Director of Finance (Remote, USA)

Who we are:

Stay AI is powered by savvy DTC industry vets, who have each been building subscription programs for over ten years. We’ve worked with over 300+ subscription-focused CPG brands that have generated hundreds of millions in subscription revenue alone. Our product is shaped by lifelong marketers who specialize in acquisition and retention, not developers—and it shows.

We have amazing investors like Telescope Partners, with participation from Boulder Food Group, Riverpark Ventures, and Vanterra Capital. Previous investments were led by Watchfire Ventures, alongside industry leaders such as Nik Sharma (Sharma Brands) and Adam Turner (Postscript).

We are not afraid of challenging work and are excited to build the next big thing. Sound good to you? Then, please read more about our role!

Our culture:

We are dedicated to our work, but equally committed to celebrating our achievements. Collaboration is at the heart of everything we do, as we firmly believe in the power of teamwork. While we are remote-first as a company, we try to create opportunities to meet each other. That's why we organize annual offsite retreats in the beautiful setting of Park City and Mexico!

Who you are:

We're looking for a Director of Finance to join our leadership team and play a key role in scaling our company. Reporting directly to Gina Perrelli, Stay’s CEO, you'll own all aspects of financial strategy and operations, ensuring we have the insights and structure needed for sustainable growth. You'll be a strategic partner in driving our next stage of expansion. If you're a hands-on finance leader with startup experience and a passion for building, we would love to chat!

What you’ll do:

• Own FP&A, financial modeling, and long-term planning

• Lead investor reporting and board-level financial presentations

• Manage cap table administration and equity matters

• Oversee upkeep and ongoing refinement of KPI scorecard reporting and financial dashboards

• Support strategic initiatives (Cross-functional strategic / analytical support, M&A, fundraising)

• Oversee legal, insurance, and compliance matters as needed

• Lead audit process

• Support variable compensation plan development and execution (i.e. monthly & quarterly commission calculations)

What you’ll bring:

• 10+ years of experience in a leadership role in finance (previously Director/VP/Head of Finance), preferably in the tech/SaaS space. Experience in the eCommerce/Shopify ecosystem is a plus

• Hands-on experience with fundraising, expertise in financial modeling, and experienced with tax compliance

• Expertise in budgeting, forecasting, and financial reporting

• Experience partnering with the CEO and executive team to drive strategic decision-making

• Experience in scaling financial systems and processes in a fast-paced environment.

• Strong communication skills to translate complex financial insights into actionable business strategies

• Ability to thrive in a dynamic startup environment, demonstrating adaptability, curiosity, and a willingness to take initiative

• Excellent problem solving skills and the ability to effectively communicate complex concepts across cross-functional teams

Why Join Us?:

• The opportunity to make a huge impact at a high-growth startup

• Working alongside Stayers who are fun and collaborative

• Contribute to the growth of our product as we scale quickly

• Own and scale our content marketing strategy and team