Raphael Tristao, Head of Strategic Accounts, HG Insights

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I’ve known Raph for a while, but I’ve never been quite sure what he does, outside of “global, high-level tech sales.” I took our interview as a chance to understand both his role, the tech industry in general and the man himself.

Raph has a strong balance between technical and personality-driven sales, as in his answers below, and he combines that with a mature view of long-cycle tech sales and the risk and rewards involved, and what’s needed to succeed at the most sophisticated high-end sales.

You can read Raph’s full biography here


Jamie: What have you found most fulfilling about your sales career thus far?

Raph: I like the goal-based element of it, that’s what keeps me driven. Money is always a good end result of that. The fact that I basically decide how much work I want to put into it, it’s simple math, what you put in is what you get out. So, you are completely in control of your own success. I think that’s the main thing for me.

Jamie: And is that equally true in your current role?

Raph: Yeah. Now more than ever. I’ve got this huge job opportunity where I’m growing extremely rapidly, we’re probably one of the fastest-growing sales companies out there, and the plan is to become even bigger. We have big aspirations.

Jamie: Your current role is global, is that something that you sought out or valued?

Raph: I’ve been in previous roles where it was restricted, I was selling to regional HQs of global companies, and it feels a bit restricted.

Sometimes, they may put rules and regulations around who you’re allowed to speak to or not, or the deal then gets passed to someone else, which is very frustrating; especially as a seller who’s putting a lot of time and effort to progress the deal. I definitely prefer a global role, to be able to really get embedded and penetrate across large global vendors. I

I’ll be calling Singapore and then the U.S or Australia on the same day, and I enjoy that part.

Jamie: What is the best thing about being in sales?


Everyone says “work hard, play hard.” I think it’s “work hard, get results, and then play hard.”

You reap the rewards, and you feel good about it. You have to know that you can be the best salesperson in the world, but if you’re only getting on one call a week, you’re not going to be successful. Being able to be in charge of your own success, and really drive your own business, and be responsible for your own book of business. That’s the way I look at it, and obviously, financial rewards are always a nice treat.

Jamie: What’s the worst thing about being in sales?

Raph: It doesn’t stop, so that can be a good thing. But let’s say, you have monthly or quarterly targets, what you did last month, on day one of the next month doesn’t matter, it’s out the window, you need to do it again. So it can be quite exhausting, and I’ve seen a lot of people burn out. A lot of people will take their foot off the gas once they’ve done a good number, a good result, myself included, and then you see that trickle-down in the later months, let’s say, two months sales cycle. It starts to hit you not that month, but a couple of months later, and then you are in the shit.

When you’re doing well, it is excellent, you get rewarded, and you get praised. When you’re not doing well, look at it as gambling. When you’re up, you’re up, and when you’re down, it doesn’t feel good. But that’s where you try to see people who are going to be successful or not. It’s what you do with that feeling of failure that decides whether or not you’re going to be a great salesperson.

Well, you didn’t do well this month, what are you going to do to smash it twice as much the next one? Versus some people get into their own heads and think, “Oh, I’m not doing it.” Then you get a little bit of self-pity and then a negative funk, and then just spirals downwards.

Jamie: How do you deal with that if you ever find yourself beginning a negative spiral?

Raph: I think having regular conversations with your teammates and being self-critical. We found that in my organisation, self-awareness and being able to break down what in the process isn’t working is important. It’s important to able to track certain things to see, well, okay, are you following the success patterns that you know work? Are you putting in enough time and enough activity to generate results and success? If you can look at yourself and be honest with yourself, rather than making excuses, and you can start to say, “Well, actually my input was not high enough for me to hit my number, that’s why I missed by a lot.”

There are things like what’s going on in the world now; I’ve had a slip from COVID-19, and that’s an exceptional case. But typically, it’s what you put in is what you get out. I think if you’ve got a good working environment, a good management team who are willing to work with you, always willing to break it down and see what you’re doing wrong and say, “Okay, we’ll work it out. Your problem is X, or you’ve missed this part of the process,” then you’ll be fine.

I actually did the same thing midway through last year. We did almost half our number in Q1, and then kept a few deals trickling in for five or six months; then I had to produce a very significant portion of my number at the end of the year. But my VP and I evaluated my deals and said, “Well look, here’s all that I did with the client let’s break it down. Let’s see what where you went wrong and then just analyse every step.” It’s also about them not giving you the answer, but them challenging you to try and figure it out yourself. Because ultimately, you can figure it out – you know the answers in the back your head but you just let bad habits get in the way – and it’s important to have that constant vigilance to not let those bad habits creep back in and get lazy and complacent.

