Manager, Sales Enablement

Summary

Join Tailscale's growing Revenue Operations team as a Sales Enablement Manager and become a force multiplier across our high-velocity, product-led sales motion. Collaborate with Sales, SEs, Marketing, Product, and Customer teams to help revenue teams effectively communicate Tailscale's value to technical audiences. This role is perfect for someone experienced in selling or enabling technical tools and understanding the IT/engineering persona. You will build programs from the ground up, utilize data-driven approaches, and navigate technical environments. The ideal candidate will develop and execute onboarding programs, build enablement frameworks, translate technical value into customer-facing messaging, and design programs supporting skill development and coaching. You will also partner with managers and leadership to identify skill gaps and create scalable enablement paths.

Requirements

• 3–6+ years of experience in sales enablement, technical sales, or sales engineering at a high-growth B2B SaaS company
• Proven success enabling both ICs and managers in GTM teams selling to IT or engineering decision-makers
• Deep understanding of (or strong curiosity about) developer tools, infrastructure, networking, or security
• Demonstrated ability to design, launch, and scale enablement programs in fast-paced, high-growth environments
• Data-driven mindset - comfortable using performance metrics, rep feedback, and tool insights to inform strategy and iterate on programs
• Excellent communication skills with the ability to distill complex technical concepts into compelling, accessible messaging
• Self-starter who thrives in ambiguity and enjoys building from scratch in a remote-first culture

Responsibilities

• Develop and execute onboarding programs to ramp AEs, SEs, and CSMs quickly and effectively
• Build a repeatable framework for ongoing product, process, and persona-based enablement
• Collaborate with Product Marketing and Product to translate technical value into clear, customer-facing messaging and content
• Design enablement programs that support both IC-level skill development and manager-level coaching capabilities
• Partner with frontline managers and sales leadership to identify skill gaps, deliver targeted programs, and empower effective coaching
• Create scalable, role-specific enablement paths that support core competencies and career progression
• Own the development and upkeep of enablement materials such as playbooks, talk tracks, competitive guides, objection handling, and demo resources
• Drive adoption of tools like Gong, Outreach, and Salesforce to reinforce best practices and create consistency across the sales motion
• Use data (e.g., performance metrics, pipeline trends, tooling insights) to assess program effectiveness and prioritize new initiatives

Preferred Qualifications

• Familiarity with Tailscale or similar products in the networking, infrastructure, or security space
• Experience in a product-led growth (PLG) environment
• Background in technical presales or sales engineering

Benefits

• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks