14 September 2022

Expert Profile: David Pagliari - Digital Transformation Specialist

David Pagliari

In a career spanning 30+ years to date, David has held senior roles at Accenture, IBM, AMEX, AOL, TalkTalk, Microsoft, and a number of PE-backed start-ups. He’s been working as an independent consultant since 2019. 

Over a thought-provoking virtual coffee with the Choix team, David shared insights from the world of digital transformation, advice on how to build successful client / consultant partnerships, and tips for new career freelancers.

Let’s jump in with a whistle-stop career overview..!

OK! Well, my specialism is digital transformation - within product development, product management and digital marketing. I typically focus on B2C customer acquisition, retention and revenue management.

Most of my roles have been international in scope, and I’ve spent time in the US and worked extensively in Europe. Scale-wise, I’m as happy in a large corporate as I am in a start-up; and as an independent consultant, I try to bring a strategic brain, a keen eye for detail (I love joining the dots with data) and finally, a genuine obsession with, and passion for, the customer. 

It’s vital to understand customers, and I love talking to them in depth - as well as trying out the product myself and identifying opportunities to create more value. On which note, it always surprises me when companies distance themselves from listening directly to their customers - for example by routinely outsourcing to research agencies. You get so many great ideas from talking to customers directly!  

Why did you decide to start freelancing? 

I’d reached a point in my career where I’d worked for a lot of different companies in similar types of roles and I felt like I was getting deja vu! I wanted more flexibility and control - both to shape my career trajectory, and to do things that I knew I wouldn’t if I was permanently employed. On which note I’m (fingers crossed) off to hike at the Everest base camp at the end of September!!

Are there any downsides to being an independent consultant? 

Obviously there’s always an ideal scenario in your head - “this year I’ll work 9 months and take 3 off to travel” but contracts don’t always fall so neatly in line! You have to be adaptable and comfortable with ambiguity. It helps if you’re financially stable too, because contracts do fall through, and you may end up not working when you’d planned to be. 

Is there a typical context a client is in when they reach out to you - i.e. growth or turnaround? 

I’ve done pretty much everything, so I can operate smoothly in most contexts: strategy design; delivery; project management; turnaround crises, where benefit delivery is critical - you name it! I’ve had clients in both situations recently - a big turnaround piece for a firm that had really suffered during the pandemic; and a rapid-growth project where I was brought in to build out a whole new digital business & operating model. 

How do you decide to take on an engagement - what makes you say yes?

It’s pretty simple. I ask: can I add value? The last thing I want to do is waste a client's time and money because I don’t have the right capabilities. That’s a fast track to getting your reputation burned. If a project is in my sweet spot and I can get up to speed quickly, then it’s probably going to be a yes.   

When you’re in discussion about a permanent role, you tend to think more about long term career path, seniority, chemistry etc. In a 3-9 month engagement, it’s about delivering successfully on an objective for the client. 

You have to be prepared to work with a real range of people - there are those you really gel with, who are excellent at what they do, and that’s fantastic. Inevitably there will also be people who need help, and as a consultant, part of your job is to take them on that journey, to make them successful within the organisation - and that’s extremely satisfying too.  

What do you do at the beginning of an engagement - how do you set up for success? 

The most important thing is to agree on what success looks like. I ask that question straight off the bat. I play it back. I make sure I’m hyper-clear on what’s going to knock it out of the park for the client, and that we’re on the same page at the outset. Then I work backwards, put the plan together, and make sure I have agreed and signed off at a very early stage. 

Then it’s about strong, consistent communication. You need to be in lockstep with your client from the beginning. I believe in keeping people updated and making sure they stay focussed on priorities. It’s also vital that clients are aware of risks upfront and as they arise: this means they'll be much less likely to be blindsided by an issue and much more prepared to make the necessary decisions to mitigate a risk.

I stay close to my stakeholders at all times, and encourage full transparency around issues / concerns so that they can be nipped in the bud. 

How do you feel about remote working as a freelancer?  

I’ve worked remote, on site, hybrid… I’m happy with all permutations. I do think it helps to have at least some face-to-face contact, if possible - particularly at the beginning of an engagement. It really helps to build relationships. 

I was on a remote project recently where my client had a weekly bonding meeting. No business chat - it was all about weekend plans, other life stuff, dogs etc! It was a great initiative, because the social layer really matters and it’s easy to lose it when you’re remote. As a freelancer, I appreciated being included, it gave me a much more 3D feel for the people and helped to build solid working relationships. I felt welcomed - a genuine part of the team. 

People say most digital transformations fail - what’s your take on this? 

Digital transformation is obviously a vast terrain, but in terms of issues that I notice cropping up repeatedly, I’d say, firstly that having cost-saving as a sole motive can be a problem. If project emphasis is only on cutting spend, companies don’t necessarily put enough thought into how to create a really fantastic digital experience. 

