Tailscale
Tailscale
51 – 200 Employees
SaaSSecurityTelecommunications
Tailscale builds secure networking software that connects people, services, and devices across locations and cloud environments. Its modern VPN is based on WireGuard and is designed to replace the complexity of traditional VPN infrastructure with fast deployment, encrypted connections, access controls, and zero-trust networking capabilities. The company operates across SaaS, security, and telecommunications, supporting use cases such as remote access, site-to-site connectivity, and multi-cloud networking for both organizations and individual users.

Customer Account Executive - Toronto (Hybrid)

Grow and retain customer accounts for Tailscale’s secure networking software in a Toronto-based hybrid role. Build pipeline, increase adoption, and deliver upsell and renewal results.

Description

  • Develop deep expertise in how Tailscale securely connects people and devices
  • Build a reliable quarterly pipeline through customer engagement focused on upsells and renewals
  • Take ownership of upsell and renewal goals across assigned accounts
  • Guide customers through Tailscale’s value proposition from evaluation through adoption
  • Deliver near-term revenue while sustaining sufficient annual pipeline coverage
  • Maintain accurate weekly forecasts and support revenue attainment
  • Develop mutual action plans and customer success plans for prospective and current accounts
  • Join recorded customer meetings to support training, collaboration, and quality improvement
  • Work cross-functionally with Solutions Engineering, Customer Success, Support, Marketing, and Product

Requirements

  • Up to one year of quota-carrying or closing experience in an Account Executive or Account Manager position
  • Strong interest in joining a fast-growing software startup
  • Experience selling developer or technical products, particularly in a product-led growth environment
  • Confidence presenting to senior managers and executive stakeholders
  • Ability to oversee multiple opportunities at different stages simultaneously
  • Demonstrated history of meeting and surpassing quota
  • Experience with Gong or comparable tools for internal collaboration and pipeline management
  • Experience working with Sales Engineering, Support, and Customer Success teams
  • Proactive ownership throughout the sales cycle from lead generation to close
  • Based in Toronto and available to work in the office three days per week as part of the hybrid arrangement

Benefits

  • Total compensation includes base pay, an equity incentive plan, and variable commission for quota-carrying positions
  • Comprehensive group health, vision, dental, and related benefits begin without a waiting period and cover you and your family
  • Flexible work environment and working arrangements
  • Remote-first perks including virtual and in-person social events and access to a corporate co-working program
  • Employer-funded retirement contributions match employee contributions dollar for dollar, up to 0.75% of eligible annual compensation
  • Annual company retreat and team off-sites
  • USD 1,500 each year for professional development
  • Mentorship, coaching, and opportunities for internal advancement
  • Flexible paid time off
  • Company-provided laptop with a Mac or PC option
  • Monthly reimbursement for home internet
  • USD 500 allowance for workstation customization
  • Paid parental leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents

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