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Account Executive (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 an Account Executive who is a driver of revenue growth and you take ownership of the full sales cycle from prospecting to closing. You’ll work in a highly dynamic, fast-moving environment where adaptability, resilience, and a passion for sales are essential. If you thrive in fast-paced environments and love solving infrastructure challenges, we’d love to hear from you!

In a typical day, you might:

  • As we scale, it is critical that you drive pipeline through self sourced channels, with marketing, from events and partnerships

  • Adopt and embody Stay AI’s sales frameworks to maintain a unified and compelling voice across the organization

  • Own the full sales cycle, guiding prospects from discovery through close and ensuring a seamless handoff for implementation

  • Deliver impactful technical demonstrations to merchants and prospective merchants 

  • Work in tandem with Stay AI team members outside of the sales organization to ensure a comprehensive understanding of the company voice and direction

  • Consistently exceed leadership established metrics and quarterly quotas

What you’ll bring:

  • 4+ years of sales experience with a proven track record of success

  • Proficient in leveraging sales methodologies like MEDDICC, with a demonstrated ability to close enterprise deals

  • Excelling in full-cycle sales—from cold outreach to seamless implementation in collaboration with our CSM team

  • Skilled in value-driven selling, effectively positioning Stay AI as the premier choice in a competitive market

  • Experience with sales prospecting and automation tools

  • Ability to thrive in a dynamic startup environment, demonstrating adaptability, curiosity, and a willingness to take initiative

  • Excellent problem solving skills and the ability to effectively communicate complex concepts across cross-functional teams

  • Enthusiasm for providing top-notch internal support with patience and professionalism

  • Experience working with the Shopify platform

Nice to haves:

  • Experience within the eCommerce and/or subscription management space

Why join us?:

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

  • To work alongside Stayers who are fun and collaborative

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

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Average salary estimate

$85000 / YEARLY (est.)
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$70000K
$100000K

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What You Should Know About Account Executive (Remote, USA), Stay Ai

Join our innovative team as an Account Executive at Stay AI! We’re a forward-thinking company based in the heart of New York City, dedicated to transforming the subscription landscape. With over ten years of experience in the DTC industry and a portfolio that includes 300+ subscription-focused CPG brands, we know how to drive revenue and foster lasting relationships. Here at Stay AI, our culture isn't just about hitting targets; we believe in celebrating our wins and collaborating as a team. As a remote-first company, we cherish the times we can come together for our annual retreats in scenic locations like Park City, Utah and Mexico. As our new Account Executive, you’ll own the full sales cycle and be a pivotal player in driving our revenue growth. If you thrive in fast-paced settings and enjoy tackling infrastructure challenges, this job is perfect for you. Your day-to-day will involve self-sourcing leads and developing partnerships while embodying our unique sales frameworks. You’ll guide prospects through in-depth sales processes, showcasing exceptional technical demos and collaborating with cross-functional teams to ensure smooth transitions. We’re looking for someone with a minimum of 4 years of sales experience, including expertise in using methodologies like MEDDICC to close enterprise deals. Familiarity with the Shopify platform and value-driven selling is a plus! At Stay AI, you’ll not only make an impact but also work with a group of talented, fun-loving professionals committed to growth and innovation. Come be a part of our exciting journey!

Frequently Asked Questions (FAQs) for Account Executive (Remote, USA) Role at Stay Ai
What are the main responsibilities of an Account Executive at Stay AI?

As an Account Executive at Stay AI, your primary responsibilities include managing the complete sales cycle from prospecting to closing. You'll be tasked with driving pipeline growth through self-sourced channels and partnerships, delivering technical demonstrations, and achieving established metrics and quotas in a dynamic environment. Collaboration with various teams will ensure a unified approach to sales and seamless transitions for client implementations.

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What qualifications do I need for the Account Executive position at Stay AI?