Jamie: What sort of characteristics are you looking for in a good manager?

Raph: I think they need to lead by example for sure. I have a colleague who, if you ask anyone, he’s probably the best salesperson in our sector.

Our VP’s and Directors too, they’re always willing to lend time, they can be busy with all their own things, but they set thirty minutes with you, and they’re willing to give you their eyes and see where you’re going wrong or come up with the game plan.

Again, leading by example, putting in that work in, , right? You feel like that’s the biggest thing because you like start taking your foot off the gas or missing numbers, then you feel like you’re letting the team down not just yourself, and that’s a big motivator for me. I don’t want to let everyone else in the room who’s working hard down by underperforming myself. Those are the key things; building that culture, being willing to lend you their time and being good at the job themselves, and having that work ethic.

Jamie: What skills do you think that people should exhibit naturally to go into sales?

Raph: You need to have a natural curiosity. One of the biggest things is digging into the real reason why and what motivates someone to make a decision. Having that natural curiosity tends to be a very good trait, as well as being competitive and being money motivated. Having that drive, the ability to bring yourself out of any bad patches, that is massively important, because otherwise, you are on a spiral down, and that’s a recipe for failure.

Jamie: Do you think there are certain personality types which are more suited for sales?

Raph: I’d say that it’s a difficult one because the natural answer you want to go for is an extrovert, someone who’s willing to take some hits and is fine with rejection. Because you are a starting salesperson, you’re probably going to be doing a lot of outbound calls to people that might never have heard of your company, might never have heard of you, your brand, or your product.

I think you need to have thick skin; have that ability to take rejection well, have the ability to objection-handle and turn things around, and convince people. Having that ability, but following a process that works, and just do it until you make it. I’ve seen quite a few more technical people who have been brilliant, just because of their natural understanding of a sector and the products. But ultimately, it comes down to whether you can stay process-driven and whether you’re able to take a few knocks because it’s inevitable; those are very good qualities for a starting seller.

Jamie: Do you feel like that a more technical salesperson might not be as extroverted? Is that more to do with your industry, to do with more insight and data selling?

Raph: They could be. You could have someone who needs to have that more strategic mindset, be willing to know that client’s mind and have two-to-three-year sales cycles. It’s very strategic, and it’s very complex. It’s not like Wolf of Wall Street where they pick up the phone, they close the deal, and it’s £5k from your credit card. We’re talking about the clients who pay millions of dollars a year for our product. Ultimately, that’s the way you can have a more technical mindset. If you don’t have patience, it can shoot you in the foot a little bit.

If you’re more of a technical person, then definitely move more towards the complex approach and a complex sales cycle. Someone willing to help can analyse what their plan is, what the strategy is, rather than just working hard to do £5k deals.

Jamie: How did you choose a product that had the longest sales cycle? Was that a conscious decision?

Raph: I had been doing it in my previous role. I come from an “opener,” which was a business development role, outbound calling to people, setting meetings, and passing it on to my director. Then, that slowly transitioned into me taking part in more control of the sales cycle, then fostering it at the end and turning it into my own deals. I started and then actually took on the client success role as more of an account management role. After that, I went into full sales.

Because I worked with my boss previously, he said, “There’s a new company, will you join and be the first employee?” When he explained what it was, I had to jump at the opportunity, but it was a longer sales cycle.

But it’s one that I am comfortable with now, and I’m quite well-placed for it. I’ve got that unique mix. I am not extremely technical, but I have a very good understanding of how we impact our client’s business processes.

Jamie: As someone who wasn’t technical originally, how did you go about acquiring that technical knowledge?

Raph: You learn it through, again, repetition is the key. It’s all a number’s game, if you do something enough times, you’ll eventually pick up. You pick up tips, you pick up industry knowledge, and then you put that back into your future sales conversations. Then you can rely on that more technical knowledge as you start picking up. But honestly, I’ve been in this industry for six years, and over time you definitely pick it up. So if you don’t have a technical background or knowledge of the industry, it’s something that can be learned over time as long as you’re willing to learn, willing to put in the hours and repeat.

Jamie: What would you say is your biggest strength as a salesperson?

