Director of Sales - East Region

Director of Sales, East Region

Employment Type: Full-Time Location Type: Remote Salary: Competitive base + variable structure tied to regional door and ARR targets

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About Sweed

Sweed is a product-driven SaaS company on a mission to “shatter the myth that cannabis software is always the best of the worst” by giving retailers an all-in-one platform that combines POS, payments, e-commerce, marketing, analytics and inventory management. Founded in 2018, the team of ~200 operates remotely across the US and internationally, serving single-store operators through multi-state enterprises with compliant, automation-first tools.

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Role Summary

As Director of Sales, East Region, you will lead a team of high-performing Account Executives and Field Marketing Reps to exceed monthly door-count, lead generation, and ARR targets across your assigned region. You’ll be responsible for coaching execution, pipeline accountability, and regional coordination, ensuring every rep hits quota and every market gets stronger.

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Key Responsibilities

Regional Leadership & Coaching

• Directly manage and develop 4 AEs and 5 FMRs in the East Region.
• Conduct weekly forecast and pipeline reviews with each team member.
• Ensure team accountability to HubSpot pipeline hygiene, lead routing, and activity tracking.
• Uphold Sweed’s coaching culture: inspect what you expect, praise progress, and hold firm on outcomes.

Revenue Execution

• Hit or exceed monthly new door targets and ARR goals aligned with Sweed’s 2025 plan.
• Analyze conversion funnels and launch experiments to improve demo-to-close rate, average ACV, and time-to-live metrics.
• Monitor quota attainment weekly and intervene early with underperformers.

GTM Cadence & Territory Design

• Prioritize coverage across tiered market opportunities (license velocity, market maturity, local events).
• Allocate AE/FMR resources accordingly and refine territories quarterly.
• Collaborate with Field Marketing, Product, and Customer Success to execute campaigns, pilots, and new market launches.

Field & Partner Enablement

• Ensure reps are effectively using Sweed's event programs, partner referrals, and local campaigns.
• Review contact-to-demo conversion rates and event ROI monthly.
• Share competitive intel and customer feedback to influence product roadmap and pricing strategy.

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Required Qualifications

• 5+ years managing quota-carrying SaaS sales teams (B2B).
• Strong leadership track record in regional or territory-based sales roles.
• Experience hiring, training, and coaching AEs and/or field teams.
• CRM mastery (HubSpot preferred); disciplined in forecast and pipeline rigor.
• Cannabis, POS, or payments industry experience highly preferred.
• Able to travel 50%+ across the East Coast for team support and events.

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Preferred Qualifications

• Experience building GTM playbooks (AE/FMR model).
• Familiarity with startup-stage SaaS operations and metrics (0 → $50M ARR).
• Background working with partner-led and event-led lead gen programs.
• Comfortable operating in dynamic, compliance-heavy environments.

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Compensation & Benefits

• Competitive base + variable structure tied to regional door and ARR targets.
• Remote-first flexibility and company-sponsored travel.
• Health, dental, vision, life, and short-term disability insurance.
• Generous PTO, holidays, and remote-first flexibility.