A note on who this is for. The piece is written for anyone navigating a Workday career, but it tends to land particularly with HRIS leaders for two reasons. First, the HRIS manager role is itself a fork in the road; the next move can be deeper into HR Tech leadership, sideways into consulting, or up into a broader IT or HR role, and the four paths below frame that choice cleanly. Second, every HRIS leader is also a hiring manager. Knowing which of these four paths your candidates have come from, and which one they are likely to want to move to next, is the most useful filter for building a team that stays together for more than eighteen months. Read it twice if it applies: once for yourself, once for your bench.

The four paths: end user (in-house, working for one company's HRIS team), consultancy (working for a partner firm that implements Workday for many clients), contracting (independent, project-to-project), and Workday itself (joining the vendor directly in sales, success, presales, product, or services). None of them is objectively better. Each makes a different set of trade-offs.

Path 1: End user

You work inside one company's HRIS team, managing and improving their Workday tenant. You build deep organisational knowledge over time. The path runs from analyst into functional or technical specialist, then lead, then product owner or platform architect, then director of HR Tech. Side paths into HR business roles, project or product management, or broader IT architecture are common.

Advantages: deep business context, full-cycle exposure from config to rollout, and a clear path into HR Tech leadership for the people who want it. You actually live with the consequences of your design decisions, which is a teacher no amount of consulting work replicates. Challenges: progression can be slow, often requiring a move to another organisation to advance. You see one Workday tenant in depth, not twenty in breadth. And if you are not proactive, it is easy to become a ticket-taker rather than a strategist.

Path 2: Consultancy

You work for a Workday partner or consulting firm. You jump from client to client, designing, configuring, and leading implementations. The path is well-defined. Functional or technical analyst to consultant to lead, then to delivery director, technical director, or partner. Side paths into solution engineering, account executive, or HR/finance consultancy on top of your technical expertise.

Advantages: rapid exposure to multiple industries and Workday configurations, clear growth paths, real budgets for professional development including soft skills, and a strong external network of clients and peers. Challenges: high pressure, fast turnarounds, work/life balance that varies a lot by firm and role, and at certain grades a shift into selling or people management that not everyone enjoys. You also rarely get to own long-term outcomes, since you roll off when the project ends.

Path 3: Contracting

You are independent. Project-to-project, choosing your own clients, setting your own rate, controlling your own schedule. The downside: you also handle your own admin, sales, billing, marketing, and tax. Most contractors go independent after three to five years of in-house or consulting experience and specialise sharply. Some stay solo. Others build small delivery teams or eventually boutique firms.

Advantages: maximum flexibility in location, hours, and clients. Often higher pay per hour or per project than permanent roles. You focus on delivery, not internal politics. Challenges: no guaranteed income between projects, no permanent team or home base, the overhead of running a business, and rarely being involved in long-term strategy or ownership. The flexibility is real. The price for it is real too.

Path 4: Workday

You join Workday directly. Either on the customer-facing side (Customer Success, Sales, Presales), in Product, or internally (Support, Delivery Ops, Enablement). Most people who join Workday HQ come from consulting firms, top-tier customers, or partner organisations. The path runs through customer success or presales into senior individual contributor or management tracks, eventually into director, country VP, or roles in the office of CHRO/CFO/CIO.

Advantages: exposure to how Workday actually works behind the scenes, access to roadmap discussions and early feature releases, strong internal mobility and a learning culture, and a working environment that is famously collaborative and people-focused. Challenges: tunnel vision (you only see Workday, not the broader HR or tech landscape), and depending on the role, you can feel distant from real customer realities. Many roles travel well to other SaaS vendors (SAP, Oracle, ServiceNow, Salesforce), so the path also opens doors outside the ecosystem.

“Most people in the Workday ecosystem fall into their next role by chance. The ones who navigate it deliberately tend to end up somewhere they actually wanted to be.”

How to think about which one fits

Three honest questions. First, do you want depth or breadth right now? End user gives you depth across one organisation. Consultancy and contracting give you breadth across many. Workday gives you depth on the product side. Neither is better, but you will be unhappy if you optimise for the wrong one this year.

Second, how much risk are you willing to carry personally? Permanent roles (end user, consultancy, Workday) carry corporate risk. Contracting carries personal financial risk in return for personal financial upside. Some people thrive on that. Some people find it draining within six months.

Third, what do you want to be known for in five years? A go-to expert on one module? A trusted advisor across many implementations? A senior product or success person inside Workday? Someone who built a small firm? The answer narrows the path quickly.

A personal note

My own career sat entirely inside consultancy until I started Incubane. I began as a data migration consultant. Shifted into functional consulting. Then led projects as a functional lead. Then ran full implementations including Extend builds. Then led a Workday practice and set up a global Extend CoE. Then started Incubane. Five distinct phases, all inside path two, ending in a sixth phase that is somewhere between path two and path three with a product layer on top.

Three things I learned along the way. You do not need to know your end game to get started. Every project teaches you something, especially the ones that are out of your comfort zone. And helping others grow is more rewarding than growing alone. None of those are profound. All of them turned out to matter more than I expected.

A short prompt for anyone reading this

If you have been in your current Workday role for more than two years and you have not deliberately compared the four paths in the last six months, you are probably overdue for the conversation. The ecosystem is changing fast (consolidation in consulting, agent-driven shifts in product, new boutique firms forming). The right move for the next two years is probably not a continuation of the last two.