Digital Transformation Strategy: A CIO's Guide to Lasting Change

By Sean Perry, Chief Information Officer at Kelly

In the 1940s, Kelly equipped receptionists with typewriters before sending them to client sites. This meant our employees could walk into an office on day one and start typing letters, preparing reports, and handling correspondence without delay. The client got value from hour one, and the receptionist felt competent and productive from the outset.

Nearly 80 years later, the technology looks different, but one aspect of our thinking hasn't changed: start with the experience you want to create, then build the tools that deliver it.

Still, most companies approach digital evolution backwards. Up to 70% of digital transformation initiatives fail to meet their objectives, often because organizations focus on implementing the latest and greatest tool rather than the concrete value it should create for end-users. Meanwhile, research shows that digital transformations focused on customer experience can boost satisfaction by 20–30% and deliver economic gains of 20–50%.

Rather than fall in love with the technology—the new platform, the AI capability, the latest system—you need to answer the fundamental question: who are you building this for, and what do they actually need? Amazon calls this 'Working Backwards'—start with the end customer experience and figure out how to deliver it. It may be a mix of technology and other tools, but focus on the experience, not the tech.

The Fedex moment: How transparency transforms customer experience.

Before FedEx revolutionized package tracking, you had no idea where your shipment was. You'd call customer service and they might tell you "it's on its way." Then FedEx showed us every single step—from warehouse to loading dock to delivery truck—and suddenly we couldn't imagine going back.

At first, customers probably would have said, "Yeah, it'd be nice to know where my package is." But once they experienced real visibility, the open rate on FedEx shipping notifications hit nearly 100%. Everyone wanted to know: where is it, and will it arrive when they said?

That's the power of transparency. FedEx showed customers the work happening on their behalf. That visibility built trust and engagement in a way that simply delivering packages never could. And research shows 71% of consumers are more likely to buy from brands they perceive as transparent and responsible in their practices.

This is where talent acquisition sits right now—in the pre-FedEx era. And at Kelly, we're working to change that.

Building digital experiences for clients, candidates, and internal teams.

Over the past few years, we've been rebuilding our technology around a simple idea: everyone involved in the hiring process deserves to know where they stand. That means creating distinct experiences for three different groups.

Client experience: Making invisible recruiting work visible through technology.

When a client works with us to fill a position, our recruiters do massive amounts of work behind the scenes. We might reach out to 300 candidates. Interview and screen 20 of them against specific requirements. Build short lists. Conduct multiple rounds of vetting. But traditionally, the client sees none of this. To them, a candidate just appears.

That lack of visibility creates two problems. First, clients don't understand the value we're delivering. Second, they can't engage in the process to help us find better candidates faster.

That's why we’re building Kelly Spark, a tool that will give clients real-time visibility into their talent acquisition.

Clients can see how many candidates we've screened, review profile characteristics of people on the short list, and weigh in on which candidates interest them most. When a client can say, "Yes, I like candidates one, three, and seven the most," that's incredibly helpful for our recruiters and fills jobs faster.

But we're also doing something else: putting our people front and center. I want clients to see their recruiter's face on the dashboard, not just a corporate logo. I want them to know that Bill has successfully placed five other people in similar roles in the past two weeks. Technology should create more opportunities for human connection, not fewer.

There's an old term I love: "digital exhaust." It refers to the data your processes naturally create while people do their jobs. In factories, it was sensor data. In our case, it's every CRM and applicant tracking activity. Our recruiters were already tracking this information—we just weren't sharing it in a way that created value for clients.

Candidate experience: Ending the recruiting black hole with mobile-first solutions.

On the talent side, people submit resumes, apply for jobs, and hear nothing. The black hole of recruiting is real, and it's gotten worse as bots started talking to other bots with nobody getting actual responses. Nearly 60% of job seekers cite lack of employer response as a top frustration in their job search.

Kelly Now, our mobile talent app, is our first step toward addressing this. Someone can apply for a job, complete full onboarding, and show up to work—all from their phone if they want to. They also get job alerts matched to their interests and can see opportunities as they become available.

This aligns with how candidates actually behave: around two-thirds of job applications are now submitted from mobile devices, and 86% of job seekers say they would use their phone to search for jobs. Yet only about 30% of employers offer mobile-friendly application processes. We're meeting candidates where they already are.

But we're not where we need to be yet. We still have work to do in giving candidates visibility into where they stand in the process, especially for roles that require more vetting.

