How to Land Big Deals: Jon Azodo’s Playbook for B2B Sales Success
40m 7s
In this podcast episode, Jon Azodo shares the behind-the-scenes strategy for landing a transformative deal, emphasizing the importance of pipeline creation and stakeholder management. Jon explains that his team adopted an ABM model with one-to-one pods, allowing him to strategically select accounts through "whale hunting" sessions with his BDR. They targeted large prospects that had previously evaluated AirCall but lost due to timing, not technical fit—filtering Salesforce for closed-lost opportunities where SEs had green-lit the deal. This approach re-engaged a fast-scaling company that had twice declined, but a referral from a satisfied customer opened the door. Jon nurtured a new, low-tenure contact over four months of monthly 15-minute meetings, focusing on rapport and delivering industry insights, which built trust and led to introductions to senior stakeholders. He used a "give-get" method to test the champion's commitment, asking for small tasks like call volume data, and coached her on internal dynamics. To manage his manager's pressure, Jon provided weekly updates to all relevant internal parties (manager, director, VP, legal, InfoSec) via a Slack channel, using a traffic-light system to track progress and align on asks. This proactive internal management, combined with patience and strategic coaching, turned a monthly check-in into a career-defining win, demonstrating how to become the quarterback of large deals.
What's up, my sales hustlers? This is Jack Niko and Jack Fox back with no big deal. The raw, unfilled to podcast with Top Sales Pros are going to reveal their strategies that close their biggest deals so you can learn from and use it in your day today. Now, with Jon Azodo, he's going to take us behind the scenes of his massive dealer, Erkall, from strategic well hunting to masterful champion coaching. You'll discover how Jon transformed a monthly check-in into a career defining win. Jon is also a massive fan of no big deal, so we've got a fan on sharing his tips. Jon, as well, actually bought the no big deal manifesto, so you're going to hear how he used the guide that me and Jack wrote last year in this deal to win it. Get ready for game changing insights and internal stakeholder management, the power of patience, and how to become the quarterback of your biggest deals. This is no big deal. Tune in, cue the intro. Jon, one of the things that is like everybody is challenged with at the moment is getting good opportunities into that pipeline. So not run rate opportunities, actual big means, the opportunities that are going to get us sort of like two and a bar then like really over exceed our number. Obviously this is one of those deals. So tell us how did you get and was anything unique about how you got a big deal into your pipeline in this instance? For sure. So yeah, I think the team had just moved to like this the ABM model of a but also more importantly one to one pods. So every AE was paired with a BDR, which meant that you could be a bit more strategic about the accounts that you wanted to pick. We also didn't get a book like you pick your own book, you define which accounts you want to go for. Luckily, I had a really tenured BDR but I was quite new to the business. So he was very familiar with like where air or winds and where we don't. So in the account selection you played like a really important role. So I have to be sure to give him his probs. But effectively in the account list we kind of we called it well hunting is the session that we kind of put in the calendar. It was basically looking for big accounts where there was a strategic opportunity they could have a start small and grow really large or they could even start with like a really big bang and kick off really quickly. So that was like the how we put together the account list. And then in terms of this opportunity we just got really lucky. So I know you you mentioned this all the time for us about how there's an element of luck with every one of these deals you have to get lucky. And so with this particular account I managed to get an intro from another very happy customer who'd mentioned that they'd really enjoyed working with me and they saw an opportunity for air quality to be valuable in that new business. But they weren't sure whether or not it was going to be the right fit. They would be happy to make the intro but then the ball was in my call at that point. So that's kind of the the genesis of that but the account was already selected. It was already on my hit list. It just made it just paid dividends that it kind of kicked off with a referral. When you do that way or on in session with your BDR. Let's say I'm but I'm just I'm literally going to do that now you just said that next year. You have like PG does the show in your account. I'm going to PG day Tuesdays the first two hours of that I'm going to get my BDR on a room and do well on it. What did you do? Did you like map in sales force like previous big customers that air call try and work out what a common it's all we've really had that process works and basically how do I do that? For sure. I think every AE wants to go to the first place they go is close one like where are we in and we want more look alike customers. I did the same thing. There were a lot of look alike customers but I think again I had to think outside of the box in that this is a this is a strategic play. So I had to think about where I'm going to find the right type of customer where we weren't the right fit. So I actually looked at lost opportunities that were kind of far down the sales process. So I guess the secret to this particular deal is that they had evaluated air call before twice over five years and decided not to go ahead because they didn't feel that the product was like ready. But they always liked the product. They was like the idea but they were super fast scaling and so they really wanted to make sure that you know the product they're going to buy into is ready day one but also is going to grow over time. So when we were whale hunting that's what we're looking for. We want to