The use of independent contractors has become a standard part of modern workforce planning, particularly for finance organizations managing transformation initiatives, systems projects, compliance demands, and specialized technical work. Yet as contractor usage expands, so does regulatory scrutiny around classification, reporting, onboarding controls, and data access.
During the recent Controllers Council and BILL webinar, Onboarding Contractors in 2026: What Finance and HR Teams Need to Know (CPE), finance leaders Christine Gu, CFO at Clarify Health, and Genevieve Hancock, principal consultant at G. Hancock Advisory, discussed how organizations can strengthen contractor oversight while preserving flexibility and operational speed.
The discussion centered on a growing reality across finance organizations: contractors can provide substantial value, but only when companies establish disciplined governance around how those relationships are structured, monitored, and eventually concluded.
Contractors Continue to Fill Critical Capability Gaps
Both panelists acknowledged that contractor usage has become increasingly common across accounting and finance functions, particularly for project-driven or highly specialized work.
Christine Gu explained that contractors are often most effective when organizations require targeted expertise or temporary support during periods of operational change.
“Contractors are most effective when the company, for example, needs a highly specialized expertise in an area.”
She pointed to ERP implementations, technical accounting projects, tax audits, AI transformation efforts, and M&A integration work as examples where external specialists can provide meaningful support without permanently expanding headcount.
Genevieve Hancock emphasized that contractors should address a defined organizational need rather than evolve into a long-term staffing substitute.
“Those contractors, whether it’s myself or the ones that I’m working with, they should be closing a gap and not becoming a business model or an operating model in and of itself.”
That distinction became a recurring theme throughout the discussion. Several examples illustrated how temporary contractor relationships can quietly become permanent operational dependencies if organizations fail to monitor engagement length, role evolution, or cost structure.
Classification Risk Requires Cross-Functional Oversight
One of the webinar’s central messages involved worker classification compliance and the growing importance of coordination between finance, HR, legal, procurement, and operational leadership.
Christine Gu cautioned against treating contractor classification as simply an HR or payroll exercise.
“Companies should not treat contractor classification as only a HR or payroll exercise.”
Instead, she explained that organizations must evaluate several factors simultaneously, including the degree of control over work, the nature of the contractor’s responsibilities, contractual documentation, tax reporting procedures, and system access permissions.
Genevieve Hancock reinforced that regulators examine operational substance rather than contract wording alone.
“The Department of Labor and the IRS are not going to ultimately care what the invoice says and what the title on the invoice is, they’re going to care what the messages say and what the intent of the individual filling the position is.”
She described situations where companies unintentionally extended temporary arrangements for years, eventually creating compliance exposure around 1099 reporting, tax treatment, and employment classification.
Both panelists stressed the importance of periodically reviewing contractor populations, engagement scope, and project duration to reduce long-term risk accumulation.
AI Transformation Is Reshaping Contractor Demand
Artificial intelligence surfaced repeatedly throughout the discussion, particularly in relation to workforce planning and evolving finance skill requirements.
Christine Gu noted that finance organizations increasingly rely on contractors to support AI enablement, systems integration, automation projects, and data analytics initiatives because many of those capabilities evolve faster than traditional hiring cycles can accommodate.
She also predicted that AI would continue shifting the nature of finance work itself.
“Most of the routine transactional work may become more automated. So, it will be handled by AI.”
At the same time, she explained that demand for strategic expertise, governance oversight, technical accounting review, and process redesign will likely increase rather than decline.
Genevieve Hancock similarly expects contractor usage to rise as organizations modernize finance infrastructure and adapt to economic volatility.
“I would expect to see that there would be more project-based consulting contracts for the next few years as technology continues to improve and be further implemented into finance.”
The broader implication for finance leaders is that contractor strategy increasingly intersects with digital modernization strategy. Organizations are no longer simply hiring temporary support. They are often acquiring specialized transformation capabilities that internal teams may not yet possess.
Onboarding and Offboarding Require Greater Discipline
The webinar also highlighted the operational side of contractor management, particularly around onboarding consistency, compliance training, system permissions, and offboarding controls.
Genevieve Hancock shared an example from a current client engagement where she discovered she had not received the same onboarding process provided to standard employees, despite requiring access to sensitive systems and operational procedures.
That experience reinforced the importance of maintaining structured onboarding processes for all external workers, particularly in regulated industries.
Christine Gu emphasized that finance organizations should build standardized onboarding and offboarding procedures that clearly define deliverables, timelines, internal ownership, access controls, and knowledge transfer expectations.
She also encouraged finance leaders to evaluate contractor ROI beyond hourly billing rates alone.
“The true value also comes from the speed, the expertise, and then the scalability of the overall business impact the contractor can bring to the table.”
Offshore Support Requires Additional Compliance Considerations
The conversation later expanded into offshore accounting support and the additional governance considerations associated with global contractor models.
Christine Gu explained that offshore teams can provide meaningful support for repeatable transactional work, provided processes are standardized and clearly documented. However, she noted that finance leaders must carefully evaluate cybersecurity, segregation of duties, communication practices, and healthcare data privacy obligations where applicable.
Genevieve Hancock added that organizations should involve legal and compliance teams early when offshore arrangements involve regulated data, export-controlled information, or cross-border transfer requirements.
“You don’t ever accidentally want to cross over those boundaries.”
The panelists agreed that offshore support models work best when companies apply them to clearly defined, repeatable workflows with strong internal oversight.
Finance Leadership Is Becoming More Strategic
Another notable thread throughout the webinar involved the changing role of finance leadership itself.
Christine Gu observed that finance organizations increasingly operate as strategic business partners rather than purely transactional functions.
“Modern finance team are no longer just transaction processing organization. We are strategic business partner.”
That evolution affects contractor strategy directly. Finance leaders now evaluate contractor relationships not only through a cost lens, but through governance, scalability, transformation readiness, and long-term operational design.
Genevieve Hancock framed the distinction similarly when discussing the two foundational responsibilities of finance organizations:
“There is the timely and accurate reporting… And there is the strategic finance, which is what are the levers to be able to make that next decision.”
As finance and HR teams prepare for evolving contractor regulations in 2026, the discussion made one point particularly clear: successful contractor management is no longer an isolated administrative function. It now sits at the intersection of compliance, workforce strategy, operational resilience, and technology transformation.
To learn more about onboarding contractors, watch the full webinar here.
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