E44: First in Region: Hard Won Lessons from Scaling Revenue in APAC with Gerard D’Onofrio

And I got on a plane with my manager to go fly to rural Iowa, which was a great experience. And we saw a couple of prospects there. And one notably where I kind of applied that mindset that we talked about before around asking what seemed like simple questions, but not overcomplicating it and just asking it. So we're in the room with this prospect. They were a tax provider and we're in the room with the CEO and 3 or 4 others. And we had the biggest contract in our company's history around the table. For them to sign. And on the plane going over there, actually, I was like, you know what? I'm leaving it all on the field. No stone gets unturned. I'm gonna ask some questions. We're gonna get on this plane going back and we're gonna know where we stand. So at the end of like an hour and a half meeting, I just straight up asked the CEO, what's gonna prevent you guys from signing this contract with Dialpad? I could feel my manager nearly falling out of his chair and I could feel the heat coming off of him in asking such a direct question to the CEO who we'd never met before. But look, the CEO said, really? If you guys go out of business? So basically not. We're ready to go.

Welcome to the High Performance Sales Leader Podcast. My guest today is Gerard D'Onofrio. He is the Managing Director of Asia Pacific at Dialpad, and I've invited him to have this conversation because he is one of the rare few people who came to Australia from the US as a country lead. He set up a business, and he has scaled it dramatically. Today, he runs teams across Australia, New Zealand, and Japan, and Dialpad is just growing in the region. So we are going to learn so much. Moreover, he's made President's Club repeatedly as a leader. And even before that, in the US with AdRoll, he was the number one sales rep worldwide. So we're in for an absolute treat. Gerard, thank you so much for joining me.

Thanks for having me, Pri. Thanks for the warm introduction.

Fantastic. Well, I have so many questions that I want to ask you, but most importantly, I guess let's jump in by saying you mentioned that you've had a bit of help with the genetic part with that. You've had your dad who was SVP of sales. So kick me off in terms of a bit of your background.

Yeah, it's kind of like being an athlete, right? You see a lot of professional athletes and their kids are natural athletes and you see all these juniors on certain teams. Yeah. So I've actually got a tweet twin brother. He's an enterprise sales rep in the US. My dad was a sales leader for his entire career in tech companies as well. So I don't think anybody naturally, most people don't naturally want to get into sales. It's not really a degree you get from university or college in the US, but that might be a little different for me. It's kind of all I know. It's kind of what I know growing up with my dad and my brother. So it's definitely a career that I think was on the horizon no matter what it came.

I love it. I've had other guests just talk about how we stand on the shoulders of others, influences that have helped us start stronger, faster, better. And your track record is so impressive. But let's start with some of the challenges as you got into your early sales career at AdRoll. What were some of the challenges that you experienced earlier?

Yeah, I mean, and just to rewind the clock, this was 2011, 2012 in San Francisco, obviously very fast-paced tech environment. Companies are growing really fast. It was my first closing role and it was very exciting. The company was hiring 10, 15+ salespeople a week and it was growing really fast and it was really an environment that You wanted to make a name for yourself, but it was difficult. And so I think one of the best ways to do it that I found is to really twofold. Number one, find a patch where there's not much traction so far, where others aren't really looking for. And secondly, be yourself. You know, I think sales is very human in nature and the best sales reps are themselves. And for me, that means having frank conversations. That means asking tough questions. It means asking questions to listen, not asking questions to be ready for your next question to be asked. And I think with that comes success. You know, I've always been one to think strategically about why is someone saying that as the answer? I don't think that that's correct. And instead of just parking it, saying it. And that's the hard part, right? You gotta make yourself uncomfortable from time to time. And, uh, if you can be yourself, look, some people are analytical, some people like to build relationships. I think I'm probably a combination of the two, but to some extent, I like to use those relationships to really, uh, help progress a deal and, uh, create a bit of friction at times, I guess.

Nice. What were some of the early wins that you mentioned about, you know, making a big difference in a team when they're hiring so many people? So what What did you do that got you your first break, so as to speak, or the first biggest break?