speak to someone who we don't necessarily have to reintroduce ourselves. It's more a case of now's the right time to speak to us because you know we've done we've made this improvement or this is we've added this new member of our senior team like we've got the right now's the right time to have this chance. That's how we build out. So you'll feel really in Salesforce closed lost closed lost app like scope or negotiation or something. Yeah. Re listing all of those and being like okay what was the problem at the end of the deal that isn't a problem today. For sure. And then also filtering by technical risk so paired to everyone of these strategic deals is an SE. SEs also have to deliver a forecast. They often have to they deliver their forecast based on the technicals and they have to deliver like a confidence level. And so there were these these accounts had typically had closed lost opportunities far in the process where the SE had green lit the deal. So it was a case of oh we know we're going to be the right fit technically. It just probably wasn't the right time. So those are those are the best accounts for us to be going after. And and in this then research on top of that clearly the clever way that you got back in was through a customer reference. How did you then find that? Yeah so I think my VP would kill us all if we don't ask for references after every call every closed one opportunity. Luckily he used to be an A so we can actually listen to what he what he has to say but whenever he he claims that back in his selling days it was it was like sort the the normal process was to ask a referral now that I've helped you out who else in your network do you think could benefit from this solution. So that kind of was ingrained in me from onboarding. But I think when you get a referral it's hard to know what to do with it and it's also hard to know who's the right person. So I think for a large transformation you're going to get an introduction to someone in the business but it's not going to be it's not going to be the CEO and even if it is the CEO more often than not with these large translations the CEO doesn't make any decision without group consensus. So if they if I had a referral or inter sort of above the line it was going to be useful but if it was below the line it was also going to be a bit tricky there was always going to be some navigate it needed. Quick one from me if you like what you're hearing today head over to nobigdeal.club you'll find a whole host of other episodes on there you'll also find the no big deal manifesto. Manifesto is a breakdown of every lesson we've learned from all the guests we've had on the show. They'll give you tips, tricks, frameworks, guidelines, templates on how to open, manage and close your biggest deal. Check it out and hey introduce this podcast to your friends it's the easiest way for us to grow and get more great guests on for future episodes. Back to the episode say for example I you know it's a good fit and you're you've got a referral if I'm the AE do I reference the old opportunity and say this was the problem is that still a problem some of you want to discuss are you going to kick off where you where you left off or are you trying to like rebuild it from scratch I'm assuming it's the former it's definitely yeah you definitely want to kick you want to kick where you left off but then you also want to have a new point of view yeah that's what you have to see when that right back you have to assume that they came to you with some problem or you went to them and discovered they had some problem but the problem either wasn't pressing enough to solve right now or not painful enough to solve right now and so you have to come in with a new point of you so even in this case where I was given the referral strangely the referral contact was someone who was external in the business but was going to have high like high visibility or visibility in the right rooms so I knew that I needed to come prepared to that call more that more so in the case of like what do I want to come out of it so I want a referral from that referee that's my ultimate goal is I want this person to intro me to other people in the business and so I need to come with something new and also more importantly the sort of the person that my contact referred me to and was also very new in the business so I knew that if she's going to make if she's going to clear the path for me I had to deliver value she I had to bring her something new that she could take up to exact and say hey guys have we looked at this is this is this still a problem this is a new way that they're solving it I also have a line to someone in the right like who's selling a solution that can actually solve our problem okay so this is something that I always hesitate with when someone's new in a business I am not very good at empowering them I often feel a little bit hesitant that they I'm maybe just a bit cagey that they haven't done like their tenure yet to build a consensus of people who might follow them on this journey to try and create change what did you what did you do to overcome that was it was this an element of luck that she was quite powerful influence or was it like you built her up in a way that made her feel powerful how do you how do you help somebody who's no to help that make change yeah that's a good one I think in this in this case we just had to take we first of all we had to take it really slow so I knew I knew they asked I knew I wanted it in sure I knew I wanted her to kind of put me in front of the teams that Eccles going to be useful for but I also knew that she probably doesn't know who those people are and even if she asked them to join a meeting they'd probably say no and so I think it was a long game the the long going to show of it was we had 15 minutes in the calendar
