📉 Selling in a recession
Gerry explains how he landed a massive logo during a recession with a hyper-targeted cold call.
He also never demoed the platform until after the deal closed.
Think selling in a down market is impossible? Gerry lays out how to do just that in this episode.
Gerry Hill began his career as a pro rugby player before arriving on the sales floor.
His early selling days were heavy individual contribution. He then moved into managing sales teams & consulting.
Gerry is now helping ConnectAndSell grow & teaching the best cold conversationalist in the world.
What problem does ConnectAndSell solve?
ConnectAndSell removes the pain of dial-by-name directories, operators, and gatekeepers.
Delivering salespeople right to the decision-maker by pressing one button at a time.
What are you selling?
- A deal at a former company. Sold management consulting & research.
Where did the prospect come from?
- Spotted an emerging business unit in a massive company using their analyst briefing.
- Massive logo in the old industry with thousands of employees. A whale account if you will.
- Cold call with a very specific pitch for one specific person. A silver-bullet idea that would only apply to one person in one unit.
Barriers to Overcome
- Gerry’s subject matter expert went rouge during their big presentation. Setting back a lot of the ground work built leading up to the meeting & eroding trust.
- Stakeholders: CEO of a brand new business unit.
Note: timestamps correlate with the full conversation
Discovery: teach today, sell tomorrow (12:29)
Demo: more white board solutions, less feature dumping (16:39)
Barriers: trust your subject matter experts, but verify you’re in lock-step (20:10)
3 Tips for Account Executives
1. Even in a down market, you can sell.
Just need to become even more targeted & confident in your messaging.
2. Team selling makes a huge difference.
Don't be afraid set your ego aside & bring in your experts to help.
3. Know what to listen for & pounce on it.
There are key phrases that should perk your ears up in every deal.
Watch the full conversation
Welcome back to How I Deal, where we discuss past, closed-won, and lost deals, how they played out that way, and provide some actionable sales tips that AES full cycle sellers anyone out there can utilize today. My name is Taylor Dolam full Cycle account exec turn content guy, and I'm joined as always by Junior, our superstar seller here at Pickle. How's it going, June?
Great. It's episode six. We're moving along here, and we're making some friends as we go. So that's not bad.
Not bad at all. A quick brief refresher on how this podcast works. Each conversation, we chat through a past deal. We want to keep all names and places anonymized as much as possible, but we want to dive deep. We want to understand that from the first time a prospect was approached or at least initially researched all the way to you get the final yes, you get the close deal. And this is an exciting one. And Junior kind of tee it up here.
Today we've got Gerry Hill. He began his career as a pro rugby player, then arrived on the sales scene building teams and consulting, and is now helping connect and sell grow. Gerry, we're glad you can make it.
Thanks for having me. Really appreciate it.
Absolutely. Gerry, give us some insight into your role and what problems connect and sell solves.
Yeah, I guess I'm sort of bridge. I go to problems in the company. So connect and sell solves the number one frustration that most sellers, whether they're top of funnel sellers or full circle, they suffer from, which is the inability to get conversations on demand with prospects that they want to speak to. It's composition of technology and human labor, which ultimately drives the voicemails, the gatekeepers, the phone trees completely out of your existence and only connects you to the people that you've got named on your list. Instead of waiting ninety minutes for a conversation, we can get you a conversation in four minutes, meaning I can have ten conversations in an hour. So that's game changing for a lot of people. The role is pretty simple. Establish the market in Europe to connect themselves so that we can go on and dominate that market. Now, it's been a brilliant two and a half years, three years now. A lot of fun, guys.
That's awesome. And obviously solving very real problems of how much phone time are you having, what's that manual labor look like, and how can we make that a lot simpler? But let's just dive in, I guess. Gerry, what deal are you walking us through today?
Yes, it was my first proper big company deal that I did about five, six years into my career. I picked this one because it was a win, but it was a win for a variety of different reasons. It wasn't the obvious win, and I think that it's a logo or a size company that most people would love to ever bring into their career. It stands out for me for a number of reasons.
