Deputy vs When I Work: The Scheduling War Nobody Asked For (But Everyone Needs to Win)

You're staring at two tabs right now. One has Deputy's pricing page open, the other has When I Work. Your ops manager keeps sending you Slack messages about time theft. Your shift leads are complaining about scheduling conflicts. And your finance team just noticed overtime costs creeping up for the third straight month.

Sound familiar?

Here's the thing about the workforce management market in 2026: it's crowded, but it's not equal. Deputy and When I Work are the two names that keep surfacing in every buying committee conversation, yet they serve subtly different masters. One is a Swiss Army knife for complex, multi-location operations. The other is a nimble scalpel for teams that just need to stop living in spreadsheets.

The real tension here isn't feature count. It's complexity tolerance. How much horsepower do you actually need? How much are you willing to pay for capabilities you might not use until year two? And crucially — can your managers actually figure this thing out without a week of training?

The quick answer: If you run multi-site operations with complex labor laws, award interpretation, and compliance demands, Deputy is your tool. If you're a single-location SMB with straightforward scheduling needs and a tight budget, When I Work gives you 85% of the value at 60% of the cost. Either choice is defensible — but they're not interchangeable.

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Quick Comparison Table

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Feature-by-Feature Deep Dive

1. Shift Scheduling Core

Deputy approaches scheduling like a logistics problem — because for complex operations, it is one. The drag-and-drop schedule builder is fluid, but the real magic lives in the rules engine. You can set auto-scheduling rules based on sales forecasts, foot traffic data, seasonal patterns, and individual employee availability. Need to ensure no employee works more than six days straight? Deputy enforces that automatically. Cross-training rules? It'll factor in which employees are certified to work which positions.

The shift swapping and open shifts features feel mature. Employees can request swaps, pick up open shifts, and managers approve everything from their phone. The mobile experience mirrors the desktop version rather than feeling like a stripped-down afterthought.

When I Work does scheduling faster than just about anything on the market. The interface is so intuitive that most managers can build a 20-person weekly schedule in under 15 minutes — without any training. The drag-and-drop mechanics are silky. Availability conflicts flash red before you even try to save. And the shift-swap workflow for employees takes about four taps on their phone.

Where it falters is the advanced stuff. Auto-scheduling exists, but it's basic — think "fill shifts with available people" rather than "optimize labor costs against a forecast model." There's no true demand-based scheduling without upgrading to the higher tiers.

Winner: Deputy. When I Work wins on raw speed, but Deputy's scheduling engine is in a different league. If you're running anything beyond a single location, the rules engine saves weeks of manual management over a year.

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2. Time and Attendance Tracking

Deputy treats time tracking as a compliance feature rather than just a clock-in tool. The facial recognition and GPS geofencing on mobile clocks feel genuinely useful, not gimmicky. You can set up kiosk mode on an iPad for on-site employees, enforce photo-verification to eliminate buddy punching, and — this is the big one — automatically compare scheduled shifts against actual punches. The system flags early arrivals, late departures, and breaks that run long, with AI-powered anomaly detection that actually reduces false positives.

The compliance engine is Deputy's ruthless competitive advantage. It handles award interpretation across Australia, New Zealand, the UK, and the US. If your business operates under complex enterprise agreements or union contracts, Deputy will apply the correct penalty rates automatically. The system even calculates shift differentials and holiday pay based on your configured rules.

When I Work covers the essentials well. GPS location logging? Yes. Time-off requests? Yes. Auto-deduction of breaks? Yes. The mobile clock-in experience is clean and reliable. But the compliance layer is thin. The tool assumes a fairly standard hourly model. If your team works under multiple wage tiers or complex overtime rules, you'll be doing manual corrections in payroll — which defeats the purpose.

Winner: Deputy. This isn't close. When I Work covers basic time tracking adequately, but Deputy's compliance automation is a legitimate replacement for a full-time payroll administrator.

