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Head of Outbound

Toronto💼 Full-time💰 $225,000–$225,000🗓 2026-05-04 → 2026-09-27

Core

Own the strategy, execution, and accountability of outbound sales motion for MSP and Accounting segments in B2B SaaS/fintech.

Role type

Senior IC Head of Outbound Sales

Builds

BDR outbound architecture, playbooks, and high-performance sales teams

Domain

B2B SaaS / Fintech / Accounts Receivable & Payable

Deliverable

production ML models | product features | dashboards & analysis | client delivery | infrastructure

Required skills

B2B SaaS or fintech sales strategy, outbound program design, signal-based targeting, sequence architecture, cold call frameworks, email positioning, BDR performance management, GTM planning, Salesforce, Apollo, Instantly, AI-driven efficiency

Preferred skills

MSP/Accounting ecosystem knowledge, PE-backed roll-ups experience, multi-vertical outbound motion, BDR-to-AE coaching, new market entry deals

Technologies

Salesforce, Apollo, Instantly, intent data platforms, enrichment tools, deliverability monitoring

Responsibilities

Diagnose and redesign outbound processes to improve efficiency, design segment-specific playbooks, build rigor and accountability across the BDR team, collaborate with Marketing/Partnerships on strategic outbound efforts, build GTM plans for new verticals, develop mid-market and enterprise outbound motions

Seniority

Senior, hands-on IC

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