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