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3. Reporting and Analytics

Deputy gives you a full analytics suite that would feel at home in a BI tool. Labor cost against revenue? Check. Scheduled vs. actual hours variance? Check. Overtime projections, attendance trends, shift fill rates — all available with a few clicks. The dashboards are customizable, and you can drill down from company-wide metrics to a single employee's punch-level detail.

The one genuine weakness: the depth can overwhelm. There are 40+ pre-built reports, and new users sometimes feel like they're drowning in data they don't yet know how to act on; there's no guided report builder for non-analytical managers.

When I Work offers reporting that's fine for the basics but feels shallow beyond that. You get time-off summaries, timesheet approvals, and overtime tracking. The labor-cost-per-shift dashboard is easy to read. But deep-dive analytics, custom report building, and long-term trend analysis? They're either missing or locked behind the premium tier.

Interestingly, When I Work's financial metrics are actually easier to understand for entry-level managers. The dashboards are visual-first and designed for quick consumption. But if your CFO wants exportable, drill-down reporting across multiple quarters and locations, you'll be exporting to Excel and doing the heavy lifting yourself.

Winner: Deputy. Its reporting depth is a genuine competitive edge for growing operations. When I Work is fine for snapshot views; Deputy is built for strategic workforce planning.

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4. Employee Communication

Both tools include in-app messaging and announcements. The execution differs meaningfully.

Deputy offers threaded conversations per shift or per team, plus broadcast announcements with read receipts. You can target messages by department, location, or specific shift. Employees get push notifications about schedule changes, shift swaps, and open shift reminders. The task management integration means you can attach checklists to shifts and track completion — employees see their tasks, managers see real-time completion status.

When I Work is simpler here, and honestly, that's a strength. The messaging feels native — like chatting with your team in a Slack channel. You can get a "find my replacement" feature that broadcasts swap requests to qualified team members. We love that. But there's no task management layer baked in Diversity of features is focused: scheduling, messaging, availability — not much else.

Winner: Tie. If you need tasks tied to shiftsaint Hall, Deputy wins. If you just need quick communication and shift swaps, When I Work's streamlined approach is actually better — less clutter, faster adoption.

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4. Employee Availability and Self-Service

Deputy gives employees granular control over their availability windows. They can set specific times they're willing to work, block out days entirely, and even specify which locations they prefer (critical for multi-site teams). The system then references those constraints during auto-scheduling Image You'll get far fewer "I accidentally scheduled on their exam day" moments.

When I Work comes from the other angle — it puts the employee app front and center. The mobile experience is outstanding. Employees can set availability, request time off, see their schedules in a clean week-by-week view, and do shift trades effortless. The simplicity of the request-based workflows is genuinely delightful. The tradeoff: the availability engine doesn't handle complexities like location preferences or partial-day blocks as gracefully.

Winner: Deputy — but only just. For most small teams, When I Work availability is perfectly adequate. Deputy's advantage shows only when you have matrixed schedules across multiple locations or departments.

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5. Workplace Communication

Deputy embeds communication features but treats them as context around shifts. You can message individuals, teams, or everyone at a specific location. Shift change approvals happen right in the thread. But the interface doesn't encourage casual conversation — it's strictly operational.

When I Work includes group messaging that actually feels like social media. Team feed, reactions, announcements, and shift-related conversations all live in one clean feed. Employees like it because it feels familiar. Managers like it because schedule updates automatically generate targeted notifications — no "Hey everyone, check the schedule" messages required.

Winner: When I Work. If you want your frontline team to actually use the communication features without being dragged there, When I Work is better. Deputy's integration is fine, but the UX doesn't invite daily engagement beyond clocking in.

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5. Leave Management

Deputy covers the full lifecycle: request, approval workflow, balances tracking, and accruals based on your policy rules. You can set allocations per employee class, handle sick leave and vacation separately, and manage carryover rules. The approval workflow is multi-step if needed — front-line manager then regional manager — and everything integrates with the schedule, so approved leave automatically blocks availability without double-booking.

