Chief of Staff

Vannin Chief of Staff has been retained by a Prop Tech company that streamlines operations for vacation rental and property management companies through global talent solutions and innovative software. Our client is seeking a Chief of Staff to serve as a strategic partner to the Founder/CEO during a critical period of organizational transformation and growth. Reporting directly to the CEO, this role will drive alignment across the organization, facilitate cross-functional execution, and act as a strategic thought partner.

The ideal candidate combines consulting-caliber problem‑solving with scrappy, hands‑on execution. You’ll thrive in ambiguity, influence without formal authority, and bring a bootstrapped mentality that values outcomes over process. This is an opportunity to be a true partner to the CEO while building and optimizing the operating rhythm, driving accountability, and leading strategic initiatives and change management as the company transitions from a traditional services model to SaaS.

This is a full-time exempt position based in Miami, FL (4 days/week onsite in downtown Miami).

• Strategic Alignment and Operational Excellence
  • Drive organizational alignment to company vision and strategic priorities; facilitate weekly leadership meetings and manage quarterly priorities across teams
  • Build accountability systems across the leadership team; hold leaders to commitments and ensure follow‑through
  • Partner closely with C‑suite executives and cross‑functional teams on strategic initiatives/special projects
  • Act as a thought partner to CEO on company strategy, organizational design, people operations, and business model evolution
  • Create and maintain operating rhythm: establish cross‑functional communication and execution cadence that scales
  • Seek areas for improvement and innovation to make the overall business run more smoothly and drive growth
• Cross‑Functional Execution and Change Management
  • Facilitate cross‑functional execution and break down silos between service and product teams
  • Own change management initiatives as the company transitions from labor‑intensive service model to SaaS/automation – tech‑enabled solutions
  • Drive organizational communication and change narratives that create clarity and commitment to company priorities
  • Build stakeholder management excellence across a distributed global team spanning multiple time zones and geographies
  • Build a new high‑performing small internal strike team in Miami that drops into the company’s highest‑leverage problems to help the company 2x in revenue in 12 months
• Hands‑on Problem Solving and Data‑driven Analysis
  • Use data to identify trends, bottlenecks, and opportunities that drive smarter decisions and operational improvements.
  • Translate analysis into clear, actionable recommendations for the CEO and leadership team
  • Leverage technology, automation, and no‑code tools (e.g., Notion, Twilio, n8n, Airtable, AI platforms) to prototype solutions and increase team productivity
  • Collaborate with the Head of Finance on Financial Planning & Analysis (FP&A) and key business metrics
  • Translate overall business objectives into specific, actionable Key Performance Indicators (KPIs) and measurable targets for each department to ensure the company achieves its strategic goals

• Prior Chief of Staff experience (or equivalent right‑hand strategic role to a CEO/Founder)
• 8 years professional work experience with prior Management Consulting experience (MBB or Big 4 preferred)
• Startup experience, ideally with bootstrapped or profitable companies (not just VC‑funded hyper‑growth)
• Demonstrated cross‑functional program ownership and project/change management experience
• Prior experience with operating frameworks (EOS, OKR, or similar)
• Strong analytical skills; able to extract and interpret data from multiple sources (SQL, dashboards, or reports) to surface insights and improve responsiveness across the business
• Exceptional written and verbal communication skills; able to translate complex ideas simply, articulate the company vision, and ensure clarity across global teams

• Experience in Prop Tech, SaaS, or…