Head of Revenue Enablement

Ashby•San Francisco, CA

About The Position

As the Head of Revenue Enablement, 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 customer-facing Sales & CS teams — this includes but isn’t limited to: fast time-to-ramp for new hires, consistent adoption of our frameworks and methodologies, strategic business partnership with GTM leadership and ultimately delightful customer experiences that drive growth. In 2026, Revenue Enablement will be a team of three. You will lead and manage two practitioners, one for each Sales and Customer Success. You will operate in a player-coach capacity, with an eagerness to roll up your sleeves to support program delivery and ensure execution against company priorities. Sales & CS will be close to 200 people by the end of next year, and so you and your team will have a high impact role on Ashby’s growth trajectory to $100M ARR and well beyond.

Requirements

You’ve helped a SaaS company scale to over $100M ARR where you lead an enablement team.
You are highly organized and have managed a small but mighty enablement team who deliver multiple projects concurrently.
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).

Responsibilities

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 LMS 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.

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.

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