Controller

About PlanSource

PlanSource is a leading cloud-based provider of benefits administration technology and services, on a mission to simplify how people choose, use, and manage benefits through cutting-edge, AI-powered experiences. As we continue to scale, we are seeking an experienced, strategic, and hands-on Controller to lead our accounting organization. This leader will be responsible for the integrity of our financial reporting, the effectiveness of our controls environment, the efficiency of our accounting operations, and the development of a high-performing remote accounting team. The ideal candidate brings a foundation in public accounting, significant experience leading accounting organizations within a software or SaaS company of scale, and a passion for leveraging technology and AI to continuously improve the accounting function.

Position Summary

The Controller will report directly to the Chief Financial Officer and serve as the senior leader responsible for corporate accounting operations. This role owns the monthly close, financial reporting, revenue accounting, audit coordination, internal controls, tax compliance, treasury oversight, and accounting systems management. The successful candidate will combine strong technical accounting expertise with operational leadership and a continuous improvement mindset. They will be expected to build scalable processes, improve automation, and identify opportunities to leverage AI and emerging technologies to enhance efficiency, accuracy, and decision-making across the accounting organization.

Key Responsibilities

• Financial Reporting & Close: Lead the monthly, quarterly, and annual close processes, ensuring accurate and timely financial reporting. Oversee preparation of financial statements in accordance with U.S. GAAP. Ensure the completeness and accuracy of account reconciliations, journal entries, and supporting documentation. Establish and monitor close metrics, service levels, and continuous improvement initiatives. Deliver reporting packages and analyses for executive leadership, lenders, and investors.
• Technical Accounting & Revenue Recognition: Own accounting policies and ensure compliance with U.S. GAAP. Lead revenue accounting and ASC 606 application for a SaaS subscription business. Evaluate complex accounting issues, commercial transactions, and new business initiatives. Prepare and maintain technical accounting memos and documentation. Partner with FP&A, Legal, Sales Operations, and Customer Success on contract review and revenue-related matters.
• Internal Controls, Audit & Compliance: Maintain a strong internal control environment and accounting governance framework. Coordinate annual financial statement audits and lender diligence activities. Manage relationships with external auditors, tax advisors, and other consultants. Ensure compliance with tax filing requirements, regulatory obligations, and debt covenant reporting. Develop and maintain accounting policies, procedures, and process documentation.
• Accounting Operations: Oversee accounts payable, accounts receivable, payroll accounting, fixed assets, treasury, and cash management activities. Ensure accounting operations support business growth while maintaining strong controls and data integrity. Drive improvements in working capital management and operational efficiency. Partner with Finance leadership to improve forecasting accuracy and reporting capabilities.
• Systems, Automation & AI: Serve as the accounting leader for NetSuite, SalesForce, and related financial systems. Drive automation initiatives that reduce manual effort and improve close cycle efficiency. Evaluate and implement AI-enabled solutions across accounting workflows, including reconciliations, variance analysis, reporting, audit support, transaction coding, and data validation. Develop a technology roadmap that improves scalability while maintaining appropriate controls and governance.
• Leadership & Team Development: Lead, mentor, and develop a geographically distributed accounting organization. Foster a culture of accountability, collaboration, ownership, and continuous improvement. Build organizational capability through coaching, succession planning, and talent development. Establish clear goals, performance expectations, and career development plans for team members.
• Strategic Support: Support acquisitions, integrations, and other strategic initiatives. Partner cross-functionally to improve business processes and enhance organizational effectiveness. Provide financial insights and recommendations to support key business decisions.

Preferred Qualifications

• Big Four public accounting experience strongly preferred; national accounting firm experience also highly valued.
• Experience in a private equity-backed software company.
• Experience supporting debt covenant reporting and lender relationships.
• Experience with acquisitions, purchase accounting, and post-acquisition integrations.
• Experience operating in a multi-entity environment.
• Demonstrated success implementing automation and AI solutions within accounting and finance.
• Familiarity with best-of-breed financial close, AP automation, reporting, and planning platforms.

What Success Looks Like

Within the first 12 months, the Controller will:

• Ensure a consistently accurate and timely monthly close process.
• Strengthen and modernize the accounting control environment.
• Improve efficiency through automation and AI-enabled workflows.
• Enhance visibility into accounting operations through metrics and dashboards.
• Develop a high-performing, engaged remote accounting team.
• Establish accounting processes capable of supporting the company's next stage of growth.

Why This Role Is Different

This is not simply a compliance and reporting role. The Controller will play a key leadership role in transforming the accounting organization through process improvement, automation, and responsible use of AI. The successful candidate will help shape how accounting operates at PlanSource over the next several years, creating a more scalable, data-driven, and efficient finance function.

What We Offer

At PlanSource, benefits are at the core of what we do, and we understand their impact on our employees and their families. That's why we've designed our benefits program to support overall wellbeing across health, financial security, career growth, and work‑life balance.

• Comprehensive health coverage with multiple medical plan options - all covering 100% of in-network preventive care.
• Employer‑funded Health Savings Account (HSA) - up to $1,000 annually for family coverage.
• Dental & Vision plans with 100% coverage for routine dental care and $250 vision frame allowance, plus employee-only vision premiums at $0.
• 401(k) with immediate vesting and a 50% company match up to 6% of contributions.
• Generous paid parental leave, adoption assistance, and fertility benefits.
• Flexible PTO, paid holidays, a strong culture of work‑life balance and Flex Fridays in the summer.
• Mental health & wellbeing support, including Employee Assistance Program (EAP), movement and wellness resources.
• Rewards and recognition programs that celebrate employees through peer recognition, awards, and quarterly recognition initiatives.

Top 5 Reasons to Join PlanSource

• #5: Be part of what's next in benefits technology
• #4: Make an impact with technology our customers trust
• #3: Be recognized, supported, and set up to thrive
• #2: Grow your career with intention
• #1: Be part of a culture built on connection and impact