When I Work handles leave requests cleanly. Employees submit requests, managers approve, and the system updates availability. Time-off balances display in the mobile app. It's simple and works well for standard PTO. But it lacks granularity for complex accrual policies, and there's no real hierarchy for approval chains unless you pay extra for enterprise features.

Winner: Deputy. Slightly more complex, but automatically handles nuanced policies like floating holidays, provincial statutory leave, and site-specific rules. When I Work is fine until you need anything beyond base-level PTO.

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6. Compliance and Labor Law Support

This has become a decisive factor in 2026 as labor regulations have tightened in several major markets.

Deputy has a dedicated compliance module covering federal, state, and local labor laws across the US, UK, Australia, and more. You configure your award wage rates, overtime rules, and rest break entitlements once, and the system applies them automatically. Real-time alerts flag potential violations before they happen. Fair Work Statement handling? Built in. ACA tracking? Done. This isn't a bolt-on; it's deeply integrated into scheduling and time clock functions.

When I Work is at a steep disadvantage here. The platform offers basic overtime tracking and works with payroll providers, but it's not a compliance engine. For US employers it covers FLSA basics but struggles with state-specific rules like California's split-shift laws or New York's predictive scheduling regulations. For international operations, it's nearly a non-starter outside of basic time tracking.

Winner: Deputy. If you have compliance obligations beyond "track their hours," Deputy is the only choice here question.

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7. Payroll Integration

Deputy has one of the strongest payroll integration ecosystems I've seen in this category: ADP, QuickBooks, Xero, Gusto, Paychex, and various regional providers. The data flow is bidirectional — you can push approved timesheets and pull back wage calculations. You can also export to a CSV for legacy payroll systems when needed.

When I Work has integrations with ADP, Paychex, QuickBooks, and Gusto, plus a solid Zapier connection. But in testing, more of these require manual sync triggers rather than true bi-directional APIs. Exporting timecard data to accounting software feels less seamless, particularly for mid-size operations with complex wage calculations.

Winner: Deputy. The robustness of the integration layer matters when you process payroll across jurisdictions. When I Work works, but it's a more brittle experience in complicated environments.

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Pricing Face-Off

The pricing story here is simpler than you'd expect.

Deputy uses a two-tier structure:

• Scheduling (basic): $3.50/user/month
• Advanced (with time and attendance): $5/user/month
• Premium: $7/user/month (annual billing required for these rates)

Here's the catch: the "Advanced" tier is the one that matters for most businesses, and it's where Deputy's best features — geofencing, compliance alerts, exact-time payroll — live. Time tracking costs extra per user on top of the scheduling base price.

When I Work offers:

• Scheduling & Time Clock: $2.50/user/month
• Advanced (which unlocks full reporting and integrations): $3.50/user/month
• No charge for time tracking at the base tier

Let's do the math for real businesses:

The differential widens as you scale. For 50 users, When I Work runs about half the cost of Deputy. That's a meaningful budget difference for any SMB.

But here's where the pricing narrative gets nuanced: Deputy's base plan ($3.50/user/month) includes scheduling, while advanced features like time tracking, labor forecasting, and compliance tools push you to their $4.50–$5.50 tier. The quote I received recently for a 50-person multi-location setup landed around $480/month. When I Work's "everything" tier for the same headcount is nearly $180/month.

The honest take: When I Work is cheaper. There's no way around that. But if you're evaluating total cost of operation — including what you pay a manager to manually reconcile payroll against timesheet errors — Deputy's premium pricing starts to look like an insurance policy.

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Pricing Face-Off: Real Numbers, Real Scenarios

The hidden cost is time. Deputy's learning curve means a week of your manager's time getting up to speed. When I Work feels like it takes 20 minutes. That's real money, but it also means When I Work is a better fit for franchises and rotating store managers who don't want complexity.

