Paul M. Caffrey (00:02.203)
And as I mentioned, I'm delighted to be joined by Rob Halligan, the co-founder and COO of Pitchdit. Rob, how are you doing?
Rob Halligan (00:09.954)
Great, Paul, thanks for having me.
Paul M. Caffrey (00:11.791)
Yeah, look, delighted that you've come on. And I guess this episode will be a little bit different than most because rather than focus on sales, we're going to talk about what you could or maybe should do, what your commission that you earn.
Rob Halligan (00:27.17)
Yeah, nice. I think we've both been through that over the years working together. So hopefully we have some good things to share.
Paul M. Caffrey (00:33.691)
Yeah, I'll be a bit of crack. Yeah. So, um, and yeah, full transparency myself and Rob did work together a number of years ago. Now it must be said, um, and George earnings have went in different directions. Uh, I'm interested in digging a bit into that. So maybe, um, you might share a little bit, uh, with our audience, um, about how you came up with the idea for pitch that.
Rob Halligan (00:56.062)
Yeah, for sure. So, um, we obviously worked together in Salesforce. I was there for six and a half years pushing seven years. Um, I think you were there similar, probably a similar amount of time. Um, we worked together for a couple of those years. Uh, yeah, I mean, I started there as a sales development rep at the time came in pretty green in the sales world and didn't really know a huge amount, didn't really know a huge amount about.
what I wanted from a career either, but was happy to be at Salesforce. Obviously, had a great reputation. And I mean, to not make the story too long, I think one thing that when you work at a big company like Salesforce, particularly in kind of big tech, right. It's very early on you're exposed to the employee stock purchase plan or stock options.
I had no idea about investing. I had an interest in the idea around finance, personal finance, but no exposure to really any of us.
And that was kind of your first port of call, right? When it came to that was your first exposure to that. And you realize very soon that everybody around you who are also starting that journey potentially for the first time or their first step into that world of investing, your financial literacy kind of comes on very quickly, all of a sudden you've kind of popped your cherry, if you will, on the investing front. And then all of a sudden you're kind of, this is now not that scary and not that big a deal.
Paul M. Caffrey (02:18.075)
Yeah.
Rob Halligan (02:23.324)
kind of looking around elsewhere and you know yourself, myself we sold into a lot of like VC backed tech companies across the UK and that's a really exciting space and you get really close to a lot of these clients and you learn such a massive amount about how they operate, their people, their various departments and how they're connected and how they do business.
But importantly, you're kind of always keeping an eye on how they're moving, right? Because these are always signals, buying signals for you as well. You're looking at, are they raising money? Are they spending money? What's been happening? Are they moving into new territories? Are they launching new products and all that good stuff? And I remember I was the account executive of a client called Pecon at the time.
and they exited to work day for nearly a billion dollars. And I just remember thinking, you know, how much money, you know, that those founders make, how many did their employees make and how do regular people like me and the people around me invest in companies like these and that kind of set off a spark that started looking into alternative assets and investing in private markets. And
Paul M. Caffrey (03:16.211)
Yeah.
Paul M. Caffrey (03:32.003)
Yeah.
Rob Halligan (03:32.97)
You know, coming up to me at the same time, my co-founder Scott, who's also my best mate of 20 plus years, was having in parallel similar thinking and similar ideas in his head. And then one day we kind of realised and came together and since then we've launched Bitch.
Paul M. Caffrey (03:50.671)
Yeah, and I guess that's a really, really key point. Two key things to mention there is, yeah, the first, I suppose, your employee stock, ESPP, stock share buy program, all of different types of names, that probably is the first time a lot of people invest. So some companies will have that. That just means you can get some stock at a discounted rate, typically on a monthly or quarterly basis.
is the first time that you invest, which just makes total sense. And then the second part, which I think is really interesting that you mentioned is, yes, selling into those startup scale up companies and seeing, as you say, the triggers. Oh, they've got investment. They've got another 50 or 100 people working there. These are all good things if you're trying to find a SaaS. But that whole world of getting a piece of a company that size.
is a little bit locked away from most of us. If we think about it realistically, if somebody is already on the stock market, they probably already had that IPO, they've already had that big jump in value. So a lot of that is somewhat locked away from, I suppose, regular people like myself and yourself.
