Customer Education Program Manager, Live Learning

Hi, I’m Jace Talamantes. I founded Ashby’s Customer Education function in 2025 and now lead the team. I am excited to be hiring a Customer Education Program Manager, Live Learning! 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. That standard shapes everything we build, and it’s what’s driven the development of our growing Academy courses, webinar program, and playbook library. We have ambitions to expand both the depth of our content and the formats we deliver it in, and this hire is a meaningful part of getting there. As our first dedicated live-learning hire, you’ll help define what this program becomes and build the practices that make it work. Our Startup Customer Success and Recruiting Operations Consulting teams already run live sessions that customers value. You’ll lead how those experiences should come together, bring a point of view on where we should invest next, and define what great live learning at Ashby should feel like. This role needs both vision and execution. You’ll shape the direction and stay close to the work: planning the calendar, simplifying registration, developing a workshop with an expert, coaching presenters, and hosting selected sessions yourself. You should be as interested in getting next week’s session right as you are in imagining what the program could become over the next year. You’ll report to me and partner with Customer Success, Customer Education, and Marketing. There’s a foundation to build on and people to partner with, alongside plenty of room to set direction and drive the work. If you enjoy forming a point of view, turning it into something practical, and improving it as you learn, there’s a lot to make your own here. What you’ll do at Ashby Own the Customer Success live-learning program, bringing existing programs together under a shared calendar, planning process, and consistent customer experience. Establish a clear process for evaluating, prioritizing, and developing new ideas. Make sessions easier to run. Own registration, reminders, session setup, presenter preparation, live production, surveys, follow-up, and recording handoffs. Build reusable templates and clear operating practices that reduce repeated work. Design learning around customer needs. Partner with presenters and Customer Education Program Managers to define the audience, intended outcome, format, and supporting resources. Develop session outlines, exercises, facilitator guides, and other materials that help customers apply what they learn. Help experts become effective presenters. Define what a high-quality session looks like, run rehearsals, coach presenters, and improve how sessions handle questions, participation, pacing, and mixed experience levels. Host and facilitate selected sessions. Lead or co-facilitate learning where it serves the program, moderate questions and activities, model effective teaching, and help test new formats. Build a program that supports multiple presenters rather than depending on you to teach every session. Own the live-learning recording library. Make useful sessions easy to find and learn from after the live event. Decide what to publish, how to organize it, and when to refresh or retire it. Partner with Academy operations on publishing and with presenters and CEPMs on accuracy, supporting resources, and opportunities to turn sessions into other learning formats. Make sessions easy to discover and join. Work with Marketing on the website experience, audience communications, packaging, and connections to broader programs. Give customers a clear way to find the right session and their next learning step. Measure and improve the program. Track registration, attendance, engagement, learner feedback, and operational effort. Define the product behavior each program is intended to support and work with partners to assess whether customers take action. Expand deliberately. Use customer needs and program evidence to recommend additional audiences and formats, including onboarding sessions, RecOps clinics, applied workshops, and customer spotlights. Our teams currently run roughly two to three sessions each week. Your initial priority is to establish reliable delivery of the existing program. You’ll work with your manager to prioritize improvements and expand formats, balancing customer needs with presenter availability and operational capacity. How you’ll work with other teams Startup CSMs and RecOps consultants will continue to lead the subject-matter content and delivery for their audiences. You’ll partner with them on learning design, preparation, and quality while owning the overall program and its operations. You’ll work together with Customer Education Program Managers to decide where live learning fits and how it connects with existing courses, playbooks, and release education. Marketing will partner on website presence, promotion, packaging, and broader program alignment. Operations and systems partners will support platform setup and integrations. You’ll define program requirements and work with those partners to improve workflows. This role focuses on scalable customer learning. Individual customer training and consulting engagements remain with the teams responsible for those services. Examples of work you might own Bring Startup and RecOps sessions into one coordinated calendar with a consistent registration and follow-up experience. Turn a presentation-heavy session into a workshop where customers practice a workflow and receive feedback. Create a presenter kit with an outline, rehearsal checklist, production plan, and guidance for handling questions. Work with Marketing and Event Ops to simplify webinar setup and connect registration and