Account Executive - Midwest

Sweed

3d•Remote

About The Position

Sweed is a SaaS company focused on product excellence, offering the premier technology platform for Cannabis retailers. Their Dispensary Operating System (DOS) is an all-in-one solution combining POS, payments, e-commerce, marketing, analytics, inventory management, delivery, and automation. Founded in 2018, Sweed is a remote-first company of approximately 250 employees serving cannabis retailers across the US. They are seeking ambitious sales professionals to expand their market presence, focusing on individuals who thrive in fast-paced environments, enjoy building relationships, creating opportunities, winning business, and contributing to a world-class SaaS company. The Account Executive role reports to the Vice President of Sales and is responsible for the full sales cycle for new and existing dispensary locations within an assigned territory. This is a comprehensive sales role involving pipeline generation, relationship building, developing business cases, conducting discovery and demos, negotiating contracts, and closing new business, with full managerial and organizational support. Success is measured by closed ARR, onboarded door-count targets, pipeline generation, territory growth, and forecast accuracy. The ideal candidate will sell a premium product through value, ROI, and business outcomes, rather than solely through relationships or discounting.

Requirements

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

Nice To Haves

Cannabis industry or retail technology experience
Success selling premium products in high-growth startup environments
Established network within cannabis markets

Responsibilities

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
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
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
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
Capture trends and feedback to influence product and GTM strategy
Refine sales playbooks and value-selling frameworks