Director of Sales

We’re Sweed, a product-driven company building an all-in-one cannabis retail platform. We’re looking for a Director of Sales to lead our account executives and turn company priorities into consistent sales results.

You’ll join a business with an established product, existing customers, and an active pipeline. You’ll coach reps, join customer calls and demos, improve how deals move, and build the processes and playbooks the team uses every day.

This is an opportunity to lead an existing team, make a measurable impact on its performance, and grow your scope as you deliver results.

What This Role Entails

• Pipeline Management — Review the pipeline with each AE every week. Require clear customer next steps, dates, decision-makers, and evidence for each stage. Define what qualifies as a pipeline with RevOps, identify stalled opportunities, and help reps move deals forward or remove them when they no longer qualify.

• Sales Process Ownership — Establish consistent qualification standards, sales stages, and exit criteria with RevOps. Build one repeatable approach from discovery and demo through proposal, negotiation, close, and customer handoff. Partner with RevOps on CRM automation and reporting.

• Sales Team Management & Coaching — Hold weekly one-to-ones and set clear activity and conversion expectations. Join and review calls and demos, give practical feedback, and track rep performance. Recognize strong results, address underperformance directly, and put improvement plans in place when needed.

• Forecasting & Reporting — Own the team’s weekly forecast, including commit, best case, and upside. Inspect deals individually, explain changes from one forecast to the next, and flag risks early so leadership has a clear view of expected results.

• Communication & Follow-Through — Run daily and weekly team communication with clear priorities and actions. Keep Sales, RevOps, Marketing, and Customer Experience informed, make handoffs clear, and escalate blockers promptly.

• Sales Enablement & Hiring — Build practical playbooks for discovery, demos, objection handling, and competitive positioning, then coach the team on using them. Use customer conversations and win/loss insights to improve the pitch and share feedback with product and marketing. Help hire and onboard reps and contribute recommendations to annual planning.

What Success Looks Like Initially

Your first priority will be to understand the product, team, and pipeline, then establish a consistent way of running sales.

During your first three months, you’ll be expected to:

• Complete a written assessment of the team, pipeline, and current sales process.
• Establish regular one-to-ones, weekly pipeline reviews, and a weekly forecast with RevOps.
• Make sure every active opportunity has a clear next step, date, and identified decision-maker.
• Put agreed sales stages and exit criteria into practice in the CRM.
• Create the first playbook materials and begin using them in coaching.

As you establish these foundations, we’ll expect improvements in forecast accuracy, pipeline coverage, conversion, and rep performance. You’ll build development plans for the team, contribute to annual planning, and help the team deliver against its agreed targets.

Performance will be measured through both sales results and leading indicators, including qualified pipeline, stage conversion, win rate, forecast accuracy, and rep quota attainment.

What Professional Skills Are Important for Us?

• Direct Sales Management Experience — 3+ years directly managing quota-carrying account executives, including at least 2 years leading a team of comparable size—approximately 10–15 reps—with measurable results in coaching, rep development, and quota attainment.

• Relevant Sales Experience — A track record of leading B2B SaaS sales, ideally in POS, payments, or retail technology. We may also consider cannabis wholesale leaders who have managed quota-carrying sales reps through a structured CRM pipeline.

• Hands-On Coaching — The ability to diagnose why a rep or deal is struggling and provide specific guidance that improves performance, supported by examples from your experience.

• Pipeline & Forecasting Fluency — Experience owning a weekly forecast, evaluating opportunities using customer evidence, and explaining your forecast accuracy.

• Process & Enablement Skills — Experience building sales processes and playbooks that reps consistently use.

• CRM & Sales Tech Proficiency — Hands-on experience with Salesforce, HubSpot, or a comparable CRM and supporting sales tools.

• Performance Management — Comfort setting expectations, having difficult conversations, and holding people accountable while helping them succeed.

• Industry Understanding — Cannabis experience is strongly preferred, particularly experience working with dispensaries or multi-location operators.

• Growth-Stage Readiness — Comfort working with involved leadership, executing agreed priorities, and improving processes as the business evolves.

What Else Matters?

• Ownership — You follow through, surface problems early, and take responsibility for moving things forward.

• Critical Thinking — You look beyond activity counts to understand what improves conversion and results.

• Adaptability — You adjust your approach when data or customer feedback shows that something needs to change.

• Communication — You make priorities clear, keep people informed, and close the loop on commitments.

• Customer Focus — You help reps understand the customer’s business and connect our product to real operating needs.