Job Overview
Location
Hybrid (Vancouver, British Columbia)
Job Type
Full-time
Category
Sales
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • Lead and develop a high-performing Sales Development Representative (SDR) team to build qualified pipeline for Tailscale’s sales organization in a fast-paced, hybrid environment.
- • Coach SDRs on prospecting strategies, refine inbound and outbound motions, and drive performance through data-informed coaching, call reviews, and pipeline forecasting.
- • Partner with Sales, Marketing, RevOps, and Enablement to align on ideal customer profiles, improve lead quality, and execute targeted campaigns.
- • Recruit, onboard, and ramp top SDR talent, fostering an inclusive, high-energy culture rooted in curiosity, accountability, and customer empathy while preparing team members for future growth into Account Executive or leadership roles.
- • Represent the SDR team in cross-functional planning to shape go-to-market strategy as Tailscale scales globally.
🎯 Requirements
- • 2+ years of experience leading SDR or BDR teams in a B2B SaaS environment
- • Proven track record of coaching SDRs, improving prospecting performance, and consistently meeting pipeline targets
- • Experience managing outbound and inbound prospecting motions across multiple customer segments and personas
- • Strong written and verbal communication skills with ability to simplify complex ideas
- • Data-driven mindset: proficient in using metrics, reporting, and tools like Salesforce, Outreach, Gong, and Sales Navigator
- • Ability to manage multiple priorities while keeping the team focused on high-impact activities
- • Passion for coaching and developing future sales talent
- • Willingness to travel 25% of the time for industry events or team gatherings
- • Hybrid role based in Vancouver with preference for 3 days/week in-office
🏖️ Benefits
- • Inclusive, flexible work environment that supports authenticity and work-life integration
- • Competitive total compensation package including base salary, equity, and variable commission (OTE: $158,120–$180,900 CAD)
- • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
- • $1,500 USD annual professional development stipend plus mentorship and internal promotion opportunities
- • Paid time off, parental leave top-ups (up to 26 weeks), and $1,000 USD home office setup stipend with monthly internet reimbursement
- • Remote-first culture with access to corporate co-working spaces (e.g., WeWork) and opportunities for in-person connection via company retreats and team off-sites
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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