AI Trainer (Part-Time / Contract) | Make Our Whole Team Claude-Powered

Company: FlatRate BookkeepingLocation: RemoteType: Part-time contractor / gigEngagement: 16 weeks (~60 hours total)Compensation: Hourly, commensurate with experience--About Us--FlatRate Bookkeeping is a modern bookkeeping firm. Our staff handles everything from monthly closes and reconciliations to customer phone calls and onboarding. We've built an in-house platform (FRB-Hub) to run our operations, and we want to layer AI on top of every role, not as a gimmick, but as a real productivity multiplier.We believe the firms that win the next decade will be the ones where every single tea ---------- mber knows how to wield AI like a power tool. We need someone to make that happen for us.--What you'll do--You will be the in-house AI coach for our staff. Your job is to take people who currently don't use Claude (or use it poorly) and turn them into confident, fluent operators who reach for it dozens of times a day.You'll work across our whole team — bookkeepers, customer service, account managers, leadership — and tailor sessions to what each group actually does day-to-day.--Topics You'll Cover Include (but Aren't Limited To)--Writing great prompts (and rewriting bad ones)Using Claude for accounting work: drafting journal entry explanations, summarizing transactions, sanity-checking reconciliations, explaining variances to non-accountantsCustomer-facing work: drafting client email s, prepping for calls, turning messy notes into clean follow-ups, handling sensitive conversationsInternal productivity: turning a wall-of-text into a checklist, generating questions to ask a client, summarizing meetings, cleaning up documentationUsing Claude.ai effectively — projects, artifacts, file uploads, the Finance plugin, Cowork, and any new features Anthropic ships during the engagement"What's new with Claude" — keeping the team current as models, features, and best practices evolveGuardrails: when not to use AI, how to verify outputs, how to protect client data--The scheduleThis Is a Structured 16-week Engagement With Two Phases--Phase 1 — Bootcamp (Weeks 1–4) — 9 hours/week2 hours Your own prep & research — staying current on Claude features, planning sessions, prepping examples relevant to bookkeeping/customer service2 × 1 hour Company-wide all-hands AI training sessions5 × 1 hour Small group sessions, one per team (we'll define the groupings together)--Phase 2 — Sustain & Level Up (Weeks 5–16) — 2 hours/week5 × 20 minutes Short, focused weekly check-ins with each small team — "What's new with Claude," answer questions, share wins, troubleshoot blockersTotal commitment: ~60 hours over 16 weeks.--We're flexible on exact scheduling — sessions need to fit our team's working hours, but the timing of your individual prep work is up to you.--What success looks likeBy The End Of Week 4Every staff member has used Claude at least 10 times for real workEach team has 2–3 documented "this is how we use Claude for X" workflowsConfidence is up, eye-rolls are downBy The End Of Week 16Claude is a default tool, not a curiosity — staff reach for it without being promptedWe have a living internal playbook of prompts/workflowsThe team self-identifies new use cases without needing you to spoon-feed them--What we're looking forDeep, current, hands-on experience with Claude (you should already be using it every day for your own work)Excellent teaching instincts — you can read a room, simplify hard ideas, and tell when someone is nodding but not understandingComfort working with non-technical professionals (bookkeepers, customer service, ops) — no condescension, no jargon dumpsStrong written communication; you'll be producing prompt templates, cheat sheets, and short-form docs the team can reference laterReliable, self-directed — this is a gig where we expect you to plan your own curriculum and just deliver--Bonus Points If You Have Any OfBackground in accounting, bookkeeping, or financial servicesExperience training staff at a small/mid-size business (not just enterprise L&D)Familiarity with Claude.ai's newer surfaces — Projects, Cowork, plugins, MCP, SkillsExperience writing internal documentation or building playbooksA track record of measurable AI-adoption results at a prior company--How we'll work together--All sessions are remote (SLACK HUDDLE)You'll get a slim Slack presence so staff can ask quick follow-up questions between sessionsWe'll give you sanitized examples of real work the team does so your training is grounded in reality, not generic prompt demos