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).ResponsibilitiesStrategic Alignment and Operational Excellence Drive organizational alignment to company vision and strategic priorities; facilitate weekly leadership meetings and manage quarterly priorities across teamsBuild accountability systems across the leadership team; hold leaders to commitments and ensure follow-throughPartner closely with C-suite executives and cross-functional teams on strategic initiatives/special projectsAct as a thought partner to CEO on company strategy, organizational design, people operations, and business model evolutionCreate and maintain operating rhythm: establish cross-functional communication and execution cadence that scalesSeek areas for improvement and innovation to make the overall business run more smoothly and drive growthCross-Functional Execution and Change Management Facilitate cross-functional execution and break down silos between service and product teamsOwn change management initiatives as the company transitions from labor-intensive service model to SaaS/automation – tech-enabled solutionsDrive organizational communication and change narratives that create clarity and commitment to company prioritiesBuild stakeholder management excellence across a distributed global team spanning multiple time zones and geographiesBuild 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 monthsHands-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 teamLeverage technology, automation, and no-code tools (e.g., Notion, Twilio, n8n, Airtable, AI platforms) to prototype solutions and increase team productivityCollaborate with the Head of Finance on Financial Planning & Analysis (FP&A) and key business metricsTranslate overall business objectives into specific, actionable Key Performance Indicators (KPIs) and measurable targets for each department to ensure the company achieves its strategic goalsRecommended Minimum QualificationsPrior 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 experiencePrior 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 businessExceptional written and verbal communication skills; able to translate complex ideas simply, articulate the company vision, and ensure clarity across global teamsPreferred Skills & AttributesExperience in PropTech, SaaS, or tech-enabled services preferredProven ability to juggle multiple projects and meet tight deadlines, showcasing strong ownership, attention to detail, and time-management capabilitiesSkilled in professional and diplomatic written and verbal communication, capable of engaging effectively with a diverse range of stakeholders with high executive presenceSelf-starter and self-motivated with a proactive approach to identifying and addressing issuesConfident yet humble; able to manage up, hold leaders accountable, and maintain composure under pressureA natural curiosity to learn more about technology, AI automation and data trendsAvailable to work onsite in Miami 4 days/weekAbility 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 restrictionsCompensation Range$160-220K/yr +bonusWhat to Expect from Our Selection ProcessThe process includes:Vannin Chief of Staff Predictive Index Behavioral AssessmentVannin Chief of Staff Screening: 15 min phone interview & 30 min video interviewClient Interview 1: Interview with Founder & CEO (in-person preferred)Client Interview 2: Virtual block interview with senior leadersClient 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 a quick, two-question, five-minute assessment—no right or wrong answers—and receive a profile readout. 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.J-18808-Ljbffr