Jobs › Stripe

Account Executive, Commercial (Grower)

Stripe · Chicago, IL · 1651 Velocity - Account Executives (NA)

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 an upsell you generated from an existing mid-market customer.

What they are checking: Grower experience in finding and closing expansion opportunities.

Tell me about a time you worked with marketing to nurture accounts.

What they are checking: Collaboration on end-to-end campaigns, a listed part of this role.

How do you build relationships with mid-market customers who are busy and skeptical of sales calls?

What they are checking: Ability to bring useful insight that earns time with busy buyers.

What would you do

How would you set strategy for a territory of mid-market customers you've just inherited?

What they are checking: Ability to segment a territory and decide where to focus first for growth.

This team is new. How would you help build its playbook?

What they are checking: Initiative and willingness to shape processes on a team still being built.

A customer you've been nurturing for months suddenly goes quiet. What do you do?

What they are checking: Whether they can re-engage a quiet customer with something useful instead of repeated check-ins that feel pushy.

About the work

How do you run a scaled sales campaign across many accounts at once?

What they are checking: Experience with one-to-many motions that efficiently drive adoption across an install base.

How do you decide which Stripe products to introduce to a mid-market customer next?

What they are checking: Matching products to the customer's stage and needs rather than pushing everything.

How do you balance quick upsells with longer, larger expansion deals?

What they are checking: Pipeline balance between near-term results and bigger opportunities.

What would make you consider a territory well managed at the end of the year?

What they are checking: How they define success, including revenue growth, retention, and product adoption.

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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  The Commercial Sales team is responsible for the acquisition, growth, retention, and expansion of mid-market customers. As a Grower Account Executive, you’ll set strategy for your territory, identify opportunities for existing customers to get the most out of Stripe, execute scaled sales strategies to grow revenue and drive end-to-end campaigns to nurture relationships and increase adoption of Stripe products. What you’ll do As an Account Executive, Commercial Grower you will play an instrumental role in fueling Stripe’s growth and expanding revenue from Stripe’s existing mid-market customers. In this role, you will also help build out a new team touching more of our install base and GTM motion at Stripe. Responsibilities • Generate upsell opportunities to drive revenue growth in your territory • Develop and implement sales strategies to grow revenue per user, adopt new products and ensure retention • Identify and understand users’ pain points to propose Stripe solutions and own the full sales cycle, from business case development to close • Own contract renewals and lead commercial negotiations to increase and retain existing customer revenue and increase Stripe share of wallet • Work cross-functionally to solve user pain points and improve Stripe’s product • You will be required to work from the Chicago office three (3) days per week 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 • Minimum of 5+ years full sales cycle/closing experience with existing business accounts • Ability to understand technical requirements and craft solutions across multiple technology  products • Ability to perform quantitative analysis and independently manage pricing negotiations  • Strong operational acumen and ability to manage and prioritize a book of 100 accounts  • Ability and motivation to operate in a highly ambiguous and fast-paced environment • Superior verbal and written communication skills • You will be required to work from the Chicago office three (3) days per week Preferred qualifications • Prior experience in a sales and/or customer-facing role at a high growth payments company

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