Manager, Sales Development Representative

Manager, Sales Development Representative – Tailscale 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% of the time for industry events or team gatherings. This role is based in Vancouver and is hybrid preferred (3 days/week in‑office). Compensation CAN Pay Range (OTE): $160,000—$160,000 CAD. 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. Benefits An inclusive, flexible environment where you can be your authentic self. A competitive total compensation package, including base salary, equity, and variable commission. Comprehensive group benefits with no waiting period—health, vision, dental, and more for you and your family. Remote‑first company, with most teams working fully remotely. Connect with other Tailscalars in person—annual retreats, team off‑sites, and travel budget. Support for personal and professional development—$1500 USD annually for development or mentorship. Paid time off and a healthy work‑life integration. Build‑your‑own home office setup—company‑owned laptop, monthly home‑internet reimbursement, $1000 USD to customize. Generous parental leave program—first day and up‑to‑26‑weeks top‑ups. Frequent statistic: 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 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, visit https://tailscale.com/scam-awareness. Referrals increase your chances of interviewing at Tailscale by 2x. Seniority Level: Mid‑Senior levelEmployment Type: Full‑timeJob Function: Sales and Business DevelopmentIndustry: Software Development Location: Surrey, British Columbia, Canada. #J-18808-Ljbffr