Manager of Sales Enablement, Tailscale

• This role is ideal for someone who has experience selling or enabling technical tools and understands the IT/engineering persona
• If you're energized by building programs from the ground up, data-driven in your approach, and comfortable navigating technical environments, we’d love to meet you
• 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

Desirable

• We’re looking for a Sales Enablement Manager to join our growing Revenue Operations team
• You'll serve as a force multiplier across our high-velocity, product-led sales motion, working closely with Sales, SEs, Marketing, Product, and Customer teams
• Your mission: help our revenue teams consistently and confidently articulate the value of Tailscale to technical audiences, especially IT and engineering leaders
• 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