Head of Revenue Enablement

About This Role

As the Head of Revenue Enablement, you'll report into our Head of Revenue Operations. We aim to keep our org design as simple as possible. We have Marketing, Sales and Customer Success and as the vertical functions with Revenue Operations as the one horizontal department within Go-to-Market to make the whole system GTM system run better! Within Revenue Operations we see three core pillars today: (1) Strategy & Ops, (2) Systems & Data, and (3) Enablement. This structure ensures tight collaboration and shared context across the pillars

You will be the business partner to our VP Sales and VP Customer Success to ensure consistently high caliber execution to support revenue growth and customer retention. You will play a pivotal role in developing and, with your team, executing programs that foster excellence in our Sales and CS organizations. Success in this hands-on leadership role is measured by the overall effectiveness of our GTM teams — this includes but isn’t limited to: fast time-to-ramp for new hires, consistent adoption of our frameworks and methodologies, close business partnership with leadership and ultimately delightful customer experiences that drive growth.

Our enablement team today is three people who you would manage, and scale based on business need. Sales & CS will be close to 200 people this year, and so you and your team will have a high impact role on Ashby’s growth trajectory to $100M ARR and well beyond.

Role Scope & Requirements

• 🤝 Business Partnership: You are innately curious about the work and priorities of our Sales and CS Leaders. You ask the hard questions to understand the nuances of the business to identify how you can have the greatest impact. You partner effectively with stakeholders including Product Marketing, Revenue Operations and Senior Leadership to deliver comprehensive programs in support of our go-to-market strategy.

• ⚙️ Program Development & Iteration: You understand business needs and identify gaps in knowledge or skills. You’re a quick learner who is at home creating and curating materials for go-to-market teams. You collect disparate information through quantitative and qualitative approaches (e.g. interviews, internal documentation, and recorded customer calls) to create tailored learning paths that drive behavior change. You have a track record of proactively eliciting feedback for program improvement and use that, along with performance data and business outcomes, to iterate, refine and scale programs that deliver measurable impact.

• 🧑‍🏫 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—sometimes less is more. You can be the master architect for role and segment specific onboarding tracks.

• 💻 Systems: You’ve managed an Enablement Stack and have perspective on which software capabilities best support learning outcomes and in-field execution. You closely follow AI-native enablement vendors and can separate marketing fluff from powerful new features.

• 🚀 Scaling: You’ve helped a SaaS company scale to over $100M ARR where you lead an enablement team. You thrive in a high growth, dynamic environment and are familiar with reinforcement learning techniques to support organizations of this scale.

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

• 👷 Team Management: You are highly organized and have managed a small but mighty enablement team who deliver multiple projects concurrently. You’re an “in the details” leader who ensures the success of your team’s work. You know when to advocate for additional resources to maximize impact.

Out of Scope

Since every organization thinks about Revenue Enablement a little bit differently, we intend 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 is not 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 have a desire to build a world-class GTM practice.

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

• Your peers would describe you as operationally excellent.

• You excel in cross-functional collaboration.

• You have strong opinions on hiring and org design for Enablement

This Role Might Not Be for You If

• You are uncomfortable rolling up your sleeves and executing. You will be extremely hands-on in this role, this is not a role for delegators.

• You are used to managing a large, layered team.

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

• You love meetings! We’re a documentation first, async friendly team that values written communication as a core mode of communication. (We’re not anti-meeting but highly value the written word).

Our Philosophy

Here are a few points relevant to go-to-market 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.