Senior Sales Development Representative Manager

Toronto, Canada

About Feathery

Feathery automates data intake workflows for insurance and wealth management companies. Our customers—including industry leaders like Zurich and Sequoia Financial—use Feathery to power mission-critical workflows such as insurance underwriting, client onboarding, and automated account openings.

Having grown revenue 6x YoY for each of the past two years, Feathery is rapidly expanding across financial services—and beyond.

About the Role

We’re entering our next stage of growth, expanding our outbound motion and moving upmarket into enterprise accounts. To accelerate this, we’re looking for a Senior SDR Manager to build, coach, and scale a world-class sales development organization at our Toronto location. You will lead by example as you will also engage with sales development.

This leader will own the top of our funnel — defining outreach strategy, optimizing processes, and driving performance across inbound and outbound channels. You’ll partner closely with Sales, Marketing, and Leadership to create a repeatable, data-driven prospecting engine that fuels Feathery’s next stage of growth.

What You’ll Do

  • Build and lead a team of SDRs, fostering a culture of accountability, curiosity, and continuous improvement.
  • Design and refine Feathery’s outbound playbook — messaging frameworks, sequencing, and targeting strategy across multiple verticals.
  • Collaborate with Marketing and Sales to align on lead handoff, qualification criteria, and feedback loops that improve pipeline quality.
  • Own SDR performance metrics — activity levels, conversion rates, pipeline contribution, and quota attainment.
  • Implement best-in-class tools and automation to improve efficiency, visibility, and scalability of the SDR workflow.
  • Train and mentor SDRs to become efficient lead machines
  • Partner with sales leadership to establish reporting and forecasting processes for consistent pipeline generation.

About You

  • 5+ years of experience in B2B SaaS sales, with 2+ years managing SDR or BDR teams in a high-growth environment.
  • Proven ability to build and scale outbound programs that generate meaningful pipeline for enterprise or mid-market segments.
  • Strong command of sales frameworks (e.g., MEDDPICC, BANT, SPIN, Challenger) and outbound methodologies.
  • Track record of hiring, developing, and promoting top-performing SDRs.
  • Analytical mindset — able to interpret funnel metrics and drive decisions with data.
  • Strong collaborator and communicator who thrives in cross-functional environments.
  • Bonus: experience selling into **financial services, insurance, or wealth management **sectors.
  • Bonus: familiarity with tools like HubSpot, Unify, Clay, Elto, Grain, and Apollo
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