Global Head of Sales Enablement

About the Company

Sierra is creating a platform to help businesses build better, more human customer experiences with AI. Founded by Bret Taylor and Clay Bavor, the company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family.

Responsibilities

• Own onboarding and ramp for all sales roles to compress time-to-productivity
• Lead sales bootcamp covering pitching, discovery, POC management, and competitive positioning
• Build a continuous learning system including certifications, coaching, and manager enablement
• Develop and maintain sales playbooks for prospecting, negotiation, and expansion
• Build a measurement framework for enablement including ramp time and quota attainment
• Build and lead a team of enablement professionals in partnership with RevOps and Sales Comp

Requirements

• 12+ years in sales enablement or GTM productivity at an enterprise B2B software company
• Experience running programs at significant scale
• Deep understanding of complex enterprise sales motions and multi-stakeholder cycles
• Proven track record of building enablement functions from the ground up
• Strong people leadership and talent development skills
• Exceptional writing and communication abilities

Preferred Qualifications

• Experience enabling teams selling into Fortune 500 or Fortune 50 accounts
• Familiarity with AI-powered enablement tools and content platforms
• Experience building vertical or industry-specific enablement programs

Benefits

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits
• Life insurance and disability benefits
• Retirement plan
• Parental leave
• Fertility and family building benefits
• Lunch, snacks, and coffee
• Discretionary benefit stipend
• Free alphorn lessons