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
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
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
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
Preferred Skills & Attributes
Compensation Range : $160-220K/yr + bonus
What to Expect from Our Selection Process
The process includes:
1. Vannin Chief of Staff
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.
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