Director of Sales

Sweed POS

. Lead the account executive team’s day-to-day work and performance .

Posted 10/13/2026full-timeRemote • United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading and developing account executive teams, with a strong focus on building effective sales processes and playbooks. Proven ability to manage forecasts, evaluate opportunities, and drive measurable results in B2B SaaS sales, particularly within the cannabis industry.

Highest-signal resume keywords

B2B SaaS Sales LeadershipSales Process DevelopmentSalesforce CRM ExperienceCoaching and Rep DevelopmentPipeline Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Quota ManagementSales ForecastingPipeline QualificationSales Playbook CreationPerformance Evaluation

Soft Skills

Clear CommunicationCritical ThinkingAdaptabilityCustomer FocusAccountability

Tools & Technologies

SalesforceHubSpotCRM AutomationSales Reporting Tools

Industry Keywords

B2B SalesSaaSPOS TechnologyPaymentsCannabis Sales

About the role

Key responsibilities & impact

Lead the account executive team’s day-to-day work and performance
Coach account executives and join customer calls and demos
Review each AE’s pipeline weekly and ensure clear next steps, dates, decision-makers, and stage evidence
Define pipeline qualification, sales stages, and exit criteria with RevOps
Establish a repeatable sales process from discovery and demo through proposal, negotiation, close, and customer handoff
Partner with RevOps on CRM automation and reporting
Hold weekly one-to-ones and set activity and conversion expectations
Review calls and demos, provide practical feedback, track performance, recognize results, and address underperformance
Own the weekly forecast, including commit, best case, and upside
Inspect deals, explain forecast changes, and flag risks to leadership
Run daily and weekly team communication and coordinate with Sales, RevOps, Marketing, and Customer Experience
Build playbooks for discovery, demos, objection handling, and competitive positioning
Use customer and win/loss insights to improve the pitch and share feedback with product and marketing
Help hire and onboard sales representatives
Complete an initial assessment of the team, pipeline, and sales process
Establish pipeline reviews, one-to-ones, forecasting, CRM stages, exit criteria, and initial coaching materials during the first three months
Contribute to sales planning, quota setting, headcount decisions, annual planning, and team development plans
Report to the VP of Strategy with a dotted line to the VP of Growth & RevOps

Requirements

What you’ll need

3+ years directly managing quota-carrying account executives
At least 2 years leading a comparable team of approximately 10–15 reps
Measurable results in coaching, rep development, and quota attainment
Track record leading B2B SaaS sales, ideally in POS, payments, or retail technology
Cannabis wholesale sales leadership experience may be considered if managing quota-carrying sales reps through a structured CRM pipeline
Ability to diagnose struggling reps or deals and provide specific performance-improving guidance
Experience owning a weekly forecast and evaluating opportunities using customer evidence
Experience building sales processes and playbooks that reps consistently use
Hands-on experience with Salesforce, HubSpot, or a comparable CRM and supporting sales tools
Comfort setting expectations, having difficult conversations, and holding people accountable
Cannabis experience strongly preferred, particularly with dispensaries or multi-location operators
Comfort working with involved leadership and improving processes as the business evolves
Ownership, critical thinking, adaptability, clear communication, and customer focus

Benefits

Comp & perks

Competitive base salary plus a performance-based variable compensation plan
Medical, dental, vision, and additional health insurance options
Paid parental leave
Generous PTO and paid company-observed holidays
Remote work environment
Occasional travel for customer visits and team collaboration
Opportunity to lead an existing sales team and build its processes, playbooks, and forecasting practices
Close collaboration with leadership and opportunity to expand responsibilities as success is demonstrated