Chief of Staff

Vannin Chief of Staff has been retained by a PropTech 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).

Responsibilities

• 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 that would help the company to 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

Recommended Minimum Qualifications

• 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
  
  

Preferred Skills & Attributes

• Experience in PropTech, SaaS, or tech-enabled services preferred

• Proven ability to juggle multiple projects and meet tight deadlines, showcasing strong ownership, attention to detail, and time-management capabilities

• Skilled in professional and diplomatic written and verbal communication, capable of engaging effectively with a diverse range of stakeholders with high executive presence

• Self-starter and self-motivated with a proactive approach to identifying and addressing issues

• Confident yet humble; able to manage up, hold leaders accountable, and maintain composure under pressure

• A natural curiosity to learn more about technology, AI automation and data trends

• Available to work onsite in Miami 4 days/week

• Ability to travel internationally up to 25% or as needed - Must have valid travel documentation and ability to travel internationally to Europe, LatAM, UK, etc. without restrictions

Compensation Range: $160-220K/yr + bonus

What to Expect from Our Selection Process

The process includes:

1. Vannin Chief of Staff Predictive Index Behavioral Assessment
2. Vannin Chief of Staff Screening: 15 min phone interview & 30 min video interview
3. Client Interview 1: Interview with Founder & CEO (in-person preferred)
4. Client Interview 2: Virtual block interview with senior leaders
5. Client Interview 3: Final in-person interview with Founder & CEO with case study

*Note: Vannin Chief of Staff partners with The Predictive Index to align workstyles with the role. All applicants complete this quick, two-question, five-minute assessment—no right or wrong answers—and receive a profile readout.

--> Please take the assessment here as you complete your application.

Our client is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves! We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.