Enablement Program Specialist – Onboarding

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

📋 Description

• Take ownership of and enhance the onboarding process for new revenue team members, from pre-boarding through key ramp milestones.

• Expand onboarding into an ongoing enablement initiative, ensuring representatives continue to develop their skills beyond initial ramp-up.

• Design, implement, and oversee recurring enablement programs that focus on skill enhancement, product launches, process rollouts, and certifications.

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

• Oversee all aspects of program logistics, including content, timing, scheduling, and quality management.

• Collaborate with frontline managers and sales leadership to pinpoint skill gaps and provide tailored programs.

• Utilize metrics related to ramp time, program completion, and competency to refine programs based on data and representative feedback.

• Administer the Tailscale Learning Management System (LMS) and ensure that materials for new hires are up-to-date and easily accessible.

• Investigate and test AI-driven learning solutions, such as an AI tutor for asynchronous onboarding.

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

⛳️ Requirements

• 2–4+ years of experience in revenue or sales enablement, with direct responsibility for program development and onboarding.

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

• Strong skills in project management with a keen attention to detail.

• Excellent written communication abilities and strong instincts in facilitation and instructional design.

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

• A data-driven approach and proficiency in utilizing performance metrics, feedback from representatives, and tool insights to enhance programs.

• High level of ownership with the capability to thrive in uncertain situations and construct solutions from the ground up in a remote-first setting.

• Experience with AI tools to create more efficient and effective learning experiences is advantageous.

• Previous sales experience, particularly with technical audiences such as IT, engineering, and security, is a plus.

🏝️ Benefits

• A welcoming and flexible environment where you can express your true self.

• A competitive total compensation package that includes a base salary, equity incentive plan, and variable commission for roles based on quotas.

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

• A remote-first workplace.

• Opportunities for virtual and in-person social gatherings.

• A corporate co-working program.

• Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible annual compensation.

• Annual company retreat and team off-site events.

• $1500 USD per year allocated for professional development.

• Opportunities for mentorship, coaching, and internal promotions.

• Flexible paid time off policy.

• A company-owned laptop (either Mac or PC).

• Monthly reimbursement for home internet expenses.

• $500 USD allowance for personalizing your home office workstation.

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