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Contingent workforce

Which roles are better as contractors? 7 skills that work best as contingent talent

Portrait of Lee Willoughby

Lee Willoughby

Senior Marketing Director, Lifted

Portrait of Lee Willoughby

Lee Willoughby

Senior Marketing Director, Lifted

Portrait of Lee Willoughby

Lee Willoughby

Senior Marketing Director, Lifted

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19 min

19 min

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Key takeaways

  • This guide covers which roles tend to work better as contingent talent and why, plus a 60-second test you can run on any role: six questions that point you toward an independent contractor, staff augmentation, managed delivery, or a full-time hire.

  • The right model (contingent vs permanent) depends less on the job title and more on the shape of the work: a defined deliverable often points toward an independent contractor, extra hands for a team you already direct toward staff augmentation, and an outcome you want a supplier to own toward managed delivery.

  • Roles tied to a project, a surge, or a defined deliverable are often better as contractors: AI and data specialists, cloud and implementation experts, creative surge talent, and security, finance, or fractional leadership roles. Full-time hires still make the most sense for sustained ownership, deep integration, and accountability that has no end date.

  • Lifted, an Upwork Company, can help with each of these situations. It supports independent contractors, staff augmentation, and managed delivery or outsourcing from one supplier, allowing you to align the engagement strategy with the specific demands of the project rather than forcing the work into a single rigid arrangement.

Start with the shape of the work, not the job title

Say you’re a VP of marketing and your company just committed to launching in three new regions next quarter. You need localized campaign creative, a few regional landing pages, and someone to set up reporting for each market.

The first instinct is to open full-time reqs. But a search like that can easily run longer than your launch window, and once the launch wraps, there may not be enough ongoing work to keep those people fully busy.

If that sounds familiar, it can help to flip the question. Instead of asking who to hire, ask what the work actually looks like, and whether a permanent employee would still be fully used once the peak passes. In the launch example from above, the localized creative is one kind of work, the reporting setup is another, and a long-running regional program would be a third. Most specialist needs fall into one of three shapes, and each one points to a different way of engaging talent:

  • A defined deliverable: An assessment, a design, a build, or a report with a clear end, like the localized campaign creative above. This often points toward an independent contractor or a small independent team, depending on the facts of the engagement.

  • A capacity gap: You know what needs doing and who directs it, but you’re short on hands or skills for a while, say two extra analysts to build regional reporting during the launch quarter. This is where staff augmentation tends to fit.

  • An ongoing outcome: You want sustained delivery of a result, with someone else accountable for how it gets done, like operating a regional marketing program or maintaining and improving a platform after launch. This is where managed delivery, usually scoped through an SOW, tends to fit.

7 skills and roles that work best as contingent talent

The roles that usually work better as contingent talent than as full-time hires tend to fall into seven skill areas: AI and machine learning specialists, data labeling and AI model evaluation, specialized project, cloud, and implementation experts, creative and design talent, niche finance, analytics, and compliance experts, cybersecurity, privacy, and risk specialists, and fractional or interim leaders. Each section below covers who you’d typically look for, a scenario where the need comes up, and the engagement model that tends to fit.

1

AI and machine learning specialists

AI is where the gap between the talent companies want and the talent they can hire is widest right now. In ManpowerGroup’s 2026 talent shortage survey of more than 39,000 employers, AI-related skills now top ManpowerGroup’s global ranking of hard-to-find skills, with AI model and application development and AI literacy leading the list.

So say you’re a Head of Product with a short window to get an AI feature in front of your executives, whether that’s a prototype, a retrieval pipeline, or a check on whether the idea is worth building at all. The ML engineers and AI developers who can build it are hard to hire and expensive to keep between projects, so the real question is how to get them for the build without committing to a permanent seat.

Building something and keeping it running are two different jobs. A build phase can need deep expertise for a few months, then much less once the system is live. If you hire permanently for the peak, you may end up with a specialist whose time you can’t fully use, and the search itself can take longer than the window you had. A useful gut check: if their calendar would look half empty in six months, that’s a hint.

In practice, the engagement usually looks like a specialized independent contractor or small team joining for a defined stretch. They take a scoped deliverable, such as an architecture review, a working prototype, or a model built with clear acceptance criteria, work with your product and engineering leads, and hand it over when it’s done. Or you bring in a couple of machine learning engineers to work inside your team through the launch. In one Lifted case study, PepsiCo worked with a lead mobile and AI developer sourced through Lifted, an Upwork Company, to build a live AI-powered ordering kiosk prototype for a brand event.

As for the engagement model, an independent contractor or small team may fit a build or assessment with a defined deliverable, depending on the facts. Staff augmentation may fit when you want extra engineers inside your own team, since you direct the work. For example, two machine learning engineers join your product team for the launch quarter and take tickets from your engineering lead, while the supplier handles sourcing, contracts, and compliance. Managed delivery may fit when you’d rather have a provider own the build outcome. For example, you agree on a working prototype, a deadline, and acceptance criteria under a SOW, and the provider decides how to staff and deliver it.

2

Data labeling and AI model evaluation

Is your AI team waiting on thousands of examples to be labeled, ranked, or reviewed before it can train or test an AI model, the system behind a chatbot, a recommendation engine, or an image generator? Picture a head of AI who just got the green light for a new release. The review work spikes for a few weeks, then drops back once the training cycle ends. The people you need are data annotators, language specialists, and subject-matter reviewers, and that up-and-down pattern is exactly why this work suits contingent talent.

Data labeling work can often come in waves. For example, volume jumps when a model is being trained or tested, then falls away, so a permanent team can sit idle between releases. And more hands alone won’t solve it: quality depends on everyone applying the same standards, which takes training, calibration, and review. Two reviewers who read the guidelines differently can quietly lower the quality of a whole dataset.

In practice, the engagement looks like a trained group of reviewers applying the same guidelines, with spot checks, calibration between reviewers, and regular reporting back to your team. In one Lifted case study, a global learning platform needed AI-generated sentences evaluated across 28 languages, and Lifted supported a fully managed linguist program with 80+ pre-qualified linguists under a single SOW. In another, a global technology company’s creative AI division reduced 150+ contracts to a single engagement model for image evaluation (results vary by engagement).

Both staff augmentation and managed delivery can work here. The choice comes down to who runs the day-to-day:

  • Staff augmentation fits, for example, when you already have annotation guidelines, tooling, and QA processes, and a lead on your side to run the day-to-day. The supplier sources and vets the reviewers and handles contracts and compliance, while your lead directs the work and checks the output.

  • Managed delivery or outsourcing fits, for example, when you want a vetted team, training, workflow management, and quality controls handled for you, with a provider accountable for delivery against agreed quality targets and timelines.

3

Specialized project, cloud, and implementation work

Got a system rollout, a cloud migration, or a data architecture redesign on the calendar? The same goes for a Kubernetes build (the setup that runs and scales your applications in the cloud) or a cost-optimization sprint. Imagine you’re an IT director with a rollout due by year-end and a team already stretched across other projects. The people you’d look for are cloud architects, ERP implementation consultants, and data engineers, and the work has a start, an end, and a point where it gets handed to your internal team to run.

Full-time often isn’t the first move here because the skills are specific, the scope is bounded, and the need fades once the project lands. Hiring permanently for a one-time migration can mean paying for expertise your steady state doesn’t use.

The engagement can look quite different depending on what you’re buying. The same project can be engaged three different ways:

  • IC or small team: may fit best when you want an outside expert to assess your current data architecture and recommend a target-state design, then hand it back to your team.

  • Staff augmentation: may fit when you, for example, want two extra engineers inside your implementation team for the length of the rollout, taking direction from your own lead.

  • Managed delivery or outsourcing: likely fits best when you want a provider to take responsibility for the migration, integration, and acceptance testing by a fixed date.

The first is a defined deliverable, the second a capacity gap, and the third an owned outcome. Many teams combine them: an independent architect designs it, augmented engineers help build it, and a provider owns a specific workstream. In one Lifted case study, Jumio’s IT team was juggling 26+ concurrent projects, some with 12-hour turnarounds, and brought in independent contractors with uncommon combinations of IT, ERP, and finance systems knowledge when that expertise wasn’t available in-house.

4

Creative and design surge work

Remember the VP of marketing launching in three new regions? The creative side of that launch is a textbook contingent need. Campaigns, product launches, rebrands, and events create short, highly visible spikes, and for a few weeks you may need a senior designer, a copywriter, a motion designer, or a creative director. That’s more creative muscle than any internal team would sensibly carry all year.

Creative demand is lumpy. A permanent team sized for launch season can sit underused the rest of the year, and the skills you need often change from one campaign to the next, from motion design to copywriting in a new language.

The engagement can be as small as one senior designer, copywriter, or creative director working on a defined deliverable, or as big as several creatives embedded in your campaign team for six weeks.

For example, Pipedrive used independent talent for copywriting, translation, design, and data work to support content for new regional launches without adding headcount. At the other end of the scale, Hitachi Energy worked with Lifted on outsourced delivery of thousands of creative, technical, and communications assets for a rebrand across 140+ markets.

