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 Own

• Build and execute a repeatable outbound prospecting motion in a greenfield territory
• Own discovery, demo, and close for consultative sales cycles with small business owners
• Close deals the year through self-sourced pipeline and some inbound leads
• Attend 10-12 trade shows annually to generate pipeline and close business
• Educate buyers on what's possible and position the platform as a system-of-record decision
• Help launch new product offerings as they roll out in 6-9 months

What 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 solutions
• Comfortable running your own demos and learning products with depth
• Consultative, value-based selling approach with relationship-driven deals
• Scrappy, high-energy, and comfortable building in ambiguity
• Strong training background from companies like Salesforce, Intuit, or similar sales orgs

Plus Skills

• Huge plus if you can commute to Shelton, CT
• Experience selling to retail, family-owned businesses, or unsophisticated buyers
• Jewelry industry background or experience at vertical SaaS companies serving retail
• POS software sales experience (Toast, QuickBooks, Square, or similar)

What You'll Get

• Competitive Comp Package: strong base commission program (quotas that are set to exceed)
• Strong benefits and incredible culture
• Opportunity to be a foundational hire and shape the sales org
• Backed by a growth equity firm investing in product modernization and GTM scale
• Hybrid 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.