How to get your CEO to invest in HR software

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Over the past decade, the perception of HR has slowly been shifting, away from support function and cost-centre towards a strategic partner and value-driver. But that’s far from the case everywhere, especially among smaller and medium-sized organisations who are usually slower to adopt impact-driving new technology.

Often, HR leaders work hard to change the perception and credibility of HR – but are denied the resources and support to amplify impact. This can be a major barrier to earning a seat at the top table.

To have an impact on the workforce and organisation, HR must be equipped with the right technology to drive change. But securing investment for this technology can be an uphill struggle, especially where HR hasn’t yet earned their stripes as a strategic decision-maker.

This can turn into a vicious cycle where HR struggles to deliver results, so struggles to build credibility, so struggles to get sign-off for the investment to deliver results. And so on.

The problem is exacerbated by the often-underwhelming state of many organisations’ current HR software. When employees, managers, and other leaders have a poor perception of the current HR system, this reflects badly on the HR team.

At the same time, many organisations have tried to solve the problem by implementing new HR technology – but these projects often fail.

If the project team doesn’t truly understand what the business needs to meet future goals, they risk under- or over-speccing software that doesn’t drive value. Or, if the team does choose good software, internal problems with implementation (usually around misunderstanding the scope of work and not planning accordingly) can mean the project never builds momentum. Adoption falters and the software also then can’t deliver value.

This too becomes a vicious cycle, because HR then faces widespread scepticism and a lack of buy-in before they’ve even begun. This impacts HR’s ability to deliver, and the organisation gets pulled into an endless buying cycle that means projects aren’t completed and don’t achieve their goals. In that context, it’s often a challenge for HR to get sign off for the investment needed to move beyond basic, legacy software towards strategic HR solutions that have a transformative impact across the whole organisation.

This is where we come in.

We’ve helped hundreds of HR leaders steer successful HR and payroll tech implementations in organisations from 100 people to 1,500 people. We know what it takes to galvanise support, secure sign off, and build the foundation for a successful implementation that serves the organisation for years to come. We’ve distilled those lessons into a series of blogs, to help HR professionals build a cast-iron proposal for your chosen HR and payroll technology and vendor, to make that all-important ‘yes’ more likely.

(We’re focusing here on helping you get your business case signed off. If
you’re looking for more detailed guidance into functionality requirements,
read this eBook.)

In this article:

Getting the CEO on-side

In most mid-market organisations, the CEO will sign off big-ticket investments like this directly.

Ultimately, the organisation’s success (or otherwise) sits firmly on the CEO’s shoulders. This new software will impact the entire business and will likely herald some big changes into established ways of working.

Get the project right and the software can become a foundation for greater organisational capability, higher performance, sustained growth and, where relevant, happier shareholders. Get it wrong, and the CEO could face considerable scrutiny about the investment they approved.

So, high stakes. In that context, how do you get the CEO’s blessing to invest in the new software you believe the business needs?

Typically, the CEO will consider two interrelated aspects when making their decision:

  1. Your ‘official’ business case, which makes the argument for HR software within the context of the organisation’s strategic and tactical requirements
  2. Your personal credibility and currency as an internal buyer

Get both of these right and you’re much more likely to get the nod for investment. Let’s unpack both of those.

1. Build a compelling business case

Although this is a high-stakes investment, the CEO typically won’t be too concerned about specific functionality or have the bandwidth to be too heavily involved with the project. This might be one of several such projects happening across the business, and that’s on top of their business-as-usual workload.

That said, this process isn’t always bottom-up. Often HR does instigate it, usually triggered by some sort of pain or problem. But where there’s an important business need — which there should be, if you’re considering new software – it’s probably on your CEO’s radar already.

Either way, this request for investment shouldn’t come out of the blue. Building a business case is the process of formalising your argument for an approach to solving known issues. It’s not the process of highlighting emerging issues for the first time.

Let’s look at some of the factors you’ll need to think about.

Tell a strong story

The root of a compelling business case is a compelling story. What’s the problem? Why is it costly for the organisation? And how does your proposed software solve it? The CEO’s decision to release investment will hinge on whether they agree with the narrative you put together

“Just because we could introduce new software doesn’t mean we should. Why do we need to do this? What’s the benefit? How will people use it? If that case isn’t clear, we won’t invest yet.

“HR is so full of fads. I’m bombarded constantly with sales messages on LinkedIn. Our job is to filter out the noise, to make sure we’re identifying a real business need.”

Darren Vann, head of HR, Paultons Park

Here are some principles to consider:

Start from data

The data is everything. As an HR professional, you already have a good idea of the macro-trends happening across HR and people management. But you’ll need to move beyond the generic and theoretical to make a compelling case. Yes, Gartner says leadership and management development is the top global HR priority for 2024.

