Head of Sales - North America (Open to Remote)

Key Responsibilities

• Sales Team Leadership & Execution
• Directly manage, coach, and develop all sales team members (BDRs, closers, and sales ops support)
• Establish clear goals and expectations by role (outbound activity, pipeline creation, stage progression, close rate, and quota attainment)
• Run structured deal strategy reviews and support late-stage deal execution (negotiation planning, stakeholder mapping, close plans)
• Drive improvements in win rate through rigorous qualification, competitive positioning, and consistent sales process adherence.
• Sales Operations, Cadence & Forecasting
• Own the sales operating cadence: weekly pipeline and forecast calls, stage-by-stage inspection, and gap-close planning
• Define and manage core KPIs (pipeline coverage, conversion by stage, cycle time, win rate, outbound activity, meeting-to-opportunity and opportunity-to-close rates)
• Ensure high-integrity CRM usage (HubSpot): accurate stage management, activity logging, close dates, and reporting hygiene
• Targeting, Playbooks & Enablement
• Refine and operationalize the ideal customer profile (ICP) and targeting approach in partnership with Chief Customer Officer and the marketing team
• Develop and continuously improve outbound and closing playbooks (messaging, objection handling, discovery, qualification, mutual action plans)
• Strengthen proposal and SOW discipline (scope clarity, pricing logic, margin awareness, and negotiation readiness)
• Standardize handoffs from BDR to closer and from signed deal to delivery/account leadership to reduce downstream churn risk
• Cross-Functional Partnership (Dotted-Line to Marketing)
• Partner with Marketing (dotted line) to align campaigns / content with ICP targets and pipeline needs
• Create a feedback system on lead quality, conversion performance, and messaging effectiveness
• Cook up coordination with Finance and Operations leadership on targets, capacity, and performance reporting

What you’ll need

• Strong business development experience (with preference for experience with performance marketing)
• 8+ years of experience in technology, advertising or a media sale with progressive career advancement and expanded responsibilities
• Experience with short and long sales cycles, and a broad range of clients spanning large enterprise-level, as well as small and midsized businesses (ecomm and financial services experience a plus)
• Track record of team building and culture development
• A motivated self-starter, process-oriented with high attention to detail
• Operates with a sense of urgency and expects his/her team to do the same, leading by example
• Possesses a very hands-on orientation and comfortable working in a resource lean environment
• Bachelor’s Degree required.

What's in it for you?

• Compensation includes a base salary plus a competitive commission/bonus structure based on performance and achievement of targets.
• Hybrid work and remote work options are available outside of head office locations
• Flexible work hours
• Summer Fridays
• Insurance coverage with cost incentives
• Paid parental leave benefits
• Opportunities to travel
• 401K contribution matching plan after 6 months