Head of Sales & Customer Success Enablement

About Ashby

• We’re building the next generation of enterprise software, starting with products that help talent leaders, recruiters, and managers unlock hiring excellence

• Raised our Series C earlier this year, and we’re growing ARR >100% YoY

• Have over 2,000 amazing customers including OpenAI, Ramp, Deliveroo, Notion and Reddit

• Built multiple products to win both land-and-expand and material new business deals

• Rapidly moving up-market with no signs of slowing down

• Implemented AI throughout the platform

• Known for our pace of innovation and advanced analytics

About this role:

As the Head of Sales & Success Enablement, you will play a pivotal role in developing and executing programs that foster excellence in our Sales and Customer Success teams. Success in this role is measured by the overall effectiveness of our customer-facing Sales & CS teams — this includes but isn’t limited to: fast time-to-ramp for new hires, strong adoption of our frameworks and methodologies, strategic business partnership with GTM leadership and consistently excellent customer experiences.

Role Scope & Requirements:

• ⚙️ Program Development: You are adept at understanding business needs and identifying gaps in knowledge or skills—you partner effectively with stakeholders across Sales, Customer Success, Product Marketing, and Revenue Operations to clarify goals and define the structure of enablement programs from scratch.

• 💡Content Creation & Curation: You’re a quick learner who is at home creating and curating training materials for go-to-market teams. You collect disparate information through interviews, internal documentation, and customer calls and create tailored learning paths that drive behavior change. You elicit feedback for improvement.

• 🧑‍🏫 New Hire Onboarding: You have experience developing onboarding programs for GTM teams that ensure new hires ramp quickly. You have a knack for simplification and prioritization.

• 💻 Systems: You’ve managed an LMS or similar and have perspective on which software solution(s) best support learning outcomes and in-field execution. (We do not yet have an LMS but have abundant internal documentation and looms)

• 🚀 Scaling: You’ve helped a SaaS company scale from <$25M to over $100M ARR and have supported a team of >100 customer-facing folks. You thrive in a high growth, dynamic environment and are familiar with reinforcement learning techniques to support organizations of this scale.

• 📈 Impact: You use analytics to assess the impact of enablement programs and make data-backed decisions.You have a proven track record of achieving measurable improvements in team performance and productivity. You iterate on your approach based on observed results, evolving company goals, and changing market conditions.

• 👷 Project Management: You are highly organized and have managed multiple projects and initiatives simultaneously. You are passionate about empowering teams and helping individuals reach their full potential. You know when additional resourcing is required for the greatest impact.

Out of Scope:

Since every organization thinks about GTM Enablement a little bit differently, we wanted to be clear about what we currently view as out of scope for this role, while also acknowledging that things may evolve, and your perspective also counts!

• Technical Enablement / Ashby Product: We have an expansive product surface area as a full-suite talent acquisition platform. Our Support, CS and Solutions Engineering teams especially need to develop deep product acumen to be effective in their jobs. We anticipate you being a partner to other owners of Technical Enablement but it not being your primary responsibility.

• Competitive Intelligence: You would not be expected to become the subject matter expert on our competitive landscape, but would partner with our PMM and Solutions Engineering teams on the creation of competitive enablement programs, leveraging existing knowledge and frameworks

You Might Love This Role If:

• You balance creative problem-solving and operational execution

• You’re a systems thinker with experience scaling enablement programs

• You have a passion for data-driven decision-making

• You excel in cross-functional collaboration

This Role Might Not Be for You If:

• You are uncomfortable rolling up your sleeves and executing. This is not a role for delegators.

• You prefer working independently vs as part of an interdisciplinary team.

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.