Account Executive (Southern California)
WFA Digital Insight
Sweed’s Account Executive role is a deep dive into the niche of cannabis‑retail technology, a space where compliance and speed matter. The position sits under the VP of Success, giving the AE a clear line to senior leadership while still collaborating across product, marketing and customer‑success teams. What sets this opening apart is the emphasis on building a four‑times quota pipeline in HubSpot and maintaining razor‑sharp CRM hygiene—an unusual focus that signals a data‑driven sales culture. Candidates will be expected to run ROI‑focused demos and negotiate bundled contracts that span POS, payments and messaging, requiring both technical fluency and consultative sales skill. The mix of outbound prospecting, regional events and partner referrals makes the day‑to‑day rhythm varied, while the travel component keeps the role grounded in the real‑world retail environment of Southern California dispensaries.
Job Description
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 ~250 operates remotely across the US and internationally, serving single-store operators through multi-state enterprises with compliant, automation-first tools.
Role Summary – Account Executive (AE)
Reporting to the Vice President of Success, the AE owns the full sales cycle for net-new and existing dispensary locations in a defined region (Southern California). Success is measured on closed ARR and door-count targets monthly supported by a best-in-class commission plan.
Key Responsibilities
Pipeline Generation
Prospect, sequence, and qualify 12+ new dispensary accounts each week through targeted outbound, regional events, and partner referrals.
Build and maintain ≥ 4× quota pipeline coverage in HubSpot, ensuring every prospect has a documented next step.
Deal Execution
Lead discovery, ROI-focused demos, and multi-threaded negotiations for SMB opportunities, tailoring value props to each stakeholder.
Structure and close bundled contracts (POS, payments, text-messaging) in PandaDoc, maximizing ACV while protecting margin and compliance.
Forecast & Governance
Keep deal stages, close dates, and action plans current in HubSpot; submit a weekly commit forecast with clear upside, best-case, and commit numbers.
Achieve ≥ 95 % CRM hygiene and deliver consistent 30-60-90-day forecast accuracy for executive reporting.
Cross-Functional Alignment
Partner with Marketing, Product, and Customer Success on regional campaigns, pilots, and upsell plays, sharing competitive intel and win-loss insights.
Co-develop account strategies that lift cross-sell rates and expansion ARR, hitting joint KPIs for adoption and retention.
Voice of Customer & Continuous Improvement
Capture product feedback, compliance hurdles, and market trends in a structured VOC log; present findings in quarterly reviews to influence roadmap.
Contribute to iterative refinement of sales playbooks, demo scripts, and onboarding materials, ensuring best practices scale with team growth.
Required Qualifications
3+ years quota-carrying B2B SaaS or retail-tech sales with a history of ≥100 % attainment
Working knowledge of cannabis retail operations and state compliance rules
Proficiency with HubSpot CRM, virtual demo tools and BANT or similar methodology
Comfortable with 40%+ travel to dispensary sites, trade shows and regional events
Excellent consultative presentation, negotiation and written communication skills
Preferred Qualifications
Experience selling POS, payments or fintech solutions to regulated industries
Prior success in high-growth startup environments (0 → $50 M ARR)
Existing network of decision-makers in cannabis markets
Familiarity with integrations and retail data analytics tools
Benefits & Comp
Lucrative variable plan
Remote-first flexibility
Medical, dental, vision, life & disability insurance options
Generous PTO, paid company holidays and paid parental leave
Career growth path to Senior AE / Regional Sales Manager as Sweed scales
How to Stand Out
- Highlight specific HubSpot pipeline metrics you have managed in past roles; recruiters will look for concrete examples of four‑times quota coverage.
- Prepare a demo walkthrough that showcases ROI for a cannabis retailer, emphasizing compliance and automation features.
- Bring data‑driven results from previous SaaS sales, especially any Excel‑based reporting you built for forecasts.
- Mention any existing relationships you have with dispensary owners or managers in Southern California.
- Be ready to discuss how you balance remote work productivity with the required 40 % travel schedule.
- During negotiations, ask about the structure of the variable plan and any equity components tied to ARR growth.
- Watch for vague language around compliance responsibilities; ensure you understand the legal expectations before signing.
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