New

Manager, Sales Enablement

Remote (Canada)

About Tailscale 

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

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.

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.

Key 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

What We Are Looking For

  • 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

It's Nice if You Have

  • 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

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE)

$268,000 - $268,000 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
  • 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. 

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

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