Your Money Line

Role Description 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. Responsibilities - 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. Qualifications - 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. Benefits - 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"

• Repurpose long-form video (podcast, radio, interviews) into short-form content for TikTok, Instagram Reels, YouTube Shorts, and LinkedIn • Clip, caption, and package content with strong hooks and clean edits • Assist in producing The Pete the Planner Show (episode prep, posting, distribution) • Draft and schedule social posts across platforms to grow engagement and followers • Reformat and redesign content to suit platform-specific dimensions, layouts, and user behaviors (e.g., vertical video, carousel storytelling, thumbnail design) • Identify trending formats, sounds, and ideas we can adapt quickly • Help maintain a cohesive look and consistent voice: smart, approachable, slightly witty, never preachy • Analyze social media performance metrics and surface insights that help improve content and campaign effectiveness • Monitor social channels to identify engagement opportunities and contribute to community interactions

About the Role Our growing company is seeking an experienced Program Manager to lead the complex, cross-functional initiatives that are critical to Your Money Line’s growth, beginning with a high priority white label partner solution. Reporting directly to the COO, you’ll own the structure, execution, and relationship management to bring a strategic partner program to life. You’ll also serve as a key client-facing leader throughout the implementation process. As the Program Manager, Strategic Implementations, you'll play a central role in how YML plans and executes high stakes partner implementations. Your time will be focused on creating and managing project plans, aligning stakeholders, managing risks and dependencies, and ensuring initiatives move from concept to launch. You will also serve as a trusted point of contact for partners and clients, bringing structure, clear communication, and strong execution to complex implementations. The ideal candidate is proactive, decisive, and exceptionally strong at creating structure in ambiguous environments. They know how to bring order to complex, evolving work, drive clarity when ownership or process is unclear, and push stakeholders toward timely decisions. They are skilled at identifying blockers early, escalating when needed, and accelerating progress across internal teams and external partner organizations. This role is remote and open to candidates based in the United States. Candidates must be willing and able to travel for internal collaboration and key partner meetings, including on site work in the Chicago suburbs for a specific partner engagement. Applicants must be legally authorized to work in the United States without the need for current or future employment visa sponsorship. Responsibilities Strategic - Lead execution for complex strategic implementations with authority to adjust milestones, manage scope changes, and make day to day project decisions. Escalate timeline shifts that affect overall launch dates or strategic tradeoffs between partner needs and YML's broader priorities. - Translate broad business goals into actionable project plans with clear milestones, dependencies, owners, timelines, and decision points. - Partner with leadership to identify implementation needs, pressure test plans, surface tradeoffs, and ensure alignment across teams. - Develop and strengthen repeatable implementation processes, templates, and operating rhythms that make future launches more scalable. - Surface risks, dependencies, and operational implications early enough to support strong decision making and avoid downstream disruption. Operational - Create, maintain, and drive detailed project plans, ensuring priorities are clear and deadlines are realistic and visible. - Create structure where process, ownership, and decisionmaking is unclear. - Lead regular status meetings and communicate progress, blockers, risks, dependencies, decisions, and next steps clearly. - Manage changes in scope or timing while preserving momentum and execution quality. - Track follow through and hold internal and external teams accountable for commitments while maintaining strong working relationships and a collaborative tone. Client Communication - Build trust and confidence with partner contacts from kickoff through launch - Lead partner facing meetings with professionalism, clarity, and strong command of the project details and business context. - Collaborate closely with Client Success and other internal teams to ensure a strong partner and client experience before, during, and after launch. - Help create a culture of accountability, transparency, and thoughtful execution around major company initiatives. - Capture lessons learned and continuously improve the way YML approaches implementations, partner communication, and cross-functional program management Requirements and Qualifications - 5+ years of experience in program management, project management, implementation management, or other similar roles. - Direct partner-facing experience in the benefits, financial wellness, or retirement advisory space is required. - Strong experience building and maintaining project plans, managing timelines, mitigating risks, and driving accountability across teams. - Demonstrated ability to create order in ambiguous, fast moving environments where process and ownership are still evolving. - Demonstrated AI fluency, with the ability to leverage Generative AI tools (e.g., Claude, ChatGPT, Gemini) to automate administrative tasks, refine program documentation, and synthesize complex data. - Willingness and ability to travel as needed, including onsite work with clients in the Chicago suburbs. - PMP or similar certification preferred. - Experience in SaaS, fintech, HR tech, health tech, or partner-driven businesses strongly preferred. About Your Money Line 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. Benefits - 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'

Location: Remote (U.S.-based) Your Money Line seeks an enthusiastic and self-motivated Financial Guide (Independent Contractor) to support our participants on an as-needed basis. Our Financial Guides provide participants with clear and empathetic financial guidance, catering to diverse backgrounds and addressing a variety of financial challenges. You will play a key role in delivering a high level of participant satisfaction while operating as an independent professional. Engagement Structure On-Demand, Part-Time: You will receive assignments as needed and are expected to respond within one (1) business day of receiving an assignment. Independent Work: As an independent contractor, you will control how, when, and where you perform your services, provided deadlines are met and quality standards are maintained. Compensation: $28/hour, paid per assignment, as agreed in the independent contractor agreement. About Your Money Line Money is stressful. We're on a mission to fix it. Your Money Line is one of the leading financial wellness benefits in the nation. We pair AI-powered software with empathetic human coaching to increase financial stability and confidence in thousands of households—from teachers to nurses and everyone in between. With YML, employees get help with their everyday money challenges, and employers see gains in team wellness, retention, and engagement. Your Money Line was founded by Peter Dunn (aka Pete the PlannerTM) and is funded by leading Midwest investors like Ground Game Ventures, Elevate Ventures, Rehab Industries, InnovateMap Ventures and Gravity Ventures. Scope of Work Listen to and discern participant needs, identify viable solutions, and adeptly communicate possible courses of action Provide Spanish-speaking participants with support by: Answering questions via phone, Zoom, email, and chat Sending necessary follow-up information outlining summaries and next steps Managing recurring counseling appointments as necessary Create and deliver educational support via webinars, short-form videos, articles, and other content Escalate questions as necessary to senior members of the financial guide team Attend training and coaching sessions as necessary to expand knowledge of services provided and stay current with industry updates such as policy changes and regulatory adjustments Requirements This is a contractor role; you will not be eligible for employee benefits. You will be responsible for your own taxes, insurance, and compliance with applicable laws as an independent contractor. Your Money Line may reimburse certain professional certification fees (e.g., AFCPE annual certification fee) as outlined in the contractor agreement. If you’re passionate about improving financial stability for diverse populations, thrive in a flexible and independent environment, and meet the above qualifications, we’d love to hear from you.

• Provide direct, licensed tax advice to participants on complex topics, including: Tax implications of income changes, life transitions (e.g. marriage, divorce, relocation), and equity compensation • Multi-state taxation, self-employment income, estimated payments, and amended returns • Filing status decisions, deductions/credits eligibility, and retirement contribution impacts • Collaborate with the Financial Guide team by handling escalated cases that exceed coaching and education scope • Educate participants using clear, jargon-free explanations of IRS guidelines and implications • Maintain accurate and timely documentation within Salesforce and align with internal case protocols • Support seasonal participant needs during tax season and contribute to internal tax education efforts • Assist in the development of participant-facing tax resources, FAQs, and training