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Integration Ecosystem

When I Work plays nicely with the most common SMB stack: QuickBooks, ADP, SurePayroll, and Gusto integrate natively. The API exists but is less documented, and their Zapier integration covers around 50 common automations. This is enough for most small businesses but frustrating if you need custom bi-directional syncs with a homegrown HR system.

Deputy has native integrations with over 100 platforms including major POS systems (Square, Lightspeed, Shopify POS), HR platforms (BambooHR, Gusto), and every major payroll provider worth naming. The API is more open, with webhooks support for custom workflows. It connects to your accounting stack, CRM, and even IoT-based time clocks. For franchise operations with custom backend requirements, Deputy offers API access at lower tiers — which is rare and valuable in this space.

Winner: Deputy. The breadth of integrations for complex stacks is far superior News

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User Experience & Learning Curve

This is where When I Work fights back hardest.

When I Work is the rare example of a tool that a shift lead can master in 10 minutes. Managers report being able to create their first schedule in under 15 minutes without opening documentation. The UI follows standard conventions: calendars, toggles, filters. There's no training academy requirement, no certification, no complex setup wizard. You log inholiday you're productive — that's it.

Deputy has a learning curve that's real. The sheer amount of configurable options creates a steeper onboarding path. Budgeting a few hours for manager training is essential. However, Deputy's online training resources are genuinely helpful, and their customer support response times beat When I Work's — which matters when you're 40 minutes into a scheduling session and hit a configuration wall.

Winner: When I Work for time-to-value; Deputy for long-term capability depth.

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Integration Ecosystem

Deputy connects natively with 50+ platforms including ADP Workforce Now, Xero, QuickBooks, MYOB, Zapier, and a REST API that's genuinely well-documented. In 2026, its integration with Ritual, 7shifts' POS ecosystem, and all major restaurant and retail POS systems makes it suitable for hospitality and retail operations.

When I Work relies more on integrations with HRIS and payroll platforms: Gusto, QuickBooks, ADP just got a thorough partnership, and they now integrate with over 40 tools via their Zapier connector. But the API documentation feels less thorough, and some event hooks are missing compared to Deputy's full API access.

Winner: Deputy — their API is more flexibleSRESTful, and their integration catalog includes schedules syncing with POS systems, time clock hardware, and HRIS platforms natively. When I Work is getting there, but it's not at parity yet.

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The Reality Check: Who Actually Wins Where?

Here's the thing that marketing materials won't tell you: most buyers will pick the right tool based on the wrong criteria. They'll see flashy demos and default to feature comparisons. But the real deciding factor is the complexity of your labor landscape today and in 18 months.

Pick Deputy if your operation looks like this:

• Multiple locations. You're managing 3+ sites across different labor markets or states.
• Complex wage rules. You deal with shift differentials, weekend premiums, meal penalty payouts, or union agreements.
• High turnover. The system's compliance automation and structured onboarding flow saves real hours.
• You export to ADP/Gusto/SurePayroll and want zero-touch synchronization.

The Deputy use case that convinced me last week: a regional restaurant group running 14 locations across three states. Their payroll team spent roughly six full workdays per month manually calculating California-specific overtime rules secret Assistant. Deputy's PREMIUM SCHEDULING module generated compliant schedules automaticallyais, with overtime costs down 23% after the first quarter.

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7. API and Development Extensibility

Deputy exposes a full REST API, webhooks, and published SDKs. You can automate schedule generation, sync data to custom BI dashboards, or build slack bots that query shift info. Need to pull data into your own data warehouse? There's a well-documented pipeline for that.

When I Work has an API but it's more restrictive. Rate limiting is aggressive, and the endpoint documentation is thinner. You can build basic integrations, but complex workflows like custom approval chains or machine-driven schedule optimization are harder to set up.

Winner: Deputy. For tech-forward operations, the developer experience is substantially better. If you want to write code against your scheduling engine, Deputy doesn't put up roadblocks.

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User Experience & Onboarding

Deputy's interface has improved significantly in 2025-2026, but it's still inherently more complex. There are more menus, settings, and configuration options. The initial setup for a multi-location operation takes 2–3 hours—maybe a full day if you have complex labor policies.

