked with GoCardless before, knew the value we were driving. So it was really about having that conversation early doors to see if this was something of interest to them. And I think when we look at the GoCardless stakeholder landscape, there's quite a wide variety of people we can speak to: heads of product, retention, growth, CTO, CIO, CFO — all of the acronyms under the sun. But for the most part, it's probably finance directors and CFOs, along with a technical capabilities piece and a user experience piece around conversion. In this instance, the finance director was identified early as a champion because of their understanding of GoCardless. 00:11:14 Pim Roelofsen: I can see why that would work so well, especially since you had worked with them before. But this deal — and I think typically your other deals as well — the stakeholders you needed involved were more than just this one person, right? So what are some of the other stakeholders you needed to get access to, and how did you get there? 00:11:40 Conor Hyland: Yeah. A huge part of getting access to stakeholders comes from that initial discovery — trying to understand what the high-level problems and pains are. In this instance, and as MEDDICC talks about, there were financial, efficiency, and people dimensions to the pain. Financially, there was high card cost. From an efficiency standpoint, they were having high failure rates with their card payments, which meant they had to chase failed payments — a lot of people in their call centers calling customers trying to get payments back into the business. And then from a people perspective, it was inefficient teams around reconciling payments coming in. 00:12:22 Conor Hyland: So when you break down those three components — from a finance director standpoint, it's about the costs they're incurring; from an efficiency standpoint, it's who's in the call center driving all those calls; and from a people perspective, it's the head of treasury and their team. And then there's the technical integration piece as well. So at a high level I'm trying to get my CFO who's my champion, get someone from treasury, get technical validation, and get someone from the call center. To get them all in a room, you need to be very clear with your champion: "I think we've uncovered something here. These are the type of people I typically see involved in deals like this — do you think now is a good time to bring them in?" If they say yes, you know you've got someone who will champion this project. If they say no, it's about understanding why and how you can overcome those reservations. 00:13:58 Pim Roelofsen: Yeah, that's thorough. And so when those stakeholders come in — are you personalizing the potential outcome with the champion, aligning what each of them is looking to achieve, almost building consensus around a shared target for a partnership? 00:14:05 Conor Hyland: Yeah, that's a really good point. I was reading The Challenger Customer a few years ago and it talked about the idea of a collection of yeses versus the collective yes. You can individually have stakeholders say "yeah, this sounds great" — and then all of a sudden you get them all in a room and it doesn't quite work. So it's about understanding on an individual level the pains and challenges each one is facing, and then bringing them all into a room and acting as a facilitator: "Here's what was important to each of you independently — does this all still make sense together, and how can we drive consensus across all the teams?" 00:14:41 Conor Hyland: The champion will help facilitate that, especially if they're in a position of influence and authority. But as a salesperson you also have a responsibility to be able to share those learnings and co-facilitate those calls. 00:15:10 Pim Roelofsen: Absolutely. And something interesting you mentioned earlier is around the different types of pain, and how that relates to metrics with this customer. The same metric can look very different from one stakeholder to the other — where a CFO might express it as a dollar amount, someone more operational might express it in hours saved. Getting clarity on that common consensus from various perspectives is important, and probably your champion is the best person to help you get there. 00:15:43 Conor Hyland: Exactly. And when you have somebody new coming into the business — CFOs are historically going to drive change very quickly in their first few months — but that doesn't always mean they have the influence from day one. Finance teams often have people who've been there a long time and understand the processes. So even though your finance director or CFO might be a champion, they probably still have to get internal consensus from some of those longer-tenured people. They have to act like internal change agents, and they have to build that momentum internally. It's about nurturing those different conversations and understanding the status quo. Stakeholder consensus is a really interesting one — even though you think you have a champ, you still can't forget about the people who may be blockers. 00:16:50 Pim Roelofsen: Yeah. So what was the total length of the sales cycle — from that initial stage all the way through to the deal being booked? 00:17:03 Conor Hyland: Around six months from outreach to close. 00:17:07 Pim Roelofsen: And if you think about that timeline from a pain perspective — how did you go about not only identifying and implicating the pain, but keeping it alive throughout so it stayed top of mind and you were able to get access to all the stakeholders across the whole cycle? 