Got you a huge logo. Sounds like a whale here. Happened a few years back. But first, enterprise deals are hard to forget. I guess to that point, the research probably was obvious target account. But what nuances went into kind of understanding the opportunity, the scale, maybe. How did you go about researching this deal? Yeah.
So I think context is everything. So this was in the last major sort of downturn credit card subprime crisis. Two thousand and eight, two thousand and nine. So it wasn't a growth year. Most sellers today are operating in growth markets, well funded companies where they don't have to necessarily worry about the macroeconomic factors at play. This was definitely not the case. Big companies at the time are squeezing and tightening belts because behind their profitability, they're exposed to a lot of toxic risk in financial markets. Right. So there was this hidden force behind why deals couldn't happen or why they were stalled or why they were just pushed out altogether. The research behind it was quite interesting in the context of everything that was there. The proposition and product in itself wasn't actually what mattered here. It was finding a unique angle to attack. You could have an opportunity to even have a conversation in the first place. So this company specifically funded and built an internal venture capital firm, corporate venture capital. So they were able to deploy balance sheet assets to invest in companies that would either benefit their operations day to day, or they could potentially scale based on their global expertise in specific markets. The company I was working for at the time was a tier two management consulting organization and market research firm. And what makes this really unique was just the depth of research that we had to find and go through in order to be able to make it all come together. It started off in an analyst briefing in a financial reporting market when the company was reporting. That was when my ears pricked up to the fact that this new business unit was coming into being, looked across the portfolio of assets that were in my business at the time and realized that there was a real sweet spot that we weren't leveraging in any way, shape or form. And it was the ability to match those two things up. Ultimately that helped me originate and prospect to them specifically with a very specific idea in mind.
I think this is really interesting, a great, interesting deal to talk about because you mentioned your ears perked up when you heard, like, analyst briefing in the details that came about there. And myself, I hear analyst briefing and I'm like, hey, that's a bore. That's a snooze for me. I'm not tuning into that, but in my cell, there are definitely events that I do need to tune into that when I hear for me the phrase as an analyst briefing. But if I hear whatever phrase it is that I'm trying to chase, I should be perking up just like you. So we know Connect and Sell is really tuned into the prospecting world. The prospecting scene, right. Connecting sales people to conversations. While this isn't under the Connect and Sell umbrella, we previously talked about this deal before, so I love where it's going. But how did you go about getting in front of this prospect? Give us some details there.
I mean it was a cold call. It was a cold call. But it wasn't like cold cold. I wasn't just sort of calling with generic pitch or value prop to create curiosity. I had a very specific thread in mind that I wanted to speak to this human being about. Now back in two thousand and nine. Whilst phone based prospecting was relatively hard, most people picked up because most people did. It was primary business. And just to give you context, we were operating on a Lotus Notes email system and we only had like a Lotus Notes chat window and we were still getting orders over Fax in two thousand and eight and two thousand and nine rather than getting PDF emailed back to you. Right. So this sets the scene from a technology point of view. So generally speaking, switchboard operators would put you through to people nine times out of ten. Back then the main friction was gatekeeper. I got really lucky one day I got one hundred percent hit rate from switchboard to the person I actually wanted to speak to. Now the person I wanted to speak to was the CEO of this newly minted business unit. Now because of the value that they were placing on it, the CEO also held nonexecutive jobs at other industrial businesses, what I would call products of an oil company, people that would require those types of things and the thread that stitched it all together to give me social proof was the fact that she was also on the board of a company. That another part of our business at Frustrating Sullivan did business with. So I was able to articulate context quite quickly. I was able to take research from that analyst call and additional pieces that I had done and threaded together and talk about some work that would help them with some very specific problem. As a start up within a big company that was looking for startups to invest in, the primary thing that I felt we could help was sort of map mega trends, five year, twenty year technology outlooks to deal flow today for areas in the value chain that they really cared about working through. She agreed and she was very patient and had the time for me to go through that narrative with her. So part of it was skill, part of it was timing, part of it was good luck. But I think the real thing from a seller's point of view was using judgment at the right time to not be fearful of job title, to not be fearful that she might say no, but to have real confidence in the idea that you're presenting. Because I'm going to be honest with you, it was a silver bullet idea. It was one idea, one conversation, one thread that I don't think there would have been many opportunities for me to go and reinvigorate that idea anywhere else inside that company.