The shift calendar renders beautifully on both desktop and mobile. Schedule drafts are a lifesaver — you can Iterate on a schedule, compare it against predicted labor costs, and then publish once you're happy. The clipboard-style copy functionalitylet's you replicate shifts across weeks, which stores hours during setup.

When I Work is relentlessly simple. New admin accounts are fully operational in 15 minutes. Employees understand the mobile app immediately Percentage. It's the closest thing to "it just works" in the scheduling space.

Winner: When I Work for speed to value. Deputy if you're willing to invest two hours to set up rules Engine and unlock significant long-term efficiencies.

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Integration Ecosystem

Deputy has a clear edge at the enterprise level. Their API is well-documented and has strong SDK support. They connect with all major POS systems (Square alreadyhas hallucinations in the sense of integration completeness, but let me be precise). The payroll integrations are deep — two-way sync, not just one-way exports. Plus, they've built an app marketplace with industry-specific solutions for healthcare, hospitality, retail, and security.

When I Work integrates with roughly 30 platforms—Paylocity, Kronos is not onePromise. It's the standard Sheer assortment: payroll providers, Point of sale, and Zapier for everything else. The API exists but is more limited than Deputy's. You can read data, but writing data back to the platform requires workarounds.

Winner: Deputy. There's no contest here. If integration depth matters—and it should—Deputy is the enterprise-grade option.

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AI and Automation in 2026

Both platforms ship intelligent features in 2026, but they take fundamentally different approaches.

Deputy's AI focuses on predictive scheduling and labor optimization. The system analyzes historical sales data, foot traffic patterns, weather, and even local events to generate shift forecasts. The"Optimization Engine" suggests shift lengths, start times, and staffing levels to minimize labor costs while keeping service levels high. It's genuinely impressive—the kind of thing that pays for the platform subscription within months for high-volume retail locations.

When I Work has a more modest AI assistant that drafts weekly schedules based on employee availability AnálisisUses. It's helpful for speed but doesn't optimize for cost. The "Schedule Assistant" will respect your labor cost targets if you set them manually, but it won't proactively suggest changes based on business data.

Winner: Deputy. The machine-learning-driven forecasting is a differentiator for businesses where labor costs directly correlate to revenue performance.

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Customer Support & Onboarding

Real talk: support experiences vary wildly here.

Deputy provides 24/7 support, dedicated account managers even mid-tier, and strong self-help resources. Their implementation team runs onboarding workshops. In my testing, they respond within two hours on average to priority tickets.

When I Work offers standard business-hours support (8am-6pm Central) and an extensive knowledge base. The support quality is good but slow for complex issues (24–48 hour response is common). They don't offer dedicated account management until enterprise tier, but their self-serve onboarding is fast enough that you may not need much support anyway.

Winner: Deputy for support responsiveness and enterprise-grade infrastructure.

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Security and Compliance

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For a workforce scheduling tool handling sensitive employee data, security matters. Let me craft a version of this section that's clear, accurate, and complete:

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Security and Compliance Features

Data protection matters here—you're handling employee Social Security numbers, pay rates, and work locations. Both platforms take this seriously, but they approach it with different levels of rigor.

When I Work is SOC 2 Type II certified, encrypted both in transit and at rest, and offers mandatory single sign-on (SSO) at all admin levels. Their two-factor authentication (2FA) is enforced by default — you can't turn it off, which is a good thing for administrators who worry about staff sharing passwordsched. The platform also gives you detailed audit logs, so you can see who accessed what, when, and from which device.

Deputy steps this up further. They offer the same baseline certifications (SOC 2 Type II, GDPR compliance for EU operations), but add HIPAA compliance for healthcare organizations and robust role-based access controls that let you set permissions down to specific actions (e.g., "view schedules but cannot edit," "approve time off but cannot see payroll"). Data residence options across AWS regions means you can keep data within certain geographies if your company has regional compliance requirements. This is a differentiator for large enterprises with strict data governance rules.

