Head of AI-Driven Sales Enablement & Onboarding

Sierra; San Francisco (CA); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Flexible time off

Medical, dental, and vision benefits

Life insurance

Parental leave

Equity plans

Job summary

Sierra is seeking a Senior Sales Enablement leader to design and run a structured onboarding program for Account Executives and Sales Engineers in San Francisco.

You will deliver live and asynchronous sessions, establish ramp metrics, and leverage AI tools to scale enablement while partnering with Product, Marketing, and Sales Leadership.

The role emphasizes hands-on work, global rollout including London, in a fast-growth, in-person environment.

Qualifications

• 6+ years in sales enablement at a high-growth B2B software company.
• Experience designing onboarding for quota-carrying and technical sellers.
• Proven ability to balance competing stakeholder requests with data.
• Ability to tie enablement work to business outcomes.
• Strong facilitation skills with executives and seasoned sellers.
• Willingness to do hands-on work early and build from scratch.

Responsibilities

• Design and implement onboarding for Account Executives and Sales Engineers.
• Deliver onboarding sessions live and asynchronously: cohorts, workshops, role-plays.
• Define AI Fluency concepts and embed in daily sales activities.
• Ensure sellers can explain and demonstrate Sierra's AI approach.
• Set ramp metrics and targets to reduce time to first meeting and quota.
• Use AI tools to scale enablement: content, coaching, self-serve answers.
• Collaborate with Product, Marketing, Sales Leadership, and Sales Engineering.
• Recruit top sellers and SEs to teach in the program.
• Gather feedback and iterate quarterly.
• Make the program global and adaptable for regional teams including London.

Skills

Sales enablement

Onboarding design

Cross-functional programs

Facilitation

AI Fluency

Tools

Highspot

Seismic

Salesforce

Gong

Job description

Sierra is seeking a Senior Sales Enablement leader to design and run a structured onboarding program for Account Executives and Sales Engineers in San Francisco.

You will deliver live and asynchronous sessions, establish ramp metrics, and leverage AI tools to scale enablement while partnering with Product, Marketing, and Sales Leadership.

The role emphasizes hands-on work, global rollout including London, in a fast-growth, in-person environment.