Head of Sales and Customer Success Enablement

Summary

Join Ashby as the Head of Sales & Success Enablement and play a pivotal role in developing and executing programs that drive excellence in Sales and Customer Success teams. You will be responsible for program development, content creation and curation, new hire onboarding, managing systems, scaling enablement programs, using analytics to assess impact, and managing multiple projects. Success is measured by the effectiveness of customer-facing teams, including fast onboarding, strong adoption of frameworks, strategic partnerships, and excellent customer experiences. The role requires experience scaling SaaS companies, managing LMS, and using data-driven decision-making. Ashby offers competitive compensation, equity with a 10-year exercise window, unlimited PTO, generous family leave, and an education budget.

Requirements

• Be adept at understanding business needs and identifying gaps in knowledge or skills
• Be a quick learner who is at home creating and curating training materials for go-to-market teams
• Have experience developing onboarding programs for GTM teams that ensure new hires ramp quickly
• Have managed an LMS or similar and have perspective on which software solution(s) best support learning outcomes and in-field execution
• Have helped a SaaS company scale from <$25M to over $100M ARR and have supported a team of >100 customer-facing folks
• Use analytics to assess the impact of enablement programs and make data-backed decisions
• Be highly organized and have managed multiple projects and initiatives simultaneously

Responsibilities

• Develop and execute programs that foster excellence in Sales and Customer Success teams
• Understand business needs and identify gaps in knowledge or skills
• Partner with stakeholders across Sales, Customer Success, Product Marketing, and Revenue Operations to clarify goals and define the structure of enablement programs
• Create and curate training materials for go-to-market teams
• Collect disparate information through interviews, internal documentation, and customer calls and create tailored learning paths that drive behavior change
• Elicit feedback for improvement
• Develop onboarding programs for GTM teams that ensure new hires ramp quickly
• Manage an LMS or similar and have perspective on which software solution(s) best support learning outcomes and in-field execution
• Help a SaaS company scale from <$25M to over $100M ARR and support a team of >100 customer-facing folks
• Use analytics to assess the impact of enablement programs and make data-backed decisions
• Iterate on your approach based on observed results, evolving company goals, and changing market conditions
• Manage multiple projects and initiatives simultaneously
• Empower teams and help individuals reach their full potential
• Know when additional resourcing is required for the greatest impact

Preferred Qualifications

• Balance creative problem-solving and operational execution
• Be a systems thinker with experience scaling enablement programs
• Have a passion for data-driven decision-making
• Excel in cross-functional collaboration

Benefits

• Competitive compensation, including equity
• 10-year exercise window for stock options
• Unlimited PTO with four weeks is recommended per year
• Twelve weeks of fully paid family leave in the US
• Generous equipment, software, and office furniture budget
• $100/month education budget with more expensive items (like conferences) covered with manager approval