Global Head of Sales Enablement

Sierra • San Francisco, CA

1d • $240,000 - $305,000 • Onsite

About The Position

Sierra is hiring its first Global Head of Sales Enablement to build the programs, content, and systems that make a world-class Sales team even better. This person will build an enablement function that is ahead of the curve — designed for the company Sierra is becoming, not just the one it is today. This is a builder role. There are strong foundations in place: an onboarding program, a sales bootcamp, core pitch materials — but the opportunity is to take everything to the next level. The right person has done this before at scale and is hungry to do it again.

Requirements

• 12+ years in sales enablement or GTM productivity at an enterprise B2B software company, with experience running programs at significant scale
• Deep understanding of complex enterprise sales motions, including multi-stakeholder cycles with a services or implementation component
• Proven ability to build enablement functions, not just run them — you've started from a foundation and built something that lasted and scaled
• Strong people leader who attracts great talent, develops it, and creates a team culture that reflects Sierra's values
• Exceptional writer and communicator — can craft a crisp playbook and a compelling training session in equal measure
• Hungry to build — brings the ownership mindset and energy of someone who wants to leave something behind that didn't exist before they arrived

Nice To Haves

• Experience enabling a team 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

Responsibilities

• Own onboarding and ramp for all sales roles — building programs that compress time-to-productivity and equip reps to tell Sierra's story credibly from day one
• Lead Sierra's sales bootcamp covering the full motion: pitching, discovery, POC management, competitive positioning, pricing, and the AE/SE/agent development partnership
• Build a continuous learning system — certifications, coaching programs, role-specific training tracks, and manager enablement — that raises the skill floor across the entire sales team
• Develop and maintain the playbooks that define how Sierra sells: prospecting, discovery, multi-threading, POC management, negotiation, and expansion
• Build the measurement framework for enablement — ramp time, quota attainment by cohort, win rates, and program utilization — and hold the function accountable to those numbers
• Build and lead a team of enablement professionals, and partner closely with RevOps, Sales Comp, and Deal Desk to ensure operational changes always land with the right enablement behind them

Benefits

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family building benefits through Carrot
• Lunch, as well as delicious snacks and coffee to keep you energized
• Discretionary benefit stipend giving people the ability to spend where it matters most
• Free alphorn lessons

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed