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 technical accounting, FP&A and forecasting, controls and governance, and hands-on AI/automation into a single charter and it's a builder's seat. You are one accountable, hands-on leader who can close the books, rebuild the controls, model the P&L's of a multi entity organization, and defend the numbers to leadership. A pure, hands-off CFO profile is not what we are looking for.

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

• Work with our Controller to own the month-end close end to end — general ledger, journal entries, reconciliations, accruals, and flux analysis. 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: Modernize and compress the close, fix the controls that a company can't scale without, and build a lean, AI-first finance function as an 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 work with our Controller to own the close and controls rebuild, not just manage it.
• Diligence-ready always — the books stay audit-clean
• One source of truth — the ERP/GL (Sage Intacct) is the system of record; if it isn't in the system, it doesn't exist.

Requirements

Basic Qualifications

• Bachelor's degree in Accounting or Finance; CPA strongly preferred
• 8+ years of progressive accounting and finance leadership, including personally owning a month-end close and an external audit relationship end to end
• Direct, hands-on inventory accounting and cost accounting experience in a product-based, distribution, or ecommerce environment
• Demonstrated ability to build controls and processes from scratch — approval workflows, spend limits, segregation of duties, exception reporting — not just inherit and maintain them
• Current, concrete examples of AI/automation changing how finance work gets done, with judgment about its limits, not hype, not skepticism
• Multi-entity experience (e.g., US + Canadian entities, intercompany) preparing standalone financial statements
• Advanced Excel and financial modeling; comfortable owning P&L forecasting and business-unit reporting
• A hands-on builder who thrives with one finance seat and broken processes — you'd rather fix and automate than staff around a problem
• Previous experience with a company selling physical goods
• Exceptional communication — you can explain what the numbers mean to leadership and defend them with evidence

Preferred Qualifications

• Transaction experience, data room, quality-of-earnings, and diligence; have supported or led a deal process
• Sage Intacct experience
• Demonstrated use of AI agent-building tools / custom workflows in finance (pulling data, reconciling across sources, flagging anomalies)
• FP&A partnership with General Managers and cost-to-serve / unit-economics modeling
• Experience in ecommerce, apparel, or product distribution
• Experience building a lean finance team at a bootstrapped, profitable, rapid-scale company

Benefits

The base compensation for this role is expected to range from $215,000 - $270,000 per year. Actual compensation will be based on a variety of factors, including skills, experience, qualifications, and overall fit for the role.

Total compensation may include base salary, performance-based bonuses, equity, and benefits. Final offers are tailored to each candidate and take into consideration their background and years of experience.

Comprehensive Benefits: Full medical, dental, and vision coverage, with a portion of premiums paid by Jiffy.

Retirement Planning: 401(k)

Wellness Support: Annual wellness benefits to help you stay healthy and balanced.

Tools for Success: Choice of MacBook or PC laptop, plus equipment for your home office setup.

Perks & Extras: Annual credit of $200 to use on our website plus more team merch drops than you will know what to do with!

Professional Development: Annual stipend to support your learning and career growth.

EEO

Jiffy is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristics. Jiffy considers qualified applicants with criminal histories, consistent with applicable federal, state and local law.