Innovative Sales Strategies in Challenging Economies with Gerry Hill
We are joined today by Gerry Hill who is RVP EMEA, Strategy and Alliance at ConnectAndSell. His company’s cloud-based dialing technology enables B2B businesses to have more conversations with their intended targets than serial dialing. With extensive experience in risk assessment, cost analysis, and market entry strategies, Gerry brings a wealth of knowledge to sales professionals navigating challenging markets.
Gerry will take us on an exploration of innovative sales strategies, diving into mastering sales lead generation in tough markets, understanding private equity’s role in business efficiency, and engaging senior prospects. He shares actionable insights on boosting sales productivity using agile teams and scientific approaches.
Topics covered during this episode include:
Why mastering sales lead generation in challenging markets is required for boosting sales team effectiveness.
The role of private equity in value creation and operational efficiency through operating partners.
Proactive strategies for slower markets, focusing on aggressive closing techniques and system improvements.
How to confidently engage with senior prospects and uncover opportunities to add substantial value.
The evolving landscape of sales strategies, emphasizing outbound sales and agile methodologies.
Benefits of small, specialized sales teams for productivity and morale.
Transforming lead generation by moving clients from fear to curiosity within seconds during cold calls.
Effective sales strategies emphasizing permission-based openers and confidence in outbound sales.
Why the emergence of operating partners in private equity is essential for enhancing company performance.
The necessity of balancing labor and valuing experienced talent in today’s market.
How trusted advisors and value articulation become vital in down markets.
Importance of selling underlying technology rather than just products in the SaaS industry.
The role of executive buy-in and structured sprints in applying agile frameworks to sales.
How nurturing relationships over time is critical for long-term demand creation in outbound sales.
Mike (00:00.086) Jerry, thanks ever so much for joining me on Higgle, the B2B Selfie Podcast. It's great to have
Gerry Hill (00:20.85) Thank you for thinking of me.
Mike (00:24.102) pleasure. I'm really looking forward to this. Lots of conversation at the moment around lead generation in a tough market, as you can imagine. So it's gonna be fascinating to hear your insights around sales lead generation. But first of all, who are you? What do you do? And anything slightly unusual about yourself.
Gerry Hill (00:41.902) yeah. So Jerry Hill, I run a business called Connect and Sell, US software company, and I have full piano responsibility for our European and rest of world programs. what do we do? We solve all of the inertia and the bottlenecks that make cold calling and top of funnel conversations with strangers feel ineffective. And we turn that waste and frustration into meaningful fun and engaging work for, for reps.
How would I describe myself day to day? I am a sales person, but moreover these days more of a sales economist. I'm helping leadership and boards and executives and private equity funds really determine risk, cost and value and assess best routes to market with an acute economic lens applied to strategy. Unusual stuff about me. I was once an extra in an art house movie
in good faith I decided to participate in as a volunteer for a friend of mine turned out it was a bit of a smut flick. My cameo was I was supposed to be playing like a big dock worker and so on and then I went along to the screening of this thing it was his student art project and everything that happened behind me was nefarious to say the least.
Mike (01:44.319) Ha ha!
Gerry Hill (02:05.642) And what I'm really concerned about is the fact that he didn't want to cast me in one of the major roles. I was just literally a wallflower in a pub scene. And what made it even worse is I'm a ridiculously large human being. I'm six foot seven and about 140 kilos. I stood out very much in the context of the
Mike (02:09.482) Exactly!
Mike (02:14.402) Brilliant.
Mike (02:20.29) Are you six foot seven? my word. Okay. I bet. Yes. Is that movie still around on the internet or do we just try and ignore that?
Gerry Hill (02:29.194) I hope not, this was -internet, this was 1999, so it would burn probably minutes after it screened.
Mike (02:32.883) Okay, fine.
Mike (02:37.024) I was gonna say it's probably buried somewhere exactly or hopefully burnt. Brilliant, Jerry. cool. Artie.
Gerry Hill (02:41.53) It was all very art noir and stuff as well. It was trying to be sort of a pirate like, you know, once upon a time in Hollywood.