every month for four months before she made a single intro. And like it was, and it was a case of every week, I'm trying to bring some new industry inside. This is what I heard is happening. And it would start, the conversations would start that way and then they'd end with, you know, what she's getting up to that weekend, what her kids are doing. Like we built a rapport, but she felt comfortable coming to those calls every week. And also there was always a little bit of a takeaway. So every week, like every month, it's, oh, I've seen that this new product is being launched, how's it going? And then again, feeding back into air could be in a phone solution. How is that impact in the phones? Are this particular problem that you're experiencing in terms of like sort of your customer support? How do, how is this new product launched affected by those problems in the support team? So just kind of coming back to it. Every month she's thinking about new ways that this is an issue. So by the time it came for me to be confident enough to say, hey, we've been talking for months now, are you okay to make an intro? I know who I want you to introduce me to. She'd already knew that I was waiting for that intro. She was like, not only do you need to speak to this guy, but you actually need to speak to her. You need to speak to this person. I think we actually need to call with these individuals. And so she was kind of integral in that process, but also her kind of me, her coaching me and me coaching her as to like what's valuable about our solution and her telling me about the dynamics internally in the business. I think that that was kind of the process. Based on this opportunity, what are the signals then on this experience that you would also look for for these types of scenarios in other opportunities? It's going to be that give-get. So I think everybody sees the post-satellite in about ease need to be in need to be a give-get in every scenario that you're constantly negotiating. But I think when you're coaching your champion, or when you're figuring out whether or not your champion is a champion, it's always going to be about those, those gets. Like how open are they to the idea of giving something back to you when they ask for something? Also, can you test them with small things? Like I think an introduction to a from a stranger to their most senior execs in the business is an incredible ask, even if you are selling something that's going to be super valuable. So you do have to build a little bit of credibility there, but there are small things you can ask for. I'd like to typically with telephony, there's always an existing solution. So we ask, "Hey, what are you using today?" But then there are more details around that. So if you're on the phones, you have volumes, how many calls are your team's making? Where are those calls going to? Where are you seeing bottom-backs? If those things that they wouldn't typically know on that call, that they have to go away and almost do a little bit of homework, that's a signal. They come back to you and they say to you, "Yeah, I did what you asked." And then I guess here's what I want in return. Then you're in a conversation already negotiating. Reminds me of Jack, Libio and Jones' episode, if you can also remember that John, as I do. We like, this is tips for sales reps, come prepared with questions that potentially that stakeholder is not going to know the answer to. And it will allow you to multi-thread into people that can get you the answers to the challenges that they're hoping to alleviate. This is a really great technique. I've actually got a deal review with Will today and we're going for an onsite me and I've got next week. You need to ask this question about the measurement, how they're going to track that? I was like, "I'll just take a lot of what I want to know that." Will was like, "Yeah, exactly." That was like, "Oh yeah." That's how you get the intro. We need to go wider. I was like, "Okay, I think about that." It's such a good point. John, how do you manage your manager when they're saying, "John, you've been speaking to this person every day, every week for 15 minutes without any, it's going anywhere." So two things. How do you manage your manager to keep them like? What are you doing? Yeah, well, yeah. Yeah. Could keep them patient, but also, how are you keeping one eye on like whale hunted and also hitting target in that instance? Because that's what your manager wants you to do. They want you to hit target. And also, we to progress that whale and you're sitting there trying to do both things at the same time, keep everybody happy. How do you do that? I'll be honest. Initially, I wasn't hitting target and my manager wasn't happy. We had one of those conversations where it's like, "I get that you want to hunt whales and I think I'm going to give you the autonomy to be able to do that, but you've got to give something to me." So, it's nice that you have these monthly sinks, but what are you doing every day? Where are the deals you're closing every week? And that was the give. I think that was the thing I knew I had to promise. And return, it was like, "Okay, after those sinks, I had to sink with my manager straight afterwards. This is what we discussed. This is what I asked for in the next session of what do you think would be like reasonable to ask for next?" And that was kind of the cadence for those, I guess, for the main bulk of it. So those four moms. That was kind of the rhythm. And then it kind of became like an internal thing. We'd have that monthly review where specifically on this opportunity, we were like, "Okay, here's the update, here's what we're doing." And it built into the long-term rhythm of this deal. So towards the end, skipping towards the end, in terms of the closing, we eventually got to a place where we were offering weekly updates. So I used to give my manager weekly updates. This is where we're going. These are the asks I made. This is what we're expecting. What asks do you think I should put forward in the next meeting? And so that was the weekly update. I went to my manager. Eventually, as you know, these big deals require lots of internal stakeholders. So I actually had to put together a weekly update for not just my manager, but our director and then our VP. And then also other stakeholders like our chief legal officer, head of security, ahead of InfoSec. It's the same. They were all in this bit, really big Slack channel