Manager, Sales Development Representative

About Tailscale

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

We are looking for a thoughtful, hands-on Manager to lead our Sales Development team. In this role, you will coach and develop a group of curious, motivated SDRs who are responsible for building qualified pipeline for the sales organization. You’ll guide their day-to-day execution, help refine our prospecting motions, and partner closely with Sales, Marketing, and Operations to align on strategy, messaging, and highest-value opportunities.

If you are passionate about coaching early-career sellers, optimizing prospecting strategies, and helping teams grow in a fast-paced startup environment, we’d love to talk to you.

Key Responsibilities

• Lead, coach, and mentor a team of Sales Development Representatives with clear goals, actionable feedback, and ongoing skill development.

• Become an expert in how Tailscale solves real customer problems, and train your team to articulate that value with clarity and confidence.

• Build, refine, and operationalize our prospecting playbook across inbound and outbound channels.

• Drive team performance through regular coaching sessions, call reviews, pipeline reviews, and weekly/monthly operational cadences.

• Partner closely with Sales, Marketing, RevOps, and Enablement to align ICP, improve lead quality, run campaigns, and accelerate pipeline creation.

• Own SDR KPIs: track performance, forecast pipeline creation, and use data to identify opportunities for conversion improvements.

• Recruit, onboard, and ramp exceptional SDR talent, helping them grow into future Account Executives or leaders at Tailscale.

• Foster an inclusive, collaborative, high-energy culture rooted in curiosity, accountability, and customer empathy.

• Represent the SDR team in cross-functional planning and help shape our go-to-market strategy as we scale.

What We Are Looking For

• 2+ years experience leading SDR or BDR teams in a B2B SaaS environment

• A 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 the ability to break down complex ideas simply

• A data-driven mindset - comfortable using metrics, reporting, and tooling (Salesforce, Outreach, Gong, Sales Navigator, etc.) to guide decisions

• Ability to manage many activities and priorities simultaneously while keeping the team focused on what matters most

• A passion for coaching, developing future sales talent, and helping others succeed

• Willingness to travel 25% for industry events and team gatherings, with week-long quarterly stays in Vancouver during the first 2–3 quarters

• This role is based in Toronto (this role will be building out a new sales hub location of Tailscale) and is hybrid preferred (3 days/week in-office). #LI-Hybrid

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE)
$160,000—$160,000 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.

• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).

• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!

• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.

• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.

• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!

• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.

• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.