An independent contractor engagement may fit one person on one defined deliverable, like a freelance copywriter writing a launch campaign, as long as they control how the work gets done. Staff augmentation may fit several creatives working inside your campaign team under your direction. Managed delivery or outsourcing makes the most sense when you’re buying an end-to-end creative production outcome, not individual creative capacity.

5

Niche finance, analytics, and compliance expertise

Facing an audit, a valuation, or a regulatory deadline and short on someone who has done it before? Niche finance, analytics, and compliance needs tend to be tied to a specific event: a valuation ahead of a transaction, an audit-readiness review, an analytics build, a regulatory remediation, or a policy rollout. Think of a CFO preparing for an audit who needs a technical accounting specialist or compliance consultant who has run this exact review many times. The need is real and deep, but it’s usually tied to the event, not to an ongoing internal function.

A permanent hire can be a poor fit here because the expertise is narrow, the window is bounded, and there may not be enough ongoing work to keep a specialist engaged once the project ends.

In practice, the engagement might be an independent expert delivering a written assessment and a remediation plan, working mostly on their own and checking in with your finance or compliance lead. Or it might be a data analyst joining your finance team through quarter-end close, working inside your processes and tools.

This is the area where the engagement model matters most, because it should reflect how the work is actually performed. An independent expert fits a bounded advisory engagement where they work independently and hand over a result. Staff augmentation fits when the specialist must work within an existing team and process. A label alone doesn’t decide the arrangement, and some regulated work carries independence, licensing, or confidentiality requirements, so it’s worth checking with your legal and compliance advisors first.

6

Cybersecurity, privacy, and risk specialists

Has a customer asked for proof of a recent security assessment before they’ll sign? Security, privacy, and risk needs often arrive just like that, as a penetration test (an authorized, simulated attack that looks for weak spots), an incident response, a privacy review, or audit remediation. Say you’re a CISO facing that request. You’d be looking for a penetration tester, a privacy analyst, or a GRC (governance, risk, and compliance) specialist, and most of this work is episodic and highly specialized.

A full-time hire is rarely the first move here, because the specialist you need for a two-week assessment is rarely the same one you need for day-to-day security operations, and incident surges are unpredictable by nature.

In practice, that might be an independent specialist running an assessment and delivering a written set of findings, extra analysts embedded in your security team for the length of an incident, or a remediation program with defined milestones and a provider accountable for hitting them.

An independent contractor or specialist may fit an assessment. Staff augmentation may fit an incident surge, since responders work inside your team and tools. Managed delivery may fit a remediation program with a defined end state. Because security work often involves privileged access, it can look more like staff augmentation than an independent engagement, so access, confidentiality, and data handling are worth settling up front. Enterprises commonly pair this with least-privilege access, activity logging, background checks where appropriate, and clear rules for handling sensitive data and systems.

7

Fractional and interim leadership

What happens when a senior leader leaves in the middle of a big initiative? Leadership gaps are one of the less obvious contingent needs, but they come up often: a leader departs and the role needs cover during the search, a transformation needs an experienced lead for a defined window, or a growing company needs senior finance or marketing expertise before it’s ready for a full-time executive. Say you’re a CEO whose VP of marketing just left right before a rebrand. You need senior marketing leadership now, not in six months. Maybe that’s an experienced interim leader you haven’t met yet, or maybe it’s a former executive you’d like to bring back while you search for a permanent replacement. Either way, the real question is how much experience you need, and for how long.

Senior hires take time, carry real cost, and are hard to reverse. When the need is a stage of the business, such as a first audit, a system change, or a reorganization, a fractional or interim leader can bridge it without committing to a permanent seat. Fractional leaders, who work part-time for a company, are most common in mid-sized and growth-stage businesses. Large enterprises more often use interim leaders to cover a vacancy, or bring in a VP- or director-level specialist to lead a defined program, so the title and structure vary widely.

In practice, that might be a fractional CMO or CFO working a couple of days a week to set up a marketing plan or a reporting and budget process, an interim VP of marketing covering a vacancy while a search runs, or a transformation lead guiding a defined program to its handoff.

An independent contractor or fractional executive engagement may fit advisory leadership with a defined scope, depending on the facts, and staff augmentation may occasionally fit interim leadership cover. Leaders often direct teams, make decisions, and sit close to the core of the business, so the degree of control, integration, and continuity involved can matter as much as the title. A fractional leader brought on in more of a consulting capacity, offering expertise and guidance the business then implements itself with its own internal team, may make sense as an independent contractor engagement. If an enterprise needs help in a more hands on way, seeking not only executive-level expert opinions but also on-the-ground leadership skills, it might explore a staff augmentation engagement if it also needs help finding that person or an EOR-supported engagement if it wants to bring back a former leader to pinch hit. It’s worth reviewing the actual arrangement carefully with your own legal, tax, and HR advisors.