Rob Halligan (05:02.878)
Yeah, 100%. I mean, historically private markets or alternative assets like private companies and hedge funds and all that stuff is world away from 99% of people, right? It's the 1% world. It's the wealthy that have access to those things. But they're also the highest performing asset classes, right? So, you know, it's kind of when you realize it, you're kind of going, well, no wonder the wealthy maintain their wealth and grow their wealth.
to such an extent is because they have access to the tools that allow them to do it. Well, the majority of us just don't have access to those same tools. You know, for, and you know, any salespeople will know that because salespeople, like I mentioned, you make that first kind of jump by investing in your stock, participating in your given stock when you join a company. Generally what I've noticed, and I'm sure you probably did yourself, is when you look around your colleagues in these companies,
A lot of them are also looking elsewhere very soon after that, like where else can I put my money? Right? So they're looking at like investing and now it's so easy. Like what I mentioned there about investing in this awkward spot, like that's eight years ago, you know, roughly when I joined Salesforce. Since then and back then there wasn't apps on your phone to make these things super easy. The first platform I started using was eToro. I was trying to buy Ethereum and cryptocurrency at the time.
But that wasn't an easy process either. I'm sure it's gotten the user experiences come on leaps and bounds since then, but it wasn't, wasn't super easy. But now it's the touch of a couple of buttons and you can do that. But yeah, it's, it's a different world for sure. In comparison to what it was. And I think.
people have come on so much in terms of their understanding of the world of finance as well. But it's still not easy to get into these private markets. It's easy for people now to whip out their phone and buy some stock on Revolut or Dejairo or a similar app like that. But it's not very easy to invest in a private company, particularly in its early days, pre-IPO or any other private market assets.
Paul M. Caffrey (07:16.707)
Yeah. And I guess that's, I mean, that's pretty much where the, where the biggest gains are to be had. And you're right. We're all in these WhatsApp groups and you're going to find yourself, maybe it's the end of Q4, you've got that big commission check. It's just, when you sit in there, you think, Oh, I should do something with this. Let's invest. It sounds cool. But very easy to, I guess go after the flavor of the month or that latest shiny object. And you can potentially lose a whole lot that way.
Rob Halligan (07:44.95)
Yeah, for sure. Look, I mean, everybody's situation is really different, right? You look across a floor and just say a tech company for the sake of the argument across the sales floor and the variety and person is in terms of demographic, we're very much the same, but the age bracket is very, it can be very different. You have people who are just out of college and you have people who are, you know, in their forties, fifties, who are also selling.
and everyone's responsibilities and priorities are vastly different, right? So if you're someone who's just out of college, you may, maybe you're not married or have a family or a mortgage or whatever.
How you spend that money is going to be vastly different right and you'll probably be more inclined to look at some of the Nice shiny things and that might not be saving or investing it could be other things I think I heard something before about sales managers and VPs love A's that go out and spend their money on you know nice new cars and whatnot because it means that they've Spent their money or rocked up some death that they go and that they go and need to
need to replace or replenish. So they're motivated again to start selling. And for the people who are maybe more further along in terms of their, their life and maybe they have kids in a mortgage.
Paul M. Caffrey (08:49.959)
Yeah.
Rob Halligan (09:03.298)
they're not quite maybe spending on the flashy stuff, but maybe they're more inclined to invest or save or whatnot. So it's obviously different for everybody. And I mean, I mean, and obviously looking back in hindsight, I would have done a lot of things differently as well, but I did always try through my own interest to make sure that certain things I was doing, some things are certain things. And when it comes to investing, I think for me, and a lot of people will be the same, you know, at the end of when I was thinking back to my days in...
SaaS sales, every month is different. Your pay packet looks different every month, right? Depending on how well you've done or every quarter, whatever way you're paid. So it can often be hard to properly plan ahead of those things.
And for me, it was always like, automate as much of this as possible. If I want to save money, or if I want to invest money, have it come out of my account automatically so that it's just gone and then I can, you know, I can do what I wish with the rest, but when it lands in your account and then it's up to you to go, where will I put some of this? That's where it's very easy to get carried away and just spend on, as you said, flavor of the month or something else. But yeah, I mean, it's obviously different, right?
Paul M. Caffrey (10:15.971)
Yeah. Like if I think about some of the stuff about Martin to NFTs for a while, that was a bit of a funny, funny time. I think that market seems to be definitely way down. I don't know if that'll ever be back.
Rob Halligan (10:25.536)
Thank you.
