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 & Operations 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, operations, and people functions, 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 and operations leader with startup experience and a passion for building, we would love to chat!

What you’ll do:

Finance & Strategy

• 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)

People Operations & HR

• Own the People Ops function, with an HR Manager reporting directly to you

• Oversee employee onboarding and offboarding end-to-end, ensuring a smooth and consistent experience across the organization

• Partner with hiring managers and leadership on people strategy, compensation benchmarking, and organizational planning

• Maintain and improve HR policies, employee handbook, and compliance with applicable employment laws

IT & Systems Administration

• Serve as IT and tool admin for all corporate and GTM software, overseeing provisioning and de-provisioning of user access

• Manage the company’s SaaS tool stack, including license tracking, usage audits, and vendor relationships

• Lead negotiations for software renewals, working to optimize cost and contract terms across the portfolio

• Establish and maintain processes for tool governance, access controls, and security compliance in partnership with relevant stakeholders

What you’ll bring:

• 8+ years of experience in a leadership role in finance (previously Director/VP/Head of Finance), preferably in the tech/SaaS space

• Expertise in budgeting, forecasting, financial reporting and modeling

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

• Familiarity navigating and leveraging data from CRM (e.g. Salesforce) and ERP systems (e.g. Quickbooks, NetSuite)

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

• Familiarity with SaaS tool administration, vendor management, and software contract negotiation

• Strong communication skills to translate complex financial and operational 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

Nice to haves:

• Experience in the eCommerce/Shopify ecosystem

• Hands-on experience with fundraising and with tax compliance

• Experience managing or overseeing HR/People Ops functions, including onboarding, offboarding, and employee lifecycle management

Why join us?:

• Own the systems, processes, and financial infrastructure that hundreds of DTC brands indirectly depend on

• High autonomy: you'll set the direction, bring the recommendations, and be the person the business looks to for answers

• Strategic impact: you'll be a close strategic partner to the executive team, brought into the conversations that shape the direction of the company

• Cross-functional influence: you'll be the connective tissue between finance, ops, and people strategy, with the scope to drive cohesion across the business