Mike (02:49.014) Yeah, brilliant. So before we get into the three questions, if you're open to it, just talk, because I think what you're doing now is quite different about, I I used to work with private equity funds. I know what they're like in terms of very focused on the economics and enterprise value creation. Do you want to just talk about the big picture context before we get into the specific questions?
Gerry Hill (03:09.578) Yeah, I think the macros are interesting at the moment. You're going to hear a lot of talking heads talk about sort of post interest rate world or a zero interest rate world. And, you know, I think that whilst that stuff matters the most, it's actually very few people have got an understanding of how the companies that they work for and serve ultimately are funded. So if I'm a company, there's a strong chance I'm owned by private investment in nine times out of 10.
that private investment is drawn from limited partners. Those limited partners could be asset management companies, or they could be our pension funds, or they could be high net worth family offices and individuals. Then that capital gets deployed around meaningful bets. If I'm investing into companies as an asset class, I'm looking at three real metrics that I care about. What are the efficiency ratios of those companies? Can I take the efficiency ratio as it is today pre -investment and make it better?
love squeezing more opportunity from my invested dollar. Can I radically transform the operating tempo of that business? You know, it's the old joke, which is private equity always takes a company from Andrex to to two sheep line. And then the other element is what the levers of value creation that I can offer and support to a company in order for them to be able to do delivery of model better.
What we found is a rise of a new and emerging job role inside private equity is called the operating partner or the operating partner executive. And they've got an acute lens on trying to support value creation within, within the portfolio companies. They kind of feel like a McKinsey kind of dude, but working in the business and around the business, their job is loosely defined, but the majority of it is working on strategy, go to market execution, finding signals, tying up operational elements.
Mike (04:35.414) Absolutely.
Gerry Hill (04:59.614) working with vendors create, you know, scale, scalability. When we talk about go to market operating partners, they're very, very good. Typically I find in marketing narrative and they're very good in what I would call discovery sales to close, to quote and measurement. But there's this little gap that exists somewhere between marketing and sales execution, which I would call pure play top of final selling. And that's gap that we're trying
trying to cover and add an additional layer of competency to their world.
Mike (05:30.658) Amazing. And that is the, that is absolutely the gap. that whether you're private equity funded, whether you're private family funded at a smaller scale or whether you're a management buyout team. I think everyone in this market has got the same problem. I mean, everyone's saying basically, I where are we now? We're now in August 24. You know, the market slowed down. It's not my fault. So, you know, we're down 30 % of budget. And I'm like, well, yeah, the market has changed.
But to just accept it's the market's fault and therefore I'm going to do nothing about it seems to me a bit bizarre as an owner. And you must face a lot of that kind of conversation.
Gerry Hill (06:10.864) we've seen a lot of do nothing this year and we found inaction and status quo much more compelling competitive than anything we'd see in the market. Typically. My sense is we probably need to do a lot more headlock and push than we've ever done before. And that's behavior change for me because I've always worked in a strong, high value consultative. If we get the scope right and the execution right, then naturally close takes care of itself. But I'm actually having to relearn right now, how to go out and aggressively close deals with people.
So that's a new skill that I'm to relearn as a result of the macros. I think the other side of it is I call it a set of fears, fascinations and opportunities that people tend to have around system, system design or process improvement. They're fearful because it means that something's going to change in their life, their day to day, the meaningful work that they do potentially be displaced or they could be made to look a little bit silly.
for having not thought of a thing beforehand. And I find that lens is even greater at the moment because people are more concerned about job preservation than they've ever been, and rightly so. I think the fascinations are real interesting curiosity sets all around what if, what if, what would, why would, possibilities. Opportunities is, how can I take my curiosities and turn that into actual future state?
Mike (07:16.492) Definitely.
Gerry Hill (07:35.174) What I fear for the industry as a whole is we've been so heavily integrated into price reduction, competitive markets, especially in my world, which is software and technology. But I think a lot of people have actually undervalued what they do and they don't have the gravitas to be able to actually go and speak to a senior prospect in a company that you want to work with and actually go, well, here are the fears that we commonly see. Here are the fascinations that we commonly see and the opportunities, which do you care about the most? And, you know, that's a radical reframe for a lot of people, especially
you know, the production line of sales development as an entry level career rolled into AE, nobody's got any business acumen anymore. So nobody's thinking about those questions. So I don't necessarily see it as a function of the market. It's more a case of nobody in market currently today, apart from a rare few of a generation like mine and yours, ever actually seen down markets before and know how to behave with women and around them and understand what it takes.
Who's teaching them that? Because the first line leaderships were not old enough to remember 2009, for example. So you've got to be very, very sort of thoughtful about what the reframe looks like, how you rebalance your labor, what you care about the most. My sense is there's a strong market right now for really experienced sort of 50 X year olds who've probably been on the beach for a few years. They're probably concerned about pension top ups and we know that they can come in and just execute on gravitas alone.
Mike (08:35.255) Exactly.
Mike (08:56.246) Yeah. Yeah.
Gerry Hill (08:58.046) and then opportunity to rehire from that pool of latent capability. But I don't think anybody's imagined it enough to start doing that kind of stuff.
Mike (09:06.274) That's a brilliant point, but I would because I'm 60. So, no, think it's really interesting is that the, did you see the recent Salesforce state of sales report that came out? Yeah. And that, you know, the trusted advisor is now back. Unsurprisingly in tough markets, people, executives want to have business conversations with people that they believe they can trust and that have got insights and have got some thought leadership
A view on the world.
Gerry Hill (09:36.498) Yeah. look, look, practical example of that is me and my CEO, Chris Beale, the other day we had a breakthrough on, we've actually undervalued what we do as a company in a lot of instances. We've got into this world of trying to create product for people and sell product and sell licenses. And that's all great, but it also comes with massive income, but challenges, is somebody needs to manage that. Somebody needs to mitigate for the churn. Somebody needs to take day -to -day ownership of making something work. Actually, if you've got underlying technology that potentially has more value to a market than your
product version of your technology does, why wouldn't you just sell the underlying technology to people that can benefit from that at scale? And so it's forcing, I think, people into being a lot more realigned to what value they provide. And it's also forcing people to think about, what can't I do today that I know I need to do? But at the moment, the gateway for a license, for a rep, for how do you monetize it? It just feels like too much of a project.
Mike (10:09.472) Yeah, yeah, exactly right.
Gerry Hill (10:31.07) But actually, if you can make it super strategic and say, well, you we've got a market exclusivity play for here. We're to do this at five weeks. We're going to take it to five of your competitors. XYZ all of a sudden, you're creating demand in the market for an underlying capability that otherwise didn't exist. If you're just trying to sell it upstream like you normally would. And I'm wondering how many other people are going to catch onto that thesis at some point.
Mike (10:53.282) Absolutely. And I think, you you talked before about the value of your products or services that you put into the marketplace. As an ex -buyer, an ex -procurement buyer, you know, one of my views was if a vendor, partner, supplier, whatever you want to call that third party, if they can't explain the value, the differentiation, the uniqueness, the ROI, the economic value creation, and why they stand out, if they can't explain that,
and I see them more as a commodity, well then I'll just treat them as a commodity. That's their fault, not my fault.
Gerry Hill (11:25.502) Yeah, I
Gerry Hill (11:31.208) Yeah, because you never want to be in the papers and pen clips and paper categories.
Mike (11:34.058) No.
Exactly what you want to do in the top right hand corner, high impact on their profit, very rare to find that capability. So you become a strategic partner.
Gerry Hill (11:47.604) Yeah, exactly right. And it takes time to get there. You know, I think people are trying to either do want to do things. I think we've got this obsession of big deal culture as well, which is unhealthy. I understand why it's necessary for a lot of companies, especially a company like mine, which is bootstrapped. You know, we like big upfront deals because that's how we fund our company, ultimately, and push off risk. But, you know, I'm not myopic enough to say
you know, a small deal that can expand to a massive deal over 12 years isn't a bad thing for you either. You've to be fairly reasonable about what you see on the ground. And I'm curious about the economic impact of lost opportunity because people got really myopic about the fact that it didn't fit within a pricing pro forma or a size of right to participate. Fascinating about that.
Mike (12:33.27) Yep, absolutely. Yep. So let's get into the questions, Jerry. So is outbound sales dead? If not, why not? So this is all kind of top of funnel stuff.
Gerry Hill (12:46.952) Yeah, is and no, it's not. think, you know, that's not a very explicit answer for you, but it's, it serves massive utility until you become market dominant. And when you become market dominant, you've got alternatives. it's still fundamentally the cheapest way that you can get your message to market. For me, companies in the innovation economy who don't have scalable marketing or channel differentiation.
is how scrappy companies can get started and be proactive about informing their own destinies. My big issue at the moment is how many bad and unworthy companies there are in the world because companies are super easy and cheap to create these days. So that's creating massive mind fog for absolutely everybody by channel. And, you know, how do you differentiate, how do you stand out? It's like an arms race for the most extreme form of messaging now, which probably doesn't do a good thing for the industry at all.
you know, whoever invented the cold FaceTime deserves to be strung up and shot, in my opinion. But that's kind of where we're getting to in terms of extremes to be able to help people get to a quota. The other reason why I think it's dead is people have forgotten what the fundamentals are, which are everybody's chasing in market opportunities today because of the short term nature of business cycles in 2024. Actually outbound is a bigger, longer term process that is designed to help you curate trust
credibility over 12 quarters of execution. So if you don't have a playbook that's designed for that, then it's always going to fail because you're constantly switching your experiments, your staff, your resources, your labor, your messaging and your models. You haven't done anything to sustain it and a sustainable outbound works and the unsustainable outbound doesn't. And also you just got to be really mindful about channels and action. Certain markets can have a high potential to email, some are going to have a high potential for socials, some are going to have a high potential.
Mike (14:24.748) Very good point.
Gerry Hill (14:41.14) For events, I regarded events as outbound by the way. And then some markets can have a high propensity for fire. And then you've to be able to be disciplined in the arts to work in the channel. My big fear about why outbound is dead though is rise of automation, has curated reasons for prospects to not engage with credible sellers. that's just made it really difficult for the people that are in the market who are credible. So it's not dead.
Mike (14:43.99) So do I.
Gerry Hill (15:09.034) those with the goods, the means, the will, the patience and the resources to be able to sustain a 12 quarter view. For everyone else that's just like trying to hunt the meeting on the first call today, it's a failure. It does nothing for your salary, does nothing for your
Mike (15:26.068) Exactly right. And just irritates people. And I think, you know, with the advent of, you know, God forbid, AI generated personalized emails, it's like, can spot them a mile off. And I think it is starting to really irritate people so that they're filtering out more and more and more from their inbox.
Gerry Hill (15:44.244) Yeah, I totally agree with you. I totally agree with you. you know, it's... I think the other big debate in our band at the moment is this sort of thesis around personalisation and relevance. And I think personalisation as a concept has been completely corrupted. Before it was show me you know me, now it seems to be show me you know me, but in a very creepy way. And nobody likes that. It's an invasive feeling.
Mike (16:07.21) Right. Yeah. Yeah.
Gerry Hill (16:13.393) The biggest fear that most
Mike (16:14.326) when you don't know them. It's like you don't know this person and yet you found out that basically they play squash and they were county champion.
Gerry Hill (16:22.322) Yeah, like all of them, right? Like it's nonsense and it's false and it's fake and it's disingenuous and some people might respond to it well because they're egos and narcissism as a prospect that's super, supernatural. But for most ordinary humans who just want to go about getting their job done, it's insane. But you can show somebody you know them by understanding their business problem and resonate with that. Yeah.
Mike (16:45.214) Exactly. The industry they're in, the kind of problems typically that those companies face in that industry.
Gerry Hill (16:51.31) And then dogs to be done. People don't look at it enough for them top profile messaging. I've got this high relevance thesis, which is understand the job to be done about the prospects that you want to engage with. And you can scale that by the way. I could look at it as the chief revenue officers and broadly speaking, no within 5 % either side of the job description, what the economic job to be done is, what the waste job to be done is, what the frustration job to be done is and what the emotional component of failure around all of those things looks
And I can turn that into 20 seconds. And then I can do that again for a rev -up person. I can do that for a CFO and so on. And am I going to get it right all the time? No, but if I get it right five to 10%, I'm outpacing the market, especially within an enhanced conversation flow, because now I've got measurement signals that I can play back into my system of design. So it becomes intentional design. It's not, I've got a feeling that we should be saying this to somebody who would know
Mike (17:45.09) So without this becoming some crazy role play, that's not what we started off with, Gerry, at all, but just talk to us about that kind of first engagement, whether it's via email or whether it's via a call. Broadly, what do you think works to get someone's attention enough to go, this person isn't an idiot, they're not being offensive, they're just trying to start a conversation?
Gerry Hill (18:08.01) the
Gerry Hill (18:11.594) If I'm writing, I'm writing like a CEO writes, which is very short emails, feel like WhatsApps or texts. They don't feel like war of peace. So my email engagements typically mean something like, Mike, wanted to discuss a breakthrough breakthrough results in about $25 ,000 in pipeline production per hour of time invested per seller. Companies like XYZ are using this to achieve breakthrough results. Sounds too good to be true. Want to meet? That would be the message.
a paragraph, half a sentence, it feels like a WhatsApp. using bad grammar on purpose. I'm using equal signs and apostrophes and stuff in the wrong places, just so that it draws people in. And it's measurable for me at that point. After that, cold calls. I'm still a great believer in one of the death spiral debates on LinkedIn is, know, permission based openers or business equal openers. Permission based, why? Because I'm a stranger.
I've never met this person. I've got to take that person from a fear state to a curious state within seven seconds or less. So I'm always asked for something. Hey Mike, we've never met. Got half a minute for me to show why I'm calling. Nine times out of 10, most decent humans are going to say yes. Great. Problem statement. You know, we're working on solving glitchy pipeline issues that most sales leaders seem to experience in 2024. Reason for my call was I believe we've discovered a breakthrough which
enables you to cover your market 1200 % faster, 85 % cheaper. Think of it as a way to get nine conversations like the one you and I are having for your sellers every single hour. And I just want to see if I could grab 20 minutes with you to discuss this breakthrough. You got your calendar available? 20 seconds or less, but there's an economic element, there's a speed element, there's a job failure element, there's a frustration element, but neatly packaged into context. Guess what I didn't do? I didn't talk about my product.
Mike (20:02.188) Yeah. And it didn't
No, correct. You just kind of said.
Gerry Hill (20:08.762) If I talk about my product, can get somebody categorizing me. If I get categorized, then they can leave the conversation with their dignity intact by saying this one thing. Now I'm covered. I'm good. How do you come back from that? So, design, think that's the key point.
Mike (20:21.186) Exactly. I mean, I've heard people recently saying, I mean, there's this crazy, I thought actually, Jerry, that's really good. Very grown up, sensible conversation, know, 20 seconds. And I can easily go, thanks. Interesting, but no. But could you send me something better than I got, I've had two or three recently. Hi, mate, you're gonna hate me. It's a sales call. I'm like, okay, you've put hate in my head.
So yeah, probably. I'm probably gonna hate you and gonna say no. I might laugh and smile and then put the phone down, but that's as far as you'll
Gerry Hill (20:50.676) Yeah exactly.
Gerry Hill (20:58.538) Well, do you remember, do you remember about 15 years ago when society probably wasn't as precious as it is now? There was the whole sort of psychology of dating with the nagging and there was the whole book thing where you deliberately be a little bit mean to girls and stuff in order to get their attention. You know, what I find with those sort of self -deprecating, you're probably going to hate me as much as I hate doing it myself kind of conversations is I'll never, ever, ever elevate in your mind's eye to business value.
business equal because I've already put myself on a lower pedestal. However, being polite to a stranger that you've never met before is completely different. And again, it's part of that nuclear arms race about how do I differentiate, how do I stand out. And you know, I think people being negative against themselves is such a fool's errand, but you know, why would they not be better?