Rob Halligan (10:30.686)
Yeah, on its knees. I'm not sure. Yeah. I didn't, I didn't venture anywhere into the NFT space, into the crypto space. My self has got quite a while ago back kind of 2016 and 17 quite a bit and did okay and held onto a little bit of it. Very small amount, but
Paul M. Caffrey (10:42.588)
Yeah.
Rob Halligan (10:53.867)
Those were pretty wild days as well, right? So it's kind of things we've seen before.
Paul M. Caffrey (11:01.54)
So I guess what I'm picking up so far is to have a plan to maybe put some of your earnings or commission aside on a monthly basis. Try automate that if you can have that going somewhere. And I guess what's the key difference with say PitchDish versus
Let's say if I was to go looking at using it as euro or a typically IPO traded company stocks
Rob Halligan (11:34.258)
Yeah, yeah, sure. So something like the Giro or even Revolut, if you're looking at just the stock or crypto purchasing element of it, or even using an exchange like E-Trade or something like that, for the most part, most of these will expose people to public market assets, so your stocks, your bonds, so the stuff that most people are familiar with.
Some of them have now ventured into cryptocurrency a little bit, which is a private market asset or an alternative asset. But it is obviously still relatively in its early days and its infancy cryptocurrency and has a lot to prove, I would say. And I mean,
If it's again, I have played in that space, but I'd be wary enough of it as well, unless you knew what you were doing. But in terms of pitching, what we do again, we expose retail investors to private market assets. So retail investor being someone like you and me, your everyday person likes to invest some of their salary. They're not considered high net worth or an accredited investor or professional investor.
And we expose them to private market assets, going to be starting with venture capital or the startup space, directly investing in young private tech companies. Now, the difference between ourself and those is probably pretty obvious then, why you're looking at stocks in publicly traded large organizations usually, or bonds, versus young startups that are in the early stages of their growth.
and you know, we'll be backed by say venture capital firms, right. And we are then moving to other asset class within the alternative space, like private debt, hedge funds and other areas as well, right. And the difference, say between us then and someone else who plays in that space, like say a Cedars, which a lot of people would be familiar with, or a Crowdcube, like a traditional crowdfunding platform.
Rob Halligan (13:36.122)
is that those platforms usually work kind of on a volume play. There's a lot of opportunities on the platform, mixed industry and vertical, mixed quality as well. The space historically hasn't been regulated is now, which is a great thing, particularly for the safety of the user. But unfortunately, what you see with platforms like that is...
Unless you know what you're looking for, unless you know how to effectively screen and analyze an opportunity, you're still just blind betting, right? You're still just taking a punt on the company and you're following generally what we see and from the research we've done is people either follow their mates because they've said, Oh, I've invested in this company. And they think that's good enough for me. And they see a brand that they're familiar with. So maybe it's a brand that they bought before they use.
or they're flicking through the platform and they see kind of loud, shiny branding that they've done a good job on their brand. And they think, oh, this company looks cool. I'm going to put some money into it. And that's not a good investment strategy, right? For 99% of people, they don't have that experience. They don't have the time to be sifting through platforms like these and trying to find a winner or a good, good company.
and they don't have the knowledge. So the one thing that these platforms have done and no shade on these platforms, they're great in giving people access, but they have allowed people to access, you know, investing in startups for small amounts of capital, but I think they still are missing two really important elements and that's around the knowledge piece and the time piece. And they're two elements that we're looking to solve through our platform by...
taking that heavy lifting away from the end user, really automating the process for them so they can build out a diverse portfolio quickly and with very little required input from them.
Paul M. Caffrey (15:34.963)
Okay, that's interesting. Yeah, look, we've all been there when you like, say, jump on cedars, every project seems like it's the next big thing, right? It's, you know, you're blown away by it. So you're then advocating for people to, I guess, diversify into the small into the smaller startups that they're going to have access to in the private market then. Is that that's the idea?
Rob Halligan (15:59.23)
Yeah, yeah. I mean, I think any good investment strategy for anybody. And like, you know, using that term investment strategy shouldn't be scary to anybody, even if people are new to investing everyone, if you're going to plan to put your money somewhere, you should have a bit of a plan and a strategy around it, right? Instead of just going on to desire revolution, throwing all of your, you know, spare cash into one stock or two stocks, there should be kind of some kind of structure around it.
And diversification is the key around that. It's like funneling your money into different spaces that give you security, right? So if one of them goes up or it goes down, the others, or goes down, or say aren't affected too badly or too negatively. And, you know, I'm not saying that you should put all of your money in public markets or all of your money in private markets. It's about having strategy where money is put in between both.