Raph: It’s a good question. I think I am quite process-oriented; I am good at following those processes. We don’t have a script, but we do have blueprints in terms of how we want things; what are the key questions that need to be asked? What are the answers that we need to know? What are the quantifiables and unquantifiables? What are the key success metrics from the client that they’re aiming for?

Then showing them how we can solve the challenges that stop them from attaining those goals and those metrics. I am quite good at sticking to the process. I think I am quite personable, but that’s just my opinion, honestly. I think that I’ve got a good amount of technical knowledge now having been in the industry for a long time. So I think it’s a bit of a combination of the three. That’s why I have a unique blend that makes me fairly good at what I do—process-driven, personable, and knowledgeable.

Jamie: What skills do you think are necessary for your industry and longer sales cycle insights that might not be necessary for other sales jobs?

Raph: I think the ability to be very organised, you need more structure, more ability to plan, and analyse situations to figure out the best route to a larger complex deal. I’m not saying that’s necessarily specific to my industry, it’s more about what’s specific to a more complex sales cycle, versus a more transactional sale.

It’s very different getting someone to sign off on a £5k deal, versus a £200k deal. But that money spent is going to help them achieve their yearly goals.

Time management planning and the ability to look at things critically and objectively once we’re caught up in something. The ability to take a step back. This is quite important for a lot of the videos that we work with or that I’d close. I think a lot of sales is transferable in across industries, you just need to spend the time to understand what the industry is. You don’t even necessarily need to have a good technical knowledge of your customer’s products per se, you need to have a general understanding of what you’re talking about. I don’t have very technical knowledge about how my customer’s products work, it’s more about what our intelligence can help them achieve with their own products.

If you are going into a transactional sales role and you are someone who just willing to pick up the phone a hundred times a day, that is great. I think everyone who says cold calling is dead is dead wrong, to be honest because it’s the biggest source for our deals.

People are just picking up and delivering a pitch that really resonates. Preparation is always key as well. If you don’t prepare, you are just shooting yourself in the foot.

Jamie: What sort of skills do you think that people need for both customer success and new business roles, and should they necessarily be separate in organisations?

Raph: You can have someone that is much more aligned to customer success and account management, than hunting, for sure. There are certain characteristics that make someone a really good at client success, managing clients on a day to day basis, building that relationship, versus hunter who has to be a bit more cutthroat with their time, a little bit more ruthless, and focused on what’s going to generate revenue for the business.

I say one thing that is important to grasp across the board is that communication is absolutely critical with any client. The biggest frustration that I’ve seen happen with clients is they tell you a need, and you don’t deliver it within the timeline, and they don’t have any visibility as to when it’s going to be delivered. Obviously, they’re going to be pissed off.

Whereas, I’ve had that conversation where we have had this issue in our own company, with our best team. It’s difficult to ingrain that in someone’s head versus when I used to do it, I didn’t have any technical knowledge. I was just really good at being on it, quick to reply, and keeping people up to date. I was for most of my clients’- their favourite account manager.

Jamie: Would you recommend your industry and the technical insight to any salesperson?

Raph: Yes. I think it’s really interesting the way that we can impact a client going to market in such a fundamental way. If you look at the clients that we have, and we have hundreds of clients, but we are working with literally 20 of the Top 20 Global biggest, most advanced vendors out there in the technology space. That tells us that we’re a critical component to their entire market strategy. We help them with everything from new market expansion plans, and what they are risking in that, by giving massive data-driven insights – how do we then plan to attack those markets in the market dynamics, helping them operationalise that data and make sure that sales and marketing are all aligned to really attack their market most effectively.

I think one thing that you’ll see is true for any company is how well can you execute a good market strategy that’s well-informed. That sends the right message to the right people at the right time and in the right market. To me, that’s the big thing because you see so many companies go out of business, they overextend in the wrong market. They attack an area that a very strong competitor is already doing really well in, and they’re not winning any businesses.

That’s the name of the game, right? The more that we can impact those decisions, it’s phenomenal to see clients telling us that we’ve helped them close extra business or change the way they go to market.

I’ll definitely recommend it for anyone even if you don’t have a technical background because I didn’t start with that technical background. I had a media communications degree, which had nothing to do with technology, IT, and insights. You pick it up at over time, and it is quite fulfilling, knowing that you would change the way all these global and multi-billion-dollar companies are going to get to market.

