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Manager of Sales Enablement

Tailscale17 days ago
Remote
Remote (Canada)
Senior Level

Top Benefits

Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
Competitive compensation, stock options and 401(k) (for United States-based employees)
Comprehensive medical/dental/vision benefits, and more

About the role

Who you are

  • 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
  • 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

What the job involves

  • 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

Benefits

  • Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
  • Competitive compensation, stock options and 401(k) (for United States-based employees)
  • Comprehensive medical/dental/vision benefits, and more
  • 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
  • An allowance for equipment to help you personalize your workspace

About Tailscale

Software Development
51-200

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