Head of Finance And Accounting

VP/Head Of Finance

We're Jiffy! We launched over a decade ago with a simple mission: use technology to combine an unparalleled level of customer service with the fastest delivery in the blank apparel, direct-to-film transfer, and custom apparel industry. We're more than a T-Shirt company; we're a support system for the creator economy, the home hobbyist, the small business owner, and more. Today, we help millions of small businesses and customers build their vision from scratch!

We are bootstrapped and profitable, no VC playbook, no burn-rate math, which means finance here is a source of truth and a competitive advantage, not a back office.

As our VP/Head of Finance, you'll own the integrity, speed, and intelligence of Jiffy's finances. This is the senior-most seat over accounting and finance: you'll own the month-end close and the general ledger, run the external audit and tax relationships, build the controls the company needs to scale, and serve as the hands-on finance partner to leadership. You'll get the books audit-clean and diligence-ready, modernize and compress the close, and stand up the forecasting and cost-to-serve visibility that tells us where the business is actually making money.

This is a rare, full-spectrum role. It blends controller-grade technical accounting, FP&A and forecasting, controls and governance, and hands-on AI/automation into a single charter — and it is explicitly a builder's seat. You are one accountable, hands-on leader who can close the books, rebuild the controls, model the P&L, and defend the numbers to leadership. A pure, hands-off CFO profile is not what this role needs today;

we will bring a deal-CFO or advisor in for a transaction process if and when we need one.

You'll work very closely with the CEO. We move fast and operate lean, so we need someone who automates instead of adding headcount, sets their own standards, and tells us what the numbers mean before we ask.

Accounting & Close

• Own the month-end close end to end — general ledger, journal entries, reconciliations, accruals, and flux analysis. Our close runs ~130 steps and has already been compressed from 4 days to 2; you'll keep re-sequencing, automating, and tightening it.
• Own the general ledger — keep accounts clean, reconciled, and well-documented, with real-time reconciliation to catch inconsistencies between actuals and what the systems report.

Reporting, FP&A & Unit Economics

• Build and deliver the monthly financial package — full P&L broken out by business unit, with line-item detail that gives leadership real visibility into what's driving results.
• Forecast the total P&L for the upcoming month in partnership with FP&A and General Managers, and stand up a weekly margin/spend signal.
• Own inventory & cost accounting across Jiffy's distribution network — valuation, reserves, shrinkage, and obsolescence — and build COGS and cost-to-serve reporting by product line, channel, facility, and per order.

Controls & Governance

• Be the controls function. Build approval workflows, spend limits, segregation of duties, and exception reporting for unusual activity from scratch — and de-risk company cards and non-approved spend.

Audit, Tax & Transaction Readiness

• Manage the external audit end to end — scope, PBC lists, timeline, auditor communication, and sign-off — and keep the books audit-clean and diligence-ready.
• Own tax compliance coordination across a multi-entity (US + Canadian) structure — serve as the internal quarterback for external tax advisors and prepare standalone financials per entity.
• Lead transaction readiness — data room, QoE prep, and the model — and serve as the finance partner through any deal process.

Cash, AI-Native Finance & Team

• Own cash and treasury — visibility, controls, and a reliable cash forecast.
• Automate instead of adding headcount. Apply AI agents and custom workflows across the finance function — reconciliation, multi-source data gathering, anomaly detection, and month-end automation. Sage Intacct experience is a strong plus.
• Build a lean, AI-first finance team in your image — hiring for both controls rigor and AI-nativeness.

Mandate: get the books audit-clean and diligence-ready, modernize and compress the close, fix the controls that a company can't scale without, and build a lean, AI-first finance function — as one accountable, hands-on leader.

Operating non-negotiables:

• Controls are non-negotiable — approvals, spend limits, and segregation of duties; no card or spend without a control.
• AI-native, not AI-hype — automate the close and reporting and extend the team with tools, with clear judgment about where AI's limits are.
• The leader is hands-on — you personally own the close and controls rebuild, not just manage it.
• Diligence-ready always — the books stay audit-clean and transaction-ready.
• One source of truth — the ERP/GL (Sage Intacct or equivalent) is the system of record; if it isn't in the system, it doesn't exist.