And I love that you're taking like you called with something so specific to this person because I have a script for my cold calls when I'm calling and when it's my list of fifty, I'm hitting that script. But when you've done your target research account, like you had this analyst briefing content and you weren't just calling to give her your script opener and run down. But you're like, hey, I've got this proposition and I see this window. I believe it can work. And I love that aspect.
Yeah. And just to give you context for the set up for the sales team that you worked in pre practice areas, ours in the energy and environment practice, oil and gas will come under energy. Then you've got a long tail of accounts that are allocated to you. Your promotion gradient was account executive. Strategic account executive. So the pool of accounts get smaller. But at that time I was still managing a portfolio of eighty accounts, five of which were globally strategic value. So five accounts required deep research and insight. The rest of my account was broader, more generic, more general value prop. And then see what happens in the melee of that eighty accounts to see if you can manufacture them into a key account. Right. So you're absolutely right, Jr. But the ones that you have been targeted against that are high value. You should always put the application and research together to make sure that your bullet lands. Right.
Yeah. And Taylor, before you take over, if you're an Ae and you're given a list of accounts that is anywhere from eighty, like Gerry said, to one hundred, just realize that you could cult eighty people in one day. You could burn that list really quickly. So if you're given a list, be more strategic and specific when you're calling because it could be one and done and then you're screwed and trying to climb the ladder back up. Yes.
Especially named accounts. These whales be as strategic as possible. One call, one close.
Yeah. Just on that as well. Like every other way, our organization in the world that can provide value to that company is also trying to prospect them. It's a vanity metric. Get the biggest logo. Right. So you've got everyone from mom and pop recruiter with some seventeen year old kid who's like Boop. I've heard of them. So Accenture that's going to sell you a billion dollars of marketing services and It services a year speaking directly to the CEO of the company. But they're still doing prospecting work. So you need to stand out amongst the noise. The more specific you can be in a big business, the more relevant you can be. It's all about relevant contextual awareness. Right? So contextual awareness is your generic but relevant contextual awareness is more important than a pain funnel because you haven't established pain at this point. You just got one idea. I'm going to give you the idea.
Let's move into that pain. Right. So you've closed at least an initial yes of, hey, my research is targeted. I've made this first encounter, this first cold call. They got the yes. They want to chat heads into the discovery kind of what did you do for that discovery and what did you learn and take away from it?
Yeah. So I think about discovery in a slightly weird way in the sense that people still don't really understand the quantifiable nature of the thing that you've got in front of them. So I don't feel it's fair to put anybody through an interview process, no matter how skillful you are at it, if they can't quantify even what it is yet. So you need expertise, you need credibility. Teach that they sell tomorrow is probably my motto. A lot of these kind of bigger company pursuits. So teaching was the first component. That was the very first step in the world. It was teaching not about the company. It was teaching about the scale of what the next twenty years look like. What does the next twenty years look like? Such a big meeting. Right. But how do you distill that into something now? Twenty five, twenty six years? I'll probably not really qualified to deliver that credibly to the type of executive. Right. So you have to bring people in, you have to bring experts, and you have to bring the grown ups in the Gray hair. Now, I follow Brenda Flirty a lot on LinkedIn. You probably know he is the life person, dude, the one million dollar a year guy. He's right. Deep work matters and bringing executive alignment into your deals matters. I'm still quarterbacking. I just need to push my ego somewhere else. I can't do it all. But the senior partner in the business can. And he's going to be like, what do we need to do? How do we need to prep? What are the contact? What are we doing? What are we establishing? How are we going to do it? My quarterbacking is this is the shape of the meeting. Is there anything else you want to add? And this is what you're going to get from it. Now, here's the thing. I had another golden moment with an adjacent business in the utility sector, and we went in and pitched. And at the end of the meeting, she said, Guys, really underwhelmed. What do you mean underwhelmed? I was expecting you to teach me something new. Given how much insight you sit on, I don't know anything.