Jamie: Do you work for the market leader?

Raph: We are in our space. Lowell really can drive sales marketing strategy enlightenment through data sets that we can provide to companies that can do things in certain regions, and it becomes more of a tactical play. We want clients to say, “Oh, we had your insights. We would have purchased this company for $45 million. We can see it probably wasn’t the best move that we would’ve made.”

 Jamie: Is it important to you to work for a market leader?


I would say it’s very rewarding to work for a market leader having come from a company that was not, by any stretch of the imagination, the market leader. It’s rewarding when you see clients coming back and saying, “this has genuinely revolutionised our sales and market strategy.” It makes it that much nicer when you’re talking about, “Okay, let’s extend the partnership. Let’s grow it this way. Let’s help here.” It’s always a warm reception.

Jamie: From here on out, are you going to be very picky regarding the products you sell?

Raph: Yeah, I’d say so. I’m not going to be jumping the boat into any random company if I don’t believe in the product, the vision, and the strategy of the company. One of the things that sold me most about where I work now is the people on your side who said, “Look, this is what we’re trying to build. This is the vision, this is where we could get to, if we do it in the way that I know we can”.

Jamie: You mentioned the vision, what are the elements of culture make an organisation a great place for a salesperson to work?

Raph: Having that shared culture is really important. I think certain things can get messy. You all have down days and good days. I think it’s the difference between the ability to incentivise someone to drive through on those bad days versus reprimanding someone—that cultural ethic works, which is in Romans:14. Everyone’s driving towards the same goal, everyone believes in the company, the product, and the vision.

We’re humans, we like to be rewarded when we do good things, and we don’t like to be reprimanded when we’re not doing that. So I think having a good balance of incentives in place that can pull you out of the funk, if you’re having an off day, or if you just had a bad month, then really drive success.

The big companies before, the atmosphere was very silent, very isolated, people in different parts, and not having the same drive and motivation. Ultimately, that energy brings down everything as a whole. Now we are being very picky and very selective about who we hire, and ensuring that they fit in with our culture.

Jamie: If an aspiring salesperson wanted to get a job like yours, how do they go about getting it?

Raph: When you’ve been in the game as long as we have, you can smell the bullshit from far away. I was at a graduate day the other day and saw a bunch of people talking about why they want to be here and a presentation about why they want to be in sales, and there’s a few that we felt like their heart really wasn’t in it. We felt they were speaking about and saying the things that they had been coached to say. It transpires through your enthusiasm, through your body language, and everything.

I think if you really want to go into sales, the first reason you need to ask yourself is why. Then why again, it can’t be the money. Okay. Why? It is important to dig into the real motivators, maybe it’s you need to do it for your family, maybe it’s that you want to be the most successful person in your friendship group. Maybe you need it, or you want to, or you need to buy your first property by the age of 30. Whatever that is, you need to find your real motivator.

Because if you don’t know the real reason “Why?” that will come across to any senior salesperson that’s looking to hire someone. Just having the ability to understand; okay, where have you overcome adversity or negative situations? How did you do that? The ability to bounce back is extremely important in sales. Resilience is something that we would look for, for our company, at least, and probably a lot of companies would look at. “Where have you been successful? Where have you not, and how did you deal with that?”

Plus, you should have a generally competitive nature, not being afraid to interact with people. Ask questions, be inquisitive, all of these things are quite important, and I’d say this to any budding salesperson.

Everything starts with motivation, and that’s what’s going to drive you on a cold winter morning in London when it’s raining, and you have an hour or two-hour commute to just get out of bed, and you’re not feeling too well. What is going to motivate you to look at it and say, “I’m going to have a fucking great day at work, and just smash it,” That’s going to turn your whole mood around.

Jamie: What advice would you have for speaking to people at the highest level of business, the C-level, something that aspiring salespeople often struggle with?

Raph: I think if you’re actually having to pitch to C-level people, it’s important to talk about corporate goals – they won’t necessarily be program-driven or budget-driven. It’s not like speaking to a Marketing Directors who will say “Oh, here is £50k, I need to solve this problem.” It’s a C-level, it’s the CMO, and if he needs to solve a business problem, he’s going to be able to get to the CEO and say, “I need this amount to solve this problem, and it’s going to return X.” So, having a very value-driven discussion with those people rather than a feature or small-time benefit.

