Head of Sales - Shopify of AI for eCommerce ($6.5MM Seed Funding / $7MM ARR in 5 Years)

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Head of Sales Seeking an outstanding Head of Sales to build and scale the company’s revenue organization. This is not a corporate sales-management role. You should be equally comfortable defining GTM strategy, hiring exceptional sales talent, and personally closing enterprise customers.

You’ll own the company’s commercial strategy top to bottom, working directly with the CEO and GTM team.

The ideal candidate has successfully sold innovative SaaS products, understands AI beyond the buzzwords, and can explain complex technology in simple business terms to executives.

What You’ll Own

• Company revenue targets and commercial execution.
• Defining and continuously refining the GTM strategy.
• Scalable sales processes, forecasting, and reporting.
• Hiring, coaching, and leading a world-class sales organization.
• Strategic enterprise opportunities closed personally.
• Building outbound, inbound, partner, and product-led sales motions.
• Pricing, packaging, and commercial strategy, developed with leadership.
• Working closely with Product, Marketing, Customer Success, and Engineering to improve product-market fit.
• Relationships with executives at leading ecommerce brands, retailers, and agencies.
• Representing the company at conferences, customer meetings, and industry events.

Required What We’re Looking For

• 8+ years of B2B SaaS sales experience, including 3+ years leading and building sales teams.
• Proven history of exceeding revenue targets in high-growth startups.
• Experience building a sales organization from an early stage.
• Experience owning six-figure enterprise deals across the full cycle, from prospecting through expansion.
• Strong understanding of ecommerce, digital commerce, MarTech, retail technology, or AI software.
• Demonstrated ability to sell AI-native or technically sophisticated products, and to explain complex AI capabilities to both technical and non-technical decision makers.
• Strong analytical and operational skills with forecasting discipline.
• Excellent communication and executive presence.
• Based in New York City and able to work from the office five days per week.
• Fluent daily use of AI tools to drive pipeline generation, forecasting, customer research, and sales execution.

We Value People Who

• Think like founders and take full ownership.
• Move quickly while maintaining an exceptionally high bar.
• Prefer solving problems over escalating them.
• Are naturally curious and continuously learning about AI.
• Use AI tools daily to become significantly more effective.
• Thrive in ambiguity and enjoy building from zero.
• Care deeply about customers and product quality.

Nice To Have

• Experience selling to Shopify brands, enterprise ecommerce companies, or digital retailers.
• Existing network within ecommerce, retail, agencies, or commerce technology.
• Experience scaling revenue through Series A–C growth.
• Experience with PLG, product analytics, or AI-first software companies.
• Experience hiring and mentoring Account Executives, SDRs, and sales leaders.

Job-3630249