Chief of Staff to CEO

Who We Are

At Bennett Data Science, we've been pioneering the use of AI, predictive analytics, and data science for over a decade for some of the biggest brands and retailers. We're at the top of our field because we focus on delivering actionable AI for our clients. Our deep experience and product-first attitude set us apart from other groups and gets us the business results our long-term clients want.

Why You Should Work With Us

You'll be exposed to a wide range of clients who are at the cutting edge of innovation in their field and get to work on fascinating problems, supporting real products, with real data. We help lots of companies, from some of the largest companies in the world to small startups in Silicon Valley who are building the next big thing.

The role:

I am looking for a full-time Chief of Staff who will become my direct extension. I run strategy, business development, and client relationships across multiple active engagements and multiple companies. I need a senior operator to take operations off my plate. The means ownership of appointments, calendars, client follow-up, pipeline tracking, document prep, HR, invoices and more. This roal carries real trust. You will be a part of maintaining client relationships, financial milestones, and business decisions.

The right candidate becomes a direct working partner with me, the delivery team, and our clients, and over the first six months grows into a deputy-COO posture that runs the operating rhythm of the firm. What you will do:

• Manage my messages as the primary daily interface: triage, draft, respond, follow up, archive
• Draft correspondence on my behalf to Fortune 500 clients, PE firms, and senior executives
• Own the weekly calendar across Pacific, Eastern, and European time zones; protect my deep work blocks; resolve conflicts without direction
• Track and prioritize every to-do or action item coming from every meeting and make sure each is completed
• Work alongside PM to keep pipeline deal stages, next actions, and dates current; flag stale deals before I do and suggest a reach-out cadence ensuring nothing gets forgotten or lost
• Prepare short morning briefs: meetings, context, open items, priorities
• Format SOWs, decks, briefing memos, and meeting prep packets; catch typos, wrong values, and unsigned attachments before they go out
• Support new hire onboarding logistics, contractor agreements, simple invoicing follow-ups, vendor coordination
• Turn weekly recaps into living checklists so the team can run without me
• Use AI tools such as Claude, Gemini, or ChatGPT to help with research, drafting, and prep
• Maintain complete confidentiality with sensitive business information
• Occasionally book travel and other personal tasks

Required:

• 3+ years as a Chief of Staff, Executive Assistant to a CEO, General Manager, or Operations Manager in services, technology, or consulting
• Senior operator background. You have run process design, ops strategy, or business process modeling for at least one growing organization
• Strong written English. You will draft on my behalf to Fortune 500 contacts and PE principals. 
• Strong calendar judgment. You think in time zones, you defend focus, and you understand which meetings can't be moved
• Financial fluency for ops. Comfortable with invoicing, contractor pay schedules, basic budgets, Google Sheets or Excel
• Proactive operating style. You anticipate needs and act before being asked
• High discretion and sound judgment with sensitive business information
• Working hours overlap with early Pacific Time
• Fluent in Google Workspace (Gmail, Calendar, Drive, Docs, Sheets); comfortable in remote teams that work asynchronously
• Ability to work at a high level without a lot of direction

Strong plus:

• AI tooling fluency. You have used Claude, ChatGPT inside a real project
• Tech, AI, or consulting industry context. You understand SaaS, SOWs, and the rhythm of a services firm
• Ukrainian language. Our delivery team is Ukrainian or Ukraine-adjacent
• Experience growing an organization with documented process work. Examples of headcount or revenue growth you helped shepherd are valuable
• Familiarity with Telegram, Slack, Jira, Confluence, or other async business tools
• Background as a founder Chief of Staff, deputy COO, or general manager at a small to mid-sized company

What you get:

• A high-trust role working directly with the CEO of a growing AI company
• Real authority over the operating backbone of the firm
• Direct exposure to major clients: PE-backed technology companies, Fortune 500 brands, global financial institutions
• Senior team to work with, no bureaucracy between you and the work
• Competitive compensation
• Long-term high-impact role