Yeah, I mean, again, this was 2012. I don't think we had a CRM of sorts at the time. It was very wild, wild west. So I found a couple of different strategies that helped me gain traction where others weren't. The first was actually calling into business outside of continental US. I actually called into Australia a lot. I think that's part of the reason why I'm over here today. I called into a lot of companies in Australia and gained some great traction there. But furthermore, there's a lot of businesses in the broader US and in any broader market that typically don't get called on. These could be, you know, these are companies not just in, not just on the coasts, right? Which I think, you know, in that time and even possibly now as a tech seller, you want to call into fast-moving tech companies because they know how to buy software and it might make your job easier. But I took a little bit of a different approach. I was calling into companies in the middle of the country and getting some good traction, building good relationships there. I mean, we talk about the best year that I had at Agrol was actually with a couple customers in Iowa. And I got on a plane with my manager to go fly to rural Iowa, which was a great experience. And we saw a couple of prospects there. And one notably where I kind of applied that mindset that we talked about before around asking what seemed like simple questions, but not overcomplicating it and just asking it. So we're in the room with this prospect, they were a tax provider, and we're in the room with the CEO and 3 or 4 others, and we had the biggest contract in our company's history around the table for them to sign. And I, on the plane going over there, actually, I was like, you know what? I'm leaving it all on the field. No stone gets unturned. I'm going to ask some questions. We're gonna get on this plane going back and we're gonna know where we stand. So at the end of like an hour and a half meeting, I just straight up asked the CEO, what's gonna prevent you guys from signing this contract with Dialpath? I, I could feel my manager nearly, nearly falling out of his chair and I could feel the heat coming off of him in asking such a direct question to the CEO who we've never met before. But look, the CEO said, really, if you guys go outta business. So basically not, we're ready to go. And it was a fun plane ride home. And we got the deal, largest deal in the company's history. And I don't think there's anything like specific that I do differently per se. I might be dumbing it down a little bit, but I think most salespeople know the things they need to do. It's just really pushing yourself to do it.

Yeah, I love that story. Thank you so much. I mean, that's the thing we as sellers play over and over in our heads. You know, you've— it's the last few seconds, you've scored the 3-pointer, you know, the crowd goes wild. And I can just see how, you know, after an hour and a half, just asking the real closing question, you can get someone to commit. And that's so interesting.

You got to do it. And it's not just closing questions too, right? It's every other— I mean, you talk to reps, you know, I manage a handful of people now, and I have reps come to me and they're like, oh man, I just ended that meeting. I really should have asked this. I really should have asked that. We're not perfect. Sales isn't perfection, but the more you can do it, the better you're going to be.

Moving forward, and I'm going to come back to discovery because I think that that is such an amazing skill that actually people are not very good at. So, I'll come back to that. Let's fast forward to your decision to take a country lead role and come out to Australia and what has happened since.

Yeah. Well, I actually, building on that success I talked about at AdRoll and calling into Australia, a couple years into my tenure there, I actually had the opportunity to come out to Australia for a 6-month stint and help open up the office for AdRoll then. Did a bunch of selling, hired our first 6, 7 to 10 people, and then went back. Absolutely. And went back to the US and kept selling and, you know, the rest is history. I loved that experience. It's very dynamic. You can do your core job, you could do a bunch of other things. You're doing interviews, you're going to conferences, you're meeting people, you're meeting partners. You know, I think I got ADD a little bit, so doing those sort of different things on a daily basis, like, really energizes me. Don't get me wrong, I love selling. It was an IC, love, care, just to book a business. But I think the ability, especially when you work for a company you love, And you really are bought into. You're bought into leadership. You're bought into the product vision. You're bought into the market fit. All of that. Naturally, I think a lot of people want to take more on, and they want to help scale the organization. So fast forward to 2020. I was already living in Australia. My wife's Australian, so I was already living out here, and I was at Salesforce as an IC. And the chief AI officer at Dialpad was my VP of sales that sent me out for Abrol, coincidentally enough. And he reached out to me and said, hey man, we're going to— we were going to send some people over to do what you did, but the borders are shut. Would you be interested? And immediately I said yes. I was the first sales rep hired, first person on the ground in June 2020. Fast forward 5 years later, We now have north of 20 employees across Australia and New Zealand. I've recently taken over the sales team of 5 in Japan. And yeah, the rest is history. It's just fun. You know, I sold for the first 10 months, carried my own target, hit my number, did well. And then the role really shifted to, you know, what is the growth and go-to-market opportunity for the broader region and what sort of roles do we need to attack that?

