Executive Assistant to the CEO + Training Coordinator

Executive Assistant to CEO & Training CoordinatorLocation: Remote (but must be U. S. -based)Status: Full-Time Employee (40 hours/week)Compensation: $55,000–$64,000/year + generous benefitsAbout How to ContractHow to Contract isn’t just a training company. It’s a trusted partner for lawyers and professionals who want to master real-world contract drafting and negotiation. Founded by Laura Frederick, a veteran tech transactions lawyer, we exist to make contract work less overwhelming and more effective. Our mission is simple: help professionals feel confident, capable, and supported.

We create practical, no-fluff training that focuses on what to say, when to say it, and why it matters. Through online courses, weekly shows, community programs, and events like ContractsCon, we combine expert insights with a human, approachable style. At How to Contract, we respect the critical role lawyers and contract professionals play. We bring clarity, confidence, and a touch of joy to one of the most demanding parts of legal and business work. About the RoleWe’re hiring an Executive Assistant & Training Coordinator to support our CEO and manage day-to-day operations.

This is a critical role that keeps the company running smoothlly. You'll be handling details, coordinating contractors, organizing content, and ensuring nothing falls through the cracks. If you’re someone who thrives on precision, gets things done quickly and correctly, and can bring order to fast-moving projects, you’ll fit right in with our growing team. We are scaland prefer to promote from within when possible.

ResponsibilitiesExecutive SupportManage CEO’s calendar, email, and key prioritiesPerform invoice and record-keeping tasksTrack action items and keep tasks performed by employees, contractors or you moving to completionTraining Program CoordinationManage and track training projects in AirtableOrganize and QA training videos, transcripts, and handoutsUpload and publish content across platforms (Kajabi, Vimeo, Descript)Relationship & Logistics CoordinationCoordinate with speakers, sponsors, partners, and customers across events, training, and contentSchedule meetings, track deliverables, and ensure all parties have what they needDraft and send follow-up emails, prep materials, and key documentsMaintain organized records for all contributors and external stakeholdersCustomer & CLE SupportSubmit and track CLE applicationsRespond to customer questions quickly and professionallyOperations & Process OwnershipMaintain and improve internal systems (Google Drive, Airtable, SOPs)Spot process gaps and implement solutionsWhat We’re Looking For2–4 years in an Executive Assistant, Project Coordinator, or similar role Must be in the U.

S. Detail-focused and highly organizedExcellent proofreader-level writing skills. Comfortable with tools like Airtable and Google Workspace Proactive, fast learner, and able to manage multiple tasks without close supervisionHiring ProcessThis is a full-time employee role with benefits for 40 hours a week (not a freelance gig). We use a paid freelance project (up to 30 days) to confirm mutual fitFreelance rate: $30/hour during this evaluation phase. Compensation & BenefitsSalary: $55,000 – $64,000/year (based on experience)Benefits:

Generous health, dental, and optical insurance, short-term and long-term disability benefits, 12 PTO days plus a company-wide holiday week off between Christmas and New Year’sForever remote with flexible hours and autonomy