Customer Success Enablement Manager

About this role:

As the Customer Success Enablement Manager, you will be a critical partner to our Customer Success organization, ensuring CSMs, Implementation Specialists, Contract Management and Professional Services teams have the skills, knowledge, and resources to deliver exceptional customer outcomes. Reporting to the Head of Revenue Enablement, you will refine and execute programs that accelerate CSM and Professional Service onboarding, reinforce customer engagement excellence, and ensure CS leaders and their teams are consistently equipped to drive retention and growth.

This is a hands-on role with high visibility, where you’ll collaborate closely with CS Leadership, Professional Services, Implementation, and cross-functional partners like Product Marketing and Revenue Operations. Your success will be measured by the effectiveness of the CS organization—knowledgeable, well prepared CSMs, stronger renewal and expansion execution, and consistent adoption of strategic playbooks (such as our Customer Outcomes Framework) that underpin Ashby’s growth.

Customer Success will be a nearly 100 person customer-facing team next year, and your work will directly impact our trajectory to $100M ARR and beyond.

Role Scope & Requirements:

• 🤝 Business Partnership: You partner closely with CS Leaders across segments to deeply understand their priorities. You ask tough questions, surface gaps, and design enablement programs that align to business outcomes like NRR, expansion, and customer satisfaction. You build trust across Product Marketing and RevOps to deliver cohesive GTM programs.

• ⚙️ Program Development: You create and curate learning paths, playbooks, and frameworks tailored to CSM needs (e.g., value discovery, partnership reviews, renewal conversations). You translate insights from calls, customer data, and frontline feedback into practical, repeatable programs that drive consistent execution.

• 🧑‍🏫 New Hire Onboarding: Near-term, you own onboarding for our Customer Success Managers , Implementation Specialists, and our Professional Services team, building on our role- and segment-specific tracks to accelerate time-to-value. Over time, we anticipate our onboarding tracks willto better support our Contract Management and Supporfunctiont as well. Through program development,you simplify and prioritize what new hires need to know, ensuring they’re ready to lead customer conversations with confidence.

• 💻 Systems & Tools: You manage enablement systems (LMS, content hubs, call libraries) to make resources easy to access and apply in the field. You bring perspective on how AI-enabled tools can reinforce learning and support real-time customer interactions.

• 🚀 Scaling Impact: You thrive in dynamic, high-growth SaaS environments. You’ve supported CS organizations at scale and know how to reinforce skills and behaviors over time (certifications, peer learning, scenario practice) to ensure programs stick.

• 📈 Impact Measurement: You partner with CS Ops to measure program effectiveness. You go beyond activity tracking to link enablement to business outcomes like faster ramp, improved NRR, and higher expansion rates. You iterate programs based on both data and observation.

• 👷 Program Execution: You are organized, detail-oriented, and comfortable managing multiple initiatives concurrently. You balance strategic program design with rolling up your sleeves to facilitate sessions, deliver training, and embed new practices in the field.

Out of Scope:

To set expectations clearly:

• Technical Enablement / Ashby Product: While you will partner with Product, SE, and CS leadership to ensure teams have the product knowledge they need, you will not own deep technical enablement.

• Competitive Intelligence: You’ll collaborate with PMM and Sales Enablement on competitive readiness, but you are not expected to be the subject matter expert in this area.

You Might Love This Role If:

• You’re passionate about enabling Customer Success Teams to deliver business outcomes via their expertise

• You love building scalable programs that directly impact retention and expansion outcomes

• You thrive in cross-functional work and enjoy building trust with leaders and customer-facing teams

• You’re known for operational excellence, clarity, and execution

• You’re energized by both designing programs and reinforcing them with Customer Success Teams

This Role Might Not Be for You If:

• You prefer focusing only on training content without engaging in reinforcement or measurement

• You’re uncomfortable facilitating live sessions or role plays with CSMs and leaders

• You need a large team or mature infrastructure to be effective—this is a lean, hands-on role

• You dislike documenting and systematizing—Ashby is an async-first culture that values clarity in writing

Our Philosophy

Here are a few key points (relevant to the go-to-market side) that should give you an idea of what it is like to work with us:

• We believe a highly differentiated product is a lot easier to sell, so we continually invest in product innovation and this has proven to be a sustainable source of competitive differentiation

• We always aim to show up well prepared and with deep industry acumen. This caliber of customer experience is another way we differentiate.

• 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 hire and compensate accordingly.

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.

Benefits

• You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks, but equally move with precision and urgency

• Competitive compensation, including equity

• 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.

• 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.

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.