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Account Executive, Product - Terminal

Stripe · Chicago, IL · 1640 Product Sales - Payments

Posted Oct 1, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a hardware or point-of-sale deal you led. What made it different from a software sale?

What they are checking: Experience with the logistics, deployment, and longer timelines that come with selling physical devices alongside software.

Tell me about a time you fed customer insight back to product and engineering that changed something.

What they are checking: Whether they act as a bridge to product teams, which this cross-functional specialist role requires.

How do you stay credible on technical topics like device management and payment security?

What they are checking: Commitment to deep product knowledge, since customers expect specialists to answer hard technical questions directly.

What would you do

A multi-location retailer worries that switching terminals will disrupt checkout during the holidays. How do you respond?

What they are checking: Ability to address rollout risk honestly with phased plans rather than brushing off a real operational concern.

You're advising an account executive on a deal where Terminal is one piece. How do you add value without taking over?

What they are checking: Skill as an overlay specialist who strengthens the core team's deal while respecting the account owner's lead.

How would you compete against an incumbent point-of-sale provider that the customer's staff already know?

What they are checking: Competitive selling that accounts for switching costs, training, and staff habits, not just price or features.

A customer asks for a hardware feature that isn't on the roadmap. What do you say?

What they are checking: Honesty about product limits while collecting useful feedback and keeping the deal alive.

About the work

How would you explain unified commerce to a retailer that runs separate systems for its stores and its website?

What they are checking: Whether they can make the case for combining online and in-person payments in terms of real operational and customer benefits.

What questions would you ask to understand a customer's in-person checkout today?

What they are checking: Discovery depth around hardware, staff workflows, offline needs, and how in-store data connects to online channels.

How would you help build a go-to-market plan for Terminal in a specific vertical like restaurants or retail?

What they are checking: Strategic thinking about vertical needs, which this lean team uses to attack a very large market.

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The full job description

As published by Stripe.

Who we are Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career. About the team Product Sales is a team of deep functional and technical specialists who both lead and advise on deals for the most strategically important products in Stripe’s portfolio.  The Terminal Product Sales is tasked with attacking a $15T market opportunity for Unified online and offline commerce. The team is lean, high visibility and highly cross-functional! What you’ll do As an Account Executive, Product (Terminal) at Stripe, you will use your sales and product expertise to help drive growth of Stripe’s Unified Commerce suite of hardware, software and payments solutions. You will collaborate with product, engineering and marketing teams to develop deep product and industry knowledge and drive strategic deals. You will be instrumental in leading in depth product discussions with existing and prospective customers – and building and executing against our go to market strategy. You are an adept salesperson, capable of engaging in business-level and technical conversations at multiple levels of the organization, including CEO and CTO. You are used to building value in competitive situations and enjoy working on products that require deep product understanding, combined with technical knowledge. You’re as comfortable working with clients as with internal stakeholders (including executives). You’re excited to become an expert and to share your knowledge. You’re an organized self-starter, an excellent communicator who is highly analytical and has a track record for improving the processes and organizations around you. Responsibilities • Drive new business growth by identifying, prospecting, and closing new Stripe Terminal customers. • Own the full sales cycle from lead generation to close, with a strong focus on expanding Stripe Terminal’s footprint. • Lead strategic sales conversations with prospective customers, positioning Stripe Terminal’s software, hardware, and payments as the best solution. • Develop and execute go-to-market strategies to outperform competitors and accelerate adoption. • Manage and expand relationships with existing customers , driving upsells and incremental revenue growth. • Act as a trusted advisor and Terminal expert , both internally and externally, to drive customer success and influence product direction. • Collaborate with Product, Marketing, and User Operations teams to refine our approach and fuel Terminal’s growth. Who you are We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement. Minimum requirements • 5+ years of sales or prospecting experience at a technology company and a track record of top performance • A proven ability to build strong collaborative working relationships with business partners.  • The ability to deal effectively with ambiguity and thrive in an unstructured, fast-moving environment. • A proven ability to be a self-starter capable of driving business results without significant supervision. • An enthusiastic “roll up your sleeves” mentality. • Excellent verbal and written communication skills. • Strong presentation skills, particularly for in-person meetings with multiple stakeholders • Proven ability to lead complex negotiations involving bespoke commercial agreements • Ability to understand complex technical requirements and craft solutions across multiple stakeholders Preferred qualifications • * 3+ years of experience specifically selling online and offline payments to large merchants or software platforms who embed it into their product suite • Proven ability to sell complex solutions involving both hardware and software

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