Director of Special Projects

Director of Special Projects / Chief of Staff
Location: New York City
Company: AI Native Operating System for Hotels

About US
We’re building an AI-native operating system for hotels, backed by Tier 1 investors including Bessemer and Sequoia, and already serving independent hotels across the US, MX, and CA. We move fast, build ambitiously, and operate with extreme ownership. This role sits at the center of that.

Role Overview
We are hiring a Director of Special Projects / Chief of Staff to serve as the CEO’s right hand and execute the highest-leverage initiatives across the company. This role is ideal for someone who thrives in ambiguity, has a strong strategic mind, and loves rolling up their sleeves to build. You will take on mission-critical projects essential for unlocking scale. You will be given clear outcomes, not long briefs, and are expected to move from problem to shipped solution swiftly. This is for someone who wants to operate like an early founder — a problem solver energized by the variety and velocity of early-stage work.

What You’ll Do
You will be responsible for understanding problems, defining success metrics, executing the work, and operationalizing it for scale. Examples include:
• Leading cross-functional initiatives requiring strategy, structure, and hands-on execution
• Building internal systems and processes that create leverage and reduce founder bottlenecks
• Analyzing data across product, customers, and GTM to surface insights and recommend direction
• Designing and implementing workflows that improve operations as we grow
• Identifying gaps in our tooling or processes and proactively solving them
• Partnering closely with product to turn customer insights into roadmap clarity
• Experimenting with creative growth ideas and running lightweight tests quickly
• Sourcing, managing, or coordinating external partners when needed
• Increasing the CEO’s capacity by owning high-trust, high-complexity workstreams end-to-end

Who You Are
You likely come from backgrounds such as:
• Top-tier consulting or investment banking with strong execution instincts
• Chief of Staff, Strategy and Ops, or Special Projects at a fast-growing startup
• A product/ops hybrid with strong analytical and systems-thinking skills

You thrive when:
• Given high autonomy and high ambiguity
• Switching between strategic problem-solving and hands-on building
• Taking on projects that cut across functions
• Being told the outcome and determining the fastest path to deliver it
• Creating structure where none exists
• Solving customer and product challenges without a detailed playbook

Traits
• Exceptionally resourceful and proactive
• High-velocity operator with an owner mindset
• Analytical, structured, and able to synthesize clearly
• Fast learner with new tools and systems
• Strong communicator and cross-functional collaborator
• Comfortable making decisions with imperfect information

Skills and Experience
• 2–5 years in consulting, special projects, product ops, CoS, strategy and ops, or similar
• Strong data analysis ability
• Experience designing or improving processes and internal systems
• Strong project management and prioritization skills
• Ability to manage cross-functional work and external vendors with minimal oversight

What We Offer
• Work directly with the CEO as a key strategic partner
• Massive impact across the business
• Competitive salary
• A front-row seat to building an AI-native vertical SaaS company
• A role that evolves as quickly as the company does

If transforming how an entire industry runs, empowering indie hotels to survive and win, and shaping the foundation of a venture-backed startup excites you, we’d love to speak.