To qualify for the Account Executive position at Stay AI, you should have at least 4 years of sales experience with a proven record of success. Familiarity with sales methodologies like MEDDICC is essential, alongside a background in full-cycle sales and experience with sales prospecting tools. Strong communication skills to convey complex concepts and the ability to adapt in a fast-paced startup environment are also crucial.

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Is remote work an option for the Account Executive role at Stay AI?

Yes, the Account Executive position at Stay AI is remote-based, allowing you the flexibility of working from anywhere in the USA. While we emphasize teamwork and collaboration, we also organize annual offsite retreats to foster relationships and celebrate successes in beautiful locations like Park City, Utah and Mexico.

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What skills are essential for succeeding as an Account Executive at Stay AI?

Essential skills for succeeding as an Account Executive at Stay AI include strong proficiency in full-cycle sales, adaptability in high-paced environments, excellent problem-solving abilities, and a deep understanding of value-driven selling strategies. Additionally, having experience with the Shopify platform and the ability to work collaboratively across teams will enhance your performance.

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Why should I apply for the Account Executive position at Stay AI?

You should apply for the Account Executive position at Stay AI to join a high-growth startup where your contributions can lead to significant impact. You will work alongside passionate team members in a collaborative culture and have the opportunity to influence the direction and growth of innovative subscription products in an exciting industry landscape.

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Common Interview Questions for Account Executive (Remote, USA)
Can you describe your sales process when closing a deal?

When describing your sales process in an interview for the Account Executive role, focus on the steps you take from initial contact to closing. Detail how you identify customer needs, build relationships, and adapt your pitch to different audiences. Providing concrete examples will showcase your experience and approach.

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How do you handle objections from potential clients?

In responding to questions about handling objections, demonstrate your ability to listen actively and empathize with concerns. Discuss specific techniques you use to turn objections into opportunities, such as providing additional information or testimonials that resonate with the prospect's needs.

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What experience do you have with sales methodologies like MEDDICC?

Highlight any previous experiences where you successfully utilized MEDDICC or similar sales methodologies. Explain how you leveraged these frameworks to maintain a structured and effective approach to sales, focusing on how they improved your efficiency and results in closing deals.

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How do you prioritize your leads and opportunities?

Discuss your criteria for prioritizing leads, such as assessing their potential value, alignment with your product offering, and the likelihood of closing. Mention tools or techniques you use to help organize and track opportunities to ensure you focus your efforts effectively.

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Can you provide an example of a challenging sale you navigated successfully?

When providing an example of a challenging sale, select a situation where you overcame obstacles through creative problem-solving and collaboration with your team. Emphasize the outcome and what you learned from the experience, showcasing both your resilience and adaptability.

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What role does teamwork play in your sales strategy?

Discuss how you view teamwork as an integral part of your sales strategy. Provide examples of how collaboration with other departments, such as marketing and implementation, has helped you achieve outstanding results, highlighting your belief in unified efforts leading to better outcomes.

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Why do you want to work at Stay AI?

When answering why you want to work at Stay AI, connect your values and aspirations with the company's mission and culture. This can include their approach to innovation in eCommerce, the collaborative environment, and the opportunity to influence the subscription market.

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How do you stay updated on industry trends and competitors?

Describe your methods for staying informed about industry trends and competitors, whether it's through attending webinars, following relevant blogs, or engaging on platforms like LinkedIn. This shows your dedication to continuous learning, which is vital for an Account Executive.

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What metrics do you use to measure your sales performance?

When discussing metrics, outline the key indicators you track regularly, such as revenue generated, number of new clients, conversion rates, and customer satisfaction scores. This demonstrates your understanding of performance analysis and accountability in sales.

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How do you build relationships with clients?

Talk about the importance of building trust and rapport with clients. Share your approach to maintaining regular communication, gathering feedback, and being responsive to client needs. Provide examples of how you have fostered long-term relationships that resulted in repeat business and referrals.

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Full-time, remote
DATE POSTED
March 7, 2025

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