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Senior New Business Account Executive

Tailscale· Sales
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full-timePosted 2w ago

About the role

Senior New Business Account Executive role at Tailscale (hybrid in Toronto, ON) responsible for inbound and self-sourced pipeline, owning the full sales cycle from prospect to close, and traveling to events to evangelize Tailscale.

Responsibilities

  • Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale.
  • Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns.
  • Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers
  • Support customers across all time zones
  • Manage and organize your activities, pipeline, and forecast in Gong and Salesforce

Qualifications

  • 2+ years of prospecting or closing experience in a door-to-door or in-person sales role
  • Ambition to build (and not just follow) a sales playbook
  • A technical background or curiosity in technology
  • Excellent communication and presentation skills
  • Proactive from lead to close - identify and engage the hiring manager, and articulate why you’re the best candidate
  • Experience self sourcing opportunities and guiding a customer from discovery to closed won with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO)
  • This role is based in Toronto and is hybrid required (3 days/week in-office)

Skills

Required:ProspectingSales playbook developmentTechnical curiosity/backgroundCommunication and presentationSelf-sourcing opportunities

Benefits

  • An inclusive, flexible environment where you can be your authentic self
  • A competitive total compensation package (base salary, equity, variable commission)
  • Comprehensive group benefits with no waiting period
  • Remote first company with opportunities for in-office collaboration as noted in description
  • Employer-funded retirement contributions (match up to 0.75% of eligible compensation)
  • Annual company retreat and team off-sites
  • Development support including $1500 USD annually for professional development
  • Paid time off and flexible PTO
  • Build-your-own home office setup (laptop, internet reimbursement, workstation stipend)
  • Paid parental leave program (20 weeks birthing, 16 weeks non-birthing)
Last updated Oct 8, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
Company profileWebsite

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