For example, “We can help you impact your marketing campaigns, or we can help you impact your bottom line by reducing effective processes and optimising your go to market. We can help you win the market share.” Those are the things that a C-level person is worried about. He doesn’t care about whether you can impact a marketing campaign or you can help us get a bit better on sales. It’s the big things that drive them like I need to hit a 30% gross profit this year. How am I going to do that? We can help them with that.

Jamie: If you had your sales career again, what would you do differently? 

Raph: I would take a few lessons. I have been definitely guilty of doing extremely well for a short stint and then getting complacent, taking my foot off the gas, and then dealing with the repercussions two to three months down the line and then having realised that too late.

I would say if I could go back and realise two things. I think one is never taking your foot off the gas, and always find motivation daily. Break it down by day, by the hour or even break it down by the client. What do you want to work on this specific day? That’s the game plan.

The second thing is as a new starter, if I were to offer one bit of advice that I’d give myself is to be okay with rejection, be okay with failure, and not spend above the necessary amount of time on each task.

If you spend fifteen minutes prepping every single call that you are going to make to a person, you are not going to get anywhere. You need to get the numbers up and repeat. Like I said, time and time again: you need to have conversations with people because what ended up happening is you spent fifteen minutes prepping perfect pitch this one guy, and he doesn’t pick up, then you’ve you just wasted fifteen minutes of your time, which could have been spent calling ten people, for example.

So not over-planning and not worrying about the minor details, especially around things like follow-ups, phone calls, if you’ve delivered a good pitch, it’s going to resonate with them, and they’re going to remember that. I’ve also fallen victim of my own perfectionism and that I’ll spend 45 minutes on a follow-up email making it spot on brilliant and then rock with what verses I could have probably done it in ten minutes, fifteen minutes, and had it 90 percent there. Don’t fret about the small details. Get the main stuff out, and realise that volume is the biggest thing.

Jamie: Tell me about a time when you didn’t make a sale that really stands out and that taught you something really valuable?

Raph:  I had a very big deal with a large technology vendor, and if we had secured it, it would have been a very significant portion of my client base. We were getting basically all the “yes'” from all the different parts of the organisation across their sales operations team, they were saying, “Yes, yes, this is amazing, this is what we need.” Then the final step was okay, “I want my marketing ops VP, I want my business intelligence team. I want the sales operations team, and I want a data analytics guy on the call.” Every single one of them has different issues, different goals, different motivators, and different levels of seniority.

Ultimately, it is impossible to tailor a pitch effectively with the right language, the right messaging, if you’re trying to accommodate for everyone. We passed every single stage, and I was committing that this deal was going to happen. Then, you know, the message that we were leading with this whole time just didn’t quite fit with the marketing ops person at all. By that point, you missed the message, you spend an hour on the phone with them, and if, after that, they’re not convinced, then it’s very hard to recover from that.

Separate your personas and separate the senior from the junior, because you need to talk a different language. So if you don’t have that, you’re going to end up sending a very mixed message trying to cater to everyone. It’s going to resonate with everyone but not really hit home as to why that person needs to make a decision right now.

One other thing that has affected deals in the past is getting an understanding of the size of the problem. If you don’t know if this is a $10,000 problem or a $10 million problem. If you’re going to sell something that’s $100k, they’ll be like, “Well, there’s no way I’m going to pay that to solve a $10k problem.” However, I might actually be impacting $10 million worth of their sales pipeline. So those are probably the two biggest takeaways.

Jamie:  Tell me about a specific time when you won a deal, and it showed off all the things you’ve learned throughout your career?

Raph: It was a very fast deal turnaround for a video that we closed within about a sixth of the usual sales cycle. I had a Sales Development Representative open the call, and he called the right contact at the right time with the right message.

The guy actually said when he got on the phone with me, “Well done to the Sales Development Representative because he called me from a number that I didn’t recognise, on the phone that I never usually pick up, at a time that I wouldn’t normally be on my phone. He delivered a very concise pitch that was spot on.” Then, again, sticking to the process of seismic challenge, I needed to find: what was the real motivator for them making the strategic change in their organisation? What was the impact that was going to make? Taking it down that path, to ensure that if I can prove that we can solve that challenge, we are in a position to do business as a six-figure deal in a twelve-day turn-around, compared to other deals that have been in the pipeline for a year? That was a pretty significant win, I have still got the celebration picture on my desk here, from me and my mate who opened the deal – I was pretty pleased about that one.




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