Mike (21:45.728) It is. I would agree. And it does it. It indicates all sorts of things to me, which is like they're not serious business people. So I'm not going to have a conversation. I'm not wasting my time. So really interesting.
Gerry Hill (21:48.979) Yeah.
Gerry Hill (21:54.942) Yeah, sure.
Gerry Hill (21:59.171) Yeah, yeah. yeah, that's it. Outbound can be optimized and can be made to work. It's hard work. Nobody seems to have any tolerance for doing hard work in order to make a very scalable and cheap route to market work for themselves. And that's the big frustration is everybody's just looking for shortcuts and hacks right now and they've set the wrong.
Mike (22:16.465) Exactly. And as someone said to the other day, your only objective really initially is to get the next conversation. What you just did. Have you got your diary? Have you got 20 minutes? That's all you're trying to do, isn't it? Is just generate the next conversation.
Gerry Hill (22:29.934) We're riffing on the stone at the moment around just brilliant basics is probably the next innovation in sales and it's going to take us back to where we all came from in the late 90s, early 2000s. Just focus on the fundamentals which is have a conversation, follow up, nurture. That's it.
Mike (22:39.222) Yep.
Mike (22:46.07) Correct. Have a conversation, follow up, nurture and do what you say you'll do. You know, if you're gonna send a, like I was taught many, many, years ago back in the late nineties about selling was, you know, simple things like, why don't I just send you our latest thought leadership paper? It's not a sales document, it's a thought leadership paper on your industry and the dynamics, the issues that people seem to be facing. Would that be helpful? Well, yeah, that sounds quite helpful. Okay, fine. So you send
Gerry Hill (22:50.876) Exactly.
Mike (23:15.81) and then you have a follow -up conversation. And so it goes on. I my longest sales cycle, Jerry's 10 years. Hopefully. Yeah, recently a few have been a bit quicker than that, but it takes time.
It just takes time to get to know people and there is no shortcut.
Gerry Hill (23:32.81) Yeah. And I think people just need to be realistic about that. You've got in -market opportunities at 3 % of the market every quarter. You've got out -of -market opportunities where you create the demand. My big fear today is with all the cleverness and the technology tricks and hacks, everybody points in all of their resource at the in -market opportunities. And then everybody wonders why they're not closing business. Well, you didn't create the demand, you
Mike (23:55.765) Exactly.
Gerry Hill (23:57.576) mopping up the soft demand in the market with people that are never going to be one of the customers because they're inherently already expert on the problem set. So, you know, what have I taught anybody? How have given everybody, anybody else compelling McKinsey level perspective? How have I shown them value economics? How have I done any of the core work as opposed to, okay, who are you competing with? Well, this is how we're different. Great. We'll send you a deck and we'll put it together in evaluation. Is it too late to enter? You know?
Mike (24:24.64) I mean, on that point, Jerry, we haven't talked about this, but just get your thought on SDRs, the role of SDRs going forward. What's your thought, Jerry?
Gerry Hill (24:37.034) I don't necessarily want to resource the sales team and SDRs at my price point at like 10 ,000 ACV because they're just grinding out too much drudgery to make that cost of acquisition worthwhile for me. Where I've probably got a mindset for them now is sort of high teams of Tiger teams, careerist SDRs, early entry SDRs, where the value to time makes sense and where I can compress as much of the worst part of the job away from them.
And that's essentially what my product and proposition offers, which is I take a really good SDR or an AE, I reduce 90 minutes of waste and I return a conversation every four minutes as opposed to a conversation every 90 minutes. That's an example of this sort of special forces hypothesis, which is starting to emerge, which is I think we've come out of like the Victorian era of warfare, which is big team set piece battle.
You know, my resources are greater than your resources. My head count equates to more coverage. Whereas now I've got potentially an opportunity to redesign a team. They're all very good at everything, but they're specialist in something. They take ownership of that specialism and then they execute accordingly. And I'll tell you, can five people and I've applied a million dollars in resource to those five and I've turned that five into 50. That would be my SAS Delta, maybe see all kind of analogy drawn against the traditional infantry, which may or may not still have a place.
