Controller, AI-Enabled Finance Operations

Job Description

Job Description:\n\nLovingly is an AI-driven emotional commerce platform serving around 1,000 independent florists across the U.S. and Canada. We provide platformed websites, point-of-sale, and digital marketing services that help local florists win in their local markets while building a consumer brand that customers return to.\nWe operate at the intersection of local commerce, technology, and emotionally meaningful moments. Our partners are florists — and the work we do for them shows up at weddings, funerals, birthdays, and every moment in between.\nWe're a B2B technology platform. We build systems, not one-off campaigns, and we use AI as a core part of how we operate, not as a buzzword. In finance, that means taking our operations from chaos to clarity — systems that just run.About the Role\nWe're hiring a hands-on Controller to own the accuracy, integrity, controls, timeliness, continuity, and daily operation of our finance function.\nThis 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.\nYou remain accountable for the finance outcome whether the underlying work is done by you, your Senior Accountant, Claire, an outside provider, or another system. The initial mix is roughly 75% finance stabilization and control, 25% systems, automation, and Claire development, shifting after stabilization to roughly 65% finance reliability and control, 35% systems, automation, team development, and leverage creation.The Operating Model\nWe're building a finance function where routine work is increasingly performed through intelligent systems, while human expertise concentrates on financial truth, judgment, controls, exceptions, analysis, compliance, and business decisions.\nClaire is Lovingly's progressively autonomous AI finance operator — not a writing assistant or optional productivity tool. Claire is being developed to independently perform defined finance workflows as she demonstrates sufficient accuracy, control compliance, auditability, and reliability. You'll be the accountable finance-domain owner of Claire's operating performance. Technical infrastructure may be built in partnership with the CEO and technology leadership, but finance-domain correctness, accounting rules, control design, workflow validation, exception handling, and operating outcomes are yours.Your Mission\nBuild and operate a finance environment that is accurate, timely, visible, controlled, documented, transferable, independently verifiable, and increasingly executed through Claire and approved systems rather than recurring manual dependency. Success means finance keeps running reliably without depending on one person's memory, private knowledge, availability, or personal workarounds.What You'll OwnAccounting & financial reporting\n\n Lead and complete monthly and annual close; deliver a reliable monthly soft close within five business days.\n Produce accurate, timely management financial statements.\n Review journal entries, accruals, reconciliations, prepaids, fixed assets, and financial reports.\n Maintain general-ledger and entity-level integrity; reconcile intercompany activity and balances.\n Investigate material variances; document significant accounting judgments and assumptions; coordinate technical questions with outside professionals when needed.\n Control and document all post-close adjustments.\nFinancial integrity\n\n Maintain zero known unresolved material misstatements — errors documented, corrected, root-caused, and evaluated for control remediation.\n Keep a correction log: error, financial impact, root cause, correction date, reviewer, whether a control must change, and whether similar transactions need review.\nCash, banking, payroll, tax & compliance\n\n Maintain current cash visibility; govern banking access and payment controls; preserve preparer / reviewer / approver / authorized-signer separation; ensure no unauthorized cash movements.\n Review payroll execution and accounting; coordinate tax filings and payments with internal and external providers; coordinate Betterment, retirement-plan, and Form 5500 requirements.\n Own compliance calendars and deadlines; process finance-related notices; coordinate audits, insurance requests, tax requests, and banking requirements.\n 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.\nRamp, payables, receivables & expense controls\n\n Govern vendor creation and approval; ensure entity, location, payment account, vendor owner, and approval path are correct before payment.\n Maintain categorization and documentation standards; govern receipt compliance.\n Maintain AP/AR visibility; review aging, exceptions, and disputed balances; resolve Ramp/Sage synchronization failures; prevent wrong-entity payments and undocumented intercompany cleanup.\n Keep approvals and supporting records in the appropriate system of record; eliminate informal Slack/email/spreadsheet workarounds when an approved system exists.\nWorking through Claire\n\n 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).\n 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.\n Claire's authority normally 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. The threshold rises with a workflow's financial risk.\nSystems, automation & capacity recapture\n\n Continuously identify recurring work to eliminate, simplify, standardize, delegate, automate, transfer into Claire, or convert into controlled exception management.\n First 90 days: 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.\n After stabilization, deliver ≥1 material finance-process improvement per quarter. Recaptured capacity converts into company value (greater output, faster completion, higher accuracy, stronger controls, less executive intervention, more time on judgment and leadership).\nWorkload transparency & escalation\n\n Maintain a current workload tracker (workstream, deliverable, owner, due date, status, effort, blocker, risk, requested support, next action, recovery date).\n 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.\nManaging the Senior Accountant\n\n 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.\n The Senior Accountant may execute assigned work — you remain accountable for quality, controls, review, escalation, and outcome.