Xero Insider: Steph's playbook for fearless payroll migration and tech-powered growth

The cosy comfort of spreadsheets

Spreadsheets are the office equivalent of a well‑worn cardigan, reliable, familiar and almost impossible to throw away. More than one billion people open Excel or Google Sheets each month according to Microsoft, and 54 percent of small‑business owners still use them to track customers, quotes or inventory. In the very earliest phase of a venture, a single worksheet can indeed feel adequate. Columns labelled Name, Email, Status and Next step look deceptively like a miniature sales pipeline.

At Yopla we greet this DIY spirit with genuine respect. We started exactly the same way, capturing early enquiries in a colour‑coded sheet, adding comments in hidden columns and emailing each other attachment updates. It worked, until it did not. As activity grew past a few dozen deals, the brittle nature of the file became painfully obvious.

See our primer on digital transformation strategy for guidance on recognising other tools that quietly outgrow their usefulness.

The spreadsheet temptation checklist

Even this table hints at why convenience can morph into chaos. Those costs remain hidden while the dataset is tiny, then compound aggressively.

Spreadsheet mayhem in full colour

If you recognise any of the following scenes, your organisation has probably outgrown the grid.

The version‑control hydra

The folder contains Clients Q4 FINAL.xlsx, Clients Q4 FINAL v2.xlsx and, infamously, Clients Q4 FINAL v2 REAL FINAL.xlsx. Nobody is sure which document drives Monday’s forecast meeting. Two colleagues edit different files over the weekend, reconciling them on Monday burns an hour and several brain cells.

A 2024 Harvard Business Review survey found that sales teams lose 12 percent of weekly selling time to manual data reconciliation. That is one working day every fortnight spent wrangling spreadsheets rather than winning revenue.

Collaborative carnage

Google Sheets allows concurrent editing, but throw five eager representatives into the same workbook and carnage ensues. Someone sorts a single column, misaligning rows. Another applies a global filter, hiding half the pipeline. Audit trails exist, yet untangling the mess is slower than dealing with the client who just called twice.

Human error roulette

Consultancy PwC estimates that 90 percent of spreadsheets contain non‑trivial errors. JPMorgan’s infamous London Whale trading scandal, which racked up a USD 6 billion loss, partly stemmed from faulty copy‑pasted formulas. Your firm may never flirt with that scale of catastrophe, but one misplaced decimal in a quote can still scupper a deal and tarnish credibility.

The reporting black hole

Management requests “conversion rate by channel for the last three quarters”. The answer involves exporting CSVs, building pivot tables and manually stitching graphs. By the time the slide deck is ready, numbers are already stale. Data‑driven decision‑making becomes wishful thinking.

Zero automation, zero reminders

Spreadsheets do not nudge reps that a follow‑up email is due, cannot trigger a task when a proposal goes unanswered for seven days, and do not consolidate activities across multiple communication channels. Reliance on personal calendars invites inconsistency.

Fragility and security gaps

One corrupted file, synchronisation glitch or unexpected ransomware incident and the entire “CRM” disappears. Backups help, but multiplying unsecured copies multiplies risk. Data protection regulators have grown less forgiving about casual handling of personally identifiable information.

For more on mitigating operational risk, explore our article on sustainable AI which covers governance principles equally relevant to data tooling.

The economics of stagnation

Hidden spreadsheet costs manifest in three broad buckets:

1. Labour drag: Manual updates, duplicate entry and error correction steal time from quota‑carrying activities. A Yopla benchmarking exercise across twelve B2B clients showed reps shackled to Excel spent 22 percent less time in live customer conversations compared with peers on modern CRMs.
2. Missed revenue: Delayed follow‑ups and opaque pipeline health translate into lost deals. Even a five‑percent slip in win rate can dwarf the licence fee of any commercial platform.
3. Poor intelligence: Decisions rely on anecdote rather than analytics. Forecasts become sandcastles, impressive at first glance yet easily washed away.

Gartner quantifies the opportunity cost succinctly in its 2025 Sales Technology Guide, noting that organisations deploying mature CRM workflows capture up to twenty per cent higher customer lifetime value versus spreadsheet stalwarts. Access the full report here.

