Enablement Program Specialist – Onboarding

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Take charge of and enhance the onboarding process for new revenue hires, from pre-boarding to achieving ramp milestones.

• Expand onboarding into ongoing everboarding enablement, ensuring representatives continue to enhance their skills beyond the initial ramp-up period.

• Create, initiate, and oversee recurring enablement initiatives focused on skill enhancement, product introductions, process implementations, and certifications.

• Develop scalable, role-specific enablement pathways that support essential competencies and career advancement.

• Handle all aspects of program logistics, content management, and scheduling while ensuring quality and adherence to timelines.

• Collaborate with frontline managers and sales leadership to pinpoint skill deficiencies and implement targeted training programs.

• Measure programs with ramp-time, completion, and competency metrics, refining them based on data and feedback from representatives.

• Oversee the Tailscale LMS to ensure that new-hire materials are up-to-date and easily accessible.

• Investigate and experiment with AI-driven learning tools, such as an AI tutor for asynchronous onboarding.

• Work collaboratively with teams across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product.

⛳️ Requirements

• 2–4+ years of experience in revenue/sales enablement, with practical program and onboarding leadership.

• Proven track record of designing, launching, and scaling enablement programs in dynamic, high-growth settings.

• Strong project management abilities and a keen eye for detail.

• Exceptional written communication skills and strong instincts in facilitation and instructional design.

• Effective stakeholder management across various functions and levels of seniority.

• Data-driven approach and familiarity with using performance metrics, representative feedback, and tool insights to refine programs.

• High level of ownership and capability to excel in ambiguity while building from the ground up in a remote-first culture.

• Bonus: Experience utilizing AI tools to create more efficient and impactful learning environments.

• Bonus: Previous sales experience, particularly with technical audiences such as IT, engineering, and security.

🏝️ Benefits

• An inclusive, flexible environment where you can express your true self.

• Competitive total compensation package that includes base salary, equity incentive plan, and variable commission for quota-based roles.

• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.

• Remote-first work setting.

• Opportunities for virtual and in-person social events.

• Corporate co-working program.

• Employer-funded retirement contributions that match employee contributions dollar-for-dollar, up to a maximum annual contribution of 0.75% of eligible compensation.

• Annual company retreat and team off-sites.

• $1,500 USD annually allocated for professional development.

• Opportunities for mentorship, coaching, and internal promotions.

• Flexible paid time off program.

• Company-provided laptop (Mac or PC).

• Monthly reimbursement for home internet expenses.

• $500 USD allowance for home office setup.

• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.

• An accessible and inclusive hiring process with accommodations available.