But I don't believe that if you've got an articulate proposition and you've got motivated and mobile reps who are very agile, business focused, scientific in the way that they approach their day in, have got the ability to execute and provision feedback at scale and use data well, why wouldn't you deploy that instead as the alternative? I think the reason being is too many people have attached their careers to big teams. And I get really frustrated when I'm looking at resumes, because we only hire in people as individual contributors to connect and sell.
if they've actually done some sort of sales leadership in B2D and number of resumes I see screening out hope which are like, I built the company from zero to a hundred million. No people. Show me the number. I'd be really impressed if you'd grown the company from zero to a hundred million with four heads. Then I'll have a conversation with you. So I want to understand how you did it. Right. So yeah, I think, I think we measure the wrong stuff too much.
Mike (26:38.038) No, people.
Exactly.
Mike (26:45.964) Yeah. Yeah. Exactly.
Mike (26:54.88) Exactly. So just like kind of moving on to the next kind of third question really about scaling. So as you've just discussed, this isn't about creating a hundred person team, but how do you scale outbound? What are the kind of economics behind an efficient ecosystem as opposed to a bloated ecosystem, I would say.
Gerry Hill (27:16.564) Yeah, I think the efficiency comes from the work product that you do day to day. We've lived in a generation which is sort of soft market expansion, engagement, as opposed to direct market penetration. Engagement is predicated on the idea that I know where my customer is going to be eventually, and I'll try and make them across all channels at all times in all ways. But that actually doesn't have any science applied to it because trying to capture the measurement points there are all proxy measures. There's nothing that I can actually relate to.
Mike (27:43.244) Correct.
Gerry Hill (27:44.968) as a fundamental lever to pull and a lot of it's sort of sentiment. It's not direct feedback. So I've been working on this sort of construct recently, which is trying to apply everything that our good friends in software engineering and agile do to create products, which is an agile framework, which means that hyper structured days, those days are revolved around three to four critical sprints. Those sprints have got a very specific team, theme, market, geo, message, or campaign pillar attached to them.
You go all out on the sprint, you decompress, you learn, you feedback, you cycle back. Then you go again on the next break, break up the monotony and then you go again and then you do it again. And then you've got consistent measurement. Now the overlay for that is gamification to make work fun because actually you're now mandating work to people again, which is a rare management principle in 2024, but actually needs to come back into fashion. And then the other thing is you're measuring on a jobs to be done measurement framework as opposed to just
quota attainment. So I've got this hyper accurate thesis now, which is if I can model time against each sprint and understand the outcomes and the behaviors that I want to apply to it, I can then burn down to a goal and I can measure everything off the deviation of that burn down. So I'm now either above the line, I'm failing or I'm below the line, I'm accelerating. And because I've got insight like
All of a sudden I know which I can scale against and where I can start to apply more resource, more investment to the bets that I need to make. It's not to neglect all the other work, but it's taking a huge amount of the sentiment and the gut feel out of the process. And it's actually framing it in a very, very specific way. Now, none of this stuff works unless you can apply velocity to it. know, scale comes with velocity and that's where your falls multiply and start to make a big difference. And I think you can only scale outbound once you've got existing
Mike (29:21.601) Yeah,
Gerry Hill (29:37.618) systems and processes in place because it's like any input lever. If it's shitty inputs, you get shitty shitty outputs. And I've probably also got one dedicated resource, not a team allocated to market exploration and finding those adjacent market opportunities, not the ones that are core today, so that we can start to model in what the potential friction points looks like. you know, that's, that's an even higher tier of special forces. It's kind of like a trailblazer roll.
somebody can collect information, synthesize it, act as a business concierge into the market, test messaging for you and with you, but actually acts very independently and separately away from the core team and is incentivized slightly differently as a result.
Mike (30:17.676) So there you're kind of scouts.
Gerry Hill (30:19.422) Yeah, I like that term, I hadn't thought about it but I'm going to start using
Mike (30:23.851) Because they are aren't they? They're out there exploring. Yeah exactly and then they're coming back with information and they're feeding that back into central intelligence.