with a weekly update. So they always knew what was going on. So that's kind of the way to manage up. It doesn't mean that you don't get the pressure. I still had all of the sessions where it's when it's closing, when it's coming in, but like being proactive about that internal management. I almost feel like you have to manage your manager as much as you would in prospects for a. What are you would ideal? It's exactly the same way. Did you have like a pro-former, like a template of how you send that update round, like the context, what change, what needs to change, block it, something like that? I did, yeah. You send it to me. Yeah, it's like. Send me the template. I have to remember. Do you remember I think what we heard from Olli was like a really good, was like the traffic light system? Yeah, I was like, I'm not sure. I'm like, red, this is not, this needs to be done at you. Green, this is fun. Do you know how I've actually taken that and used it into a different part of my sales process? When I'm delivering like decision criteria, I actually try, I've renamed it to testing criteria. I feel like it resonates with the buyers that have better at the moment. It's like it's what you're testing really on your brief of concept. I have it in a table format on a slide. On the left hand side will be the like the overarching description. So let's say genericly it could be like the AI features of your platform, which probably everyone has now wrote. And on the right hand side is just like a high level description of like specifically what they're going to test, like what would demand, what would regard as success. And I traffic light the decision criteria with my buyers at the beginning of every weekly check in on the proof of concept. So I say, okay, we're going to start at the top. Like, let's go and I give it like six. You can basically be one of six dark red one is like really not doing well. All the way to like a lighter red lighter orange and it really helps to then formulate when you go and take it to the senior stakeholders that sign up. We've done this proof of concept. This is where we did really well. And it lets you, but I've seen buyers have the slide on a zoom call like actively talk like this is so good. This is how different it is here. And this is here. I don't know that I just thought of that as like quite a nice way of. Is it in like a G sheet or like a word doc or something? It's in a Google slide that I have a template of. And I actually another way of doing it. And I could share this with you afterwards as generically is I actually give it as a descriptive thing per industry. So let's say I've got one for the three major, we work with like 20 industries at Vacada, but like the three major ones I go, by the way, generally when we go and prove the concepts, this is the testing criteria. And you know it's the six ones where we went. Yeah, yeah, so obviously. And I'm like, you probably don't need that one. We can add in this one. I know you spoke about this one, adding this one. So it's like a really nice way of presenting it to the client. And then always going to track it through the travel. Anyway, I rambled on a bit there, but hopefully someone found that valuable. Yeah, I mean that's what I'm pleased. Yeah, cool. Actually, definitely I'll send a dude both of you. I actually want to go back to the deal and something that we talked about like after you got this referral, John, is like, how your champion ended up coaching you? Tell us more about that experience and the result of it. For sure. I got really lucky, I think, with a really nice champion. So not that we don't love all of our customers, but like I feel like it was a real pleasure speaking to every month. Like I actually look forward to hearing about what she got up to the last day days. So that was, I think that was the first piece, but I think also
It always felt like she was moving in the right way. So it felt like she wanted to help me, and in turn, I wanted to help her. I wanted her to show up to those management meetings and look good. And so I always tried to show up with something new. And in turn, she would give it back to me. So I remember one month, she showed up to the call and we were talking about the weather or whatever. And then out of nowhere, she explains to me the procurement process. And she's like, hey, just to let you know, we've just bought something. And this is the steps that we took to buy. And like, when I'm telling you, it's not just, it's everything, not just, oh, you know, it has to go to security or somebody who needs to see some certificate. It was like, maybe I shouldn't say, but she shared like 18 steps for three different teams. This is how it works. This is in real time, it's happening right now. So I can took this is exactly how it works. And I found out that this is how we buy everything. So this is the format that you need to prepare or your summary in. Otherwise, it's just not going to move. And I remember walking away thinking, whoa, like again, this is not something I could have possibly asked for. Well, I mean, I guess I could have asked, but she probably would have said no. But like, I don't think I would have thought to ask for that. And I think sometimes reps ask those questions, what is your process in that initial discovery? And then we're a bit disheartened when they play their cards close to their chest. But I think she shared that willingly. And then also in the next catch up, I brought the summary. I was like, okay, well, you told me this is how you guys buy things. This is exactly, I've followed it to the tee, helped me fill out this stock, like helped me spot where the errors are. And again, it's an ask, she gave it back to me. I was like, yeah, I'd remove this. They don't care about this. You should add this. And so I was like, wow, like this is these are the pieces that you need. Also helping me know who that needs to go to. So in the initial stages of my BDR, when we kind of, we had that well hunting session, we do obviously we have an account mapping session. So we know who the key contacts are. In the business, it's very funny that the ultimate decision