Account Executive - Midwest
Account Executive – Midwest About Sweed Sweed is a SaaS company focused on product excellence. We have developed the premier technology platform for Cannabis retailers, dedicated to creating a retail operating system capable of rivaling the top mainstream POS solutions. We provide dispensaries and multi-state operators with DOS, a Dispensary Operating System, which is an all-in-one platform that combines POS, payments, e-commerce, marketing, analytics, inventory management, delivery, and automation into a single solution. Founded in 2018, Sweed is a remote-first company of ~250 employees serving cannabis retailers all across the US. As we continue to expand our market presence, we're looking for ambitious sales professionals who thrive in fast-paced environments and enjoy building relationships, creating opportunities, winning business, and being part of growing a world-class SaaS company.
About the Role
Reporting to the Vice President of Sales, the Account Executive owns the full sales cycle for net-new and existing dispensary locations within an assigned territory. This is a true 360 sales role: You'll be responsible for generating pipeline, building relationships, developing the business case for Sweed, running discovery and demos, negotiating contracts, and closing new business. You have full responsibility for the above with full managerial & organizational support on each of these elements. Success in this role is measured through closed ARR, onboarded door-count targets, pipeline generation, territory growth, and forecast accuracy. We're looking for someone who can successfully sell a premium product through value, ROI, and business outcomes—not simply through relationships or discounting.
What You'll Do
Pipeline Generation - Prospect and qualify new dispensary accounts via outbound activity, events, and referrals - Maintain ≥4x quota pipeline in HubSpot with clear next steps for every prospect - Consistently generate new opportunities while advancing active deals - Create territory plans to target high-potential market operators - Cultivate relationships with key cannabis retail stakeholders Deal Execution - Lead discovery, ROI-focused demos, and complex negotiations with decision-makers - Close bundled SaaS contracts covering POS, payments, and e-commerce - Build business cases proving operational and financial value - Position Sweed as a premium, outcome-driven solution - Navigate multi-stakeholder buying processes across retail and executive teams Forecast & Pipeline Management - Manage accurate deal stages and action plans in HubSpot - Submit weekly forecasts with commit, best-case, and upside projections - Ensure high CRM hygiene and consistent forecast accuracy - Monitor funnel metrics and overall pipeline health Cross-Functional Collaboration - Partner with Marketing, Product, and Success teams on campaigns and strategic deals - Share market insights, customer feedback, and competitive intelligence - Support regional growth and account expansion initiatives Voice of Customer & Continuous Improvement - Capture trends and feedback to influence product and GTM strategy - Refine sales playbooks and value-selling frameworks What We're Looking For - 3+ years of quota-carrying B2B sales experience with a proven track record - Proficiency in full-cycle sales, from prospecting to closing - Experience in SaaS, fintech, or retail technology - Ability to articulate ROI and business impact to stakeholders - Skilled in HubSpot, virtual demos, and BANT methodologies - Excellent communication skills and high emotional intelligence - Willingness to travel for regional events and meetings Preferred Qualifications - Cannabis industry or retail technology experience - Success selling premium products in high-growth startup environments - Established network within cannabis markets Travel Requires 25–50% regional travel for customer meetings and industry events. Why Join Sweed? - Competitive base salary plus uncapped commission - Remote-first flexibility with comprehensive health benefits - Generous PTO and parental leave - Clear career path into leadership as we scale What Success Looks Like By 90 days, you will have established a pipeline and key relationships. By 6 months, you will be closing business and hitting ARR targets. Top performers are proactive, accountable, and outcome-oriented. Apply To This Job