Director of Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the daily operations and performance of the account executive team.

• Mentor account executives while participating in customer calls and demonstrations.

• Conduct weekly reviews of each account executive’s pipeline, ensuring clarity on next steps, dates, decision-makers, and stage evidence.

• Collaborate with RevOps to define pipeline qualification, sales stages, and exit criteria.

• Create a consistent sales process that encompasses discovery, demos, proposals, negotiations, closures, and customer handoffs.

• Partner with RevOps for CRM automation and reporting initiatives.

• Conduct weekly one-on-one meetings and establish activity and conversion benchmarks.

• Review calls and demos, offer actionable feedback, monitor performance, celebrate achievements, and address any underperformance.

• Manage the weekly forecast, including commitments, best-case scenarios, and upsides.

• Analyze deals, clarify forecast modifications, and identify risks for leadership.

• Facilitate daily and weekly team communications and coordinate with Sales, RevOps, Marketing, and Customer Experience.

• Develop playbooks for discovery, demos, objection management, and competitive positioning.

• Leverage customer insights and win/loss feedback to enhance pitches and relay insights to product and marketing teams.

• Assist in the recruitment and onboarding of sales representatives.

• Perform an initial assessment of the team, pipeline, and sales procedures.

• Set up pipeline reviews, one-on-ones, forecasting, CRM stages, exit criteria, and initial coaching resources within the first three months.

• Participate in sales planning, quota determination, headcount decisions, annual planning, and team development strategies.

• Report to the VP of Strategy with a dotted line to the VP of Growth & RevOps.

⛳️ Requirements

• Minimum of 3 years of direct experience managing quota-carrying account executives.

• At least 2 years of experience leading a similar-sized team of approximately 10–15 representatives.

• Proven track record of measurable success in coaching, developing sales representatives, and achieving quotas.

• Experience leading B2B SaaS sales, preferably in point-of-sale, payments, or retail technology sectors.

• Leadership experience in cannabis wholesale sales may be considered if it involves managing quota-carrying sales representatives through a structured CRM pipeline.

• Ability to identify underperforming representatives or deals and provide targeted performance enhancement guidance.

• Experience in owning weekly forecasts and assessing opportunities based on customer evidence.

• Skilled in developing sales processes and playbooks that are consistently utilized by representatives.

• Proficient with Salesforce, HubSpot, or comparable CRM systems and related sales tools.

• Comfortable setting expectations, engaging in difficult conversations, and holding individuals accountable.

• Strong preference for candidates with cannabis experience, especially with dispensaries or multi-location operators.

• Ability to work collaboratively with engaged leadership and enhance processes as the business grows.

• Demonstrates ownership, critical thinking, adaptability, effective communication, and a customer-centric approach.

🏝️ Benefits

• Competitive base salary along with a performance-based variable compensation plan.

• Health insurance options including medical, dental, and vision coverage.

• Paid parental leave.

• Generous paid time off and company-observed holidays.

• Flexible remote work environment.

• Occasional travel for customer meetings and team collaboration.

• Opportunity to lead an established sales team and develop its processes, playbooks, and forecasting methods.

• Close collaboration with leadership and potential to expand responsibilities as performance is demonstrated.