Gerry Hill (30:25.182) Yeah, that's I you were coming to say.
Gerry Hill (30:32.49) But the big way for it to work, the only way for it to work is it requires executive buy -in. And I think for sales development and outbound in 2024, it's become a highly tactical job and people have forgotten the fact that it's got massive strategic value. And it's kind of like this ongoing debate at the moment. Who should rev ops report into, should be the CFO in my opinion, because they own the data and the cost and risk. It shouldn't be the CRO, because I don't think every function deserves its own operational concierge.
Mike (30:58.583) Yeah, yeah.
Gerry Hill (31:00.252) in much the same way that I think sales development should actually report directly through to the CEO because it's first contact with the market. And for me, the most important job is first contact with the market.
Mike (31:10.726) Absolutely. I mean, and just to kind of draw this together, any business with an investor of some kind, be that a person investor or be it a PE fund, you've got to grow. Well, to grow, you need to drive sales and you need to deliver high quality results to your clients so they stick with you at an efficient cost base. And we seem to have forgotten the entire, not forgotten, people just...
Gerry Hill (31:34.814) Yep, that'll be right.
Mike (31:38.956) They don't want to talk about the entire sales bit and how difficult it is.
Gerry Hill (31:42.058) It's interesting, isn't it? It's interesting, isn't it? There was a turn in the market at some point, and I don't think it quite when it happened, but you when I left university, I didn't want to get into sales. I wanted to be in a hedge fund or an investment bank or a trader. That was where all the glamour was when I was a 21 year old man. And now people are rejecting those careers in favor of early entry tech sales.
And there's a huge amount of blow as a result and the compensation model has got completely out of whack with the value. And it was just getting a foot in the door so that they can do the next job, not the job that we need them to do today. And that compounds cost because there's hidden management burden there associated, there's term burden associated, there's, you know, but unfortunately everyone in the world reads the same fucking books and read the same fucking books and do the same fucking things. So yeah.
Mike (32:20.319) Exactly.
Mike (32:33.11) Yep, precisely. Correct, exactly. We're just scaling shit. A guy I had on the other week was saying that he does a outbound, he's got a small outbound team himself, it's like six, people. And he says, the worst thing that happens to us is we get people that want to become the sales director and the CEO and their entry point is, well, I'll start on outbound calls. And he said, they always fail. You want people who are career salespeople.
in one aspect of the sales value chain. And then you'll succeed.
Gerry Hill (33:05.256) Yeah, it's like the Reed Hastings hypothesis, right? Which is Netflix doesn't promise anybody anything other than the job that they're applying
No career paths, nothing. You get paid really well to do that. Really high area of specialism, really well. And if you don't do that and you get frustrated or you want to do something else, there might be a home for you here, but actually I'm not going to mismanage your expectations and promise you with those.
Mike (33:33.248) Yeah, exactly. Jerry, it's been amazing. Genuinely interesting, thought provoking, amazing, thoroughly enjoyable. Thanks for joining me on the Higgle B2B Sales for podcast. Really enjoyable. Where can people find out more about
Gerry Hill (33:37.418) Let's do
Gerry Hill (33:44.49) My pleasure. My pleasure. Thank you. Yeah, so I always give my phone number out because I hate email. I hate getting email. So my numbers UK 07782034081. I take pretty much any call that anyone ever makes. LinkedIn, I'm quite visible. Jerry Hill, Connector Cell. My avatar's a chat GP generated version of what I would be if I was a superhero. So it's been, yeah, it's been continued for me.
Mike (34:09.898) I saw that. It's quite fun.
Gerry Hill (34:12.97) And yeah, that's pretty much it. Those are the two places you'll find me. Quite active in our revenue scenes in the United Kingdom. Sorry if you belong to Pavilion, Revenue Collector, CRO Connector, South London Leaders of the Mayor. Probably knocking around in those places as you go.
Mike (34:29.174) Brilliant. Jerry, it's been a real pleasure.
Gerry Hill (34:30.954) Thank you Mark. for having me.