Quick reference: which engagement model fits which role?

Which engagement model fits which need? Find the kind of role you’re hiring for, then see which model usually fits and why. Your own facts, jurisdiction, and advisors should shape the final call.

If you need…

Example roles

Best-fit model

Why it fits

A scoped AI or architecture assessment with a recommendation

AI/ML engineer, solutions architect

IC or small team

Defined deliverable, bounded scope, your team owns what comes next

Extra ML or data engineers to hit a launch date

Machine learning engineer, data engineer

Staff augmentation

A capacity gap inside a team you already direct

A labeling and evaluation program with quality targets

Data annotator, linguist, AI trainer

Managed delivery (staff augmentation if you run the workflow)

Consistent judgment, training, and QA matter more than extra hands

A migration delivered by a fixed date

Cloud architect, ERP implementation consultant

Managed delivery

The provider owns the outcome, delivery approach, and acceptance criteria. Use staff augmentation if your team directs the engineers.

One senior designer or copywriter for a launch

Senior designer, copywriter

IC may fit, if the facts support it

One person, one defined creative deliverable

Several creatives embedded in a campaign team

Designers, copywriters, motion designers

Staff augmentation

Capacity you direct day to day

A valuation, audit-readiness review, or policy build

Technical accounting specialist, compliance consultant, financial analyst

Independent expert for a bounded advisory engagement

Time-limited expertise, not an ongoing internal function

A security assessment, incident surge, or remediation program

Penetration tester, incident responder, privacy analyst

IC for the assessment, staff augmentation for the surge, managed delivery for remediation

The model follows the shape of the work

A fractional or interim executive

Fractional CFO or CMO, interim VP

IC or fractional executive for a defined advisory or consultative scope; staff augmentation or EOR for interim coverage

Deep expertise for a defined window

When a full-time hire is the better choice

Contingent talent isn’t always the answer. A full-time hire usually fits when the work is sustained and has no natural end date. It also fits when someone needs to own a system, a roadmap, or a team over years, and when the role depends on deep integration with your culture, your people, and your institutional knowledge.

Accountability matters too. If the role carries ongoing responsibility for outcomes, direct management of employees, or decisions that need continuity, permanence usually serves you better. Contingent talent can still help here, as a bridge while you hire or as a way to try a working relationship before committing, which is the territory covered in our guide to contract staffing vs. direct hire. Many teams use both: a full-time owner supported by contingent specialists for peaks and projects.

How to choose between a contractor and a full-time hire in 60 seconds

You don’t need a long framework. Run these six questions against any role you’re trying to fill. Each one tells you which way to lean, toward a contractor or toward a full-time hire.

  • Is the work temporary or ongoing?

    Surge, seasonal, or project-based work often points toward a contractor. Sustained ownership of a system, a team, or a result with no end date more likely points toward a full-time hire.

  • Is there a defined outcome with an end date?

    A clear deliverable and finish line may point toward an independent contractor or a SOW-based engagement. A vague, evolving scope usually points toward embedded capacity you can redirect, or sometimes toward a full-time hire if the work will keep evolving for years.

  • Does the role depend on deep knowledge of your company?

    Roles that need years of context, internal relationships, or decisions that shape your culture lean toward a full-time hire. Roles where a specialist can learn what they need quickly and deliver probably lean toward a contractor.

  • Can the person work independently, or do they need to sit inside your team?

    If they can work on their own and hand over a result, an independent contractor may fit. If they need to work inside your team, tools, and process day to day, think staff augmentation, or a full-time hire if that integration will last.

  • Who should own the result?

    If you want to direct the work and own the outcome, staff augmentation or a full-time hire are likely your best fits. If you want a defined deliverable from someone who controls how it gets done, an independent contractor engagement may fit, depending on the facts. If you want a provider accountable for delivery and quality, managed delivery may fit.

  • How fast do you need to start, and how likely is the scope to change?

    Urgent timelines and uncertain scope point toward flexible, contingent options. Stable scope with no rush leaves room for a full-time search.

Here’s a quick way to read your answers:

  • Temporary need with a defined outcome: start your search with an independent contractor or a SOW-based engagement.

  • Temporary need with extra hands inside your team: start by exploring staff augmentation.

  • Temporary need where you want a provider to own the result: start by considering managed delivery.

  • Ongoing, business-critical need: give a full-time hire equal consideration.

  • Regulated or classification-sensitive work: bring in your legal, HR, and tax advisors early, so the model you choose matches how the work will actually be done.

