Sales Development Representative

Position Overview

Tailscale is seeking motivated and curious individuals to join our Sales Development Representative team. In this role, you will be instrumental in building a qualified pipeline for our sales organization. If you are passionate about sales, educating customers, possess a technical aptitude, and are eager to contribute to a fast-growing startup, we encourage you to apply.

Key Responsibilities

• Become an expert in Tailscale's value proposition and how it benefits customers.
• Identify and engage prospective customers through tailored messaging that addresses their interests, pain points, and business challenges.
• Utilize a multi-channel approach to generate qualified meetings.
• Coordinate and schedule meetings for Account Executives.
• Manage and organize sales activities and tasks across a broad range of accounts.
• Represent Tailscale at conferences and industry events to generate leads and identify new prospective customers.

Requirements

• Demonstrated aptitude for delivering exceptional customer experiences, characterized by urgency, curiosity, and a focus on adding value.
• Excellent written and verbal communication skills.
• Proven ability to manage multiple activities and tasks concurrently.
• Willingness to travel to industry events approximately once per quarter.
• Must be located in Vancouver or Denver.
• The team collaborates in a WeWork space three days a week (Tuesday-Thursday).

Nice to Have

• A technical background, such as a STEM degree or completion of a coding bootcamp.
• Experience with sales engagement platforms like Outreach, Gong, or CRM systems like Salesforce.

Compensation & Benefits

• Pay Range (OTE): $108,000 - $121,500 CAD (On-Target Earnings, inclusive of base salary and variable compensation tied to quarterly sales targets).
• Inclusive & Flexible Environment: Tailscale fosters an environment where you can be your authentic self, valuing diverse voices and backgrounds. Flexibility in work arrangements supports work-life integration.
• Competitive Compensation: Includes base salary, equity incentive plan, and variable commission for quota-based roles.
• Comprehensive Benefits: Group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
• All-Remote with Co-working: Enjoy the flexibility of working from anywhere with Wi-Fi. Participate in virtual and in-person social events, and utilize the corporate co-working program for access to WeWork or similar spaces.
• In-Person Connection: Opportunities to connect with colleagues through an annual company retreat, team/department off-sites, and an individual travel budget for meetups.
• Professional Development: Annual budget of $1500 USD for professional development, plus access to mentorship, coaching, and internal promotion opportunities.
• Paid Time Off: A flexible PTO program designed to support personal needs and promote healthy work-life integration.

About Tailscale

Tailscale is building the future of the Internet by providing software that simplifies secure interconnection for people and their devices, regardless of location. Teams of all sizes, from individuals to large corporations, rely on Tailscale daily to secure their networks, share access to internal tools, and more. We are committed to creating an Internet that is easy, sensible, and safe. Founded in 2019 and operating as a fully distributed company, Tailscale is supported by leading investors including Accel, CRV, Insight, Heavybit, and Uncork Capital.