00:17:36 Conor Hyland: Yeah, it's a really good question. A huge part of uncovering pains is having a champion who's bought into the problem they're facing. I often hear about customers not giving enough information or being closed off — and I think for us as a business, we're never going to be the cheapest. So it's imperative that we build business cases demonstrating where we provide value and ROI. We really need to get good at uncovering what's really going on. 00:18:00 Conor Hyland: I feel like there's a misconception around discovery-type questions. What often happens with AEs is we teach them to listen for keywords — so they've identified a pain, but they don't necessarily know how to indicate that pain or implicate it. What we're trying to do is be conversational, be facilitators. We're going to the call having pre-hypothesized, so some of those questions are going to be validation questions, some are going to be deeper discovery questions, and others are going to be consensus-building questions. And then once we have that information, we need to drive momentum. 00:18:51 Conor Hyland: The momentum piece is getting the right people in the room at the right time — speaking about the customer service piece, the treasury issues, the technical integration, maybe in parallel to maintain momentum. Understanding when they want to go live and working backwards from that date. That's really the "why now" — what is the compelling event, and how do we get to it? If you have that compelling event, it becomes easier to gain momentum. And implicating the pain is really going to get you to the "why now." So it's about driving momentum, understanding the pains, holding people accountable to the "why now," and keep circling back to that. 00:19:34 Pim Roelofsen: Yeah, absolutely. I want to pick up on something you said — the go-live plan. Working back from the moment the customer needs to go live, which is tied to the pain they're trying to solve, underpinned by metrics. And sometimes I hear the best sellers talk about the early introduction of MSA terms and conditions to save time later in the deal. How do you go about that? 00:20:07 Conor Hyland: Yeah. A long time ago one of my old bosses — an MD at Dell — said to me: if the contract's not out, it's never going to be closed. The earlier we can get that in front and uncover objections, issues, or challenges that might come up, the better. But there's also a very fine line — "why are you sending this over to me? I've not even confirmed I want to move forward with you." So it's almost about getting a sense of: "We've uncovered some pains here, I think we both agree this is something we want to proceed with — as part of that process, legal is going to be involved. Do you think it would make sense to send over the MSA now so we can work in parallel?" 00:21:10 Conor Hyland: I think a huge part of this, in my ten-plus years of sales, is that we very often don't get legal involved early enough. They've got a huge stack of contracts to get through; they don't want to start looking at things until they're sure it's going to close. And it can be challenging to get your champion to push that MSA to the top of the legal team's list when they're overwhelmed with work. So yes, in theory, it's great to get it out early — but whether you can actually get it to the top of their list is another question. It's a tricky one to navigate, but yes, the earlier you get it out the better. 00:22:01 Pim Roelofsen: Yeah. I think it was interesting how you talked about getting introduced to other stakeholders — by explaining to your champion: "Here are the typical individuals we'd see as part of your team that we'd need together to make this a success." It becomes a common goal. And I think the same applies to the paper process and the go-live plan — you tie it back to when they need to start getting value from the solution. If you build in the MSA review a bit earlier, it's a great way for sellers to get ahead of delays later in the process. 00:22:31 Conor Hyland: Yeah. And another part of that is around board approval as part of the decision process. In this example — the CEO and the board would ultimately make a decision. And a lot of the time we'll just naturally say "great, it's going to the board" — but actually, maybe the board only meets once a month, or once a quarter. And if you don't have that in your timelines, all of a sudden you've said legal is going to take a week, but actually you needed to give yourself a month's wiggle room for the board meeting. And if you miss that one, you're out by a month. So board meetings, and understanding the decision process in full, are really important to be mindful of. 00:23:43 Pim Roelofsen: Yeah, that's a great point. So I think we've uncovered a lot here — especially about the initial stage and throughout the selling cycle. What stood out for you specifically when it came to stakeholders and bringing this deal home? 00:24:07 Conor Hyland: I reflected on this at the time, which I think is a really important thing to do — because if we're not reflecting and being deliberate about what we do, we make the same mistakes. Two reflections I had on stakeholders: one was C-level alignment. Sometimes it can feel unnatural to bring in that C-level executive sponsor to a deal, because you've got such a good relationship with your champion, everything is moving smoothly, you feel like you're on course. It's not to say the deal slipped because I didn't do it — but I feel like if I had gotten that C-level alignment earlier, it may have moved things forward by a couple of weeks and given me that foothold I needed at key moments in the deal. 00:24:41 Conor Hyland: The other piece is around legal and boards. Although I was able to uncover the board meeting, I was not able to uncover the priority legal was giving us. We just weren't a priority for legal to get through. You don't know what's happening in the business — maybe they'd just acquired a new company and legal was working 18-hour days on due diligence. Yes, you can have a contract sitting with legal, but where is it on the desk? Is it at the bottom of the pile or the top? That's a hard question to ask — "yes, it's with legal, but where is it on the priority list?" — because they don't care about your deal. They care about the macro picture: "I need to close this new acquisition we've just done." So for me in this instance, the two key stakeholder lessons were C-level alignment and legal. 