Customer Education Program Manager, Live Learning - Ashby

Ashby is looking for a Customer Education Program Manager, Live Learning to help shape and scale its live learning experiences across Ashby Academy.

Our team is built on a simple belief: Ashby Academy should feel like every customer's personal CSM. Regardless of tier or team size, every Ashby customer deserves content that meets them where they are — practical, accurate, and genuinely useful. As our first dedicated live-learning hire, you’ll help define what this program becomes and build the practices that make it work.

What you'll do

• Program Ownership: Own the Customer Success live-learning program, bringing existing sessions under a shared calendar, planning process, and consistent customer experience. Establish a clear process for evaluating and prioritizing new ideas.
• Operational Excellence: Make sessions easier to run. Manage registration, reminders, session setup, presenter preparation, live production, surveys, follow-up, and recording handoffs with reusable templates and clear practices.
• Learning Design: Partner with presenters and Customer Education Program Managers to define audiences, learning outcomes, formats, and supporting materials (exercises, facilitator guides, session outlines).
• Presenter Coaching: Define what a high-quality session looks like, run rehearsals, coach presenters, and improve question handling, participation, pacing, and mixed experience levels.
• Facilitation: Host and facilitate selected sessions, moderate questions, model effective teaching, and test new formats while building a sustainable multi-presenter model.
• Recording Library: Own the live-learning recording catalog. Organize, publish, update, and retire sessions, partnering with Academy operations to repurpose sessions into other formats.
• Discovery & Growth: Work with Marketing on website discovery, audience communications, packaging, and program alignment to help customers find their next learning step.
• Measurement: Track registration, attendance, engagement, learner feedback, and downstream product behaviors.
• Program Expansion: Use customer needs and program data to launch new audiences and formats, such as onboarding clinics, applied workshops, and customer spotlights.

How you'll work with other teams

• Startup CSMs & RecOps Consultants: Partner on learning design, preparation, and quality while they provide subject-matter expertise and delivery.
• Customer Education Program Managers: Coordinate on where live learning integrates with existing courses, playbooks, and release education.
• Marketing & Event Ops: Collaborate on promotion, platform setup, packaging, and integrations.

You may be a great fit if:

• You’ve owned recurring live education or a comparable customer-facing program and demonstrated measurable improvements in reliability and scalability.
• You have a background in customer education, product training, customer success, enablement, learning design, or webinar program management.
• You manage recurring calendars, contributors, deadlines, and dependencies reliably.
• You can translate complex product workflows into clear, practical learning experiences.
• You are a skilled live facilitator who can handle dynamic audiences and unexpected situations.
• You can provide constructive coaching to help internal subject-matter experts teach effectively.
• You quickly learn software products firsthand through documentation and hands-on testing.
• You have operational experience with virtual learning platforms, webinar tools, and CRM/marketing systems (e.g., HubSpot).

You may not be a great fit if:

• You want to focus exclusively on presenting rather than operations, production, and coaching.
• You want pure strategy without hands-on setup, follow-up, and troubleshooting.
• You measure success solely by event volume rather than customer learning and application.
• You require a pre-established playbook for every decision.

Interview Process

• Introductory Call: 30-minute conversation with Recruiting.
• Hiring Manager Call: 45-minute conversation about programs you’ve owned.
• Take-Home Exercise: Bounded exercise with one week to complete.
• Final Round (2 hours):
  • Take-home exercise review (45 mins)
  • Facilitation and presenter coaching discussion (30 mins)
  • Cross-functional partnership conversation (30 mins)
  • Closing questions with the Hiring Manager (15 mins)

Benefits

• Stock Options: 10-year exercise window for stock options.
• Unlimited PTO: Recommended minimum of four weeks per year.
• Paid Family Leave: Twelve weeks of fully paid family leave in the US (expanding internationally).