maker on this deal was one of the first contacts we called who told us, nope, we're not interested. We don't want it. It's not for right now. Hey mate, hey again. (laughing) That was, and it was so, we were obviously, we've been laughing about it for weeks at this point, but yeah, we remember. And also more importantly, he mentioned it on a call the other day and was like, yeah, do you remember when you called me and I said, we weren't buying this thing and now we're trying to implement it. It's insane to think of, but like, when we initially mapped those contacts, it made sense to take that to my referral and be like, this is how I think your organization is shaped. These are the power players I think are at the table. Tell me where you see, tell me where I'm wrong. And initially, I think she was a bit hesitant to share, but eventually it was like, bring it up slowly. She came back to me. I think maybe in our fourth or our fifth meeting, these are the people that you need to win. And this is what they care about. Like, feel free to, feel free to prospect into those accounts, feel free to prospect into those contacts. Tell them you're speaking to me. 'Cause I guess she was building credibility also. - Yeah, I was gonna say, what's the get for her there? Why would she, I would find it hard to get that? - She must have been called a man. - Desk from customers. 'Cause I don't know why they would give it to me. - She must have desperately wanted to buy Erkall. - 100%. So the company she came from bought Erkall and they'd like, almost revolutionized their support team. - Do you know what I'm thinking is that, on those calls that you were having the monthly check-in and sort of like the delivering insights, the industry and so on, I actually think maybe you're a modest or something, maybe you're just not explaining it. I actually think you were doing way more, to impressing upon her way more, like your ability and capabilities as a person to help her make change, then perhaps you're letting on. And I think that is something that goes unsaid in most sales cycles. It's like the element of credibility that you deliver across a Zoom call frequently. Like you build up to position where someone's like, yeah, trust his person, your respective, where they work with me or for me or for a different company. I think that's probably something that happened here. And I think, I thought I was comes of experience, I don't do that regularly. I mean, I have to do that. - Yeah, and then when you do do it, you're like, it deals on a bullet train now. - You need to come, I think it's all in preparation as well with these calls, like, come prepared, come look like you've, you know what you're talking about. Not like you've just been jumped from call to call and look a bit nervous and you're scrabbling around for water, like, come prepared, deck well presented, tell the buyer, you know, this is the agenda we're going to follow in this call because this is how you bet generally by this software. And it adds so much credibility. And you can imagine from the buyer's perspective, you're like, well, I trust this guy, because he obviously knows, he obviously knows what they're doing. They've done this before. - I think leveraging what we'd done before was the most important part, because obviously this deal came about right at the beginning of my time at AirCool. So I think the beauty of the conversations we were having every month, I feel like every month I was getting one more confident at selling the product, but two more confident about the industry. So as I'm learning, I'm sharing every learning with her. Like, there's things I'm interested in to left for me. I'm interested in called calling. I'm interested in understanding how you get more out of your phone solution. So I'm excited when I show up to those calls. I'm prepared in a way that she obviously couldn't be. And I'm looking at the problem in a different angle. I would also say probably it benefited me that the deal was underpiped in my pipelines. That it was probably a bit less pressure from management. So like, it didn't feel like I needed to push to her every week. Like, it didn't feel like I needed to push to them every month. What are you gonna buy when you're gonna buy? Because I knew that once the light bulb moment kicked in, like once that switch kicked in, we'd move from that push to pull motion. And it almost happened overnight. She made it into-- What was the switch? Data experienced, obviously, with telephony, you always have a phone solution in place. So they'd had a negative experience with their existing provider. And I think it was like a light bulb moment for her. But also it just made it-- they had a crisis, like a crisis meeting. And at the end of the meeting, the solution was we need to change. She already knew exactly what we would be changing to. She just needed to tick box effectively the criteria. So this existing solution can do these 10 things. These are the 10 things you need to be able to do. And then these are the four or five other things that our team care about. And it'd be nice if you could do three or four of those things. And so I think that moment, it was probably like a system-wide outage that affected them. That they were like, this also has a monetary value, this problem. Let's take this more seriously. And almost it was like a night and day difference. The following week, she made four intros. We sat down. We had a demo before the demo. She was like, hey, let's have a prep call. I'm going to prep you on everyone who's in the room. This is how you need to speak to the problem. And then after the call was complete, she did a handoff. So ultimately, she wasn't the key stakeholder in this scenario. She was just a true champion of the product. She made a handoff. And was like, this is who you need to be speaking to. He eventually was like, yeah, I remember saying no to you guys. I'm familiar with you. I'm happy to be back at the table. This is a real problem for us. We need to solve this today. And then I built up that same cadence. So instead of monthly things, it was biweekly things. And I let him know that this is not