Remote Chief Operating Officer Insurance Jobs in Indiana

Our growing company is seeking a Director of Finance to lead finance strategy and operations. Reporting directly to the COO, you'll own financial planning, strategy, budget management, A/P, A/R, and day-to-day financial operations.

As the Director of Finance, you'll play a central role in how YML creates a growing, sustainable business.

The ideal candidate is proactive, communicative, and analytical. They can zoom out strategically while executing on tactical items day to day.

This role is remote or hybrid.

• Serve as a key financial thought partner to the COO, contributing to strategic planning, resource allocation, and long-term financial direction.
• Manage and refine our financial model, ensuring accurate planning and forecasting.
• Manage the end-to-end fundraising process, including financial modeling, investor relations, and coordination of due diligence activities if applicable.
• Oversee relationships with external accounting, tax, and advisory firms.
• Manage routine tax filings and payments across jurisdictions, and coordinate with the company's tax firm on compliance and planning matters.
• Collaborate with department heads to create, monitor, and manage budgets.
• Prepare and deliver financial reporting packages for board meetings, investors, and banking partners, including required quarterly reporting.
• Oversee the accounts payable process, ensuring timely and accurate vendor payments.
• Manage accounts receivable and collections, ensuring timely invoicing and follow-up.
• Serve as the point of contact for customer billing inquiries.
• Ensure bookings data reconciles across systems (e.g., CRM and billing platforms).
• Administer the company's expense and T&E program, including credit card spend limits, positive pay monitoring, and expense approvals.
• Consult with sales and CS leadership on pricing, ensuring we are protecting margin and value.
• Complete month-end, quarter-end, and year-end close of income statement and balance sheet, recording journal entries, reconciling accounts, managing cash, and handling G/L analysis.
• Lead the evaluation, implementation, and ongoing management of financial systems and software.

• Bachelor's degree in Accounting, Finance, or related field. CPA or other relevant certification is a plus.
• 5-7 years of accounting experience, with at least 3 years in a management role.
• Strong knowledge of financial principles, accounting standards, and regulations.
• Proficiency in financial software and tools, including revenue management, bookkeeping software, and CRM.
• Exceptional analytical and problem-solving skills.
• Excellent communication and interpersonal skills, with the ability to work effectively with cross-functional teams.
• Detail-oriented with a high level of accuracy in financial reporting and analysis.

Your Money Line (YML) is a leading financial wellness platform that provides employees with essential tools and guidance to manage financial challenges, plan for the future, and achieve their goals. Through an all-in-one mobile app, access to certified financial coaches, and AI-driven tools, YML empowers employees at every life stage. Trusted by organizations across industries, including corporations, school districts, and healthcare systems, YML is transforming lives and improving financial well-being nationwide. Founded by financial expert Peter Dunn, also known as Pete the Planner, YML is dedicated to making impactful, positive changes in the lives of employees and their families.

• Medical Insurance (Company pays 75% of the premium for all tiers)
• Health Savings Account with employer HSA contribution
• Dental and Vision Insurance
• Company Equity
• 401K with Company Match
• Hybrid Office Model
• Unlimited Wellness Time Off
• Unlimited Paid Time Off
• Unlimited access to YML platform and resources
• Elective Accident, Disability, and other non-medical insurance coverages
• Monthly Technology Stipend (Remote Employees)
• Group-Life & AD&D Insurance
• Paid Paternity, Maternity, and Adoption Leave
• Flexible Spending Accounts and Dependent Care Flexible Spending Account
• Voted a "Best Place to Work in Indiana"