Incredible. I love it on so many counts. So, congratulations. I can see how that constant progression that's come out of the ethic and the resilience that you talked about earlier. So, that's really impressive.

Don't get me wrong, it's not easy. But I think just to add to that, I think what's interesting, you talk about earlier, you know a bunch of people that kind of do something similar to me, country manager, country lead, et cetera. I think what's helpful for me is being an American, but over in Australia, I think one of the problems that, and you probably see this all the time, Pri, speaking with businesses that are trying to grow in region, is they think Australia, perfect market for us. Similar economy, similar businesses. Let's just go do the exact same thing. We have seen success in America. Maybe Canada, they typically do EMEA second or third. Australia's usually the next cab off the rank. And they say, cool, let's just go hire 15, 20 people from day one, call it a day. But that's not the case. And so I think, you know, some of us that have lived and worked in other, in other countries, we're able to share that unique perspective. Like, hey, Australia's different. It may seem the same. It's even more different in New Zealand. Let's start small. Let's build relationships. Let's build a partner ecosystem, let's get close to our customers, and then we can scale up versus starting too big and then having to scale down. So I think I've talked to others that are in similar roles and they've lived and worked elsewhere, and I think that's a kind of a common trait, unfortunately, of US businesses that want to come over here. They just say, hey, cool, let's go launch in Australia and hire 20 people and hire a recruiter and call it a day and they'll 10x revenue in a couple of months. Not the case.

That is really good. So I'm gonna dig a little deeper into that. What are the top 3 things that a CEO, CRO of an early-stage company needs to know when it comes to the, when they think about Australia as a region to expand in?

Yeah, I mean, the first is relationships are always important in sales, but relationships in Australia, I think, are second to none. And that's not just who you know in the industry, who you're friends with. It's what is your name in the industry? Who uses you? What networks are you in? Where can you gain referrals? What is the partner channel community like? Have you built that community up? I mean, Australia's got 26 million people. The US has 330 million plus broken out across 50 states. I mean, California has the 5th largest GDP in the world, right? So it's night and day. You know, especially in Australia where the populations are for the most part centered in 2 large cities, and then you drill down even further into the particular industry that that vendor is in. Everybody for the most part knows everybody, and you gotta build those relationships early in order to gain good traction and gain good momentum. I would say the second piece that is also really important is your first couple of hires. need to be people that are used to very dynamic and ever-changing environments because they're not going to be well supported. They are going to have to do a lot of things on their own. They're going to have to introduce and create a lot of their own processes, and they're going to have to operate for the most part independently and figure out how to get stuff done. And so typically, at least from my experience, that starts with finding people And almost overstretching a little bit into the role that you're hiring them in because you wanna push them and give it an op— give them an opportunity to grow. Maybe it's someone from in industry, maybe not. But, you know, for example, if you're hiring a mid-market rep, maybe you hire someone that's been in SMB for a couple years who's kicked butt, has been in a small team, and is ready to take on a new challenge and doesn't make any excuses. The other thing is, is, you know, probably more of a technical standpoint. There's definitely nuances in, in the local market around how products can and can't work. I know very specific to our industry and, you unified communications and contact center. There's a lot of differences in how things work. I'm sure it's the same with any industry, whether it be security, et cetera. There's a lot of regulation in Australia, especially compared to the US and elsewhere.

Fantastic. And you've really outlined that really well around the market, the people, and the technology. And I guess, Those first 10 months as an individual contributor selling, how critical has that been for you in terms of being able to feed that information back and create an understanding and alignment? Because I know a lot of cases where it didn't work because there was a vital information gap.