uncommon. I've been speaking to your colleague for the last six months. We have a monthly check-in in the calendar. With you, we're going to need to move a bit faster. If we want to get this in place, we're going to put this in the calendar for every two weeks. And then maybe towards the end, when it feels like you want to go ahead, we'll move to weekly things. We eventually moved to Slack. We're in a Slack channel. So we now speak almost all the time. But the cadence was already there. And the framework was already in place. So it was really just more of the set. What one thing as well, John, probably-- did you have a really-- how long was the critical event of the contract end date from when this potential tipping point happened? That's a good question. Did you have a good critical event with the contract end of the convention? No. So they were in a monthly rolling contract. So they could have left at any point. They had no incentive to. That was the effect. And that's often the case with air call. There's always a critical event. There's always a compelling event that we're looking for. But more often with these strategic opportunities, there isn't one. You have to build that case over time. You have to encourage them to think outside of the box. And you also have to look for-- we'll see the future. Where do they want to go? And how does their existing solution stop them from getting there? That's one layer of the conversation. And then the next bit is like, oh, OK, if you're telling me that this solution isn't going to help me get there, how are you going to do it? You already have the answer to that question. So it felt like that was where we were going, where we were working with them. When you went from that push to poor motion externally-- and obviously you said you underpiped the opportunity entirely-- Yeah. --to have a human. You started to actually like, fess up a bit about it. I didn't. What was what it was? How did you-- You said not $1,000. Yeah. Exactly. Well, after the year for six months. How did he, because obviously that's when you built in these weekly check-ins in the Slack check-in.
with the legal team or the rest of the other stakeholders. How did you go from a push to pull motion internally as well? What kind of gears do you switch? How do you start like leverage people? Are you like, I'm just, I'm very fascinated by how we communicate internally as well as how we communicate externally. So I'm just interested in what you did internally as well. For sure. I think I have to, before I start to, my own who I have to credit my director James, like I think he made it clear once I'd been honest and said, hey, there's a large opportunity I'm working on and this has real potential. I've taken me very seriously, one, but then also clear in the path. So I think I let him know again with those updates what was going on. But then also once we were in that, we were in closing motion, what I would need. He sat down with me, we had like a 10 minute chat and he mentioned, he made it clear to me that I'm the quarterback of this deal. My job is to know exactly who I need, who I need and what I need from each person. And he will make it happen for me. And I think that was like so essential and it would be my advice to any rep that wants to make it happen. Like you're not going to be able to make this make it happen by yourself. It is a team game that you're going to have to play. But you're the captain of that team. You need to tell everyone where to go. And so there was a moment internally we had where I explained to him where we are. And he mentioned, you know, one, we need a channel. And we need to involve teams as and when. And we also need to preempt their involvement. So again, on the legal side, we know that deals die and they end up in this legal hell where, you know, procurement illegal, go backwards and forwards. He mentioned that this is something you need to prepare our legal team. So I sat down with our chief legal counsel and there was like, you know, I'm going to need your time in a month. I'm going to need at least like two or three hours of your time in a month's time. These are the things that they're going to want dealt with. These are the parts of our contract that they've already indicated might not be interesting to them or might need a little bit of work. You need to be prepared for what I call on you. They appreciate the heads up because they have obviously lots of deals in flight. And so it meant that they could prep ahead of time. They were offering calls like tell the customer we're happy to jump on a call. We've already allocated the time this week to look at red lines. We're already we're already ready to kind of build out the SLA or just the SLA if need be. And so there was a moment internally that we all had to just kind of sit down and accept that this is a deal that we're working to make happen. And then that it was kind of on me but mostly like using my director as like my mouthpiece to say, I need this team ready. I need this document prepared. I need these these individuals on this call and full credit to him he made it happen. I think John something I want to touch on before we wrap up is you actually bought the big deal manifesto the guide that Jack and I wrote in halfway through this deal. And you said it had like a massive positive impact on helping you to close like a transformative deal on this occasion. Could you tell us more about which parts of the guide like you found particularly effective when deploying it in your sales process? 