Head of Finance

The Story

Our founders, Alec and Sajan, started Laylo after watching the music industry get strip-mined by platforms that owned the fan relationship and rented it back to artists. We're building the infrastructure for the next generation of entertainment: a direct messaging and CRM layer that lets creators own their audience, drop products to them, and drive real revenue without paying a middleman tax.

Laylo is the drop CRM powering some of the biggest names in music, live events, and entertainment. We replace the patchwork of email, SMS, presave, and tour announcement tools with one platform that lets creators message their fans directly and drive real revenue. Over 10,000 creators use Laylo to drop more than $1B in tickets, merch, and music to millions of fans, including artists like Zach Bryan and Sabrina Carpenter and festivals like Outside Lands.

We're a 24-person team based around the world. We went through Y Combinator (S20) and are backed by Eldridge, Sony, and other top-tier investors.

The Role

You'll be our first dedicated finance hire. You won't be inheriting a team or a playbook. You'll be building the financial infrastructure of a profitable, fast-growing SaaS company from scratch, reporting directly to the CEO.

This role is equal parts operational and strategic. On any given day, you might be modeling the unit economics of a new pricing tier, renegotiating a vendor contract, pressure-testing our hiring plan against runway, or building the framework that tells us whether a $40K SaaS tool is actually earning its keep. Almost every major decision we make has a financial dimension, and you'll be in the room for all of them.

If you get excited about being the single source of truth for a company's financial health, and you want to do it at a company where the product actually matters and we work with the artists you listen to, this is the role.

What You'll Do

• Be a strategic partner to the CEO and department heads on budgets, headcount planning, vendor negotiation, and unit economics. Not a reporter of numbers. A thought partner who happens to know where the money is.
• Lead budgeting and planning cycles. Work with team leads to set budgets, track actuals, and flag variances before they become problems.
• Drive pricing strategy and analysis across our subscription tiers and our AI Agents product (which uses hybrid pricing: $1 + 3% of cart value on successful recoveries). Build the unit economics framework that lets us scale this confidently.
• Audit and optimize our cost structure across headcount, software, infrastructure, and vendor contracts. Know where every dollar goes and whether it's earning its keep.
• Own all financial operations: bookkeeping (we use Pilot, you own the layer above), AP/AR, payroll coordination, expense management, and monthly close.
• Build and maintain our financial model, including revenue forecasting, cash flow projections, and scenario planning.
• Prepare monthly financial reports and investor materials that tell the real story, not just the numbers.
• Build the financial systems and processes that scale with us. Infrastructure that works at 2x and 10x our current size.
• Handle tax compliance, audit prep, and relationships with external accountants and tax advisors.
• Be ready to lead fundraising or M&A workstreams (data rooms, diligence, cap table management) if and when we decide to.

What Makes You Great for This Role

Must haves:

• 5+ years in finance roles, with meaningful time at a venture-backed startup (ideally Seed through Series B).
• You've been the primary or sole finance person before. You know what it means to own everything from AP to board decks.
• Strong financial modeling skills. You can build a model from scratch, not just maintain one someone else built.
• Deep understanding of SaaS metrics: ARR, net revenue retention, gross retention, LTV/CAC, gross margin, magic number, burn multiple, Rule of 40. You think in these terms naturally.
• Experience as a strategic partner to department heads on budgets, headcount planning, and unit economics. You've built budget processes from scratch and held team leads accountable to them without becoming the budget police.
• Track record of meaningful vendor renegotiation and spend optimization. You can name specific wins.
• You're comfortable saying "I don't have enough data yet, here's my best estimate and what would change my mind."

Nice to haves:

• Experience at a profitable or capital-efficient company. Most SaaS finance people only know the burn-and-grow playbook.
• Experience at a company in the creator economy, music, or entertainment space.
• Familiarity with the cost structure of messaging platforms (SMS/MMS costs, infrastructure scaling).
• Direct experience with hybrid or usage-based pricing models for B2B SaaS.
• Experience with fundraising mechanics: SAFEs, convertible notes, priced rounds, cap table management, 409A valuations.
• CPA or equivalent, though we care more about what you've built than what credentials you hold.
• Experience with tools like QuickBooks, Ramp, Carta, Mosaic, Pry, Runway, or similar modern FP&A platforms.

Example Projects

• Pricing overhaul: Analyze our current pricing tiers against usage data, COGS, and competitive positioning. Recommend and model changes that improve gross margin without hurting conversion. Build the unit economics framework for our AI Agents product as it scales.
• Vendor audit: Audit every recurring software and infrastructure cost across the company. Identify redundancies, renegotiate contracts, build the renewal calendar, and create a framework for evaluating new spend.
• Hiring plan: Model the financial impact of our hiring roadmap. Help leadership understand the tradeoffs between speed of hiring, gross margin, and capital efficiency. Build the headcount-to-revenue logic that holds across multiple scenarios.

Growth path

This role is a Head of Finance position with a clear path to VP Finance and CFO as the company scales. If you execute, you grow with the business. We'd rather invest in someone who wants to be here at $30M ARR and $60M ARR than hire a senior person to replace you.