‍A migration that rewired my career

Before Yopla existed I ran finance at a different start-up and resolved to ditch FreshBooks for Xero. I devoured both Xero and Payroll certifications over one weekend, migrated the ledgers myself and discovered a truth that still fuels my work today, finance teams can and should own their data. Costs shrank, insights ballooned and the confidence I gained later shaped Yopla’s people-first framework for change, explored in our post on investment in technology for growth.

The email that rearranged my week

In spring 2025 Xero’s global research team sent me a survey on payroll-switch pain points. My answers, grounded in dozens of client migrations, earned an invite to their London HQ. Five accountancy practices and one digital-first consultancy would unpack why businesses fear change and how Xero might remove friction.

First impressions: espresso, skyline, purpose

I checked in through a secure glass booth, swapped the heat of Bishopsgate for air-conditioned calm and accepted a flat white from an in-house barista. No glossy tour, just a boardroom with panoramic views, a whiteboard and one instruction, help us name the rocks that block progress. The absence of corporate theatre set an honest tone that lasted all day.

Inside the panel: cost is noise, fear is signal

Most invitees resell Xero yet still run payroll on legacy apps. Price dominated their vocabulary, yet the subscription delta between Xero, QuickBooks and Sage is negligible. What truly paralyses teams is the fear of mis-paying staff and the drag of re-keying historic data. My own migration taught me that the first live pay run is the emotional cliff edge, get that right and adoption soars.

The wizard on the horizon: automated payroll migration

Xero’s product lead lifted the lid on a new migration wizard that parses HMRC filings, ingests employee records, leave balances and statutory history, then guides users through a reconciliation checklist before the first pay run fires. The prototype echoes steps published in Xero Central’s guidance on preparing payroll changes   and its migration-filing tool for reporting previous payroll data  . For Yopla, the wizard promises smaller risk windows and tighter timelines, for finance teams it converts midnight spreadsheets into routine clicks.

Planday and the single source of truth

The room then pivoted to Planday from Xero, a workforce-management platform that will soon feed approved hours straight into payroll, unifying scheduling, time capture and wage calculation   . We see the same theme in many transformation projects, when people data flows without manual hops, managers trade guesswork for margin control. Our article on digital transformation and the journey to net zero shows how integrated data streams accelerate sustainability gains too.

HubSpot + Xero: lessons from the alpha trenches

Two years ago HubSpot asked Yopla to co-pilot its native Xero connector. We mapped fields, stress-tested VAT, insisted on two-way tax handling and helped push the project from alpha to the current public beta  . What still excites me is the untapped potential, payroll contacts are relationship gold. Sync that data back into HubSpot and HR, sales and finance finally share one narrative spine.

Why many accountants still resist the cloud

Legacy billing models reward manual intervention, automation compresses hours and feels like a revenue threat. That tension surfaced repeatedly during the panel. The irony, of course, is that time saved on data entry can fund higher-value advisory work. Our guide to the return on investment from digital transformation walks through the maths that proves it.

Yopla’s seven-step blueprint for fearless change

1  Map reality with ruthless honesty

Shadow every spreadsheet and email thread until the hidden process map emerges.

2  Quantify pain

Translate manual steps into hours, errors and opportunity cost. Numbers secure budget.

3  Visualise the destination

Swim-lane diagrams of lead-to-ledger flows turn risk into solvable design.

4  Select tech on fit, not fashion

Small licence deltas never outweigh lifecycle ROI.

5  Prototype and iterate

Sandboxes crumble resistance faster than slide decks.

6  Automate migration

Leverage Xero’s conversion tools today and its payroll wizard tomorrow.

7  Embed continuous improvement

A living knowledge base keeps the lessons visible and the wins sustainable  .

Five provocations for finance leaders

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Inside Xero’s research culture

Every external delegate was paired with an internal specialist, UX, data science or engineering. Instead of nodding politely they probed assumptions, photographed every sticky note and promised to share updates. Vendors that listen like that build roadmaps worth betting on.

