Ross Holliday – Spotlight Interview

by | Oct 1, 2024

Get to know Sales Director Ross Holliday! He talks spearheading Expert Thinking’s growing Sales function, becoming the best cloud consultancy – not by size, but by reputation – and the trends in cloud, AI and data worth knowing about. 


As co-founder Ben Fry said:

“Never, ever, ever underplay the importance of marketing and sales. You can have the strongest delivery capability, but if you have a poor sales and marketing function, you’re in trouble.”

You joined Expert Thinking as Sales Director a year ago to do exactly that. Can you tell us a little bit more about your role? 

I spearhead our sales function, and in close collaboration with marketing, the practice leads and customer success, I manage our direct customers, channel partners and software partners and bring new customers and partners on board. 

When I joined, the main goal was to mature our sales and marketing capabilities. Expert Thinking are brilliant. They’re an amazing company, but they weren’t great at telling people how good they are. So, I probably spent the first four or five months treating them a bit like a startup. Going right to back to basics: evaluating who we are and what we do. We now have a new website, new partner agreements, LinkedIn campaigns, etc. and it’s really paying off.  

Expert Thinking’s growing more than ever before. What do you think has contributed to that?  

I’d say three things have played a part in that. First of all, we’re better at telling people how good we are. So, we are now getting opportunities directly from the website, our network and from LinkedIn. Secondly, we have an extended partner network, which has brought exciting new opportunities and customer interactions. And thirdly, we have seen a big increase in recommendations from existing and past customers. 

On top of that, I would say that people are more confident in us. We have more visibility in the market and it’s obvious to people what we do and how we can help. We know what we’re good at and we don’t move outside of it. 

You’ve only been here a year, but you’ve accomplished a lot already. What’s one of your proudest achievements so far? 

There are probably a few, but I would say the fact that we’ve won 2 industry awards just this year alone and we’ve been shortlisted or finalists for another 6. We were also awarded AWS Advanced Partner, AWS Well-Architected Partner and AWS Ambassador status, which is massive. So, we’re really starting to see that recognition. 

And the recognition is great, because not only does it give customers confidence, internally it’s also brilliant because there’s a lot of hard work that goes into that.  

Expert Thinking’s mission is to be the best cloud consultancy, not by size, but by reputation. How do you ensure success? 

Two big things. Number one, we know what we do, and we don’t go outside it. So basically, we qualify really hard. We don’t pretend we can do something and just build the capability as it comes. Lots of competitors will say they can do it and hope for the best and put contractors in, we don’t do that.  

Secondly, the consultants who are on the presales calls with potential customers are usually the people who will also deliver the project. Bigger consultancies will often put their A team on the sales calls and their B team on the delivery. We don’t A/B team. And for customers, there’s nothing better than that. Our consultants understand the customers’ need from the get-go, and there are no communication issues with handovers. 

With that in mind, what would you advise someone looking to propel their career in tech consulting? 

Sales is about listening. People just don’t listen. There are a lot of people who think they know everything, and they don’t. They just reiterate stuff and ChatGPT made that really easy to do. Listen to your customer, understand their need, come up with a suitable solution.  

The other thing is, be a specialist in your field. There are a lot of people who sell everything. They sell hardware on one call, and on the next, they’re trying to sell a cloud migration strategy. We don’t do that. We understand what cloud is, and it’s all we do. 

Expert Thinking lives and breathes cloud. What’s one thing you wish people knew about cloud that they don’t?  

That cloud can be really expensive if you do it wrong. And when it’s done wrong, people start talking about going back to on-premise. But the problem isn’t the cloud, it’s the way you’ve gone about it.  

Cloud should change the way the business operates and help the business change, but for so long, it’s just been a lift and shift job. Taking data from the data centre, shoving it in the cloud and thinking you’ll save some money. 

A lot of businesses are now stuck in a hyperscale trap where, as they grow and expand, their cloud services are just getting more and more expensive and people make business cases to move back to on-premise, which is kind of crazy. 

It’s so important to make sure that everything’s right for what your business needs, not for what you think you need or what sounds fancy. That’s where we come in.  

Speaking of, what’s your biggest pet peeve in the tech industry? 

I’d say GenAI. We’re very early days. Assessing what it’s going to do, where it’s going to go, and it feels like everyone thinks that it’s about a year more mature than it is. It’s still very much in its early development stages. The bit that annoys me is when people say that GenAI has been around for 10 years. That it’s just machine learning. That’s not right. 

GenAI and Machine Learning are totally different. GenAI is a new revolution and it’s going to fundamentally change the way the world works. Don’t underestimate its impact. One thing GenAI will do is massively speed up everything. You’ll see startups evolve to full blown IPO unicorns in weeks. Older businesses or businesses that aren’t using its benefits will fall behind.  

At Expert Thinking, we get involved in the next level down: we work with customers on GenAI and what the use cases might be. We’re looking at a lot of data, data warehouses, data projects, and do data assessments, because the mature businesses understand that in the end this is going to come down to data. GenAI or large language models are great, but they mean nothing if the data’s not there, so we’re doing a lot of work with our customers in that space. 

What are some of the trends you’re seeing when companies want to get more out of their data? 

The first trend is making sure that their data is secure and compliant with what they’re meant to do, like GDPR and NIST, for example. That’s quite high on the agenda, because if you’re going to expose data to any form of AI interface, then you should make sure it’s compliant.  

The second trend is that a lot of data warehouses and data lakes have been built that aren’t in good shape. They’re on premise, they don’t really work very well, and they want to be moved to the cloud. 

Then the third one is related directly to Gen AI. In essence, it’s about making sure that what goes into whichever structure you’re going to put in place is clean and good data. 

Your journey with Expert Thinking didn’t actually start a year ago. It goes back a bit further. What made you join Expert Thinking? 

Basically, about seven years ago, Ben Fry, John Shortt and I were talking about Expert Thinking. But the time wasn’t right. And then just over a year ago, I was looking for a new challenge, a new kind of role. I was running a £40 million-pound global sales force, and that was fun, but I wasn’t involved with the customers, and that’s what I enjoy the most. So, I went back to Ben and John and told them it might be a good time to have another chat. Now, I get to do both, which is sell and work with customers, but also help grow a business, so it’s perfect! The timing was good.  

But it wasn’t just the timing. The biggest thing in sales is if you believe in what you sell, it’s so much easier to sell. There are so many salespeople out there that really don’t believe in what they’re really selling and just holding on and hoping for the best. But at Expert Thinking, you sell, and you know it’s going to be really good. It’s quite a technical sell. And the level of technical expertise we have here is unparalleled. We just get repeat business all the time, because we are really good at what we do and that makes the job a lot more enjoyable. 

Even though we’ve been around for seven years, it still feels like a startup, which is great. It’s fast-paced, everyone’s friendly, everyone wants us to succeed, and we’re continuing to grow. 

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