Chief of Staff

Raspberry AI is a generative AI design platform built for fashion brands and retailers. We help design, merchandising, and product development teams move faster — from concept to market-ready assets — using industry-leading AI. Some of the world's top fashion brands rely on Raspberry AI to streamline their workflows and accelerate product development.

We closed $24 million in Series A from a16z, plus $5 million seed rounds from Khosla Ventures and Greycroft Ventures. Other investors include REVOLVE and Reformation founders, and the President of Saks Fifth Avenue. For more information, visit raspberry.ai.

• Be an owner: We take responsibility for outcomes, not just tasks. We don't wait for permission — we step up, move fast, and hold ourselves accountable to results.

• Bias to solution: We're solutions-oriented at heart. We go beyond identifying problems to actively unblocking ourselves and others.

• Customer obsession: Everything we build starts with the customer. We listen deeply, move quickly, and obsess over delivering tools that make their work faster and more creative.

• Lowest level of detail: We're not afraid to get in the weeds. Great work comes from people who notice what others miss and ask deeper questions.

• 1% better every day: Progress compounds. We stay curious, ask for feedback, and look for the small improvements that make tomorrow better than today.

• AI first: We use AI across the entire company — from product to growth to operations — to move faster and produce higher-quality work.

• Innovative culture: A generational opportunity to define the role of AI in one of the world's largest industries.

• Growth paths: Opportunities to drive impact well beyond your immediate role as the company scales.

• Learning & development: Annual discretionary stipend for professional development.

• Annual company offsite: We bring the whole team together once a year

We are looking for a Chief of Staff to work closely with the CEO and executive team on the most important strategic and operational priorities of the company. This role sits at the center of the organization and helps translate company strategy into execution across product, go‑to‑market, finance, and operations.

Responsibilities

• Partner directly with the CEO to drive the company’s highest‑priority initiatives

• Translate strategic goals into structured execution plans across teams

• Lead cross‑functional projects spanning product, finance, operations, and GTM

• Develop internal operating cadences including planning cycles, OKRs, and executive reporting

• Build analytical models and decision frameworks to support company leadership

• Drive investor and board preparation including materials, metrics, and analysis

• Identify operational bottlenecks and implement scalable processes

• Act as a connective layer between leadership and the broader team to ensure alignment and clarity

• 6+ years of professional experience in highly analytical and fast‑paced environments

• Strong financial modeling, analytical, and structured problem‑solving skills

• Experience working closely with senior leadership on strategic initiatives

• Comfort operating in ambiguous startup environments with high ownership

• Excellent communication skills and ability to influence across teams

• Demonstrated ability to move between strategy and hands‑on execution