Job Overview
Location
Hybrid (Toronto, Ontario)
Job Type
Full-time
Category
Sales
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Manager of Sales Development Representative at Tailscale Inc., you will lead and develop a team of SDRs responsible for building qualified pipeline for the sales organization, playing a critical role in scaling the company’s go-to-market strategy.
- • Day to day, you will coach and mentor SDRs, refine prospecting playbooks across inbound and outbound channels, conduct call and pipeline reviews, partner with Sales, Marketing, and RevOps to align on strategy, and own SDR KPIs including performance tracking and pipeline forecasting.
- • Tailscale is building the new Internet by making secure device interconnection easy and safe for users ranging from hobbyists to multinational corporations. Founded in 2019 and fully distributed, the company is backed by top-tier investors and operates with a remote-first, hybrid-flexible culture.
- • In this role, you will develop leadership and coaching expertise, deepen your understanding of B2B SaaS sales motions, and have the opportunity to shape Tailscale’s sales hub in Toronto while growing future sales leaders and contributing to scalable pipeline generation.
🎯 Requirements
- • 2+ years experience leading SDR or BDR teams in a B2B SaaS environment
- • Track record of coaching SDRs, improving prospecting performance, and consistently meeting pipeline targets
- • Experience in outbound and inbound prospecting motions across multiple segments and personas
- • Strong written and verbal communication skills with ability to break down complex ideas simply
- • Data-driven mindset — comfortable using metrics, reporting, and tooling (Salesforce, Outreach, Gong, Sales Navigator, etc.) to guide decisions
- • Ability to manage multiple activities and priorities while keeping the team focused on high-impact goals
- • Passion for coaching, developing future sales talent, and helping others succeed
- • Willingness to travel 25% for industry events and team gatherings, including week-long quarterly stays in Vancouver during the first 2–3 quarters
🏖️ Benefits
- • Inclusive, flexible environment where you can be your authentic self
- • Competitive total compensation package including base salary, equity, and variable commission
- • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
- • $1500 USD annually for professional development, plus mentorship and internal promotion opportunities
- • Paid time off supporting work-life integration for any life situation
- • Build-your-own home office setup: company-owned laptop (Mac or PC), monthly internet reimbursement, and $1000 USD for workstation customization
- • Generous parental leave program from day one with top-ups for up to 26 weeks
- • Remote-first culture with access to WeWork co-working spaces and intentional in-person connection through 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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