Head of Sales - North America (Open to Remote)

Head of SalesGen3 Marketing is seeking a Head of Sales, reporting to the CEO, to lead the strategy, operations, and execution of our commercial sales team. This role oversees inbound and outbound sales, driving a disciplined operating cadence, improving pipeline quality and conversion, and ensuring consistent achievement of new business and total sales targets.The ideal candidate combines strong sales leadership with hands-on deal execution, guiding late-stage opportunities to close, elevating qualification and follow-up discipline, and improving forecast accuracy.This role partners closely with Marketing (dotted-line) to align lead generation, targeting, and conversion insights, creating a feedback loop that fuels growth.Key ResponsibilitiesSales Team Leadership & Execution

• Directly manage, coach, and develop all sales team members (BDRs, closers, and sales ops support) to drive consistent performance and accountability
• 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
• Coordinate 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

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