The result is that customers fall into a void - the digital experience is average or it breaks down, but there’s no-one left at the end of the phone / skeleton staff and queues a mile long. This damages customer satisfaction and brand. I won’t name names, but I’ve definitely been on the receiving end of what’s clearly been a badly thought-through digital transformation initiative, with a pure cost-cut agenda! 

Then there are companies who’ve gone overboard, tried to digitise everything at the same time and ended up with a load of holes. 

I think it’s strategically more sensible to approach digital transformation from a growth perspective. To ask how do we use digital to a) make an experience better and b) open up new revenue streams? Digital is BAU for customers now - they expect a great experience. Thinking from a growth perspective means you’ll give more attention to making that experience great vs average, and you’ll differentiate yourself in the market. At the same time, cost reduction will come naturally.

(I think it's also important to note here: when I talk to my teenage children and their friends, there seems to be quite a lot of anti-digital sentiment brewing, especially with regards to data privacy and social media impacts on mental health; and the fact that there are many people - often more vulnerable members of society - who don’t have access the digital world. We need to create strategies that addresses these issues effectively.)

Are there any other mistakes you see companies making?

I’ve seen clients spend far too much on digital transformation, because they’ve brought in an expensive consultancy to advise on the obvious, rather than investing in the digitisation capabilities (usually engineering and design resource) that the organisation lacks. 

There are a lot of top quality digital specialists in the market now - people who have delivered real, lasting change in multiple contexts and industries and know how to facilitate that change, from within. I think clients can often achieve their objectives more quickly, and more cost-effectively, by going down the interim expert route.

Also, it’s an obvious one, but sometimes it’s simply the case that the wrong people are leading major initiatives. You can end up losing a couple of years because a strategy hasn’t been thought-through properly, then when you come to execute, it doesn’t work, is significantly delayed, or there's an unexpected bill shock. I think stress-testing a strategy with external expertise is always good value for money, even if you’re looking for peace of mind that you’re making the right call on big decisions.

Finally, clients often overestimate project benefits in order to secure the investment they need. This invariably ends up in a vicious cycle of over-promising and under-delivering. In most cases it’s much better to be realistic about the benefits - it builds confidence and trust in the long term. Of course I understand that people want to be optimistic - it creates excitement and buy in - but there’s a balance to be found. 

As a consultant, I’ll sometimes need to reset a project if the benefits are misaligned. This can be a really difficult conversation. You can give the bad news in one go, or you can drip-feed, it depends on the scenario, but it’s part of the job to be objective and pragmatic. On the other hand I always look for as many opportunities for push and stretch as possible, to ensure maximum value creation. 

What advice would you give to clients in terms of building a successful working relationship with freelancers?

Make sure you know and agree on what success looks like. Do this as soon as possible. Make sure you have strong communication processes set up from the off, and stay in constant contact around issues and progress. As a client, you need to get on top of issues super-fast or you won’t get value for money from your interim freelancer.

Make sure your freelancers feel part of the client-team decision-making throughout. Again, you’ll get more value if your freelancers understand the decision-making context. Give some real thought to how you do this, it’s vital but often overlooked. 

Make the most of your freelancer’s fresh pair of eyes. Someone with experience across different industries and companies will see things you can’t - I mean beyond the scope of the project. As a consultant I’ll always proactively flag things that I’ve noticed / ideas I’ve had for a client that go beyond my remit. This is almost always extremely well received and on many occasions has led to further improvements for a client. But I’m very rarely asked. So clients, actively open a space for discussion here, invite your freelancer’s POV and insights while you can!

And finally... what advice would you give to freelancers who are starting out? 

Keep moving into new markets / areas. This is so important - it’s a massive risk to do the same thing over and over again as whole disciplines can become redundant. I’m always asking myself: what are the growth areas? what are the new trends? what’s going to be hot in the market? Identify these things and double down on the learning you need to do to move into them. 

Keep up-skilling yourself. As a freelance consultant you’re going to be someone who can pick up and run with things quickly - you can adapt and learn as you go. You’ll do this naturally on a contract, but it’s important to make this a continual process - i.e. when you’re between contracts as well. If you’re continually up-skilling, you’ll be in a really strong position - and it’s pretty straightforward  because you can learn SO MUCH online (it was considerably slower and harder in the analogue world!) 

Work in different industries. It means you have a really diverse perspective to leverage. You can apply learning from other contexts, spot gaps more easily, and often drive more creative solutions. 

Finally, be your own CEO. You need to push the agenda. Don’t be a victim or quick to blame if things aren’t working out. I’ve seen a lot of people doing that over the years and it’s not constructive. Take responsibility, take ownership, be accountable - you’ll drive benefits with far greater success. 


I think it’s strategically more sensible to approach digital transformation from a growth perspective. To ask: how do we use digital to a) improve customer experience, and b) open up new revenue streams?