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Deal Strategist

Stripe · Remote · 1510 Global Business Services

Posted Sep 25, 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 commercial construct you designed or improved that led to more revenue.

What they are checking: Whether they can think creatively about deal structure rather than just processing paperwork.

Describe a time you coordinated Legal, Finance and Sales on a deal where each wanted something different.

What they are checking: Whether they can broker agreement among partners with competing interests and keep the deal moving.

Tell me about a deal that fell apart. What did you learn about how you run deals?

What they are checking: Whether they reflect honestly on failure and changed how they work afterward.

What would you do

A sales rep wants a pricing exception that falls outside policy, and the quarter closes Friday. What do you do?

What they are checking: Whether they can protect deal discipline under pressure while still helping the rep find a path to close.

You notice the same deal blocker showing up across many regions. What would you do with that?

What they are checking: Whether they turn repeat friction into process or policy change instead of solving it one deal at a time.

A rep tells you a customer will walk if they don't get a discount today. How do you test that claim?

What they are checking: Whether they can pressure-test urgency with evidence rather than simply reacting to it.

About the work

Walk me through how you'd manage a large custom deal from first pricing request to signed contract.

What they are checking: Whether they understand the full deal lifecycle and where approvals, legal review and risk usually slow things down.

How would you decide whether a non-standard contract term is worth agreeing to?

What they are checking: Whether they can weigh revenue, margin, operational burden and precedent when judging a contract term.

How do you keep track of a portfolio of open deals so none slip without anyone noticing?

What they are checking: Whether they have a reliable system for pipeline hygiene and escalation across many deals at once.

How would you measure whether the team is improving deal cycles across Stripe?

What they are checking: Whether they think in metrics like cycle time and win rate and understand what actually drives them.

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The full job description

As published by Stripe.

Who we are About Stripe 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 GBS's primary goal is to ensure operational excellence across deal cycles, increase revenue through the development of transformative commercial constructs, and drive closure of Stripe's deal portfolio. The team's reach is widespread across Stripe, not exclusive to one sales segment or geographical region; GBS drives change across go-to-market, positively impacting Stripe users and cross-functional teams. GBS's priorities are set through the direction of Stripe leadership and executive vision, partnership with sales and cross-functional organizations, as well as user feedback and market insights. What you’ll do Stripe's Global Business Services (GBS) team is looking for a Deal Strategist to focus on the closure of custom and standard commercial deals. You will be responsible for deal lifecycle management and supporting cross-organizational alignment. This role requires a background in driving custom deals to closure, a strong understanding of pricing frameworks, and experience supporting sales through negotiations. The candidate will have experience with SaaS products, pricing strategies, and supporting selling motions, along with strong communication skills. You will love this job if you are a natural relationship builder and process architect. Responsibilities • Manage end-to-end customer deals—drafting, editing, and reviewing agreements—while supporting the sales cycle to ensure deal terms align with business goals, reflect strategic priorities, and close as forecasted. • Act as the primary point of contact between Sales, Legal, and other cross-functional stakeholders for deal-related questions, approvals, and escalations. • Work directly with sales teams, sales leaders, services/support teams, and customers to advise on deal structures, establish compelling commercials, and drive resolution of customer issues. • Advise sales teams on the best approach by understanding customer and partner requirements, while balancing custom terms with internal system constraints. • Remove internal blockers and drive alignment across cross-functional teams including Product, Legal, Finance, and Accounting. • Support complex negotiations involving bespoke commercial and legal agreements. • Support the pricing and structuring of multi-threaded product use cases in all segments and industries, especially in highly competitive sales cycles. • Quickly build credibility and trust with internal stakeholders. • Demonstrate strong communication and persuasion skills when working with cross-functional partners and senior leaders. 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 • BA/BS degree in Business, Technology, Finance, or Economics • 6+ years of experience in deal strategy, procurement, pricing strategy, financial consulting, or legal • Experience working in ambiguous, fast-scaling environments and comfortable operating with high agency • Strong communication, presentation, negotiation, and project management skills • Experience working in Payments and/or SaaS

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