Controller, AI-Enabled Finance Operations

About the role

We're hiring a hands-on Controller to own the accuracy, integrity, controls, timeliness, continuity, and daily operation of our finance function. This is not a traditional Controller role built around managing a large accounting department or reviewing work from a distance. It's a working finance-leadership role for someone who can personally own the accounting function, directly manage a Senior Accountant, and progressively operate finance through Claire — our AI finance operator — and modern financial systems.

Responsibilities

• Lead and complete monthly and annual close; deliver a reliable monthly soft close within five business days
• Produce accurate, timely management financial statements
• Review journal entries, accruals, reconciliations, prepaids, fixed assets, and financial reports
• Maintain general-ledger and entity-level integrity; reconcile intercompany activity and balances
• Investigate material variances; document significant accounting judgments and assumptions; coordinate technical questions with outside professionals when needed
• Control and document all post-close adjustments
• Maintain current cash visibility; govern banking access and payment controls; preserve preparer / reviewer / approver / authorized-signer separation; ensure no unauthorized cash movements
• Review payroll execution and accounting; coordinate tax filings and payments with internal and external providers; coordinate Betterment, retirement-plan, and Form 5500 requirements
• Own compliance calendars and deadlines; process finance-related notices; coordinate audits, insurance requests, tax requests, and banking requirements
• Log deadline-bearing records within one business day, assign an owner, set a due date and risk level, escalate before deadline risk, and close with evidence
• Ramp, payables, receivables & expense controls
• Govern vendor creation and approval; ensure entity, location, payment account, vendor owner, and approval path are correct before payment
• Maintain categorization and documentation standards; govern receipt compliance
• Maintain AP/AR visibility; review aging, exceptions, and disputed balances; resolve Ramp/Sage synchronization failures; prevent wrong-entity payments and undocumented intercompany cleanup
• Keep approvals and supporting records in the appropriate system of record; eliminate informal Slack/email/spreadsheet workarounds when an approved system exists
• Develop and govern Claire's finance workflows (categorization, receipt compliance, vendor/GL mappings, reconciliations, follow-ups, close-checklist administration, recurring reporting, exception identification, compliance monitoring, and more)
• Define source of truth, accounting rule, required evidence, approval boundary, normal/exception logic, completion criteria, accuracy standard, audit requirement, and failure response
• For each workflow, define source of truth, accounting rule, required evidence, approval boundary, normal/exception logic, completion criteria, accuracy standard, audit requirement, and failure response
• Ensure Claire's authority expands only after a workflow demonstrates ≥98% accuracy on a meaningful sample, no unauthorized material actions, complete logs, reliable exception identification, correct escalation, and human confirmation of stability
• Identify recurring work to eliminate, simplify, standardize, delegate, automate, transfer into Claire, or convert into controlled exception management
• Inventory recurring workflows; rank improvements by value/risk/feasibility; put ≥2 improvements into production; move ≥3 workflows into Claire-assisted/operated execution; establish ≥1 bounded-autonomy Claire workflow; demonstrate ≥1 measurable reduction in time, manual touches, errors, cycle time, or executive intervention
• Deliver ≥1 material finance-process improvement per quarter
• Maintain a current workload tracker (workstream, deliverable, owner, due date, status, effort, blocker, risk, requested support, next action, recovery date)
• Escalate before a deadline is missed — naming the outcome, deadline, blocker, impact, options/tradeoffs, your recommendation, the decision/support needed, and a proposed recovery date
• Set responsibilities, priorities, deadlines, and quality standards; maintain a role-based responsibility matrix; hold weekly 1:1s; review work; track errors and rework; give direct, evidence-based feedback; develop accounting judgment and systems competence; transfer appropriate recurring execution; build backup coverage; address performance issues within the same operating cycle
• Execute assigned work — you remain accountable for quality, controls, review, escalation, and outcome
• Document & continuity
• Every critical workflow has a primary role, backup role, reviewer/approver, escalation path, source-system references, completion evidence, current operating instructions, and company-controlled access/credentials
• Provide a full handoff before planned time away so finance stays operable during reasonable absences
• Avoid unapproved workarounds when an approved system exists
• Avoid waiting until after a deadline to explain a blocker
• Move quickly without compromising financial integrity
• Build systems that survive personnel changes
• Make yourself less operationally indispensable by strengthening the finance system

Requirements

You'll thrive here if you:

• Are the company's authoritative finance expert
• Personally own outcomes rather than merely advise
• Stay hands-on through the transition
• Lead and develop a Senior Accountant
• Convert recurring work into durable systems
• Treat AI as an operating capability, not a novelty
• Know when human judgment or approval is genuinely required
• Challenge assumptions with evidence and respond constructively when evidence contradicts an initial conclusion
• Escalate risk before it becomes failure
• Move quickly without compromising financial integrity
• Build systems that survive personnel changes
• Make yourself less operationally indispensable by strengthening the finance system

This role is not a fit if you:

• Want to manage a large team
• Require a complete checklist before taking ownership
• Treat automation as IT's job
• View Claire as optional or a threat
• Relate to personal memory or undocumented knowledge
• Wait until after a deadline to explain a blocker
• Protect manual work to stay indispensable
• Have AI enthusiasm but lack Controller-level accounting judgment
• Resist changing how finance work is performed
• Avoid direct performance management
• Can't commit to the schedule, onsite cadence, close standard, and accountability model

Qualifications

Qualifications include:

• Minimum of 5 years of progressive experience in accounting, finance, or a related field
• Experience leading and managing a finance team
• Strong understanding of GAAP and IFRS
• Experience with financial systems and processes
• Excellent analytical and problem-solving skills
• Ability to communicate complex financial concepts to non-financial stakeholders
• Strong attention to detail and ability to manage multiple projects simultaneously
• Experience with financial reporting and analysis
• Experience with budgeting and forecasting
• Experience with financial modeling and analysis
• Experience with financial statement preparation and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis
• Experience with financial risk management
• Experience with financial regulatory compliance
• Experience with financial reporting and analysis