How Yopla converts insight into advantage

Our services span strategy, build and optimisation:

• Vision and roadmap – horizon scanning aligns digital spend with long-term strategy.
• Implementation – certified consultants configure Xero, HubSpot and Planday, delivering documented workflows rather than black-box magic.
• Continuous improvement – quarterly retros and analytics dashboards keep systems, people and climate goals in sync.

Clients who adopt this cadence report faster close cycles, clearer decisions and teams free from spreadsheet purgatory.

Practical steps you can start tomorrow

1  Run an internal “fear audit”, list every payroll scenario that scares the team, rank by likelihood and impact.

2  Book two half-days for Xero certification, competence dismantles anxiety.

3  Ask your Xero account manager for early access to the payroll wizard, influence beats waiting.

4  Pilot Planday with one department, real numbers trump vendor slides.

5  Activate the HubSpot connector in read-only mode, watch duplicate data disappear.

The road ahead

The next twelve months will see Xero launch its payroll migration wizard, deepen Planday integration and, I predict, extend the HubSpot connector to employee data. Waiting will not make that wave easier to surf, it will only widen the gap between pioneers and passengers. Courage costs nothing, hesitation taxes growth.

Ready to migrate from fear to momentum? Start the conversation with Yopla today

So, what exactly is a Learning Experience Platform? Think of it less like a rigid, top-down library and more like a personalised, on-demand streaming service for skills. It’s a digital tool that puts the user first, delivering training content that’s intuitive, engaging, and directly relevant to their individual growth and, crucially, your business goals.

Why Your Current Training Is Not Working

Many leaders pour significant resources into training systems, only to watch engagement flatline and see zero real impact on performance. If you’ve ever felt that sinking feeling of frustration, you are not alone. It’s a common symptom of a much deeper problem plaguing many organisations.

The real issue isn't a lack of content. It's the fundamental mismatch between how people actually learn and how most companies traditionally deliver training. This is one of the biggest challenges in aligning people with learning platforms.

The Limits of a One-Size-Fits-All Approach

Your traditional Learning Management System (LMS) was built for a different time. They are fantastic at administration, think efficiently pushing out mandatory compliance courses and ticking the boxes for completion. They are built around the organisation's need to document training, not the individual’s desire to actually develop skills that matter to them.

This top-down model often fails to connect with modern teams. It treats learning as a chore, a separate and often inconvenient event, rather than something woven into the fabric of the workday. The result? Abysmal adoption rates, forgotten logins, and training that feels more like a punishment than an opportunity.

True transformation starts with people, not platforms. The assumption that new technology alone will solve learning challenges is a critical misstep. Progress begins with understanding your team's real-world workflows and needs.

When a platform does not align with how your people actually get their jobs done, it just creates friction. It becomes another system to wrestle with, another password to remember, and another task on an already overflowing to-do list. This is precisely why so many well-intentioned training initiatives fall flat.

Before we dive into the solution, take a moment to see if any of these common pain points sound familiar.

Signs Your Learning Platform Is Underperforming

This table highlights common symptoms that indicate your learning and development approach isn't delivering the desired outcomes for your people or the organisation.

If you are nodding along to more than one of these points, it’s a clear sign that your current system is working against you, not for you.

Bridging the Critical Gap

The challenge isn’t about piling on more content or finding a fancier platform. It’s about closing the gap between your people and the learning process itself. To turn Learning and Development (L&D) from a cost centre into a strategic asset, we have to move away from rigid, administrative systems and embrace more dynamic, people-first solutions.

This is exactly where a Learning Experience Platform comes into its own. It’s designed from the ground up to fix this disconnect by:

• Meeting users where they are. An LXP integrates learning directly into their daily flow of work, making it accessible, timely, and relevant. This is the core benefit of engaging people where they already work.
• Personalising the journey. It curates content based on an individual’s role, existing skills, and career goals, not just what the organisation mandates.
• Fostering genuine engagement. It uses social features and a user-friendly, almost consumer-grade interface to create a more compelling and collaborative learning environment.

By putting the user experience front and centre, an LXP helps you move beyond merely tracking compliance. It empowers you to build a genuine culture of continuous learning, giving your team the tools and the autonomy they need to drive their own development. This approach doesn't just boost engagement. It builds a more agile, skilled, and capable workforce ready for whatever comes next.