00:25:48 Pim Roelofsen: Yeah. And which brings the power and influence of your champion back into focus — because it becomes super relevant there. If you think about that go-live plan and legal is super busy, how powerful is your champion to get something from the bottom of the pile to the top — because together with them you're able to articulate why it's imperative to still hit that go-live date? That's where you really need a champion. If they don't have that power and influence, it's not going to happen, and your deal slips. 00:26:50 Conor Hyland: Yeah. And that's a really good point — your champion can have power and influence in many departments, but that one department where you need them to have it, they may not. Internal conflicts, internal politics, they just don't have a good relationship with that person in procurement or legal — and that slows everything down. And they're probably not going to volunteer that. "By the way, I don't have a great relationship here and this might go slow for us" — it's just going to be a slow burn. I've had that in the past with certain deals where you just don't fully understand the internal dynamics. 00:27:32 Pim Roelofsen: Gotcha. Great insight. So I think we've heard a lot of useful things today — the tools at the beginning like Sales Navigator and Salesloft; the M1 to M2 transition approach, where you take the quantifiable, impactful value you've already delivered for current customers and translate them to the prospective customer in the early stage to earn the right to do discovery. Because that's what it really is, right? The customer will say "I don't know you yet" — so underpinning your pitch with quantifiable value from customers you've already had success with is extremely powerful. 00:28:19 Pim Roelofsen: And one key takeaway I also have is: preparation is key. The number of times you still see people going into a meeting without an agenda, without any sort of preparation — if you start doing that, you're already ahead of most. And then pain throughout the entire cycle, getting access to teams like legal early — some really differentiating points there. 00:28:51 Pim Roelofsen: So the last thing I'll ask you specifically about this deal — before I go to the closing question — is: if there's one piece of advice you could give yourself from a year ago, specifically on this deal, to potentially do differently, what would it be? 00:28:55 Conor Hyland: That's a good question. I think it's about trusting the process. When, you know, we're in a macro environment where the market is tough and we need to be better, faster, more efficient than we've ever been — sometimes when a deal falls into our laps, we think "happy days, let's run with this and get it through as quickly as possible." But it's about taking a deep breath and saying: let's go through the process, and let's deliver each stage and each step — not only from a sales process standpoint, but also from a buyer's process standpoint — to make sure we're delivering what our customer needs at every engagement level. If you do that, at the end of the deal, nine times out of ten you'll be successful. 00:29:51 Conor Hyland: If you start to get desperate, if your pipeline is looking a bit thin and you start trying to skip steps to get a deal in quicker, they normally just dissipate and disappear. So the advice I'd give myself — and still give myself going into this macro environment — is trust the process, get your systems in place, and deliver deliberate execution every day. 00:30:16 Pim Roelofsen: I think that's beautifully put. And in a lot of ways it's saying similar things to how we think about deal confidence, right? I've found myself in places before where I wasn't sure what's going on, what we need to do next, how we're ultimately going to be successful. And that can mean different things — not just winning deals, but spending your time on the right things in the right deals. And in a lot of ways, that's what the MEDDICC qualification framework did for me — giving you a way to understand what to focus on in each deal, and a follow-up process to ultimately eradicate that feeling of uncertainty. 00:31:05 Pim Roelofsen: And so Conor — a moment ago you said you've been in this career for ten-plus years. If you could go all the way back and give Conor from ten years ago one piece of advice, what would it be? 00:31:15 Conor Hyland: I think one would probably be kind to yourself. Salespeople probably put the most pressure on themselves more than most — we're constantly beating ourselves up over every little thing. So being kind to yourself is something I'd reflect on. But looking across ten years, two things jump out at me. One is: how we do anything is how we do everything. That's really about personal brand, and your personal brand starts from the day you enter a sales organization to the day you finish your sales career — not just within that organization. It's a very small market. People talk. How you show up every day is how people will talk about you. What do people say about you when you're not in the room? As a young person coming into a sales career, we sometimes forget about that. Money's coming in, everything's great — but we forget about what people think of us and how we're showing up. 00:32:33 Conor Hyland: And I think the other one — and I guess the main one — is around focusing in on your brand, focusing on delivering every day, and being kind to yourself when things don't go right. Because as the saying goes, we're really living for the 20%, or the 30%, or whatever that win rate is — the other 70% of the time you're losing. So you need to have thick skin and be ready to get up every day and go again. 00:32:51 Pim Roelofsen: Yeah. No, I think you put that beautifully. And it really resonates with me too. I used to feel pretty bad if something didn't go the way I wanted — but sometimes it was because of poor qualification and I shouldn't have been in that deal in the first place. It's a great piece of advice, especially for individuals who are a bit earlier in their career. So I appreciate that — I really, really appreciated all the insights you gave us today. 00:33:35 Conor Hyland: Thanks a lot. And, to the next episode of Elite Dealers! Thank you very much for watching, and tune in next time. 00:33:43 Pim Roelofsen: Thanks, Conor!
