VP of Sales

A best-in-class platform. A market to win. We’re hiring a VP of Sales.

Hi there!

We’re Sweed, and we bring everything cannabis retailers need into one platform. Now we’re looking for a sales leader with the ambition to match—to lead the team, win customers, and help us set the standard for cannabis retail.

You’ll join a business with an established product, existing customers, and an active pipeline. Working directly with our CEO, you’ll build the structure, coaching, and execution that make the team consistently successful—with the opportunity to expand your leadership scope as you deliver results.

Team Structure

We’re a global team of over 250 people. Our development organization operates in cross-functional product teams, while our CEO, account management, and customer success teams are based in the United States.

You’ll report directly to our CEO and lead the sales team’s day-to-day execution and performance. You’ll work closely with our VP of Strategy on business development and relationships, and with our VP of RevOps on reporting, forecasting, and sales operations.

As you establish yourself in the role, there is an opportunity to expand your remit to include enterprise sales and partnerships.

What This Role Entails

• Sales Leadership & Execution — Turn company priorities into clear plans, ownership, and action. Stay close to the team and its opportunities, remove blockers, and follow through on commitments.

• Sales Team Management — Manage and coach account executives, set clear expectations, and help each rep improve through regular one-to-ones, deal reviews, and practical feedback.

• Product & Customer Understanding — Learn our product, spend time with retailers, and understand their operating challenges. Use those insights to sharpen the team’s pitch and approach to selling.

• Process & Playbook Ownership — Build, document, and reinforce repeatable processes from prospecting and qualification through close and handoff to onboarding.

• KPI & Reporting Cadence — Partner with RevOps to run weekly pipeline reviews, forecast calls, and performance reporting. Make sure leadership receives timely updates with clear actions when results fall short.

• Deal Desk & Commercial Discipline — Help the team advance opportunities while following standard deal terms and approval workflows.

• Cross-Functional Accountability — Coordinate with marketing, partnerships, enterprise sales, and customer success so opportunities move forward with clear ownership and effective handoffs. Keep sales engaged beyond signature to support successful customer launches.

• Sales Planning & Talent Development — Help develop the 2027 sales plan, quotas, and resource needs. Assess team capabilities, recruit where needed, and develop future sales leaders.

What Success Looks Like Initially

Your initial priority will be to establish yourself as the team’s leader and demonstrate meaningful improvements in how sales operates.

You’ll be expected to:

• Understand the product, market positioning, team, and existing pipeline.

• Build relationships with the team and customers, including time together in person.

• Establish consistent coaching, pipeline reviews, forecasting, and follow-up with RevOps.

• Improve how the team uses data, manages priorities, and executes on opportunities.

• Contribute to the 2027 sales plan and targets.

For a 2026 start, we’ll agree on initial milestones together, focused on team leadership and operational impact. Formal sales targets will begin in 2027.

What Professional Skills Are Important for Us?

• Sales Leadership Experience — 5+ years in sales leadership, with a track record of managing and developing account executives and improving team results. You may already be a VP or be a Director or Head of Sales ready for broader ownership.

• Operational Rigor — A structured approach to building sales processes, establishing accountability, and making sure plans translate into action.

• Hands-On Coaching — The ability to identify why a rep or deal is struggling and provide specific guidance that improves execution.

• Reporting & Forecasting Fluency — Confidence owning pipeline reviews, forecast accuracy, and KPI reporting, and translating data into decisions.

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

• High Ownership & Accountability — Reliable follow-through, clear communication, and a willingness to surface problems early and take responsibility for resolving them.

• Industry Understanding — Cannabis experience is strongly preferred. We’re also open to exceptional leaders from POS, retail technology, or adjacent markets who can learn a complex industry quickly.

• Growth-Stage Readiness — Comfort working closely with an involved CEO, building structure as the business evolves, and staying personally engaged with customers and the team.

What Else Matters?

• Proactivity — You identify what needs attention and move it forward.

• Critical Thinking — You question assumptions, diagnose problems, and make decisions grounded in evidence.

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

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

What We Offer

• 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.

• A remote work environment, with travel for customer visits, industry events, and team collaboration.

• Direct collaboration with our CEO and the opportunity to shape the sales organization, influence the next annual plan, and grow your leadership scope.

Hiring Process

1. Recruiter Call — Discuss your experience, expectations, and interest in the role, and learn more about Sweed.

2. Sales Leadership Interview — Meet our sales leadership advisor to discuss your experience, proposal, and approach to execution.

3. Sales Leadership Exercise — Prepare a short proposal outlining how you would organize and lead the sales team.

4. Final Interview — Meet our CEO and a member of our leadership team to discuss priorities, mutual expectations, and fit.