But that’s not enough. Rather, look to your own internal data to answer specific questions like:

  • Why is solving this problem a priority for your organisation?
  • What are – or aren’t – you doing at the moment?
  • How long has this been a problem?
  • How does your data compare to wider best practices or industry averages?
  • What are the consequences of solving this problem, short- and long-term?
  • What are the consequences of not solving this problem, short- and long-term?

Focus on organisational priorities (both short- and long-term)

When you make your case for new tech, frame your story against your organisation’s specific requirements. Go beyond the people priorities and put this in a wider context. Look at both immediate, tactical priorities, as well as medium-to-long-term strategic goals.

For example, not just “poor employee experience is contributing to churn”. But “poor employee experience is contributing to 27% churn – 17% over the industry average. If this continues we’ll struggle to meet this year’s expansion plans, which will threaten territory coverage. Projections suggest that’ll leave us 30% behind our sales revenue growth targets for the year. If this continues, we’ll struggle to scale our workforce to meet our target growth plan for future investment events.”

Show how you’ll measure success

To release budget, the CEO wants to feel as certain as possible that this project will be a success. To build certainty here, you need to know what success actually looks like. How will you know if the project has been successful? What will you measure?

Showing you’ve given considered thought to this aspect proves you’ve gone beyond pie-in-the-sky thinking. New technology is exciting. But beyond the excitement, have you given real, serious thought to what execution looks like?

“It’s only been more recently that HR and HR systems have been taken more seriously. Businesses often see HR as a support function, not fee earners. But your people are your biggest asset and your biggest cost: if you don’t understand them and can’t pull data about them, you’ve got a real problem.”

Katie Thompson, head of HR operations, Insight Investment

Incorporate broad perspectives

When you approach your CEO for investment, one of the first things they’ll likely do is talk to their senior leadership team. As Ciphr CEO, Sion Lewis, points out: “of course, business isn’t a democracy. But I’d still want broad consensus, to avoid widespread conflict. Be ready for robust conversations.”

To some extent, this introduces a ‘politics’ element. The CEO might have final sign off for investment, but theirs isn’t the only perspective that matters. Make sure when your CEO seeks input, other leaders aren’t blindsided but on side.

Before you take your case to the CEO, rally the support of other senior leaders to ensure this investment makes sense and is feasible, not just for HR but more widely. Has the CTO given their blessing from a tech perspective? And the CFO from a finance and risk perspective? And so on. Show how your proposed new software benefits other functions and helps solve their problems and/or contribute to their goals.

If your proposed investment seems like ‘just’ an HR priority, it’s likely to get sidelined for other investments, particularly in revenue-generating functions. Better people data has a positive impact across the business. It enables smarter data-driven decision-making that drives better outcomes at every level. Help leaders see this.

It’s through this process of collaboration that you’ll build the context you need to tell a compelling story to the CEO. Look back at the example above. You’d get that information because you’ve talked to sales and understand their challenges, targets, and priorities. That’s invaluable.

Don’t get hung up on format

If you haven’t put together a business case before, it’s natural to worry about what the CEO expects to see from you. Or even if you’ve done this lots of times, to feel uncertain about expectations for this organisation or CEO.

Don’t worry too much about format though. Business cases can look wildly different depending on your house style and CEO’s preferences. In some organisations, an email with bullet points might be brilliant. For others, the CEO might expect to dig into a 50-page PowerPoint deck.

Likewise, the actual process might (or might not) be spread over a few stages. You might present an early stage one-pager to float the idea and get the ok to assess the market. And, later, prepare a full business case that could need shareholder or investor approval.

Don’t wait until you’ve been through a time-consuming selection process and stressful pitch to the board to discover you’ve got the process or format wrong. Be clear about expectations from the start.

You’d also be smart to lean on colleagues in other departments who’ve recently made a successful case for similar-scale projects. Remember – they’re your colleagues, not your competitors. You’re all working towards the same goals (even if it doesn’t always feel like it)

Show you’ve conducted commercial due diligence

The CEO probably won’t want the same level of granular detail into vendor selection as other stakeholders. But they’ll almost certainly want some assurances that you’ve conducted appropriate commercial due diligence, to protect the business from bad investment decisions.

This overlaps with the next section we’ll dive into, about your personal credibility and currency. In many cases, the CEO cares less about the specifics of the vendor’s credentials as much as trusting that you care a lot about the vendor’s credentials.

Are you being swayed by snazzy sales brochures and good salespeople? The HR and payroll tech space has hundreds of providers, many of them with very good sales materials, processes, and people.

Are you looking past that to make a fair and balanced assessment of what software and vendor is the right choice for your organisation? The CEO wants to trust that you’re making good decisions.

2. Build your personal credibility and currency

You need to persuade the CEO that the business has painful issues and you’ve chosen a solution that can resolve them. But you also need to show that you are personally capable of delivering the project.

The reason you’re considering new technology is because it’ll be transformative for the organisation. The impact can be astronomical: careers are made on projects like this. But, at the same time, the adverse impact if the project doesn’t deliver value can also be huge.

