TL;DR

Manager, Sales Development Representative (SaaS): Leading and coaching a high-performance SDR team to build qualified pipeline with an accent on refining inbound/outbound prospecting playbooks. Focus on data-driven performance management, team mentorship, and cross-functional alignment to scale sales operations in a growing hub.

Location: Must be based in Toronto, ON. This is a hybrid role requiring 3 days/week in-office.

Salary: $160,000 CAD (Target OTE)

Company

Tailscale is a distributed, fast-paced startup building secure, easy-to-use software for interconnecting people and devices across the internet.

What you will do

  • Lead, coach, and mentor a team of SDRs through regular call and pipeline reviews.
  • Develop and operationalize comprehensive inbound and outbound prospecting playbooks.
  • Drive team performance by tracking KPIs, forecasting results, and optimizing lead conversion strategies.
  • Partner with Marketing, Sales, and RevOps to align on ideal customer profiles and accelerate pipeline creation.
  • Recruit and onboard exceptional talent, fostering a collaborative and high-energy culture.
  • Represent the SDR function in cross-functional planning and go-to-market strategy development.

Requirements

  • Must be based in or able to commute to Toronto, ON (Hybrid).
  • 2+ years of experience leading SDR or BDR teams in a B2B SaaS environment.
  • Proven track record of improving prospecting performance and hitting pipeline targets.
  • Strong data-driven mindset with proficiency in sales tooling like Salesforce, Outreach, and Gong.
  • Demonstrated ability to manage multiple priorities in a fast-paced environment.
  • Willingness to travel 25% for industry events and team gatherings.

Culture & Benefits

  • Comprehensive health, vision, and dental benefits starting from day one.
  • Flexible work environment with parental leave top-ups for up to 26 weeks.
  • $1500 USD annual professional development budget and $1000 USD home office stipend.
  • Monthly home internet reimbursement.
  • Annual company retreat and regular team off-sites for in-person collaboration.
  • Inclusive, flexible culture that supports work-life integration.