Executive AI Enablement Lead

Role Overview You are the Executive AI Enablement Lead at AIVC, the person whose job is to make the executives at AIVC’s client businesses true power users of Claude, Cowork, and code- and agent-driven workflows. AIVC partners with operator businesses to drive AI-led EBITDA growth, and part of that work is bringing each company’s most senior leaders up the AI curve. You’re the person who personally designs and runs that path on every engagement: assessing where a given client executive is today; curating the right materials, videos, and course content; running 1:1 coaching; building executive playbooks; and acting as their daily operator-in-the-loop until the new workflows stick. The first concrete instance is already lined up, a named client managing partner has explicitly asked for the fastest path to becoming a power user of Claude, Cowork, and Claude Code / Skills. From there you scale: same treatment to additional client executives across the portfolio, then a documented set of executive-grade playbooks and patterns that compound across every future engagement. You are bias-toward-results – a win is the client executive’s calendar-week looking different, not a beautifully written rubric nobody uses. What You’ll Own (Outcomes) • Within 30 days of pairing with the first client managing partner, they have a working daily routine in Claude, Cowork, and Code/Skills that’s already replacing or improving how they handle at least three recurring tasks • Within the first quarter of the engagement, the client executive is a true power user — running multi-step workflows, custom Skills/Projects, and agent-assisted tasks without needing coaching scaffolding for the basics • A documented set of executive playbooks (research, writing, analysis, synthesis, workflow automation, agent-assisted tasks) that compound across every client engagement, not one-offs • A curated, current library of learning materials, videos, example workflows, and Claude-native patterns — including a clear point of view on which external courses, tutors, or expert resources are worth plugging in • Observable change in how client executive cohorts use AI: from reactive chat to repeatable, structured, outcome-oriented workflows • A foundation of training assets and patterns that scales beyond executive coaching into broader client teams in year two • A reputation among AIVC’s clients as the trusted go-to for “how do I do this better in Claude” — measured by inbound demand and engagement expansion What You’ll Do (Responsibilities) • In the first weeks: build the first client managing partner’s tailored upskilling plan — assess current usage, identify the highest-leverage workflows for their day-to-day, curate the right mix of materials / videos / course content, and recommend any tutor or expert-guided support to fold in • Provide 1:1 coaching for client executives — managing partners, founders, C-suite leaders — on Claude, Cowork, and code- and agent-based workflows • Design tailored training plans per executive that go beyond basic onboarding into advanced usage, with explicit progression from chat → workflows → agents • Curate the best external materials (videos, courses, blog posts, example projects) and rewrap them into client-ready, AIVC-flavored learning paths • Teach practical, high-leverage use cases live: research, writing, analysis, synthesis, workflow automation, and agent-assisted tasks • Help client executives move from general chat usage into repeatable workflows — Claude Projects, Skills, scheduled Cowork tasks, MCP integrations, custom agents • Serve as a real-time tutor and expert resource for client executives — over Slack, in meetings, on-site, and in async written feedback • Run office hours, workshops, and informal Q&A sessions inside client teams to keep adoption sticky between coaching sessions What We’re Looking For (Required) • Deep hands-on expertise with Claude across every surface (Claude.ai, Claude Projects, Claude Code, Claude Skills, Claude API) — and an active habit of pushing the edges of each • Strong working fluency with Claude Cowork specifically, including scheduled tasks, connected apps / MCPs, and the broader workflow surface • Strong capability with code-enabled AI workflows: you can write Python and/or TypeScript, build agents, configure MCP integrations, and ship a working internal automation end-to-end without needing an engineer • Demonstrated ability to teach non-technical but highly demanding users — you’ve made executives, founders, or senior operators meaningfully better at something complicated, not just trained engineers • Strong workflow design instinct — you can translate messy business questions into clean prompts, workflows, and systems • Polished, discreet, and effective in high-touch client executive settings — high EQ, low ego, comfortable representing AIVC inside senior client environments and around senior decision-makers • Strong bias toward practical results over theoretical AI knowledge — the metric is the client executive’s behavior change, not the elegance of the explanation • Excellent written and verbal communication; you can write a playbook a client executive will actually read and use • Comfort with significant travel to client sites and embedded, on-site engagement work • 5+ years of professional experience across some mix of: applied AI / ML, technical training and enablement, developer relations, solutions engineering, executive coaching, management consulting, or chief of staff / senior operator roles to executives Helpful If You Have (Preferred) • Prior experience coaching or supporting C-level executives, founders, or managing partners as a client-facing professional — executive coach, principal solutions engineer to executive customers, chief of staff to a CXO, or partner-level consultant • Background that combines technical depth with people skills — developer relations, solutions engineering, technical training, or learning & development at a frontier AI or developer-tools company • Direct experience building executive-facing training programs or curricula that demonstrably moved adoption inside other organizations • Hands-on familiarity with the Anthropic product surface specifically: Claude Projects, Claude Skills, Claude Code, MCP server development, Claude API • Track record of getting non-technical users to genuinely adopt a technical tool — i.e., users who chose to keep using it after the training ended • Background in management consulting, professional services, executive coaching, or learning & development — especially in environments where the customer was a senior external client • An active personal portfolio of AI work (workflows, automations, blog posts, talks, open-source contributions) you can point to • Comfort building light tooling (a Notion playbook system, a Claude Skills catalog, a small dashboard) without needing engineering support • Familiarity with AIVC’s model — operator business engagements, EBITDA-led measurement, and the broader compounding intelligence layer — or eagerness to come up the curve quickly