Remote Controller

DescriptionAbout UsClever Benefits is a growing healthcare technology company on a mission to simplify how healthcare and employee benefits are managed. Through a combination of technology, AI, and deep industry expertise, we build solutions that make benefits more accessible, transparent, and effective for employers and their employees.As part of a broader portfolio of operating companies, our finance team supports multiple businesses at various stages of growth—from established operating companies to newly launched ventures. This creates a unique opportunity to work across a diverse set of businesses while helping build scalable financial infrastructure that supports long-term growth.We're a collaborative, entrepreneurial team that values ownership, continuous improvement, and practical problem solving.About the RoleWe are seeking a hands-on Controller to lead accounting operations, financial reporting, internal controls, and accounting compliance across our portfolio of companies.This role combines strategic controllership responsibilities with direct accounting ownership. The Controller will personally own the accounting function for Clever Benefits, including day-to-day accounting operations, month-end close, financial reporting, and cash management, while also serving as the overall owner of accounting operations, accounting policy, financial reporting, and accounting controls across the broader portfolio.This role is ideal for an experienced accounting leader who enjoys rolling up their sleeves, thrives in a multi-entity environment, and takes pride in producing accurate, reliable financial information.The Controller will report directly to the Chief Financial Officer (CFO), manage a small accounting team, and work closely with company leadership, external accountants, legal counsel, banks, and operating teams across the portfolio.This is a remote position. Candidates located near our offices in the Phoenix, Arizona or Charleston, South Carolina areas are welcome to work from those locations, but proximity to an office is not required.Accounting & Financial ReportingOwn the monthly, quarterly, and annual close process across the portfolioOwn reconciliations, intercompany accounting, allocations, and accounting review processes across the portfolioPersonally own day-to-day accounting operations for Clever Benefits, including accounts payable, accounts receivable, reconciliations, journal entries, month-end close, and financial reportingPrepare and review financial statements and supporting schedulesEnsure financial reporting is accurate, timely, and increasingly aligned with GAAPReview transaction coding, classifications, reconciliations, and journal entriesEstablish and maintain accounting policies, documentation standards, and review proceduresResearch and resolve accounting issues involving debt, equity, acquisitions, ownership transactions, stock-based compensation, and other non-routine activityRetain accountability for accounting accuracy and financial reporting regardless of delegated executionMulti-Entity AccountingOwn intercompany accounting, allocations, shared services charges, and related-party transactionsMaintain accounting consistency across multiple legal entitiesOversee accounting treatment for loans, advances, promissory notes, convertible instruments, equity issuances, and stock option plansOwn revenue recognition, deferred revenue accounting, commission liability accounting, and other complex accounting areas across the portfolioSupport accounting setup and integration of newly formed entities and incubation initiativesOwn the accounting structure, financial controls, and accounting processes for newly formed entitiesEnsure balance sheet integrity and proper reconciliation of all significant accountsDirectly perform accounting activities for Clever Benefits while directing, reviewing, and overseeing accounting execution across other portfolio entitiesControls, Risk Management & ComplianceStrengthen internal controls, approval workflows, and financial governance processesEstablish appropriate segregation of duties and accounting review proceduresImprove cash disbursement controls, spend management controls, fraud prevention processes, and payment authorization standardsOwn payroll accounting review, payroll allocations, and payroll approval processesServe as primary accounting liaison to external CPA firms and tax advisorsSupport annual tax filings, compliance projects, 409A valuations, R&D credit studies, and accounting-related diligence effortsMaintain documentation and records necessary to support investor, lender, and transaction diligenceEnsure accounting practices can withstand the scrutiny of outside investors, lenders, and potential acquirersLeadership & Team ManagementDirectly manage and develop the Accounting & Operations ManagerEstablish accountability, priorities, and operating rhythms for the accounting functionProvide guidance on accounting treatment, close support activities, and process executionReview and oversee accounting work performed throughout the portfolioDelegate accounting projects and execution activities while maintaining ownership of accounting outcomesHelp define appropriate ownership between bookkeeping, accounting operations, business operations, and controllership responsibilitiesBuild a scalable accounting function capable of supporting continued growth across the portfolioEqual Opportunity EmployerClever Benefits is an equal opportunity employer committed to building an inclusive workplace where everyone can do their best work. We celebrate diversity and are committed to creating an environment where all employees feel respected, valued, and supported. We make employment decisions based on qualifications, merit, and business needs without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other protected characteristic under applicable law.Work AuthorizationThis position is not eligible for employer-sponsored work authorization. Applicants must be legally authorized to work in the United States without requiring sponsorship now or in the future.RequirementsRequiredBachelor's degree in Accounting or Finance8+ years of progressive accounting experienceExperience leading month-end and year-end close processesStrong knowledge of GAAP and financial reportingExperience managing accounting operations within a multi-entity organizationExperience leading or mentoring accounting staffAudit ExperiencePreferredCPA licenseExperience in healthcare, insurance, SaaS, or venture-backed companiesExperience with acquisitions, equity transactions, and complex accounting mattersExperience implementing or improving accounting processes and internal controlsExperience leveraging AI tools for productivity in finance/accounting functionSkills & AttributesHands-on leader who enjoys owning both strategy and executionHigh attention to detail with exceptional organizational skillsStrong analytical and problem-solving abilitiesExcellent written and verbal communication skillsComfortable working in a fast-paced, entrepreneurial environmentAble to manage multiple priorities across several businesses simultaneouslyHigh degree of ownership, accountability, and integrityContinuous improvement mindset with a passion for building scalable processesBenefitsWork on meaningful projects that improve healthcare and employee benefitsCompetitive salary and equity opportunityFlexible work hours and remote-first environmentCollaborative, entrepreneurial culture with significant ownership and autonomyOpportunity to help build and scale a growing portfolio of companies alongside experienced leadershipThree weeks (15 business days) paid vacation time offNine paid holidaysEmployer-paid health benefits for employee and family members