Says Lewis: “It’s as much about you as the system. It’s a personal recommendation. It’s your personal brand at stake; your internal currency. How well this project goes determines whether you’ll ever get money for another.”

Your personal credibility as a buyer is critical to securing investment — and you personally will play an enormous role in ensuring the project’s success.

Here are some questions to consider.

Is your business case robust, credible, and pragmatic?

Your business case and your personal credibility are intimately connected. However informal your business’ internal pitching process might be, don’t be fooled into taking it lightly.

Make sure you’ve rigorously prepared and have considered as many questions, perspectives, and possible future scenarios as possible. Have you identified potential roadblocks or where a contingency budget might be needed, for example?

Will you own the project from end-to-end?

A worst-case scenario for most CEOs is someone who initiates this process then leaves it half-baked to someone else. The selection and purchase process is exciting – but implementation is where the magic happens.

“Lots of people start things they don’t finish, so the system winds up not quite integrated – not quite working as you thought,” says Lewis. “Ideally, the person buying the system should complete the project. It’s about taking ownership.”

Show you’re committed for the long-haul – or have a good backup plan if you can’t be. If you personally don’t have enough bandwidth to manage the project, could (or should) you hire a dedicated project manager?

Does the project have longevity beyond you?

While it’s important to show you can own the project implementation process, it’s also important that you’re not a gatekeeper. If nothing can happen without you, it creates risk.

That’s often how organisations get sucked into an endless buying cycle. Someone runs an implementation project but there’s not wider involvement and buy-in, so nobody else is up to speed. They leave for whatever reason and adoption quickly goes downhill. Then someone else comes in, and instantly thinks new software is needed because the old system isn’t working.

Show the CEO that you’re not (only) thinking of building your own career with a big-ticket project. You’re focused on long-term organisational health.

Do you have a realistic roll-out plan?

A successful tech implementation isn’t just about selecting the right solution for the business and navigating the purchase process. You can do all that right – but if you don’t get implementation spot on, the project will fail. And the CEO knows that.

You’ll need to show that you’ve given appropriate thought and consideration to the roll-out plan. It’s usually best to show how you’ll deliver incremental value fast and then scale. “When you’re building a system, don’t boil the ocean”, advises Lewis. “Just get it live and go from there.”

“A lot of HR teams have to implement HR and payroll software themselves, rather than with the business. It’s ridiculous. HR tech costs the same as other business systems, but usually doesn’t have anywhere near the same support. For implementation to work well, [the whole] business need to take the project seriously.”

Katie Thompson, head of HR operations, Insight Investment

What’s your internal currency as a strategic thinker?

Securing buy-in – and money – for a large-scale project like this is hard if you’re not already trusted as a strategic business partner. If you’ve never had strategic conversations at C-suite level about people issues and how they impact the business, you’re asking ‘blind’.

If that’s because you’re new to the organisation, share previous success stories to boost your credibility (if you’ve got them). Otherwise, lean on data and gather the support of other C-suite leaders who’ll vouch for you.

If you haven’t had the opportunity to build strong internal currency yet, you’ll need to work extra hard to ensure you tick all the other boxes. Or else the CEO might feel the project is too risky right now.

“Our team are strategic partners, because we have the data to help us to make a real impact for the business.”

Katie Thompson, head of HR operations, Insight Investment

Are you enthusiastic and tenacious?

“All other things being equal, being tenacious and enthusiastic can be the final nudge to getting approval,”, says Lewis. Your belief in the project should inspire confidence in your ability to execute.

(That’s not to underestimate the importance of being measured and pragmatic, though. Think through potential roadblocks and identify contingency budget. Enthusiasm and tenacity are great; over-enthusiasm and doggedness aren’t.)

For example, if you asked once and got a ‘no’, did you address the initial reservations thoroughly before you came back for another try? Do you genuinely believe this is the right decision for the business — and that doing nothing would be the wrong decision?

When you tick both of these boxes – a credible business case and personal credibility around your ability to deliver – it puts you in a great position for the CEO to agree to investment.

Ultimately, it means you’ve shown that the organisation faces a costly problem (more costly than inaction), that there’s a viable solution, and that you’re the right person to oversee the project to ensure success. And that the rest of the C-suite are on side too. That’s what the CEO needs from you.

Elevating HR: from support function to strategic partner

To achieve organisational success, HR must shift from a support function to a strategic partner. But smaller enterprises often struggle with technology adoption and investment. HR leaders face a vicious cycle of limited resources and outdated perceptions, setting back impactful change. To break this cycle, HR must build a compelling, data-driven business case aligned with organisational goals and secure CEO buy-in. This involves demonstrating clear benefits, gaining cross-functional support, and showcasing a realistic implementation plan. By doing so, HR can elevate its role, secure necessary investments, and drive long-term success for the organisation.

Download our full eBook on getting the C-suite on board with your HR and payroll software proposal to learn more, or book a meeting with one of our expert advisors today. Let's work together to drive meaningful, long-term success for your organisation.