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Tailscale

Sales Development Representative (Outbound)

Tailscale · Hybrid (Vancouver, British Columbia)

Posted about 3 months ago

or apply directly on Tailscale's site. We never take the application ourselves.

Is this posting real?

This role has been open
80 days
Tailscale's roles stay open a median of 76 days
Reposted
No
Salary listed
No
2% of Tailscale's roles list one
Ghost-job risk at Tailscale
high
60 stale, 2 reposted of 60 open
Hiring momentum
113 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-10-22

Measured from postings appearing on and disappearing from Tailscale's own greenhouse board since 2026-08-03. Full hiring picture for Tailscale.

About this role

As an Outbound Sales Development Representative at Tailscale, you will generate new business opportunities by proactively reaching out to potential clients through various channels such as phone, email, and LinkedIn. You will manage a portfolio of target accounts, conduct research to identify key decision-makers, and collaborate closely with Account Executives to schedule meetings and build a sales pipeline.

Our read on this posting2.6out of 5
benefits
4/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Tailscale as an employer.

What you need

  • 1+ years of sales, business development, recruiting, or other customer-facing experience preferred
  • Excellent verbal and written communication skills
  • Comfortable spending a significant portion of your day making outbound phone calls
  • Strong organizational skills and the ability to manage a large portfolio of prospects
  • Competitive, resilient, and motivated by achieving goals
  • Curious, coachable, and eager to continuously improve

Nice to have

  • Experience in SaaS sales or outbound prospecting
  • Experience with Salesforce, Outreach, Gong, Apollo, or LinkedIn Sales Navigator
  • Experience selling to technical audiences or an interest in cybersecurity, networking, or cloud infrastructure
  • Bachelor's degree or equivalent professional experience

What you get

  • A competitive total compensation package including base salary, equity, and variable commission
  • Comprehensive group benefits with no waiting period for health, vision, dental, and more
  • Employer-funded retirement contributions with a match up to 0.75% of eligible compensation
  • $1500 USD annually for professional development
  • Flexible paid time off program
  • Build-your-own home office setup with a company-owned laptop and monthly internet reimbursement

Worth weighing

  • No specific mention of salary beyond the range provided
  • Role involves high-volume outbound prospecting, which may not suit everyone
  • The position requires in-office work three days a week, which may not appeal to those seeking fully remote roles

Summarised from Tailscale's posting. Read the full original.

Listed by Tailscale on their greenhouse job board, last confirmed open on 2026-10-22. PitchMeAI is not the employer.

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