Director of Special Projects/ Chief of Staff
About Autumn
We’re building an AI-native operating system for hotels, backed by Tier 1 investors including Bessemer and Sequoia.
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 that are essential for unlocking scale.
This role is for someone who wants to operate like an early founder, a problem solver who is energized by the variety and velocity of early-stage work.
What You’ll Do
You will be responsible for defining the problem, setting success metrics, executing the work, and operationalizing it for scale! Examples incl.:
- Lead cross-functional initiatives that require strategy, structure, and hands-on execution
- Build internal systems and processes that create leverage and reduce founder bottlenecks
- Analyze data across product, customers, and GTM to surface insights and recommend direction
- Design and implement workflows that improve operations as we grow
- Identify gaps in our tooling or processes and proactively solve them
- Partner closely with product to turn customer insights into roadmap clarity
- Experiment with creative growth ideas and execute lightweight tests quickly
- Source, manage, or coordinate external partners when needed (designers, vendors, contractors)
- Increase the CEO’s capacity by owning high-trust, high-complexity workstreams end-to-end
Who You Are
You likely come from one of these backgrounds
- Top-tier consulting or IB with strong execution instincts
- Chief of Staff, Strategy & Ops, or Special Projects at a fast-growing startup
- Former founder or early employee who enjoys broad responsibility
- 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
- Creating structure where none exists
- Solving real customer and product challenges without a detailed playbook
Traits
- Exceptionally resourceful and proactive
- Analytical, structured, and able to synthesize clearly
- Fast learner, especially with new tools and systems
- Strong communicator and cross-functional collaborator
- High-velocity operator with an owner mindset
- Comfortable making decisions with imperfect information
Skills & Experience
- 2–5 years in consulting, special projects, product ops, CoS, strategy & ops, or similar
- Strong data analysis ability (Excel/Sheets, funnel analysis, cohorting, win/loss, etc.)
- Experience designing or improving processes and internal systems
- Strong project management and prioritization skills
- Comfort learning and using tools (CRM, billing, automation, no-code, analytics, etc.)
- 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
- Ownership and 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 this sounds like you or someone you know: email Maura (Co-founder & CEO), maura@autumnplatform.com