Head of Sales (Remote, USA)

Who We Are:

Stay AI is powered by savvy DTC industry vets, who have each been building subscription programs for over ten years. We’ve worked with over 300+ subscription-focused CPG brands that have generated hundreds of millions of dollars in subscription revenue alone. Our product is shaped by eCommerce experts who specialize in acquisition and retention—and it shows.

We have amazing investors like Telescope Partners, with participation from Boulder Food Group, Riverpark Ventures, and Vanterra Capital. Previous investments were led by Watchfire Ventures, alongside industry leaders such as Nik Sharma (Sharma Brands) and Adam Turner (Postscript).

We are not afraid of challenging work and are excited to build the next big thing. Sound good to you? Then, please read more about our role!

Our Culture:

We are dedicated to our work, but equally committed to celebrating our achievements. Collaboration is at the heart of everything we do, as we firmly believe in the power of teamwork. While we are remote-first as a company, we try to create opportunities to meet each other. That's why we organize annual offsite retreats in beautiful Park City, Utah and Mexico!

Who You Are:

We are looking for a Head of Sales to lead and scale our sales function. You’ll be responsible for owning the full sales cycle—from outbound strategy and pipeline development to closing and expansion. You’ll work closely with our CEO, Gina and cross-functional teams to shape our sales strategy, build foundational processes, and grow a team that can scale with us.

This is a high-impact, strategic role that requires a self-starter who can build, execute, and refine a scalable sales engine. If you thrive in fast-paced environments and love solving, we’d love to hear from you!

What You’ll Do:

Sales Leadership & Strategy

• Own the entire sales function, with a focus on new customer acquisition and revenue growth

• Develop and optimize a scalable outbound motion targeting mid-market and enterprise subscription brands

• Establish clear sales metrics, reporting processes, and forecasting tools to measure success

• Partner with marketing on integrated campaigns and outbound programs

Pipeline & Deal Execution

• Prospect, qualify, and close high-value deals while creating and managing a robust pipeline

• Build relationships with senior-level decision-makers at fast-growing DTC and eCommerce brands

• Sell consultatively, educating customers on our value prop and differentiators throughout the sales cycle

• Own pricing conversations, handle objections, and negotiate contracts to close deals

Team Building & Coaching

• Hire, coach, and lead a team of BDRs and AEs as the company grows

• Create onboarding, training, and enablement programs to level up team performance

• Foster a high-accountability, high-autonomy culture that rewards execution and customer obsession

Cross-Functional Collaboration

• Partner with Product and Customer Success to bring voice-of-customer insights into roadmap decisions

• Inform positioning and messaging based on real-time feedback from the market

What You’ll Bring:

• Proven experience leading SaaS sales at a high-growth startup (ideally Series A–C)

• A strong operator who can both build systems and close deals

• Experience selling to eCommerce brands, ideally with knowledge of the Shopify ecosystem

• Data-driven, deeply organized, and a creative storyteller

• A true self-starter—motivated by challenge and excited by what hasn’t been built yet

Who This Role is NOT For:

• Someone who needs a playbook instead of building one

• Someone uncomfortable with ambiguity or fast-moving environments

• Someone who prefers closing alone versus leading a team to win

• Someone who shies away from high expectations or healthy pressure

Why Join Us?:

• For the opportunity to make a huge impact at a high-growth startup

• Build the sales function at one of the most exciting companies in eCommerce

• To work alongside Stayers who are fun and collaborative

• To contribute to the growth of our product as we scale quickly