Remote Head of Customer Education

Head of Customer Education

Hi, I’m Casey, and I lead Customer Success Management and Customer Education at Ashby. I’m excited to be hiring our Head of Education at Ashby — a role that will drive forward our Recruiting Operations Consulting, Academy, and Product Enablement functions. You’ll inherit a team of strong, motivated people and take on the work of further unifying them under a coherent educational strategy: one that serves customers directly through consulting engagements and Academy programs, and serves Ashby internally through how we train and enable our GTM teams to teach, demo, and demonstrate the value of Ashby.

About This Role

The goal of our Education team is to act as a CSM for every customer and GTM employee. We are principled in how we operate and create content and experiences that are truly useful to our audience. Our Academy consists of public-facing content and digital programs that aim to meet customers where they are — whether that’s a Recruiting Manager just getting started with Ashby or a Head of Talent looking to improve Quality of Hire. Our RecOps Consulting team brings deep operational expertise to customers who need more than product guidance, through both 1:1 and scaled experiences. And our Product Enablement function exists to close the gap between what the product can do and what CS and sales teams can confidently apply in practice.

As Head of Education, you’ll manage across all three of these functions and own the operating model that ties them together. At the start, this will mean being close to the work — managing ICs alongside early leaders and building out the leadership layer over time as the organization scales.

Day-to-day, this looks like:

• RecOps Consulting

  • Overseeing RecOps Consulting, ensuring 1:1 customer engagements are driving real value, and that insights from direct consulting work find their way into Academy content rather than staying locked in individual engagements.

  • Partnering with Professional Services on scoping and delivering paid RecOps engagements — including how packages are structured, where the line sits between complimentary and paid work, and how the consulting model evolves by segment.

• Academy

  • Partnering with the Manager of Academy on content strategy — what gets built, how it’s organized, and how the library evolves as the product and customer base grow.

  • Building out new Academy programs, including a product certification path, centralizing the webinar function under CE, and launching a Digital Programs capability that brings education directly to customers through in-app and email experiences.

• Product Enablement

  • Building out Product Enablement as a distinct function — translating the last 20% of product context for CSMs and AEs, addressing the continuous shipping problem for our field teams, and designing a new hire onboarding experience that’s more durable than what we have today.

• Team

  • Building the operating infrastructure that lets all three functions scale: intake processes, engagement frameworks, capacity planning, and the connective tissue that keeps the functions working together rather than in parallel.

  • While you’ll start by managing a mix of Managers and ICs across Consulting and Academy, you’ll be responsible for identifying where additional layers are needed to effectively scale the org — either by developing from within or hiring externally.

  • Representing CE externally through webinars, industry events, and customer sessions — and synthesizing what you hear back into credible, specific product feedback.

There isn’t one standard background that defines success in this role. If your experience includes building and scaling Recruiting Operations, Customer Success, or Customer Education functions, we’d encourage you to apply.

You Could Be a Great Fit If

• You think from first principles about education. You’re skeptical of “best practices” as a starting point and more interested in what actually serves the specific audience in front of you — whether that’s a recruiter trying to figure out offer approvals or a CSM trying to explain a product release.

• You’re a strong leader of leaders. You develop the people beneath you deliberately, hold a high bar without micromanaging, and create an environment where your team does their best work.

• You think in operating models. You can look at three distinct functions and figure out what they need to share, where they need to stay separate, and how to build systems without over-engineering.

• You’re energized by being close to the work. While you’ll eventually have a leadership team in place, you’ll start by directly managing our RecOps Consultants and Academy team.

• You build strong cross-functional relationships. You’ll need to partner closely with leadership counterparts across CS, Sales, Product, and Marketing — and the ability to show up as a credible, collaborative peer in those conversations is as important as what you build within CE.

• You’re comfortable with ambiguity and motivated by building. This is not a standard Education role and the team is still early — we need someone who can figure out how we scale and help build toward that.

• You communicate with clarity and operate well in a writing-heavy culture. At Ashby, proposals, frameworks, and documentation are how decisions get made and work moves forward.

• You think carefully about the full customer spectrum — from the team of one setting up their first ATS to the enterprise org navigating complex integrations — and can build programs that serve both without defaulting to just one end.

• You’re comfortable hopping into new tools and figuring them out. You won’t necessarily be building, but you’ll engage directly enough to support your team — whether that’s understanding how an in-product journey gets configured or evaluating a new LMS feature.

• You have a perspective on how consulting fits into an education strategy — where 1:1 expertise should scale into content, where it shouldn’t, and how the two motions reinforce each other.

You Might Not Be a Great Fit If

• You prefer to set strategy and hand it off. This role requires staying close enough to the work to build the systems and infrastructure that support it — not just directing others toward a vision and stepping back.

• You’re not comfortable in front of customers. There will be moments where you’re supporting a RecOps Consulting engagement in a leadership capacity, or take the stage during an Ashby-hosted event.

• You don’t enjoy reviewing content. You’ll be the final bar for what the team publishes and the experiences they create, and that means staying close enough to the work to know when something isn’t ready.

• You rely on industry playbooks to tell you what an education function should look like. We have strong opinions about what effective CE should be, and we’re looking for someone who is principled and will build from first principles.

• You find it hard to thrive when the scope is shifting. This function is constantly evolving as business needs shift, and you’ll need to be genuinely energized by that rather than stabilized by a fixed remit.

Interview Process

• Recruiter Screen — 30 minutes

• Hiring Manager Interview with Global Head of Customer Success — 45 minutes

• Presentation with CE team leads and cross-functional partners — 60 minutes

• Final Panel:

  • VP of CS — 30 minutes

  • CEO Interview — 30 minutes

  • Closing Questions — 15 minutes

Benefits

• Opportunity to work with a talented and passionate team.

• 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 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, and an automatic 401k match.

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.