But take the learning, right? Take the learning, absorb it, move on. I'm now dealing with an adjacent job title in a bigger company with a much longer storied history of success. Got to execute. So now you over prepare. Give yourself the credibility. Now we get an opportunity to do discovery because guess what that person has given me permission to do. Go and meet my experts around these four things that I think you're going to be most valuable to. Now we can get to discovery with those emails.
Awesome. So you had mentioned previously and kind of while we're chatting here, but you're bringing like the big brain people, the people that are thinking about the next twenty years and listening to this, I'm thinking like I'm going into discovery too narrow minded. So even just hearing that makes me think a lot more. So post discovery you've made some promises on what you can deliver while you are selling a platform. You're also selling additional services and more. So like that partnership aspect. So you never actually tapped into a demo of the platform during this whole sales process. This is untraditional probably to our typical SaaS listener. So even I am curious, where do you take it from here?
Yes, again, context. So this is Gen one hosted platform of PDFs and market research content. Some really boring stuff, right? The generator market for alternators in the Middle East and water applications. Right. About thirty five people in the world care about that. It's actually really valuable because it's such big money markets. I think sometimes in SaaS we get skewed by valuations and stuff and think we're big business. We're not big business. The people will make alternators from massive utility companies. Now that's a big business. But you never heard of them. So there's a market for this stuff. By moving everything to platform, your cost of delivery goes down. So it's a gem. One research as a service product because it was cloud hosted. Now every other seller in the world that was selling sort of similar stuff from like Data Monitor, the Gardener to anything was obsessed with this delivery mechanism, which was SaaS. But it never really got to the end of the problem. And it's a problem that permeates in selling today, which is we throw up and show up on our demo in our slides. Right. We're not actually quantifying anything meaningful. So I've always believed in the power of a diagnostic session before you get to that point where you get your major person to bring people together. And what do we do here? We do whiteboards and I'm proudest thing in the world is that this deal led to nearly eight figures in revenue over ten years with this company. Right. But we never ever showed them the product until they agreed to buy the product. And the first interaction they had with the product was in the onboarding call. All right, what do we do? We just whiteboard it. This is what it does. How valuable would that be to you? But actually we reframed it. We had twelve people in the room and we said, right, tell me your top ten problems about accessing information and insight in these markets right now. And they would quantify the problem. They would tell us stuff and you write it out on the whiteboard with them, and then you draw out some stuff on the whiteboard about what you could do. And then you start kicking off with this solve. With this solve. Yeah, brilliant. We're now seventy five percent of the way to solving all of your collective problems. What's that worth? Brilliant. Now you can have a conversation around Monetization. And actually, that's still not the most interesting bit because what do they care about? The platform is just the gateway mechanism into an outcome. The outcome for them is still access to the expert. Right? It's not about the power of the PDF. That's good. But so what about the underlying numbers? What about the figures? What about the person who conducted the primary research? So in SaaS, the equivalent is why aren't we leveraging our customer success teams a bit more in our presales endeavor or in our sales endeavor? Because they are expert. They're the shining star in your business that helps with net retention. Reason I picked this deal, again is because we're about to head into down markets. So in a down market context, deep research on your most strategic accounts with a new perspective is potentially the thing that keeps your career motoring in the face of people freezing budgets. Second thing teamwork and displacing your ego ultimately ties it all together because now you're the quarterback and the facilitator you're trusted because you can be trusted to bring in the right person at the right time. Thirdly, allow your post sales people to shine earlier up in your sales process because they're the people that are going to be the crutch and the strategy for making sure that your product works after the deal is done. So if you can give them the full feeling of being a customer before you've even sold them a Penny, why wouldn't you? But far too much amount of time have committed to doing the deal. Do the deal. Do the deal. Now I get it. If your economics aren't great, right? If I'm selling fifty five dollars a month on a license, you can probably go through the cycle. But you do need to put an extraordinary amount of effort to create a high quality process for somebody in a way that they've never thought possible before. They're not feeling like they're being particularly exploited, which I think most discovery does set people up for.
