Director, VMS Operations & Cash Applications
Overview
Position Summary:
Insight Global seeks a strategic, data-driven, people-focused leader, process change agent, and curious individual to oversee our Cash Applications and Accounts Receivable
operations. This role is critical to optimizing our Order-to-Cash process, reducing unapplied cash balances, and driving operational excellence across a high-volume, fast-paced staffing organization.
The ideal candidate will bring deep experience in managing AR operations within environments that rely heavily on Vendor Management Systems (VMS). These platforms, while essential for client engagement and billing workflows, often introduce complexities such as delayed invoice approvals, fragmented remittance data, and inconsistent payment cycles. Experience navigating these challenges is highly desirable.
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This leader must embody Insight Global's Shared Values:
- Everyone Matters - Lead with empathy and inclusivity.
- We Take Care of Each Other - Foster a supportive team culture.
- Leadership Is Here to Serve - Empower and develop others.
- High Character and Hard Work Above All Else - Model integrity and resilience.
- Always Know Where You Stand - Communicate with transparency and clarity.
People Leadership:
The Director must be a strong people leader who inspires and empowers their team. This includes developing talent through coaching and mentorship, setting clear and achievable goals, and fostering a culture of accountability. Equally important is demonstrating care and empathy-creating an environment where team members feel valued, supported, and motivated to perform at their best. The ideal candidate will balance high expectations with genuine concern for individual growth and well-being. They must be able to analyze
performance data, set measurable goals, and track progress to ensure continuous improvement. Additionally, the Director should possess the ability to influence peers and cross-functional leaders to align priorities and drive strategic initiatives.
Responsibilities
Leadership & Strategy:
Lead and develop a high-performing team of ~30 professionals across onshore and offshore locations.
Establish and execute short-term and long-term strategies to reduce unapplied cash and improve AR performance.
Foster a culture of accountability, continuous improvement, and collaboration aligned with Insight Global's values.
Operational Excellence:
Oversee the cash application process for 5K+ staffing clients with various paymentmethods (Check, ACH, Ariba, etc.).
Drive automation and process improvements to enhance efficiency and accuracy.
Leverage tools like HighRadius or similar platforms to streamline payment matching and reduce manual effort.
Monitor and report on key AR metrics related to the cash application process (e.g., STP Straight Through Processing rate, average time to apply cash, invoice-to-remittance match rate).
Driving improvement or resolution on multiple cash application challenges: missing or incomplete remittance information, bulk payments without invoice-level breakdowns, client portal limitations, frequent client disputes, and short pays.
Providing solutions to common VMS-specific challenges, such as delayed invoice approvals due to client-side workflows, inconsistent schedules tied to VMS cycles, and limited visibility into client-side payment status.
Goal Setting and Achievement:
Use insights from data analysis to set measurable and achievable goals for employees that align with the Revenue Operations Department's and Insight Global's overall objectives.
Help direct leaders create detailed action plans that outline the steps employees need to take to achieve their goals, along with the specific tasks, deadlines, and resources required to support their progress.
Measure and provide feedback often. Adjust goals as necessary.
Analytics & Reporting:
Conduct root cause analysis to identify and resolve systemic issues.
Develop and present actionable insights using financial data to influence business decisions.
Partner with IT and Finance to enhance ERP and AR system functionality.
Stakeholder Engagement:
Collaborate with Sales, Customer Service, and Operations to resolve billing disputes and ensure invoice accuracy.
Build strong relationships with clients to encourage timely payments.
Influence internal stakeholders to align priorities and resources with AR goals.
Qualifications
Qualifications:
Bachelor's degree in Accounting, Finance, or related field (MBA preferred).
8-10+ years of progressive experience in AR and cash applications, preferably in staffing or professional services.
Proven experience managing large teams and offshore operations.
Strong analytical skills with the ability to interpret complex data sets.
Hands-on experience with HighRadius or similar cash application automation tools.
Expertise in ERP systems (e.g., Workday, Oracle, SAP).
Experience working with Vendor Management Systems (VMS) such as Fieldglass, Beeline, or IQNavigator.
Excellent communication and storytelling skills using financial data.
Experience with KPI development and performance management.
Preferred Skills:
Familiarity with AI tools and technologies, including Python for data analysis and automation, machine learning and deep learning frameworks (e.g., TensorFlow, PyTorch) for predictive modeling and process optimization, and data visualization tools (e.g., Power BI, Tableau) to enhance reporting and insights.
Why Join Insight Global?
Competitive compensation and bonus structure.
Comprehensive benefits package including medical, dental, vision, and retirement plans.
Opportunity to lead transformation in a dynamic, high-impact environment.
A culture rooted in Shared Values that prioritize people, purpose, and performance.
Perks and Benefits
Health and Wellness
- Life Insurance
- Health Insurance
- Dental Insurance
- Vision Insurance
- FSA With Employer Contribution
- HSA
- HSA With Employer Contribution
- On-Site Gym
- Pet Insurance
- Mental Health Benefits
Parental Benefits
- Fertility Benefits
- Family Support Resources
Work Flexibility
- Remote Work Opportunities
- Hybrid Work Opportunities
Office Life and Perks
- Commuter Benefits Program
- Casual Dress
- Happy Hours
- Snacks
- Some Meals Provided
- Company Outings
- On-Site Cafeteria
- Holiday Events
Vacation and Time Off
- Paid Vacation
- Paid Holidays
- Personal/Sick Days
- Volunteer Time Off
Financial and Retirement
- 401(K)
- 401(K) With Company Matching
- Stock Purchase Program
- Performance Bonus
Professional Development
- Promote From Within
- Mentor Program
- Shadowing Opportunities
- Access to Online Courses
- Lunch and Learns
- Leadership Training Program
- Associate or Rotational Training Program
- Internship Program
Diversity and Inclusion
- Employee Resource Groups (ERG)
- Diversity, Equity, and Inclusion Program