So that's what we want to give people access to. People already have easy access to the public markets. As I said, we can whip out our phone anytime and easily buy some stock, but people don't have access to the private market asset classes and they're the ones that have historically outperformed the public market. So why shouldn't everybody have access to those is our question. The wealthy have access to them and use them to their benefits and grow their wealth every year. Everybody else should be able to do the same so that's what we're
Paul M. Caffrey (17:23.235)
Yeah, so I guess it's, I suppose, further levels of diversification. So things that maybe could probably go without saying, but should get a mention is, you know, maximizing pension contributions or, you know, if you're in different parts of the world, that's 401k or whatever that is. Obviously there's tax efficiencies there. And yeah, I mean, the diversified portfolio, I guess what it really comes down to is.
If you pick one business or one stock or one thing to invest in, you probably should know that inside out. You probably should know the market they're selling to inside out, which means that you are very knowledgeable to know if the good times are going to continue or if there's any risk on the horizon. And let's face it, most of us just don't have the time, bandwidth to actually do that for any company. So if you don't have that, then yeah, diversifying makes sense. And
If you're thinking about like, let's say you're going, okay, great. So maybe I go into, you know, the existing public markets and maybe I go into the, into the private market as well. Um, are you thinking of talking 50 split? Does it matter on your age or it's a very difficult question. What would be a good starting point for people?
Rob Halligan (18:35.818)
I mean, it's hard to say. I guess it all depends on everybody's situation, right? And like, you know, I can only think about my own situation and how I've, what I've done in the past and everybody will be different. I can't tell anybody, you know, this is what you should or shouldn't do. But like you mentioned there, like, you know, pensions and whatnot. Like if I think back to my own time at Salesforce, you know, I definitely didn't take advantage of those things to, you know, the effect that I showed.
Paul M. Caffrey (18:50.204)
Mm.
Rob Halligan (19:04.378)
I think if I was going back and doing all that again, I probably would do it vastly different and, and max out or close to max out, you know, pension contributions, your stock purchase plans. At the time it's kind of, I found it very easy to just be like, ah, you know, no big deal, like, you know, or I want to spend my money on myself and other things, or like when I say myself, you know, on more material things on a month on basis or going out and enjoying myself. Um, but.
you know, where's that money now? It's gone, right? I can't get it back. So I think if I was going back or if I was advising anyone who was in a similar situation or at the start of that would definitely be to make sure that, you know, the two easiest places you can probably invest your money is in your pension. If you're in a company that offers it to you and also those stock purchase plans, right. And take advantage of them.
And then after that, it's about like, right, okay, they're the two easiest ones. They're also fully automated as well, which was always important to me. It's like, I don't want to do have to worry about, you know, the work around things like that. So if someone can do it for me and make that really, really simple, the money's gone out of my account before I even see it at the end of each month. All the better.
after that it's kind of like, well, what else can you do? And if I think, and again, only thinking about it from my own perspective, I was kind of going, you know, I had my first son was born three years ago. And at that time I was kind of going, right, what else can I do to kind of build up my own wealth for the future? And you kind of realize pretty quickly, these things are long term games, right? They're not gonna happen overnight. And you have to be willing to sit and wait and kind of forget about it. I'm not gonna get rich day.
trading, right? So unless you have that skill set and the time and knowledge to do it, then you're probably going to be in a similar situation and going to have to come to terms with the fact that it will take time. So I was looking at, you know, what else can I do? And I found an opportunity, a fund that anybody can do. It was actually with Zurich. It was through a guy, a brand called Ask Paul, which is PAC's financial advisory.
Rob Halligan (21:17.522)
And they just did a, it was like an investment club. You can invest from as little as 90 euro. I think it was a month, but again, it's fully automated. All of they, they set it all up for you. You're investing into a massive global managed fund of billions. You know, the benefit of that is that there's a very experienced and well established fund manager sitting there managing that money. And again, it went out of my account automatically. I didn't have to worry about it. And I just let it roll, you know,
So for me, it was always about finding opportunities like that. As I said, I had bought crypto years ago. I traded a bit at the very start and then I just kind of left it on my left to sit there.