If I'm honest with these problems that you're listing out kind of whiteboarding having these conversations you're getting. Yeses. Along the way and we'll talk about this in a second. But curious throughout that process, what major barriers even no matter how many problems you were solving or talking about, there had to be something that came up that maybe almost lost the deal. Right? What did that look like?
Yeah, I mean trusted expertise matters in a business like that. The people behind the content needs to stand up as an expert and they generally do, but you can't control certain dynamics. So they asked us to facilitate a very specific workshop that was a four day workshop that was already in play that they had organized internally. We were able to get a quick monetization win by charging out some of the time for the prep and for the execution. But there was a larger piece of the puzzle which was the management consultants, the ability to facilitate these work streams. That's where the real money happens for you. And we put our best expert up in front of them. We did the prep work. We thought we had the narrative nailed last minute unspeigned to anybody expert decides to go absolutely rogue in front of a room of forty of the most astute scientists and innovators in this market on the planet. First slide numbers. We only had a thirty minute slot, by the way, in this workshop. First slide numbers absolutely turned into a cluster. Yeah, I can still remember it. It's really visceral. I'm looking around the room, you've got like a woman who's now the adjacent emeritus professor to the US government of physics who was the chief science officer at the time for this company. She's just like a GOG. And you've got like these people who've got strong opinions going. Your numbers are wrong and he's now spending thirty minutes justifying his numbers. The narrative that we prepared for is this nice gentle story until we get to we believe projections before anyone actually has a time to be contentious about it. So all of a sudden all credibility is off the table. Your owner, your product owner inside that business is like, oh my God. So you've got to backtrack from that immediately and lean into the problem and recognize it because if you just hide from it and say sorry to your stakeholder, you're done right. So now you need to go and find out why it was so bad. So we basically went back individually to every single person in the room and offered to do a ten minute synthesis for all of them individually and get their feedback and make sure that they felt that we were able to go back and correct the problem. Still show that we have value to them. What does that mean? It means ten minutes of senior partners time at two thousand dollars a day for free now. So we're now extracting the cost from the time that they put into this and the money that they spent. But it was good. It ultimately showed that we were willing to work hard for them, which they respected. And because of the nature of the platforming piece, it's all margin at that point anyway. So you're able to re push it through in your cost of sale somewhere else. But at the time, it was one of those sort of coming up the session. And here's the thing, the lack of self awareness from my colleague at the time was really stunning because he was like, nailed it as he walked out of the room and I was just like, oh, my God. And I basically said to him, can you please get in a separate taxi? I'm going to get a separate taxi. Don't come and speak to me for the rest of today, but we'll deal with it tomorrow is essentially my message.
Yes. So losing credibility in this case, right, extended this deal quite a bit because now you're reorchestrating, we're reorchestrating everybody that you've previously had under your umbrella.
We're reorchestrating. But actually it probably benefited us. If I think about our maturity at that time, it probably was actually the right thing, because if they had actually given us the bigger bit of work there and I don't think we would have executed it as well. And the longer term, six, seven, eight year revenue run that came from that first win probably wouldn't have happened in the way that it did. So we were able to slowly eco our way up the value chain as a business. And the net retention was awesome, the upsell was awesome. And we were penetrating parts of the company that had we gone in with our traditional conventional value proposition at that moment in time, we still wouldn't have acquired them as a customer for at least two years. So I think you've got to be able to take some of the hits along the way. You just need to be able to displace your ego, be fair, be equitable, stand up to bullshit challenges. But when you're wrong, you're wrong. Own it and solve it quickly. I think that's the other message.