When someone applies for a specialized position, they deserve to know: did we review their resume? Are they being considered? If not, why? That transparency exists on the client side through Kelly Spark, but building the same level of visibility for candidates is still on our roadmap.

Now, that doesn't mean every position should be filled through an app. For many roles, especially more specialized ones, somebody's going to talk to you. Somebody's going to have to convince you that this particular opportunity is right for you. No bot's going to do that. But for positions where speed matters and the candidate wants immediate action, we can deliver that experience.

And for all positions, candidates should know where they stand.

Employee experience: Internal technology that matches modern skills and expectations.

There's a trap that's easy to fall into when you're focused on digital evolution: you pour all your energy into customer-facing technology and ignore what your own people are using every day.

This is how you become the employer of last resort.

The hidden cost of outdated internal systems

You can hire people who've used current, capable systems at their previous jobs. They know what good technology feels like. Then you bring them into an environment running on legacy systems, hand them what feels like a chisel and stone tablet, and watch them get frustrated. That delta—between what they used to have and what you're giving them—is why you start losing your best people to companies with better internal tools.

Nearly 80% of employees report frustration with outdated technology at work, yet only about half of executives recognize this problem. In addition, 42% of employees say they're likely to leave a job due to insufficient or outdated technology. When your best people can go elsewhere and get modern tools that respect their time and skills, they will.

Research consistently shows that improving employees’ experience with technology directly improves both customer experience and revenue. When your team is fighting with outdated systems, they have less energy to focus on what matters—serving clients well.

Our internal evolution

We've got significant work ahead here. We're moving to Workday, and the capabilities that platform ships quarter over quarter are light years ahead of our current internal stack. Our users are moving from legacy systems to cutting-edge technology in one weekend.The challenge isn't the technology—it's getting people trained fast enough so they don't fall back into old habits like extracting data to Excel for pivot tables when they could just ask the AI to do it for them.

We also built Grace, our internal AI interface that now supports close to 5,000 users for about $700 a month in AI spend. But here's what we learned: Grace as a separate website was a good first step. Now we're working on embedding AI contextually into the actual tools people use—Bullhorn, Workday, our other platforms. Why should someone copy information from one system to another when AI could surface what they need right where they're already working?

3 digital transformation strategies every CIO should implement.

If you're leading technology change at your organization, here's what I'd focus on:

1. Plan for wild success, not just failure

We launched Kelly Now with what we thought was a manageable pilot. There was a small defect we knew about—something that created extra manual work on our end. We figured we'd fix it during the pilot phase before scaling.

Then the business saw the results. Kelly Now was radically successful. They wanted to scale immediately.

Suddenly we were chasing that defect for almost a year, manually handling cases while trying to solve a complex underlying problem that required coordination with our vendor. The wheels didn't fall off, but they wobbled quite a bit.

When you're testing something new, ask yourself: what happens if this works better than we hoped? What will break if we need to scale this by 10x next month? Because sometimes the best problem to have is still a problem that needs solving.

2. Don't neglect your internal technology

We've delivered some industry-recognized solutions—Helix and Helix Analytics for client visibility, Kelly Now for candidate experience, Grace for internal AI access. But if I'm being honest, we've got as much work to do internally as we do externally.

Your employees are your first customers. If they're struggling with outdated tools while your competitors offer modern systems, you'll lose talent to companies that respect their time and skills. And those departures will show up in what you deliver externally.

3. Never get comfortable

It's not in my DNA to feel satisfied. As soon as you get comfortable with where you are, you're going to watch the next company roll right past you.

Right now, we're working on contextual AI, learning from our acquisitions like Motion Recruitment (which had already implemented a modern tech stack with Workday, Bullhorn, and a connected CRM), and asking hard questions about whether the "Kelly Core" should change to accommodate more capable technology. Sometimes the smaller, newer company has already solved problems you're still wrestling with.

The question is always: what's next?

Your company is the technology you ship.

I’ll reiterate my main advice to other CIOs trying to evolve their technology: don't fall in love with the tech itself.

Yes, Gen AI is exciting. Yes, there are a dozen new platforms that promise to revolutionize your operations. But none of that matters if you don't know what experience you're trying to create for the people who interact with your business—whether they're customers, candidates, employees, or partners.

Figure that out first. Be specific about it. Then work backwards to the technology decisions.

Because right now, your company is the technology you ship. Make sure it's worth shipping.