Software Account Executive | SMB Retail

Are you an SMB Account Executive who excels in selling SaaS to small business owners or retail businesses? Have you closed software sales into retail or family-owned businesses where you educate buyers along the way? Are you and Account Executive or Sales Rep who thrives in consultative sales helping unsophisticated buyers make smart decisions? If you're an Account Executive or SMB SaaS Sales Rep interested in selling a software product with exceptional product-market fit, please read on.This PE-backed software company builds all-in-one software for independent retailers across the US. The platform runs critical functions like inventory, POS, and operations for roughly 4,000 stores in their niche. After 20+ years of founder-led growth and inbound sales driven by an incredibly strong product market fit, they were acquired by a growth equity firm and are building out their first true outbound sales motion. This hire will be the first Account Executive under new leadership, will own an enormous territory, and will help stand up the outbound sales engine.What You Will OwnBuild and execute a repeatable outbound prospecting motion in a greenfield territoryOwn discovery, demo, and close for consultative sales cycles with small business ownersClose deals the year through self-sourced pipeline and some inbound leadsAttend 10-12 trade shows annually to generate pipeline and close businessEducate buyers on what's possible and position the platform as a system-of-record decisionHelp launch new product offerings as they roll out in 6-9 monthsWhat You'll Need This role is a strong fit for Account Executives who have sold SMB SaaS and are comfortable educating unsophisticated buyers.History of software/SaaS sales success for 2-3+ yrs (into small business or retail buyers)Closed system-of-record software sales, not point solutionsComfortable running your own demos and learning products with depthConsultative, value-based selling approach with relationship-driven dealsScrappy, high-energy, and comfortable building in ambiguityStrong training background from companies like Salesforce, Intuit, or similar sales orgsPlus SkillsHuge plus if you can commute to Shelton, CTExperience selling to retail, family-owned businesses, or unsophisticated buyersJewelry industry background or experience at vertical SaaS companies serving retailPOS software sales experience (Toast, QuickBooks, Square, or similar)What You'll GetCompetitive Comp Package: strong base + commission program (quotas that are set to exceed)Strong benefits and incredible cultureOpportunity to be a foundational hire and shape the sales orgBacked by a growth equity firm investing in product modernization and GTM scaleHybrid flexibility with 3 days per week onsite (remote considered for the right candidate)If this opportunity aligns with your background, apply to learn more about the role and company.