100% I think it's the first chapter actually is around having a mindset having the right mindset for closing these big deals. And I think reading that was immediately like it kind of hit me it was like a shot to the brain in that they really they you do have to think about these things differently. And it requires like a like a deep resolve like you've got to be confident that you're you're really going to make this make this happen. And so that was a it just open in that kind of helps me understand I'm going to have to think about this problem differently. And I think there's there was other pieces in the about relationships and stakeholder mapping. I think there's a piece in in the manifesto where it mentions relationships are not just nice to have like they're truly the most valuable currency. This is this deal was truly sold on the relationship on the report that I built with my my champion and then their ability to build champions in the business their ability to build relationships and then in turn to leverage those relationships. That was externally but then also internally like I was working with teams I never would have worked with speaking to leaders that perhaps wouldn't have sat down unless we were able to like communicate why this was valuable. And so I think that kind of changed the way I was thinking about it. The value pyramid and like mapping stakeholders in that pyramid is the same thing I had one internally about the teams internally that we're going to need to be required to make the deal a reality. And then just finally the the the bit at the end about being like introspective and like looking back. It kind of kicks like the whole process kind of came about because we were introspective because I was thinking about how where we've lost business and why we've lost that business. So I was I was thinking about it as like this is a this is also a blueprint moving forward. If this opportunity didn't go ahead why would we have lost it. What what could we have done differently what changes could be made. So I think yeah it was it was truly my guide the podcast where my like my daily commute every day and then the guide was like on my computer from time to time when I had a tough call I'd open up and see okay this is this is where we are in the deal maybe we should try and do a bit more discovery maybe we should figure out who the right people are. I may honestly you make it worth it. I know I'm actually when you're saying that I was like oh I should apologize for taking a break. Sorry about being here can you and now John you get to listen to your dulce at tones on the tube deliver absolute and I am not joking here fire on how to close transformation on big deals. I think before we wrap up Jack unless you have one more question I'd love to understand like and you've already heard us finish with this. What's your favorite sales memory? Favorite sales memory. There's have to be in this role. Oh yeah so I guess it favorite sales memory is so I used to sell kind of empty pop-up shops in and around central London. I'm a big sneakhead so I managed to I worked with like this creative agency on this really top secret brief that they wouldn't let me know about. So my favorite sales memory was I did this pop-up for ikea and Virgil Ebblo and it was really cool in Gov and Garden and so in the end they wouldn't tell me what the brief was but I had to kind of communicate to the landlord that you know this is what's going to be going on and so I had to find out the brief eventually and in return for you know looking after them and making sure they got a great deal when they got into the venue early I got early access so I got to see this really cool receipt rug and in the end I didn't get anything apart from a really cool ikea bag but I use it from time to time to go to the gym I think people look at me like I'm crazy but that's my favorite sales memory because I get to carry it with me. Amazing man and one more question before we wrap up as well is there anything from this deal one standout thing that you do now in future deals and from then that you're like that was because of what happened in the in the deal we just spoke about. Yeah that internal stakeholder management like I think you can prospect really hard you can say all of the right things you can prepare for a demo you can do lots of discovery but if you don't have the internal I guess internal cloud slash internal network to make it happen it's never going to get off the ground so I think what I've changed now is after I do all of the things I'm supposed to do externally I make sure that all the right teams are kind of geared they're all ready to go they're in that starting they're must in the starting blocks they're just ready for the that gun sound to be told to run that's kind of what I'm doing with all of my strategic ops now. Love it amazing. Love the attention. Thanks so much for joining us. No worries. Thank you. MbD out. Wow what an episode as I reflect back on that recording which we did a couple of days ago. Island seven really key things from John we were really lucky to have him on. So let's recap what every A.E. should have been taking away from John's deal just then. Number one well-hurt hunting actually works strategically target those accounts that previously evaluated but didn't buy because they're going to be these tier ones that you're going to make your year on. Number two champion cultivation takes a lot of time John spent four months of monthly check-ins before a single intro into one of these accounts like be consistent with your process. Number three always deliver value in every interaction to build credibility when you're prepping for these calls you're having ask yourself what do you bring me to the table what are you teaching this buyer on this call rather than just coming in willy nearly so to say. Number four ask questions your contact won't know the answers to it helps you multi thread and this is something that we've touched on a no big deal in other episodes. Number five be the quarterback of your deal know exactly who you need internally and what you need from them and keep updating them in a really succinct manner. Number six manage up effectively with consistent structured updates to keep leadership all aligned on your deal you win and lose together and finally seven internal stakeholder management is as crucial as external relationships that you're building remember big deals don't close by themselves they require patience preparation and the mic mindset until next time this has been no big deal thank you for listening Jack Neacon Jack Fox out tune into no big deal next week we're turning
massive deals into reality is easy. Or we try and make it as easy as possible. Thanks for listening, bye.
