Chief of Staff

About JotPsych

JotPsych develops software tailored for behavioral health practitioners. Their scribe solution has already generated over 2.5 million patient notes and reduces administrative workload by approximately 90%. The company is expanding its offerings beyond notes to include practice management features such as billing, audits, prior authorizations, and e-prescribing. Based in New York, JotPsych is a small team where every non-engineering role begins as Chief of Staff.

Role Overview

This dynamic position requires addressing the company's most urgent needs weekly, whether it be in sales, operations, product, or bridging gaps between founders and various functions. The Chief of Staff utilizes advanced tools and AI (such as Claude) to intervene across marketing, sales, analysis, product development, partnerships, and operations, delivering comprehensive solutions with real impact. The role promises significant growth and the opportunity to transition into an executive leadership position.

Key Responsibilities

• Identify and solve complex, high-stakes business challenges without merely providing analyses or options, but by delivering fully implemented solutions.
• Engage deeply with company processes, communicate with stakeholders, and conduct research leveraging AI and sound judgment to design scalable operational systems.
• Work across departments including marketing, sales, analytics, product, strategy, partnerships, and operations to build dependable frameworks and drive growth.

Examples of Typical Projects

• Develop a comprehensive attribution and tracking system for tens of thousands of weekly visitors to JotPsych.com to accurately map customer journeys and optimize demo bookings.
• Analyze onboarding data for new clinics to identify and resolve points where user adoption stalls, proposing actionable improvements.
• Map the onboarding-to-prescription funnel for prescribers, identifying bottlenecks and defining concise next steps for the engineering team.
• Design and execute repeatable marketing experiments to convert clinician referrals into new signups, evaluating channel effectiveness rigorously.

Who We Seek

• An analytical systems thinker skilled in breaking down complex problems into clear, manageable parts without overlap.
• A technically curious individual capable of creating scripts, automation, prototypes, and tools to address challenges, even without formal engineering training.
• A self-starting professional who confidently tackles ambiguous challenges, determines when to escalate issues, and works independently.
• A polished communicator comfortable engaging with customers and partners in high-stakes situations, earning their trust quickly.
• A persistent and detail-oriented person willing to meticulously refine systems to ensure high quality and reliability.

Who This Role Is Not For

• Candidates seeking defined roles with predictable schedules.
• Individuals who prefer to submit recommendations without leading execution.
• Applicants who would rely on unreviewed AI outputs.
• Anyone looking for hybrid or fully remote positions; this job requires full-time presence in the New York office.

Growth Opportunities

This role offers exposure to all parts of the company and direct visibility with the senior leadership team. Previous hires have advanced quickly into significant growth and operational leadership roles, with promotion expected within the first year.

Logistics and Compensation

• Full-time position, based in the New York City office, working five days per week.
• Annual base salary between $130,000 and $160,000, supplemented by equity participation.
• Health and dental insurance coverage.
• 401(k) retirement plan.
• Stipend provided for laptop and office setup.
• Role is within a serious, fast-paced startup environment—not a casual, lifestyle job.

How to Apply

• Record a voicemail introducing yourself, explaining your interest in the role, including the word "keystone" to demonstrate attention to detail; this voicemail serves as your application essay.
• Complete a brief form providing your full name, LinkedIn profile, email, and phone number. A resume is not required.
• Subsequent hiring steps include a 30-minute introductory call, a 2–3 hour case study assignment, an in-person half-day review and written exercise in New York, followed by a half-day working session alongside the team. Throughout the process, candidates receive prompt feedback.