Chief of Staff, Product & Operations

Dragin is looking for a Chief of Staff to work directly with the founder on product direction, team execution, communication, and organizational rhythm. This role is located in Cedarhurst, NY and is a full-time in-office role.

This is a unique role for someone who is highly organized, deeply curious, people-oriented, and excited to sit at the center of a fast-moving product company. You will act as a force multiplier for the founder: helping clarify priorities, keep teams aligned, organize product thinking, manage follow-through, and make sure the right things are moving forward at the right time.

While this role carries the title Chief of Staff, it has a strong product and strategy component. You do not need to come in as a traditional Head of Product, but you should be comfortable getting close to product decisions, understanding what is being built, asking sharp questions, and helping translate ideas into priorities, plans, and execution.

You will work closely with the founder to keep the company organized, aligned, and focused.

Your responsibilities will include:

• Helping organize and prioritize product ideas, customer feedback, internal requests, and founder-led initiatives.
• Staying on top of what is being built across the company and ensuring priorities are clear.
• Acting as a communication bridge between the founder and the team.
• Preparing notes, agendas, follow-ups, and decision summaries so that meetings turn into action.
• Helping manage staff communication, team expectations, and internal operating rhythms.
• Tracking key initiatives and making sure owners, deadlines, and next steps are clear.
• Helping the founder think through what should be prioritized, paused, delegated, or clarified.
• Identifying gaps in process, communication, or execution and proposing better ways to operate.
• Supporting product strategy by learning the business, the customers, and the company’s long-term vision.
• Creating structure around fast-moving ideas without slowing down momentum.

You are someone who brings order to ambiguity.

You may have worked in product, operations, strategy, consulting, startup leadership, project management, or a founder-facing role. Your exact background matters less than your judgment, communication style, and ability to keep many moving pieces organized.

You are likely a strong fit if you:

• Have impeccable organizational skills.
• Communicate clearly, directly, and thoughtfully.
• Are comfortable working closely with a founder or senior executive.
• Can turn scattered thoughts into clear priorities and action items.
• Are good with people and can manage relationships with maturity and discretion.
• Are curious about product and willing to learn the details of what we are building.
• Can understand technical/product conversations even if you are not an engineer.
• Are proactive and do not wait to be told what needs attention.
• Can keep track of many parallel workstreams without losing the details.
• Know how to push back respectfully when priorities are unclear or unrealistic.
• Are comfortable in a fast-moving environment where the answer is not always obvious.

Required:

• Excellent written and verbal communication skills.
• Strong organizational and follow-through abilities.
• High judgment, discretion, and emotional intelligence.
• Ability to work in person from our office.
• Comfort working across product, operations, and team management.
• Ability to synthesize conversations into clear decisions and next steps.

Nice to have:

• Experience at a startup or fast-growing company.
• Experience in product management, product operations, business operations, consulting, or strategy.
• Experience working directly with a founder, CEO, or executive team.
• Familiarity with software development workflows.
• Comfort with AI, automation, or productivity tools.

In this role, success means the founder is clearer, the team is more aligned, and the company is moving faster with less confusion.

You will help make sure that ideas do not get lost, priorities do not remain vague, and people know what matters most. Over time, you should become someone who deeply understands how Dragin thinks, builds, and operates — someone who can anticipate what needs to happen next and help drive it forward.

Dragin is building quickly, and the company needs someone who can sit close to the center of product, people, and execution.

This role is for someone who wants responsibility, context, and influence. It is not a narrow administrative role. It is a high-trust position for someone who can help shape how the company operates and how decisions become reality.

Please apply with your resume and a short note explaining why this type of founder-facing, product-adjacent Chief of Staff role is exciting to you.

In your note, we would especially love to hear about a time when you brought structure to a messy or fast-moving situation.