The 3 Capabilities Every Digital-First Executive Needs

The pace of technological change can tempt leaders into chasing trends rather than charting a strategic path through the chaos. It’s understandable. But in a digital-first environment, clarity is everything. Without a figurative north star, initiatives risk becoming siloed experiments, rather than what they should be: enterprise-wide transformation. 
 
So what does that mean in practise? Well, a digital-first executive doesn’t just approve new systems or greenlight app development. They actually define how digital connects to business outcomes. Whether that’s accelerating customer growth, improving operational efficiency or expanding into new markets. This means aligning technology investment directly with specific, measurable goals – and constantly mapping your progress along the way.

Technology is not just an executional component, It’s integral to the strategy and the idea creation itself.

- Michael Titshall, CEO R/GA

Remember, strategy is only useful if your people understand it. And what it’s for. Executives need to reinforce this digital-first ethos at every single level of the business, so teams know why change is happening and (just as importantly) what’s in it for them. 

“That human element, that’s not going away any time soon,” Sarah says. “Being able to grow leaders who can translate tech into human terms, and really understand what this means for our employees, our customers – it’s important to get that shared language across the organisation.” 

“Don’t try to do everything at once, either,” Michael adds. “The biggest lesson is not to wait for a Big Bang Digital Transformation moment. Do those small incremental things, and be absolutely clear on what you want the outcome to be.” 

Overhyped bubble or not, the truth is that artificial intelligence is no longer optional. From predictive analytics in supply chains to generative AI in customer service, the future will consist of businesses that leverage AI, and ones that no longer exist.

But here’s the key point: the leaders who succeed aren’t those rushing to adopt AI for AI’s sake. They’re the ones integrating it with intent. Let’s not forget the recent MIT Media Lab/Project NANDA study, which found that 95% of investments in gen AI have (so far) produced zero returns.  
 
So what does intent look like? AI-savvy executives always ask: What problems can AI solve that deliver tangible value? They also build governance frameworks to ensure innovation is responsible and sustainable. They understand the risks of bias, privacy and security, and they make sure the appropriate safeguards are in place.

“Being really clear in terms of what you want the business outcome to be, how you want to connect your brand with customers, that’s absolutely critical,” Michael says. “There's so much hype and jargon around tech and AI, it’s easy to lose track of the result you actually want.” 

A good rule of thumb is that it’s always better to start with a use case, rather than the technology. In other words, don’t ask “How can we use AI?” Instead, ask, “Which challenges could AI help us tackle, and how will we measure its impact?” 

For us at Sharesies, we see AI as a really amazing opportunity in terms of personalisation at scale. We’ve built these really clean databases, so we can basically ask AI anything about our customers, and then feed those learnings back to them to make their experience more personal.

- Brooke Roberts, CEO & Co-founder Sharesies

Technology might be the enabler, but as Nigel Dalton from Thoughtworks taught us this week, people are still the differentiator. No digital strategy or AI tool will succeed without good teams and good talent. That’s why building agile, human-centered teams is (ironically) the third essential capability for tech-savvy executives in the digital era. 
 
A digital-first executive tries to foster a culture where experimentation is encouraged, failures are treated as learning opportunities, and cross-functional collaboration is just an ordinary day at the office. They recognize that agility isn’t just about speed; it’s about resilience and adaptability. Keeping people at the centre of transformation. 

“We have this saying at Sharesies,” Brooke says, “’Computers doing computer work, and humans doing human work.’ And that’s the most important part of tech at the end of the day; how we level up and help humans become even more human.” 

Sarah agrees. “Transformation is not about technology,” she says, “it’s about people. We know from experience that transformation tends to fail when people just talk tech, but it succeeds when you talk impact. And impact is typically felt at the human level.”  

The truth is, you should be investing in culture just as much as technology, because the latter is pretty useless without the former. Encourage cross-department collaboration so digital initiatives aren’t owned by IT alone. And prioritize the wellbeing of your staff. Digital transformation shouldn’t burn people out – it should empower them.

We did a survey of CTOs recently, and the majority of them say they wish they’d spent more money on the human side of digital transformation. The trick is not to get too caught up in the tech, and instead really think: what’s the impact of the tech?

- Sarah Rogers, Partner at Deloitte

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