Rob Halligan (22:01.886)
I think in terms of how you make up your overall portfolio, whatever it is, it's not really, it doesn't really matter. It's entirely up to you what makes sense. But I think it's about finding like what is it, what's your strategy? Are you willing to sit on it for a long term? Do you want it just to be automated? Are you more active in it? And then, you know, directing your money accordingly. But I think if, you know, I think more and more opportunities are opening up in the
That's what we're focusing on giving people access to. I think when those opportunities are available to people, I think it's, you know, an important to look at all available opportunities and see does it make sense to move some of the money into that.
Paul M. Caffrey (22:45.347)
Yeah. Now I'm totally with you. And I guess a way that I've adopted to it, if I think back, I guess we continue on what we've done is focusing on those, like whether it's a Vanguard or whatever it is, 10% SMT, 500, you know, let's say 8% per year. So there's a chunk there which you kind of...
feels like, you know, everyone's, oh, last hundred years it's continued, always has a positive return. So you can somewhat relax and have a chunk in that. And then, yeah, I mean, the other side of it is there is sometimes then a part of cash which is nearly fun money in the sense of, right, you're going to invest in maybe something that could bring a five, 10, 20 extra turnover a shorter period of time, but could also go as well. You know, that's also, and that also happens in...
in the publicly traded markets. I mean, there are a number of companies that I'd invested in who, you know, ended up getting delisted as a result of, you know, the tech that they sell didn't actually catch on. So I don't think you're necessarily safe even in the public markets. I mean, things still go wrong. And there's something to be to be mindful of if you go into an individual stock. But so what I'm taking away from that is having the everybody has a strategy.
not having a strategy is a strategy, a very bad one, but you do have that, right? And there really should be a plan for, you know, what kind of financial stability slash freedom do you want in five years, 10 years, 20 years, 25 years, because touch wood, you should get there, you know, where everyone's living healthier lives, longer lives. So, you know, you'll probably get there sooner than you imagine.
Rob Halligan (24:29.93)
Yeah, for sure. Yeah, big time.
Look, as I said earlier on, like everyone's situation is different and some people will care more or less about these things. You know, I'm in my mid thirties now with two kids and a mortgage. And, you know, I'm at that point in my life and, you know, you're similar there. Whereas you do have these priorities that you're planning for. Again, if you're in your early 20s, mid 20s and don't have those priorities, maybe it's not as important to you. And that's absolutely fine as well. So we are like you mentioned, public markets, they go up and down as well.
depending on what the asset class is. But if you think about something like, venture capital, investing in startups, it's definitely high risk, high reward. But yeah, you're not immune when it comes to the public markets either. Like if we look at the last couple of years, the problem with public markets is they're way more.
closely tied to the wider economy. So when the economy takes a hit, you'll really notice that in the public markets, it kind of flows with that. Private markets are a lot less heavily correlated. So you don't necessarily see the same sort of dips if the economy sort of takes a hit.
And that can be, you know, that's kind of a safety net that a lot of investors use. It's kind of having a percentage of their portfolio within private market assets that can ride out those sort of bumpy times within the economy. Things like art generally, you know, is an alternative asset class is something that generally doesn't move with the economy. So if the economy dips.
Rob Halligan (26:12.802)
the art, you won't see that same correlation in art. So a lot of people will leave a lot of their money tied up in art. Now people are probably thinking, who the hell can invest in art, right? But there's actually companies that are making it really, really accessible for people like you and me who want to invest again, maybe a couple of hundred quid a month or less in really high ends, well-known artists, famous artists. There is companies that are doing these things. So
Again, it's really, I think the next few years, the next decade are going to be super exciting for many reasons in technology, but I think around this particular space around.
personal finance around investing, I think, we'll definitely see a massive jump in that as well, because we are starting to see these sort of access points open up for a lot of people, right? So I think it's gonna change a lot, which is really exciting. And that's what we're getting involved in at Pitch Did. But yeah, I think again, you know, just to go back to that point around public markets, they're not immune, they will.
they will, you will see those shaky times and I guess private market assets may be less correlated won't see the same peaks and troughs.
Paul M. Caffrey (27:26.055)
That's pretty cool. So you're saying we might be able to find a way to own the tiniest speck of paint on a Picasso. That's amazing, it will be a great moment.
Rob Halligan (27:35.05)
Oh, literally. Yeah. Or a bankruptcy or something like that. Yeah. There's a, there's companies that are doing that. So basically they, um, what's the tokenize or secure securitize the assets. So that essentially, yeah, what you're doing is you're buying one tiny fraction of it and they hold it for a certain amount of years and then they make a decision, you know, after a certain amount of years is this, and that based on the market, how popular is the artist right now?
is it a good time to sell to make a return for the underlying investors? And yeah, I think it's really cool to be able to do that, you know, and again, it's just different avenues that people can take to put their money like we're not.