  • Employee-type role, person already identified: consider an EOR, so they’re employed compliantly without the sourcing and vetting of staff augmentation.

Getting specialist capacity without opening a full-time req

Once you know the shape of the work, the next question is how quickly and cleanly you can engage the right person or team.

Engaging talent cleanly starts with matching the model to how the work will actually be done. It can be tempting to treat “independent contractor” as the default for any project-based work, but that generally isn’t how worker classification works. Assignment length alone typically doesn’t decide it. Authorities such as the U.S. Department of Labor and the IRS often look at the substance of the relationship, and the answer generally depends on the totality of the circumstances, not any single factor. Control, integration, exclusivity, duration, and whether the person runs an independent business often come up across these frameworks, in varying forms.

Different jurisdictions apply different frameworks, and this is general information, not a test applied to your facts, so develop the model with your own legal, tax, and HR advisors. Rules and enforcement priorities can also change over time, so it helps to revisit worker classification practices periodically rather than treating an earlier decision as permanent.

Where talent is engaged through an Agent of Record (AOR) or an Employer of Record (EOR), responsibilities differ again, which is why many teams review those options alongside the models above. For more on how enterprises approach this operationally, see our guides to independent contractor compliance and AOR vs EOR.

It helps to look for a supplier that can support more than one model, so you aren’t forced to fit the work to the only option on offer. For example, Lifted, an Upwork Company, is a tech-enabled contingent workforce supplier that supports engaging independent contractors, staff augmentation talent, and managed delivery, with an average time-to-fill of under 3 days, depending on role, location, and compliance requirements. If you want to speed up the sourcing side, see 6 different ways to accelerate your contingent talent sourcing.

Need specialist capacity without opening a full-time req? Talk to Lifted about the right engagement model.

See why leading enterprises choose Lifted

Explore Lifted's full CWMS platform or review our client case studies to see how enterprise organizations are transforming their contingent workforce programs with Lifted.

See why leading enterprises choose Lifted

Explore Lifted's full CWMS platform or review our client case studies to see how enterprise organizations are transforming their contingent workforce programs with Lifted.

See why leading enterprises choose Lifted

Explore Lifted's full CWMS platform or review our client case studies to see how enterprise organizations are transforming their contingent workforce programs with Lifted.

Frequently asked questions

  • Which roles are better as contractors?

    The roles that are often better as contractors are the ones tied to a project, a surge, or a defined outcome, including AI and data specialists, cloud and implementation experts, campaign creatives, security and privacy specialists, niche finance experts, and fractional or interim leaders. Core, ongoing roles that own a system or team usually fit full-time better.

  • What is the difference between staff augmentation and managed delivery?

    The difference between staff augmentation and managed delivery is who directs the work and who owns the result. Staff augmentation supplies capacity that you direct, while managed delivery transfers responsibility for an outcome to the provider. With staff augmentation, you manage the work day to day. With managed delivery or outsourcing, typically scoped through a SOW, the provider is accountable for the agreed result, quality, and timeline under the terms of the SOW.

  • Can the same role be engaged as an independent contractor, through staff augmentation, or through managed delivery?

    Yes, the same role can often be engaged as an independent contractor, through staff augmentation, or through managed delivery, because the right model depends on the shape of the work, not the title. A security specialist might be an IC for an assessment, staff augmentation during an incident, and part of a managed remediation program. Each model carries different responsibilities, so it helps to match the model to how the work will be done.

  • When is a full-time hire the better choice?

    A full-time hire is usually the better choice when the work is ongoing, the role owns a system or team, and deep integration or continuity matters. If you expect the need to last for years, and accountability has no end date, permanence tends to serve you better than a series of short engagements.

  • Should AI and data roles be full-time?

    AI and data roles can be full-time when the work is core, ongoing, and owned by your team, such as maintaining a production model. They often work well as contingent talent for builds, assessments, labeling, and evaluation, where demand rises and falls with each project or training cycle.

Author

Portrait of Lee Willoughby

Lee Willoughby

Senior Marketing Director, Lifted

Lee Willoughby is the Senior Marketing Director at Lifted, an Upwork company helping enterprises source, engage, and manage contingent talent across every contract type. With a background as a co-founder and workforce technology entrepreneur, Lee focuses on the future of contingent workforce management, helping organizations navigate the complexities of global talent, compliance, and workforce transformation.

This content is for general informational purposes only, and is not intended to be and should not be viewed as legal or tax advice. Readers should contact their attorney or tax professional to obtain advice with respect to any particular legal or tax matter. Information discussed can change frequently, and Lifted cannot guarantee that all information is current at all times.

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