Podcast Summary
Key Points:
Jon Azodo secured a major deal by combining strategic "whale hunting" with his BDR, focusing on previously lost opportunities where the product was technically approved but timing was wrong.
He leveraged a referral from a happy customer to re-engage a prospect that had evaluated AirCall twice over five years without buying, using a new point of view to reignite interest.
Jon built a relationship with a new, low-tenure internal contact over four months of monthly 15-minute check-ins, prioritizing rapport and value delivery before asking for introductions.
He used a "give-get" approach to test his champion's commitment, asking for small homework tasks (e.g., call volume data) to gauge engagement and build momentum.
To manage his manager's impatience, Jon provided proactive weekly updates (and later to senior stakeholders like VP, legal, and InfoSec) via a Slack channel, using a traffic-light system to track progress and align on next steps.
He adapted the traffic-light framework into "testing criteria" for proof-of-concept evaluations, helping buyers visualize success and facilitating stakeholder buy-in.
Summary:
In this podcast episode, Jon Azodo shares the behind-the-scenes strategy for landing a transformative deal, emphasizing the importance of pipeline creation and stakeholder management. Jon explains that his team adopted an ABM model with one-to-one pods, allowing him to strategically select accounts through "whale hunting" sessions with his BDR. They targeted large prospects that had previously evaluated AirCall but lost due to timing, not technical fit—filtering Salesforce for closed-lost opportunities where SEs had green-lit the deal.
This approach re-engaged a fast-scaling company that had twice declined, but a referral from a satisfied customer opened the door. Jon nurtured a new, low-tenure contact over four months of monthly 15-minute meetings, focusing on rapport and delivering industry insights, which built trust and led to introductions to senior stakeholders. He used a "give-get" method to test the champion's commitment, asking for small tasks like call volume data, and coached her on internal dynamics.
To manage his manager's pressure, Jon provided weekly updates to all relevant internal parties (manager, director, VP, legal, InfoSec) via a Slack channel, using a traffic-light system to track progress and align on asks. This proactive internal management, combined with patience and strategic coaching, turned a monthly check-in into a career-defining win, demonstrating how to become the quarterback of large deals.
FAQs
Jon used strategic 'whale hunting' sessions with his BDR to select target accounts, focusing on those with strategic fit. He got lucky with a referral from a happy customer, which kickstarted the opportunity.
He looked at closed-lost opportunities that had progressed far in the sales process, especially those where the SE had green-lit the deal technically but the timing wasn't right. This indicated the product was a fit but the buyer wasn't ready.
He used a customer referral to get an introduction, then came prepared with a new point of view and value to the new contact. He focused on delivering something new that the contact could take to senior stakeholders.
He took a slow approach, scheduling 15-minute monthly calls for four months to build rapport and provide industry insights. This helped the champion feel comfortable and eventually make introductions to key stakeholders.
He looked for a 'give-get' dynamic, where the champion was willing to provide information or take actions in return for value. He tested with small asks, like getting detailed information about their current phone system, and saw if they followed through.
He balanced it by committing to daily sales activities and weekly deal closures. He also provided regular updates to his manager and later to senior stakeholders, using a structured template to keep everyone informed and manage pressure.
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