Head of Sales - North America (Open to Remote)

Head of Sales Gen3 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 Responsibilities Sales 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