Again, these things weren't available, right? Not even that long ago. Like I said, eight years ago when I joined Salesforce, I had no idea about any of, not a huge amount about investing in general. The stock purchase plan was kind of the first thing. And then it was, then I came across the Toro and then it was crypto. And then in just even in the last five years, if you think about your mobile phone, if you think about if you're on an iPhone or otherwise on a smartphone, what apps do you have and what you can access?
and is pretty incredible and that's only going to get, you know, that's only going to speed up. So yeah, I mean, if you're a, where are we now? We're in November. So if you're an AE into Q4, depending on when your Q4 runs till December or January, you might be thinking about where you can funnel some of that money. I think again, the only thing I found with commission was that
You're never guaranteed to know exactly how much you're going to make until the very end, right? So you can't always plan accordingly. And it can be tough to make the mature choice of putting it away in savings or investing it in something when you get a nice payday, right? So I'm sure people will have their eyes on some shinier things.
Paul M. Caffrey (29:39.575)
Yeah, I think that's going to be really useful because that is some of the questions that I get from account executives, because I'm coaching them and they're like, OK, I've smashed my number and it's great. But what do I do with this cash? And so they just leave it stacking up in a bank account, maybe not doing what it could be for them. So I think this would have opened their eyes to the fact that, you know, there's private markets to maybe go after.
There's the world of art and also some of the different areas of the stock market as well that are there. But most importantly, having a strategy or having a plan in play. Yeah, that is pretty cool. I was just thinking, so if we fast forward or pull it back to where we are now, other people are looking to close out their quarter, looking to close out their year. And we've got a mix of county executives, mix of founders who are in that situation.
You interestingly are in a foot and boat camps and have had experience there. So I guess from a prospecting perspective, what's the number one tip that you would give somebody for looking to find new opportunities?
Rob Halligan (30:44.83)
Yeah. Um, I think something that, uh, worked for me in sales and actually that I've carried forward into what I'm doing now when it comes to reaching out to potential investors is it's a, it's actually the same process really, like, you know, trying to raise capital is a sales process. You run it the same way I would have ran a sales prospecting cadence or a sales cadence back then. Um, so it's funny to see that come through.
Um, for me, I am a kind of routine person and for me to be successful in my day to day and productive, I have to kind of have certain things set up properly and that I can just make things easy. So when I was in sales force, it was always about just preparation, right? It was, and it was always, you know, the very start of the year going through your whole account base, current customers and prospective customers.
And in detail, like it took a while, it usually took a few weeks of work, but it was always worthwhile having that done before you re-kicked off the FY. And really in detail, building out every single account, who they are, what's their current contract look like.
What, what are they using? How many seats, who are the main stakeholders in the company across the various departments, when is their contract start, finish, all that stuff. So you can actually properly go after them. Okay. And similar for your prospect accounts as well. And that's the same with me. So it's just a bear like doing all of that setup. And like, even though it's painful and monotonous and, you know, repetitive.
it stands to you in the long run to make sure that all of that is built out and done. Cause then it's just about action, right? Then it's just about, you have all of the information in front of you and you can just start chipping into it and you can just start going after it. And it makes life way, way easier. It's a bit of pain at the start, which is, which is not nice to go through, but then once it's done, you're kind of like, I have this ammo that I can use to go after these clients and go after these people.
Rob Halligan (32:51.902)
and it just makes life so much easier. So that was always one that stuck to me back then. And when I talk with me, it's putting in that preparation early, you make sure that you have all of that data, all of that information you need, and then you can just start going after it so much easier, and action is so much easier.
Paul M. Caffrey (33:07.603)
Cool makes total sense. Preparation key, do the work and get yourself set up for success. I like it.
Rob Halligan (33:14.27)
Unfortunately, nothing new that people don't know. It's kind of the obvious stuff, right? That's why people keep saying them. They tend to work.
Paul M. Caffrey (33:20.451)
Yeah. Well, look, it's what works. Rob, what's your number one sales tip?
Rob Halligan (33:28.903)
I had a manager in Salesforce once who was talking to me about one of his managers, who's a very well-regarded salesperson there and commercial leader. And he said, he had a funny saying for me, he said, he has a neck like a jockey's bollocks. Basically, like, he will ask, he has no problem asking the tough questions and sticking his neck out.