Yeah. Well, it's around— it's a great question, Priyank. I mean, it's around feeding it back in 2 ways. It's around feeding it back to the people you hire, and then it's around feeding it back to headquarters. Now I'll start with the, with the, with the, with the first point first. As the first person in market, I think you need to be an end-to-end product expert. You need to be good at selling, but you really need to know the technical nuance of your product, especially if it is technical like Dialpad's product is and can be at times. And so one of the things that helped me in my first 2, 3 months was meeting with as many people in the US and elsewhere as possible to ensure I knew everything about cloud telephony and contact center. I knew nuance about the old models and the new models. I knew nuance about carriers and phones, et cetera, et cetera. That way I could answer questions on the spot with prospects without having to wait overnight for someone in the US to answer that question. I've then taken that feedback and given that to my team when I've hired them over time and say, hey, I need you to be a great seller like you've always been, But I need you to know a lot of the product over time, right? So month 3 to month 6, after month 6, you should really know the product inside and out because the best sellers, I think, should be as technical as possible without much reliance on SEs. And then to the second point, yeah, you gotta go out there and meet people, meet competitors, meet industry experts, and get as much information as you can to then feed that back to the executives in the business. If the competitor has been in market 5 longer, 5 years longer than you, go talk to them. They'll be, they'll, they'll be open to talking with you. If there's industry bodies, join them, go meet people. If you've got partners that are powering, you know, part of your technology in region, go meet them, go talk to them. You've got customers like we fortunately had before we opened up, go meet those customers. I got on a plane and met a bunch of customers my first couple of months and got some product feedback around what might or may not be different. And then you got to share that early and often with executives, and you got to make sure they're actually being held to account on any sort of changes as well. Because again, when you're one person, 2 people, 3 people, you know, it's very easy to get lost in the shuffle. So I would say persistence with executives is crucial from the start.

Absolutely. And I can see, you know, when I talk to people who've had successful experiences scaling in region, versus those who didn't for a number of things that you've just spoken about. And I think that this is critical both for US leadership as well as people in country manager, country lead roles to connect. And I cannot agree with you more that a technically competent seller is going to be a confident seller.

Yes, definitely.

Now, let's shift gears and I know that you're a big believer in that deals are won or lost in discovery. So, you know, what makes this phase so pivotal in today's sales cycles?

Yeah, for sure. I mean, I completely agree. I mean, discovery is where deals are truly won. I mean, of course, from time to time, there'll be deals that come down to price, but the best ones, I think, the most defensible ones, the most valuable ones are really won by understanding and amplifying pain. And discovery is the best place to understand and unpack that pain. If we can understand it and quantify it early and what the impact of that is on the business as well as the individuals involved, that's where you really build momentum. I think another piece that's important around discovery, especially in today's market, is deals are competitive. Deals are very competitive. Competitors you know and competitors you don't know. And I think we too often assume that our competitors are running great processes just because the deal is competitive. But the truth is, unfortunately or fortunately, whichever way you look at it, many sellers are average and that's totally fine. There's a place for average sellers. They'll do okay. They'll make money. Their businesses will grow. But I want our team to be different. I want the people that I lead to be different, and I want to lead from the front to show them how it's different. And so if that means introducing friction into a deal to challenge someone's assumptions or slowing a deal down to make sure that we're meeting with the right people, we gotta do it. They're not easy to do, but they make a lasting impact. You know, at the end of the day, I think great sellers are comfortable being uncomfortable. That's kind of a phrase that I learned from a friend of mine that's a professional runner. professional marathoner. And, you know, we see these guys running, right? And they're running insane clips for these races and their heads aren't moving most of the time. They look calm and collected, but they're in the pain cave. They're hurting. But they've put in the hard yards before into training. They know where their bodies can go. And so the analogy might seem a bit far stretched, but I think it's kind of the same with sales. You know, you build this muscle of discomfort. You know, and I think part of that is, you know, getting reps to do things before they're ready to do it, you know, and making small improvements over time. It's really what it comes down to. You improve, you know, I think it's Atomic Habits says you improve 1% every day, compound that, 37% over a year. Just little things day to day to get better.

I couldn't agree more with you. I think one of the most memorable things, one of my early-stage sales managers— I used to be an account exec and then a sales leader before being a recruiter— was that he said variations of, if you look after the numbers, the numbers will look after you. And basically, his focus was just make today your masterpiece. Be as good as you can at every step and every stage that you're going to work on today. If you are outbound, Make sure you're really good from your rapport building to questioning to closing. And the same goes for discovery. I think that people who stay in the comfort zone, the only way to cruise is downhill. So, yeah, look—

I'm going to use that. I haven't heard that before. I'm using that one for sure. I'm going to write it down.

Yeah, he got into my head. And I think that I ended up building a few more examples around that with my team when we're talking about being uncomfortable. So, yeah. Anyway, and now tell me, you know, in terms of the challenger mindset, I heard you say that. So, tell me more around how do you see that philosophy, you know, just pushing the boundaries with your team, pushing the boundaries with your customers to actually get the information that you need to help them and yourself make an informed decision?

