Provide financial analysis support to enhance property performance, oversee internal controls, coordinate cash flow forecasts, and assist with budget reviews while training accounting teams on company systems.

Role Description The Accounting Assistant will work in partnership with the Accounting Team, Accounting Manager, and third-party accounting firm to verify and complete payable and receivable transactions by assisting in the preparation and collection of invoice documents. This role is also responsible for working with Customers to collect past due payments and preparing Customer aging reports for internal review. Qualifications - Bachelor’s degree in Accounting, Finance, or related field preferred - 2 years of Accounts Payable and/or Accounts Receivable experience - 1 year of customer service experience Requirements - Assist with Accounts Payable and Accounts Receivable - Generate and send Customer invoices - Communicate with Customers and Volition Account Executives to advise on invoice statuses - Analyze Vendor invoices for accuracy confirming all required documents are provided - Assist third-party accounting firm in issuing vendor payments after all requirements are met - Build and maintain Accounting reports to show real and projected figures - Continuously track delinquent invoices and actively contact customers for payment - Maintain orderly Customer and Vendor invoice files Physical Demands & Work Environment The work schedule of this position will be determined based on the organizational needs; it will be subject to change based on business demands and will require work outside of standard business hours. The job is performed in a general office environment with the option to work remotely as needed.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About the RoleAs Headway's Senior Accounting Manager, you will lead day-to-day accounting operations and help establish scalable financial processes during a period of rapid growth. You'll manage a team of four accountants, owning month-end close, financial reporting, and technical accounting under US GAAP. This is a hands-on leadership role: you'll coach a high-performing team while partnering cross-functionally with Finance, People, Legal, Data, Product, and Engineering to ensure accurate and timely reporting. This role offers an opportunity to apply strong leadership, technical accounting expertise, and creative problem-solving to make a lasting impact on Headway's operations and audit readiness. You will: - Manage and develop a team of four accountants — setting priorities, reviewing work, providing feedback, and coaching them on technical accounting and process improvements. - Take a lead in automating accounting workflows using AI and LLMs (e.g., journal entry preparation, reconciliations, flux analysis, audit support), and lead the team in adopting these tools responsibly. - Own the month-end, quarter-end, and year-end close process end-to-end, ensuring journal entries, reconciliations, accruals, and account analyses are accurate, complete, and delivered on schedule. - Review and approve journal entries, balance sheet reconciliations, and flux analyses prepared by the team. - Lead technical accounting research and policy setting under US GAAP, including documenting accounting positions and memos for complex transactions - Support the annual audit by coordinating PBC requests and responses across the team, partnering with the Assistant Controller (who serves as the primary point of contact for external auditors.) - Partner with the People team to oversee payroll accounting and reconciliations, and with cross-functional teams (Finance, Data, Engineering, Product) to scale accounting operations. - Drive process improvements and automation initiatives across the accounting function, leveraging tools like Netsuite, Workday, and Ramp to reduce manual work and improve controls. - Lead or sponsor strategic accounting projects, coordinating cross-functional partners and delivering measurable business impact. You'd be great for this role if you have: - 10+ years of accounting and/or audit experience, including at least 5 years managing a team - A Bachelor's degree in Accounting, Finance, or another relevant field (CPA preferred but not required) - Strong working knowledge of US GAAP and experience leading month-end close in a high-growth environment - Public accounting (Big 4 or large firm) and/or in-house experience at a high-growth or pre-IPO company - History of utilizing LLM’s such as Claude to automate processes. - A track record of coaching and developing accounting talent - Hands-on experience with Netsuite (and ideally Numeric and Ramp), and a bias toward using technology to scale accounting operations - Strong communication and interpersonal skills, with the ability to influence senior stakeholders and partner effectively across functions - A proactive, ownership mindset and the ability to thrive in a fast-paced, ambiguous environment We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

Role Description PrizePicks is seeking a Senior Manager of Accounting Systems & Internal Controls to help us build the financial infrastructure that will power the next phase of our growth. In this role, you’ll own the systems and controls that keep our accounting function accurate, efficient, and audit-ready. You’ll work at the intersection of ERP administration, internal controls evolution, and process automation — partnering closely with Accounting, FP&A, IT, and Legal to design and operationalize scalable solutions. This is a high-impact role for someone who thrives in a fast-moving environment and wants to leave a lasting mark on how a company builds its finance function the right way. What You’ll Do - Accounting Systems & ERP Ownership - Serve as the primary business owner of our ERP platform (NetSuite), driving configuration, optimization, and roadmap decisions. - Partner with IT and external vendors to manage system upgrades, integrations, and data integrity across the financial tech stack. - Lead the evaluation and implementation of new accounting tools and automation initiatives that improve close efficiency and reporting accuracy. - Maintain chart of accounts, system hierarchies, and financial data structures to support both current operations and future scale. - Strategic partner with Finance to design, maintain, and evolve management and external reporting packages. - Internal Controls - Key owner of relationship with third party accounting advisors. - Design, document, and maintain a comprehensive internal controls framework (ICFR) aligned with best practices. - Own the controls risk matrix (CRM); ensure controls are properly designed, implemented, and operating effectively. - Cross-functional partner, able to translate technical control language into value-add business acumen. - Coordinate with external auditors and serve as the primary point of contact for controls-related audit requests. - Drive a proactive controls testing program, track deficiencies, and manage remediation plans to closure. - Process Improvement & Automation - Serves as PrizePicks Accounting and Finance AI Champion by continually identifying opportunities to embed AI in systems and processes in order to build for growth and implement AI-powered solutions to complex business problems. - Identify and prioritize opportunities to eliminate manual processes across the accounting close, reconciliations, and reporting workflows. - Lead cross-functional projects to standardize and automate recurring finance processes, ensuring scalability as the business grows. - Establish and maintain process documentation, including desktop procedures and workflow diagrams for key accounting cycles. - Champion a continuous improvement mindset within the Finance team, bringing structure and rigor to how we operate. - Cross-Functional Collaboration - Act as a trusted advisor to the Controller and CFO on systems strategy, controls design, and operational risk. - Partner with the broader Finance & Accounting team to support the monthly, quarterly and annual close processes. - Collaborate with Legal and Compliance on regulatory reporting requirements and control obligations. Qualifications - 7+ years of progressive experience in accounting, finance systems, or internal controls, with at least 2 years in a management or lead role. - Deep expertise in ERP platforms (NetSuite strongly preferred); hands-on experience with system configuration and cross-system integrations, including data flow and integrity. - Strong working knowledge of internal controls compliance, ICFR design, and controls testing methodology. - Experience building or significantly maturing an internal controls program at a high-growth company. - Proven ability to manage multiple complex projects simultaneously with a high degree of accuracy and attention to detail. - Excellent communication skills — able to translate technical systems and controls concepts for non-technical stakeholders. - CPA, CIA, or CISA preferred; Bachelor’s degree in Accounting, Finance, or related field required. - Experience with tools such as Workiva, Floqast, Blackline, or similar accounting operations platforms is a plus. Benefits - Company-subsidized medical, dental, & vision plans. - 401(k) plan with company match. - Annual bonus. - Flexible PTO to encourage a healthy work/life balance (2 weeks STRONGLY encouraged!). - Generous paid leave programs, including 16-week paid parental leave and disability benefits. - Workplace flexibility and modern work schedules focused on getting the job done, not hours clocked. - Company-wide in-person events and team outings. - Lifestyle enhancement program. - Company equipment provided (Windows & Mac options). - Annual performance reviews with opportunities for growth and career development.