And what he was getting at and the lesson that he was teaching was like, do not be afraid to ask for the deal. If you've done your job, if you've put in the effort, the work you've run your sales cadence, you've run the sales process effectively and correctly.
then the client or the prospective client should have been given everything that they need. They should have all of their questions answered and they should be well aware that they are in a sales process. Obviously that's tracking towards a date where you're going to close it out. Obviously when you get close to that date, things can get a little bit jumpy with clients and you know, you're, you're wondering whether or not you're going to get it over the line or not. If you've done your job, you've earned the right to ask for that deal essentially to say, look,
we've worked through this sales process. You know, the plan was working towards this sign off day. We've answered all of your questions. We've ticked all of your boxes essentially, you know, can we get this done? You know, and I think salespeople, and I was one of them as well, and I fell victim to it. Sometimes you shy away from the hard questions because there's a fear of losing a deal. And you don't want to push a client too hard because you're...
You forecasted a deal and in your head, you're already spending the commission and you're just scared of, you know, you know, ruffling feathers and pushing somebody out of the process. But if you've done your job correctly and you've managed that right, you've ever you've ran just like correctly, you've ever right to ask that for that deal. So I think salespeople need to have that confidence towards the end of that process to know that they can ask for that.
Paul M. Caffrey (35:31.507)
Yeah, I think that's a great piece of advice is not being, I mean, one way to look on it is shouldn't be afraid to ask for a deal, but you're just speaking to another person as well. Sometimes you might be speaking to a VP of this co-founder CXOVA is just another person. And as you say, if you've done your job, if you've understood their desired outcome, if you understand the negative impact it's going to have every day or for the longer that they don't actually go with your solution.
You can also use that as a way to reiterate and ask that question as well. So sometimes it doesn't have to be so direct, but it can, you know, call out that you're missing out on such and such. We're planning to go ahead on this date. It feels like that's not going to happen. You know, what's changed your side? And there's a hundred different ways you can ask it, but asking it because what's going to happen?
Rob Halligan (36:20.734)
Absolutely.
Paul M. Caffrey (36:23.451)
You'll just get to the end of the month, the end of the quarter, and you're just going to get those questions asked by, I guess, a aforementioned leader. And what are you going to say? I don't know, because I didn't ask. You know, that's not a good place to be.
Rob Halligan (36:30.647)
Yeah.
Yeah, absolutely. Yeah. No, there's a number of different ways asking the question. You don't have to be super direct with us, but nonetheless, salespeople need to know they, they deserve, they put in the work and they've, you know, they've earned the right for it. So are they should have at that stage?
So definitely not to be scared of it. And that's, you know, I went through that experience myself and you get to the end and you're just like, you know, you're worried about pushing the deal too hard, but you know, you're, you need to know what is it in or is it out right?
Paul M. Caffrey (37:05.231)
Makes sense. Absolutely. And I guess a question I typically ask people and I'll maybe ask you in a two prong way is number one is what's your number one promotion tip? But then I guess if you think about what that might be for someone working internally. But another question I'm going to try to watch as well is, you know, what tip or advice would you give maybe a sales professional who's considering?
stepping out and founding their own business as well.
Rob Halligan (37:37.45)
Yeah, so in terms of the first question first, I think play the game, right? If the term, when it comes to career progression.
your job, your, the job description and what you were hired for is really just the cost of entry, right? That's the expectation on a day-to-day basis of, of how you, what you need to do to maintain your job. But I think people need to realize if you want to move up, if you want to move up fast, and if you want to do well outside of just your number or your target.
There's a lot more that needs to be done. And that usually comes down to the extra effort. It's putting your hand up, asking for that extra work. It's the extracurriculars. And I wasn't always amazing at doing it myself in my time, because, you know, a lot of, and it's easy to just say, look, my focus is on my job because that, that can be hard enough, right? Especially when you're in sales and there's a target over your head that you're trying to chase down every month. Sometimes it can, you kind of have the blinders on and you're thinking, look,
I have a lot on my plate right now and you don't even think about the potential extra, you know, work that you could be doing. But when you look, if you think about thinking back to my career in, you know, Salesforce and looking at a lot of the people who have done really well and have moved on since then into leadership roles, maybe still in Salesforce or other country, other companies, a lot of those are the people who put their hand up and kind of did the extra bit, you know, and, and
put themselves sometimes in uncomfortable situations, in situations where they didn't feel super confident, but they thought for the better good. So I think, you know, if you're in that type of career and you wanna go far and you wanna do well, you do have to play the game. It's just, it's part and parcel with it. As you said, was,
Paul M. Caffrey (39:25.531)
Cool, I really like that.