Yeah. I mean, I think challenger and the principles around challenger selling really needs to be baked into Every customer conversation. If we go back to the point of discovery, just because the prospect surfaces a few issues, that doesn't necessarily mean those are the most important ones. We shouldn't accept them at face value, but instead we should dig deeper. You know, sometimes, you know, maybe 2 of the issues they called out are really just symptoms of a deeper issue that they didn't call out. And so we need to find out what that root cause is, even if it's not what the customer initially thought. I think that's even more important today and more relevant today to have that mindset, especially in this AI hype cycle that we're in where everyone wants AI in their tech stack. But I think few truly understand the business outcomes they want from it. They may tell you they understand, they may tell you what they think they want, but I think very few understand truly what they want. So I think it's our job as sellers to educate businesses to reframe and sometimes tell the customers what they think they need and what they do truly need. And what they think they need may not be the priority. And honestly, I think that's where we build credibility and where deals grow beyond features and turn into, I guess, a true partnership between the 2 orgs.

Yeah, that's very true. Tell me a little bit more about the SPICED framework from Winning by Design. You know, just walk me through it. And, you know, how does this help reps structure a high-impact discovery call?

I think one of the great things about SPICED is that it's very practical and complete, and it combines elements of, I don't know, MEDIC, SPIN, Challenger, etc., to where you, you've basically taken the best of, best of breed of all the methodologies. You got your situation, your problem, your impact, your critical event, and your decision. And so Putting that back into discovery, it's really a blueprint. It's a structure. It's not a script, but it's a blueprint of what you need to get out of that call to really drive that conversation. And I think when used, when used well, it really helps you move past surface-level issues and helps you dig deeper into what's really driving the buying journey. I think there's also great opportunities that are presented to sellers to build layered questions when following. in that methodology. They can really drill down, gain clarity on situations, and then hopefully the customer sees you as a consultant and not a vendor. And I've seen more often than not customers even coming back to us mid-cycle to say, hey, we're actually also looking at a new CRM, you know, what do you think is best? And then that's when you really build a good relationship with customers. And so I think SPICE really helps give us a blueprint For how to run a deal from start to finish. And even when broken down, can be used in every single conversation you have with a customer, whether it's a formal meeting or whether you pick up the phone to call somebody.

Right. So for those who don't know what SPICED is, what does that equate to? Tell me a little bit more.

Yeah, so it stands for situation. What's the situation the customer's in? You know, what vendors are they currently using? When's their contract up, et cetera, et cetera. What's their problem? What problem are they facing? Why are they looking to leave? How long has that been a problem for? What have they done to solve that problem? The impact, either the impact of the problem or what impact they're trying to have by upleveling what they're doing. It can be both, but it can be one of the two as well. What's the critical event? And that doesn't necessarily mean when is their contract up or when does our offer expire. It should be something a bit more tangible. When are they looking to actually make this change and why? You know, are they— do they plan on hiring 50 sellers before the end of the year and they need a communication system to help support those sellers so they can get more intelligence out of those conversations? And then what's their decision process? Who's involved? How do you procure? Who signs, et cetera?

Fantastic.

Yep.

And again, it just goes back to informed sellers are confident sellers, right? So, I think that You've talked about the power of difficult questions. A lot of people stay in the safety of relational bliss and don't take the chances that you talked about as an early rep, asking the CEO the question. So how does someone go from asking safe questions to difficult questions? And, you know, what are some of the steps that you'd coach someone on doing that?

Yeah, I mean, I think you hit the nail on the head. Asking uncomfortable questions or difficult questions is a skill set that separates good sellers from great ones. Um, we talked before, I think every seller has regrets at coming out of a meeting or thinking about a deal I wish I had just asked them X. Why didn't I just ask that one question? Right? Those are the moments that have really unlocked, would have really unlocked, you know, real insight or removed a hidden objection. And so I think, you know, that is critical, but it doesn't come easy. So I think that's where it takes a leader to really come in and understand what type of seller somebody is. You know, do they build relationships? Are they more analytical? Are they more transactional? You know, whatever it might be. And then you don't just tell them what to do and leave them off to their own devices. Like, you get involved, you get your hands dirty, you lead from the front. And does everyone need to be perfect at it? No. I mean, that's why myself and our frontline leaders, like, that's why we join calls. You don't have to do all of it. Let us do some of it for you. In fact, it might have more impact if it comes from a leader and you just need to quarterback the deal sometimes, get the right people in the room and let us come in and help you do it. And then, you know, over time you're working alongside someone for 6, 12, 18 months. They've seen you do it enough times and they've seen it work a couple of times, maybe a few times it hasn't, but they understand at least how to do it. Maybe they'll start doing it themselves.