attendance data with our reporting. Package a useful session into a recording, a short practical resource, and a clear next step in Academy. Review a series with strong attendance but limited follow-through and recommend what to change before running it again. You may be a great fit if: You’ve owned recurring live education or a comparable customer-facing program and can show how you made it more useful, reliable, or scalable. You come from customer education, product training, customer success, enablement, learning design, or webinar program management. What matters most is evidence that you can combine strong operational ownership with thoughtful teaching and a strong understanding of customer needs. You own recurring work reliably. You can manage a calendar, multiple contributors, deadlines, and dependencies while keeping the customer experience consistent. You’ve helped people learn something complex. You can explain clearly, use practical examples, and check whether someone can apply what you taught. You’re comfortable facilitating live. You can guide participation, respond to questions, adjust your approach, and keep a session useful when something unexpected happens. You help other people teach effectively. You can give specific, constructive feedback and help an expert turn deep knowledge into an accessible learning experience. You learn products firsthand. You explore workflows, use documentation, test your understanding, and know when expert validation is needed. Prior Ashby experience is helpful, but not required. You’re comfortable with the operational details. You’ve worked with webinar or virtual-learning platforms and understand registration, communications, recordings, surveys, and reporting. Experience with HubSpot or a comparable system is useful. You bring a point of view and turn it into practice. You can assess an existing program, recommend what to keep, change, or build next, and personally drive the work with the right partners. You use evidence to improve. You can use learner feedback and behavior to assess whether a session helped customers apply what they learned. You may not be a great fit if: You want to focus exclusively on presenting. A substantial part of this role is planning, production, systems, and supporting other presenters. You want to focus on program strategy without staying close to delivery. This role includes hands-on setup, production, follow-up, and troubleshooting alongside improving how the program runs. You measure success primarily by the number of events delivered. We care about whether the right customers participate, learn, and apply what the program teaches. You need an established playbook for every decision. There is a foundation to build on, and you’ll help determine how it develops. Interview process We want the process to give you a clear picture of the work and give us practical evidence of how you approach it. Here’s what you can expect: An introductory conversation with Recruiting (30 minutes) A hiring manager conversation about programs you’ve owned (45 minutes) A bounded take-home exercise (one week to complete) Final Round interview (two hours) A discussion of your approach to the take-home exercise (45 minutes) A conversation about facilitation and presenter coaching (30 minutes) A cross-functional partnership conversation (30 minutes) Closing questions with the myself, the Hiring Manager (15 minutes) We’ll share the full schedule, preparation expectations, and evaluation criteria before the exercise. About Ashby We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better. Learn more on our website: https://www.ashbyhq.com/ We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. Following our Series D in 2025, we’re continuing to grow ARR at more than 100% year over year, serving over 5,000 customers, including industry leaders like Snowflake, OpenAI, Shopify, Ramp, Notion, Reddit, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers. We’ll share more details once we meet. In short, it’s the perfect time to join! 🚀 About Go To Market We view our Support team as an extension of the product itself, one that ensures an optimal customer experience for customers ranging across all market segments. Here are a few points that should give you an idea of what it is like to work with us: We spend a lot of time building best-in-class products since we believe a highly differentiated product is easier to sell. We also spend a lot of time building a best-in-class customer experience. We aim to offer deep expertise whenever we interact with prospects and customers. We strongly believe that small teams with very talented people and the right work environment deliver much better performance than teams with large headcount. We value a strong sense of ownership, principled thinking over experience, and thoughtful communication (we put a lot of effort into using the right communication channels) - we’ll get into these and other values during the hiring process. You can take a look at our Leadership Principles to get a sense of what we value in People Leaders at Ashby. Benefits 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable. Unlimited PTO with four weeks is recommended per year . Expect “Vacation?” in our one-on-one agenda until you start taking it 😅 Twelve weeks of fully paid family leave in the US . We plan to expand this to employees in other countries as situations arise. Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! $100/month education budget with more expensive items (like conferences) covered with manager approval. If you’re in the US, top-notch health insurance for you and your dependents with all premiums covered by us. Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.