Enterprise Customer Enablement & Training Specialist

AirOps•San Francisco, CA

About The Position

We're looking for a senior customer enablement leader to own and scale our Content Engineer certification program. You'll lead live cohort sessions that transform marketing professionals from "One-Shot Prompter" into Content Engineers—professionals who think in systems, build intelligent workflows, and create compounding value through automation rather than relying on manual AI interactions. This isn't just platform training. You're fundamentally reshaping how marketing teams approach content work in the AI era, building the profession that will define the next decade of marketing. You'll design progressive curriculum across Foundations, Intermediate, and Advanced tracks, facilitate hands-on 90-minute sessions where participants build real workflows solving their actual problems, and create the educational experiences that lead to promotions, raises, and measurable team transformation. Your impact extends beyond the classroom—participant struggles become product insights, cohort feedback directly informs platform development, and you'll be the critical bridge between customer learning and our engineering roadmap.

Requirements

3+ years in customer enablement, technical training, or marketing operations with a track record of teaching complex technical concepts to non-technical audiences
Exceptional public speaking and facilitation skills: You're energizing on camera, think on your feet during live troubleshooting, and create "aha moments" through interactive demonstration rather than lecture-style presentation
Technical fluency: You learn platforms rapidly, understand systems thinking and workflow logic, and can build alongside participants in real-time. Bonus if you have experience with marketing automation tools, APIs, or workflow builders like Zapier, Make, or Clay.
Teaching philosophy grounded in application: You believe in "show, don't tell," prioritize hands-on building over theory, and design for immediate micro-wins that build confidence before tackling complexity
Curriculum design experience: You've created structured learning progressions that scaffold from foundational concepts to advanced techniques, with clear learning objectives and measurable outcomes
Bias toward action and iteration: You embrace "Version 0" thinking—shipping adaptable foundations that improve through use rather than pursuing perfect initial implementations
Strong written communication: You distill complex workflows into clear documentation and can create concise, memorable educational content (session summaries, troubleshooting guides, expansion opportunities)
Customer empathy: You recognize when participants are struggling, adapt your approach in real-time, and celebrate their wins as your own success metrics

Nice To Haves

Prior experience in B2B SaaS enablement or customer education roles
Background in content marketing, SEO, or marketing operations
Familiarity with AI tools (Claude, ChatGPT, Perplexity) and prompt engineering principles
Experience with community management platforms (Circle, Slack communities)
Understanding of semantic search, knowledge management systems, or content workflows
PST time zone preferred (for optimal cohort scheduling and team collaboration)

Responsibilities

Live Cohort Facilitation: Lead 2-week cohort sessions across multiple skill levels (Foundations through Advanced), delivering interactive, demonstration-heavy experiences where participants build workflows in real-time. Run both public cohorts and private enterprise training sessions for 20+ person teams.
Curriculum Development: Design and continuously evolve educational content across three certification tracks, creating session materials, builder exercises, homework assignments, and comprehensive takeaway documents that meet learners where they are.
Hands-On Workflow Building: Guide participants from simple 2-4 step automations to sophisticated 15-25+ step orchestrations, teaching the foundational "Gather → Analyze → Extract" pattern and progressing to liquid query syntax, iterator patterns, and intelligent quality assurance systems.
On-Site Enterprise Training: Travel to deliver in-person enablement sessions for enterprise customers, adapting curriculum to specific organizational needs and use cases while maintaining the core Content Engineer philosophy.
Product-Education Feedback Loop: Synthesize cohort pain points, feature requests, and learning barriers into actionable product insights. Your observations from where participants struggle most directly inform platform improvements and documentation priorities.
Outcome Measurement: Track and report on participant success metrics including workflow implementation rates, time savings achieved, team efficiency gains, and career advancement outcomes (promotions, raises, new titles).
Asynchronous Content Creation: Develop self-serve learning materials, micro-certifications, and university-style resources that complement live instruction and enable scalable knowledge transfer.