Absolutely. I am a huge believer on, you know, the power of mentoring and standing on shoulders. I was very fortunate myself to start in a large sales team early in my career. So, I had great examples of the people that I wanted to be like, as well as the ones I didn't want to be like. So, I think that that's critical. Okay. Wrapping this up, this has been fascinating, and I could ask you questions for hours. But I think that you mentioned when we spoke about being relationship-driven versus being relationship dependent? Because I think the moment you say, oh, relationship, then people immediately say, oh, you're just too dependent on the person, not the process. So, give me a— how do you nuance that out with your experience over the years?

I think my answer might be a little bit frank or direct at times, but I think this is a really important topic. Being likable is table stakes. I can't think of an example where someone bought a piece of software from a vendor But they did it with angst because they hated the sales rep, but they just had to do it. Maybe that's happened. I don't know. I'm sure it has, but you gotta be likable.

That's—

but like I said, that's a table stake, but the relationship alone isn't gonna get you the deal. You have to use it to earn influence. And I think it starts obviously with building relationship, showing you understand their business, asking thoughtful questions. But again, that's the point of challenging. Being willing to challenge them when it matters most. You know, you can, you can run the first third of your sales cycle off relationship, but the two-thirds is not relationship. The two-thirds is taking it to the next level. You know, I share with my team all the time, being liked opens the door, being trusted keeps it open, but the influence that you have, the influence is what really moves the deal forward. And, you know, to the point of being blunt, like, we're not here to make friends. And I share that with my team as well too. I mean, you can make friends with your employee, with your coworkers, but we're really not here to make friends with buyers. Sometimes we do, and that's fantastic, but that's not the core part of the job. We're here to make a difference in their organization and we're here to hit targets. And, you know, a strong relationship can give you access and can give you honesty, but it's not just about building rapport. You gotta ask those questions. You gotta push for timelines. You gotta shape the decision criteria. And then again, you do truly become a trusted advisor, not just another vendor, again, setting you apart from the competition. And this requires trust as well as likability, but not just likability.

Thank you. That's really well articulated. I too believe that, you know, rapport with influence equals a relationship. You can have rapport with someone at a coffee shop or in the elevator, but until that influence can actually move things forward in the direction that you want, you don't actually have a real relationship.

Yep. The coffee conversation is a perfect example. You know, I think too often you hear people on your team like, oh yeah, I'm going to get coffee with so-and-so from X organization. And you're like, hey, well, make sure it's actually a sales meeting and you're not just buying them a latte and having a chat about what they did over the weekend. It's very easy to do that. Their guard's typically a little down when you're over coffee. So There's nuance, right? You don't wanna be too direct. You're over coffee. Face-to-face can be difficult for prospects or customers sometimes. So there's nuance in terms of how things are delivered, but that's a great opportunity to use that relationship to, you know, have more of a different conversation.

Absolutely. As a sales VP that I was a while back, one of the most important things I would look for in a CRM note in Salesforce that we used was, after the meeting, what are the next actions? Because it doesn't really matter if you've had coffee or not. It's what's going to happen after that meeting that will actually tell me whether you were just going out for coffee and lunches, or were you actually moving deals forward? So, yeah.

Exactly.

Gerard, this has been such a fantastic conversation because I think this is going to be so helpful to both people who want to be that country leader, build a business in the region, as well as those who are currently in the trenches and struggling at some stage, or CROs and CEOs who are thinking about expanding in regions. So I want to thank you for your time, your generosity, and your authenticity above all. Thank you for telling us your story. It's going to be so useful. Thank you.

I really appreciate the time, Preet. It's been a very enjoyable conversation, and hopefully someone gets something out of it. If not, Been great to chat, just me and you, kind of like, like a coffee conversation.

Fantastic. Thank you.