\nDocumentation & continuity\n\n 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.\n Within 90 days, all critical workflows documented or on an approved remediation plan, and independently executable by a qualified backup without private narration from you.\n Provide a full handoff before planned time away so finance stays operable during reasonable absences.\nSystems & policy adoption\n\n Adopt and actively use all approved company systems, policies, security requirements, communication tools, and standard workflows. Escalate genuine blockers promptly; unapproved workarounds aren't acceptable when an approved system exists.\nWork Schedule & Onsite Cadence\nFull-time, exempt: Monday–Friday, 8:00 a.m. – 5:30 p.m. Eastern Time (paid-lunch policy applies). Onsite Monday, Tuesday, and Friday at our Hopewell Junction, NY office; Wednesday and Thursday ordinarily remote unless business needs require more onsite presence. Remote days carry the same availability, responsiveness, meeting, output, and deadline expectations as onsite days. Because this role owns deadline-sensitive operations, occasional evening/weekend availability may be required during close, payroll, tax deadlines, audits, banking incidents, compliance events, or material finance issues — event-driven, not a substitute for planning, backup coverage, or timely escalation. Schedule/cadence exceptions must be approved in advance.What Success Looks Like\n\n 30 days: finance-workflow inventory, close map, source-system map, access/authority matrix, risk register, workload tracker, Claire assessment, and a responsibility matrix across Controller, Senior Accountant, Claire, executive, and external providers.\n 60 days: completed a close on the documented calendar; weekly finance heartbeat; ≥2 Claire-assisted/automated workflows in production; updated critical SOPs; established preparer/reviewer/approver/signer/escalation paths; Senior Accountant responsibilities and review standards set; ≥1 source of recurring manual work or rework reduced.\n 90 days: reliable five-business-day soft close; ≥3 workflows in Claire-assisted/operated execution; ≥1 bounded-autonomy Claire workflow; measurable improvement in time/touches/errors/cycle time/backlog/executive intervention; critical workflows documented or on remediation plans; measurable Claire standards; Senior Accountant development plan; six-month finance-systems and Claire roadmap.\n Ongoing: an evidence-backed monthly scorecard (close, integrity, reconciliations, corrections, compliance, cash controls, backlog, escalation, Claire performance, manual-work reduction, documentation, continuity, Senior Accountant development, executive-intervention reduction).\nThe Person We're Looking For\nYou'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; and make yourself less operationally indispensable by strengthening the finance system.\nThis role is not a fit if you want to manage a large team rather than stay hands-on; define success as completing tasks without owning the outcome; require a complete checklist before taking ownership; treat automation as IT's job; view Claire as optional or a threat; rely on 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; or can't commit to the schedule, onsite cadence, close standard, and accountability model.Role Evolution\nAs Claire and other systems earn more responsibility, your operating mix evolves toward financial judgment, exception management, control governance, financial analysis, cash and risk decisions, compliance oversight, Senior Accountant development, finance architecture, and governance of Claire's authority. Transferring routine work doesn't reduce the role's importance — it raises the altitude at which you operate.Selection Process\nExpect an evidence-based process that may include a Controller accounting/close exercise, a finance-control design exercise, a Claire workflow-design exercise, a Senior Accountant management scenario, verification of significant résumé claims, structured references, verification of claimed licenses/credentials, and a written acknowledgment of the schedule, onsite cadence, close standard, reporting structure, and AI-enabled operating model.Final Accountability Standard\nYou own the finance outcome. Delegation to the Senior Accountant, Claire, approved systems, or outside professionals doesn't transfer final accountability for financial accuracy, close reliability, controls, evidence, compliance, escalation, continuity, team performance, Claire's operating quality, and reduction of avoidable manual dependency. You'll be evaluated not on whether tasks got done, but on whether Lovingly has a finance operating environment that is accurate, timely, visible, controlled, documented, transferable, independently verifiable, AI-enabled, and resilient.\nRequirementsRequired experience\n\n Significant accounting-operations experience — ideally as a Controller, Assistant Controller, or senior Accounting Manager.\n Demonstrated ownership of month-end close and financial reporting.\n Strong practical knowledge of general accounting and GAAP.\n Experience reviewing journal entries, accruals, reconciliations, prepaids, fixed assets, and financial statements.\n Experience with cash, banking, payroll, AP, AR, and tax coordination.\n Multi-entity accounting or equivalent complexity.\n Experience managing, reviewing, or developing accounting employees.\n Experience improving finance processes and systems.\n Ability to document complex procedures and accounting judgments clearly.\n Strong judgment on materiality, approvals, controls, evidence, and exceptions.\n Ability to operate both strategically and hands-on.\n Comfort working directly with AI-enabled systems, and the discipline to test AI output against source evidence rather than accept it at face value.\n Ability to operate effectively in a lean environment without a large support team.\n Willingness to meet the required schedule and onsite cadence.\nPreferred experience\n\n Ramp, Sage, ADP, Betterment, KeyBank, J.P. Morgan bill pay, Adyen, or comparable platforms.\n Implementing accounting automation or workflow systems.\n Working with AI agents, generative AI, or structured automation.\n Growing, privately held company