So you've got outcomes coming along the way. Some are great, some cause ten additional minutes per person that you're trying to get back to credibility with. But you get the yes, right? You eventually get like a yes. We'll partner together, we'll do this thing. So where did the yes come from? And more importantly, in our eyes is like, what did the yes mean?
The yes was always at the right level. We sort of threaded into the right level initially. We maintain consistency by consistently elevating after every single meeting and engagement to report back. So there was always visibility and control for them. We weren't running around using their name, causing reputational damage, particularly because we were so over communicative with them. There was stuff they didn't need to know. But there'll be a text message at ten o'clock at night going, I met Hannah today. She was nice. That was the extent of the message. But making sure they knew. So the check, the DocuSign wouldn't have been a DocuSign, but there was actually a Fax came through and it came from the same person that we sort of engaged with in the very first meeting after that initial prospecting approach. But it meant that they showed enough value and trust in us to be able to give some of their slush money because it wasn't budgeted to us and we were able to then execute a much broader engagement. What do you mean? For me it meant I was a little bit aware that I wasn't sure whether or not I was cut out for this sort of enterprise selling lock at that time because it was the context of a down year. I've seen people around me who'd been in the business a lot longer still seeing consistent success because they've done a good job on their accounts. I was still trying to graft and grind. Right. But it was a transformational win for me because it made me believe I was in the right place. So sliding doors, if I hadn't the one that, who knows, I could be a greenkeeper out of the local golf course, not living the life that I want to, but that's fine be living a different life and I wouldn't know any different rate, but I'm grateful ultimately. And then thirdly, it did a huge amount for my career inside that organization. It elevated me because this was one of those albatross accounts. No matter what anybody ever did, they couldn't win it, they just couldn't win it. And I stitched that together, I curated it, I orchestrated it. I learnt a huge amount. It wasn't perfect or flawless by any stretch, but it gave me a huge amount of credibility in my peer group, but more importantly in the partner stratosphere, because now every single partner is going, how do we get into the account with you? Right, so they were coming to you rather than you going to them for help. And it wasn't the biggest deal. It was high five figures, which in the context of the business at the time and their spend, it wasn't huge. It was probably about zero one percent of their total global spend on anything. Right. They spend trillions of dollars and stuff. It was good. And I think the key takeaway was the company rewarded me for it. I want best deal of the year in a company that would write twenty thousand bits of business a year globally in a two thousand sale organization. That meant a huge amount to me and it was peer nominated, which is the most important part of it.
Yes, that's huge, massive win, Gerry. And I think at the end of the day, anything that's going to raise your profile, like winning a deal or approaching certain things where partners are asking, hey, how can I get in? It's going to be a good thing, but let's go ahead and wrap this thing up. What are three things? Three tips based maybe within the context of this deal that any sales pro out there can use today to enter closer to that closed one.
Yeah. Don't be scared to spend the extra time finding out like, what are the things I should be listening out for? I think that's quite important because you never know where that sort of idea is going to come from. Don't be scared to be confident in the idea once you've had it both internally and with the prospect. And I think the third thing is be comfortable with being an orchestration piece the quarterback. You don't necessarily need to do all the work yourself. Bringing the team in, showing the quality of the team and orchestrating those people at the right time is probably one of the most underrated skills. I think in fairly complex or big companies selling today to failure ego push it somewhere else, be confident in your idea and then orchestrate all the resources behind you to make sure that you deliver high quality all the time and you generally can get quite far on that basis.
That's great, great insights, great tips. At the end of the day, hopefully we can use some of these in our own deals that we're working today. Gerry, it was great to have you. If you tuned in today, go connect with Gerry on LinkedIn. Quick note, I guess two of his tips. One, was it's possible to sell in a down market and it looks like we might be headed that direction. Set your ego side, pull in and team cell secure where you are today based off of the people around you. But, Gerry, again, great to have you.
Just like that. Yes. Thank you, Gerry. Another episode of how ideals and the books. Thanks for tuning in. Please subscribe give us a couple of stars if you enjoy this pod and we'll see you next time.