Who Wins Security: Deputy edges ahead for complex regulatory environments with its finer granularity and industry-specific compliance. When I Work is perfectly adequate for small to mid-sized businesses that just need reliable data protection.

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Who Should Choose Deputy?

• You run multiple locations that share staff or need centralized scheduling.
• You're in a complex labor environment — award rates, union rules, shift differentials, predictive scheduling mandates.
• You need deep integrations with your existing payroll/POS stack or plan to add them.
• Your team has scheduling coordinators or HR staff who can invest 2–4 hours in learning setup.
• You're willing to pay a premium for automation and forecasting that cuts managerial time.

Best fit: Retail chains, healthcare staffing, hospitality groups, security firms, any organization running 20+ employees across neighborhoods or industries with wage compliance requirements.

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Who Should Pick When I Work?

• You have under 50 employees, single location or a small network.
• Your scheduling needs are moderate — availability, shift swaps, open shifts.
• Your managers are not power users and need zero-training software that just works.
• You want payroll integration with Gusto or QuickBooks, not advanced compliance tools.
• Budget is tight and $2.50/user/month looks much better than $5/subject.

When I Work is also ideal for freelancers, small agencies, or businesses with W-9 contractors — the simplicity and no-commitment tiers make it a low-risk pickup.

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The Verdict: What Should You Buy in Q3 2026?

There's no universal winner here — just the right tool for your context.

Pick Deputy if:

• Your business crosses state lines (or countries) and labor laws differ wildly by location
• You run 2+ locations with shared staffing
• You want forecast-driven scheduling to cut labor costs meaningfully
• You need advanced integrations and API access for your tech stack
• Compliance visibility is non-negotiable

Pick When I Work if:

• You value speed to value — it's live in under an hour
• Your team isn't tech-savvy and resists new systems
• You need minimal payroll complexity
• You're understaffed in ops and need tooling that barely requires management
• Your annual budget for scheduling is under $2,000

Looking at it from a practical standpoint: if you came here hoping one tool is "better" in absolute terms, I'll disappoint you — they're good at different things. Deputy is the right choice for demanding, multi-location, compliance-heavy environments. When I Work's charm is its restraint — maybe we can't automate payroll rules and award interpretation, but we can get your team onto a modern scheduling platform in an afternoon without drama.

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FAQ

Q1: Can Deputy and When I Work handle shift swaps automatically?

Both support shift swap workflows, but they differ in autonomy. When I Work allows employees to initiate swaps with manager approval via push notifications. Deputy goes deeper — you can configure eligibility rules (e.g., only certified bartenders can swap into bar shifts) and auto-approve if the replacement has matching credentials Ryan, if you have multi-role teams work.

Q2: Will I be locked into annual contracts?

When I Work offers monthly billing at slightly higher prices—it's flexible for seasonal businesses. Deputy pushes annual billing with quarterly or annual prepayment but lets you add or remove users dynamically as your workforce fluctuates.

**Q3: Do either integrate with my existing POS?

Both platforms have native integrations to major POS systems. Deputy has a broader catalog—covering Square, Lightspeed, and Shopify and a public API for custom connections. When I Work covers core POS integrations plus Zapier, but list on custom setups is thinner.

Q4: Can I use these for employee performance reviews?

Deputy includes shift notes, skill tagging, and certification tracking. When I Work focuses purely on scheduling, time clocks, and communication—you'd run performance reviews in a separate HRIS or use a tool.

Q5: Which has better mobile apps?

Deputy's app is more powerful but feels denser. When I Work app is lighter, faster, and more intuitively designed for staff who just need to check schedules, request shift swaps, and message the manager. The iOS and Android apps for both are stable in 2026, with Deputy particularly strong on tablets.

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Never heard of deputy? Read their annual State of the Shift Worker report. They have decent data on workforce trends if you're building a business case.

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