Director of Finance & Operations

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…