So you're thinking of going from, let's say, being an account executive and taking that step to starting your own company. Any tips or advice you give someone.
Rob Halligan (39:40.794)
Yeah, yeah, probably need another podcast episode to go through it all to be honest, but it's, you know, to try and keep it as short and concise as possible. The obvious stuff first is imagine yourself doing that. Can you support yourself financially? What are your, you know, what priorities do you have outside of yourself, you know, from a financial perspective, you know, family mortgage or whatever it might be? How long can, if you were to...
to do it and step out, imagine yourself not earning a salary for six, 12, 24 months, you know, there's that potential there. And it's always more than it's always longer than you think it's going to be. So do you have the finances in place to allow you to do that? So that's kind of the obvious ones, right? So just to keep a roof over your head and food on the table type of stuff. And what outside of that is, look, something that you'll hear, you know,
constantly rattled off and because it's important and true is around validating the idea that you have or the problem that you're trying to go after. And it's all well and good to come up with what you think is a great idea and go and ask your mom or, you know, your brother or your sister, or, you know, your close friend, what they think. And they tell you, Oh, fantastic. Well done. That's a great idea.
And then you go off all confident and you're kind of going ho into trying to chase this, this idea down or this problem. Validation has to run broad and deep and it has to go far outside of your own social circle and really, really try and test your hypothesis. Is this something that actually has legs? And you'll find that it might not, it might, or it might have to change slightly, but
really, really make sure that you stress test what it is you want to do with a really broad and diverse group of people. And, you know, whether that's one-to-one interviews with strangers that you think could be, would fit the kind of demographic of your, you know, future customer profile surveys, whatever it might be going and speaking to people on the street, you really do need to actually put that, put in the legwork there to make sure of that.
Rob Halligan (41:59.718)
Um, the last thing you want to do is leave a comfortable job and quickly find out that this is not something that people will pay for. So make sure that work is done and plenty of it. And that's something that doesn't end, right? So you don't validate an idea and then go right time to build this company. And then, you know, it stops. The validation continues throughout the process longterm. So, um,
I think that's probably the two important areas. It's make sure that you can survive financially and actually, and manage this for a certain amount of time longer than you probably think you're gonna need. And then make sure that whatever that idea is that you're going after the problem you wanna tackle, make sure you've done the legwork, make sure you've done all of that heavy lifting on validating it.
Paul M. Caffrey (42:48.999)
Cool. That is really helpful. So I guess that'll give people good insight into it. And everybody thinks of the more glamorous side, but I mean, the reality of, you know, how long can you go until you, you know, start getting steady cash coming back in? That's a big change. Okay. And finally, before I let you go, I know you read a lot. What one book would you recommend people check out?
Rob Halligan (43:06.984)
Yeah.
Rob Halligan (43:17.938)
I recommend two if that's okay. One that's purely kind of more personal developments or more business related-ish would be Mindset by Karl Dweck, which is kind of all geared towards growth mindset. It's a really, really interesting book.
is relevant to anybody really, because you can think about your own situation and how your own brain works throughout as you're reading it. And you will recognise quite quickly how you think in certain situations and whether or not is that grow mindset or is it not. So that's a really interesting one. And then another one is less kind of business-y or personal development.
style is The Boys in the Boat, which is a true story. It's about the US Olympic rowing team during the Berlin Olympics back in the 40s. So it's a bit more about kind of overcoming challenges and adversity, but it's a fantastic book as well and definitely worth a read.
Paul M. Caffrey (44:22.775)
Excellent. I have not read either of those books. I look forward to checking them out. Rob, thanks so much for coming on and if people want to connect with you, find out a bit more about Pitch what's the best way for them to do that.
Rob Halligan (44:36.362)
Yeah, no worries, my pleasure. And yeah, absolutely love to chat to anybody, just even casual conversation or interest in what we're doing. Reach out to me on LinkedIn is the best place. So I check it regularly. So anyone who reaches out to me there, adds me there, happy to chat either on LinkedIn or set up a call, whatever suits.
Paul M. Caffrey (44:56.219)
Great, well once again, thanks very much, Rob Halligan.
Rob Halligan (44:59.466)
My pleasure, mate. Thank you.
