Chief of Staff, AI Strategy at 404 Not Found in New York City

Job description

• Application
• The role
• Valkai is compressing drug and device development timelines from months to days, working inside some of the largest pharma and medical device companies in the world. We have grown by staying close to our customers: serving them well, shipping quickly, and deploying agents that become part of how they work every day. The next chapter is scaling that for the growth stage, so the systems, data, and habits behind the business keep compounding alongside the product.
• That is the job. As Chief of Staff, you will own and scale the operating machinery behind the business side of Valkai. The right data reaches the right person when a decision needs it. What we learn on one account shows up on the next. Our interview process selects for the people each role needs. Our own operations are as AI-native as the product we sell. You will work directly with the founders and the AI Strategy team, and you will own the problems that sit between functions.

Responsibilities

• Business operations: Capture what we learn across accounts and functions, turn it into playbooks, templates, and reusable materials, and make them available right time, right place. Ramp new strategists and sellers on how we work.
• Commercial strategy: Own our point of view on the market. Sharpen the approach and differentiation, run competitor benchmarking, keep the team current on the industry, and maintain the positioning, pricing inputs, and materials the commercial team runs on.
• GTM engineering: Build the data and tooling layer behind our go-to-market. Make sure the right account, contact, usage, and market data is available to the right person at the right time, and automate the work that gets in the way of selling and serving.
• Revenue operations: Organize and systematize the commercial motion. Define pipeline stages and conversion metrics, run the forecast, and assess where we win by segment, territory, and buyer so we can decide where to invest.
• AI-native operations: Treat Valkai as customer zero. Make Valkai context and knowledge accessible to people and to our AI, set the approach for how we build internal automations and agents, and hold the bar on what good looks like.
• Recruiting: Partner with our Talent team so the process selects for the people each role actually needs. Define what great looks like, design the cases and evaluation tools, and instrument the loop so we can see what predicts success.
• Operating cadence and corporate: Run the rhythm of the business: planning, goals, the company scorecard, and leadership meetings. Build board and investor materials, clean up and scale our people functions, and help the founders map where the company goes next.

Requirements

• Thoughtful problem solvers: You start with a clear and accurate picture of the context. You break messy, cross-functional problems into concrete plans, and you think about second-order effects before you ship a process for other people.
• Builders of systems, not one-offs: You measure yourself on whether the system still runs and improves without you, not on the deliverable you produced. You would rather fix the root cause than run the report again.
• Organized and self-sufficient: You manage yourself, navigate ambiguity, and create measurable impact. You turn loose goals into concrete execution plans, and nothing falls through the cracks on your watch.
• AI-native by default: You reach for AI tools first and you build with them. You are comfortable going from a rough idea to a working automation, and you notice when a manual process should not exist.
• High judgment, low ego: You work across every function and with senior people, hold your own on substance, and are happy for the win to belong to the team you made faster.
• Range: You move between data plumbing, strategy work, recruiting design, and board materials in the same week without dropping any of them.
• 4 to 8+ years of experience (responsibility can flex with tenure), ideally a mix of consulting, banking, or investing and time at an early-stage startup. A straight professional-services track also works if you were a top performer.
• A track record of building systems or processes that other people actually adopted, such as a CRM, a dashboard, a hiring loop, or a planning cadence.
• Comfort with data and systems: spreadsheets and data, a CRM, an ATS, and a knowledge base.
• Exposure to enterprise B2B software and how it is sold. Life sciences experience is a plus, not a requirement.
• Daily, hands-on use of tools like Claude Code and Codex in your own work, and some experience building with them.

Skills

Required

• Thoughtful problem solving
• Building systems and processes
• Organization and self-sufficiency
• AI-native tool usage
• High judgment and low ego
• Range and adaptability

Preferred

• Early-stage startup experience
• Exposure to enterprise B2B software
• Life sciences experience

Benefits

• Competitive compensation, including meaningful equity.
• Medical, dental, and vision insurance for employee and dependents.
• Generous PTO policy.
• Paid parental leave.
• Chief of Staff, AI Strategy
• $220K – $280K • Offers Equity