Braun Board

Strategic Accounts Sales Leader, AI GTM

Stripe · San Francisco, CA

Base
Not disclosed
OTE
Not disclosed
Posted
1mo ago

Still open · checked 2h agoon Stripe's careers page

What Stripe sells

Sends money to sellers and contractors in many countries

When a marketplace has to pay sellers, contractors, and creators around the world, each one may be in a different country. The problem is, every country has its own currencies and rules for moving money. Stripe Payouts lets businesses send funds to recipients around the world, with instant and next-day options, so the money arrives faster.

In plain English, from their own job posts. Something wrong? Tell us

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The Braun Read

Proceed with caution

A few things here deserve a hard look before you spend time on it.

Pay
No pay listed at all.
Transparency
Says nothing about quota, attainment, deal size, territory or sales cycle.
Pipeline
Doesn't say where pipeline comes from. Ask.
Time on market
Open 44 days. Normal, but not fresh.
Company hiring
93 sales roles open, hiring at a steady pace. Ask how many reps they hired last year and how many are still there.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

  1. 1.

    What percentage of fully ramped reps hit quota last year?

    OTE is what you could earn. This is how likely you are to earn it.

  2. 2.

    What are the base and the OTE for this role?

    No point investing hours before you know the number.

  3. 3.

    What's the annual quota, and how was it set?

    A quota built from real data is a target. Otherwise it's a hope.

  4. 4.

    Where does pipeline come from: inbound, SDRs, or me?

    Tells you how much of your week is prospecting versus selling.

  5. 5.

    How long is ramp, and what's the quota during it?

    Full quota on day one means you start behind.

  6. 6.

    Why is this role open? Did someone leave, or is it new?

    New headcount is growth. A replacement means someone left. Ask why.

When the offer comes

Save these for later. They land better once they've said yes to you.

  1. 1.

    Can I see the full comp plan in writing, including clawbacks and accelerators?

    What's in writing is what gets paid. Read it before you sign.

  2. 2.

    Can I see the actual comp distribution for the team last year, not just the OTE?

    The spread shows what most reps really take home. OTE is just the target.

  3. 3.

    I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?

    Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

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The role

Leads a team of Account Executives selling Stripe payments, billing, and marketplace products to large AI companies like OpenAI and Anthropic. Covers both expanding existing accounts and winning new strategic business.

Strategic · Mixed

Selling motion

Mixed

Who you're selling to

Buyer:
CEOs, CFOs and CTOs of AI-native companiesIn their words: “Build strong relationships with customer executives (CEO, CFO, CTO) and serve as a trusted advisor on how Stripe can support their growth.”
Industry:
AI industryIn their words: “The AI GTM team is focused on helping AI-native businesses monetize and scale.”
Company size:
Strategic

Pipeline expectations

Not stated in the posting.

Compensation

The posting doesn't list pay.

What is not disclosed

This posting doesn't tell you:

  • Base salary
  • OTE
  • Quota size
  • Quota attainment
  • Average deal size
  • Territory
  • Sales cycle length

The questions above cover the big ones.

Full posting
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 Stripe is building the economic engine for AI – and it’s working. Today, 88% of the Forbes AI 50 are building on Stripe (and most of the remaining 12% are pre-monetization). The AI GTM team is focused on helping AI-native businesses monetize and scale. We're in a unique position—partnering with the world's most ambitious AI companies (like OpenAI, Anthropic, ElevenLabs, and NVIDIA) to help them grow. This is one of the fastest growing parts of the business, and we need more great people to help us continue to accelerate. What you'll do As a Sales Manager on the AI GTM team at Stripe, you will leverage your sales leadership and product expertise to drive growth through new and existing strategic AI customers. Reporting to the Chief Revenue Officer of AI, you will lead a team of Account Executives responsible for expanding Stripe's relationship with some of the most important AI companies in the world—across payments, billing, and beyond. You will be instrumental in leading in-depth product discussions with customers, developing consultative and solution-based sales strategies, and building deep knowledge of the AI industry and its unique monetization challenges. You will collaborate closely with Product, Marketing, Product Marketing, and User Operations teams to develop and execute against our go-to-market strategy. Responsibilities - Develop the long-term vision for a growing AI GTM team and scale day-to-day operations. - Lead and manage a team of Account Executives managing existing AI accounts (driving revenue expansion, product attach, and retention) and looking for new business opportunities. Establish strategic plans and objectives to drive growth across the AI GTM business line, guiding execution to KPIs. - Build and develop a high-performing team, fostering a strong culture of energized and engaged Stripes while investing in the growth and development of your team. Coach and guide the team in developing consultative and solution-based sales skills throughout the sales cycle. - Be accountable for driving revenue, increasing product attach rates, and growing existing clients at high rates. - Engage with Product, Marketing, and User Operations teams to influence our product roadmap (you are on the frontier!) and accelerate our growth trajectory for our AI industry users. - Serve as both an internal and customer-facing expert on Stripe's products, particularly as they apply to AI-native business models (usage-based billing, marketplace payments, embedded finance, agentic commerce). - Build strong relationships with customer executives (CEO, CFO, CTO) and serve as a trusted advisor on how Stripe can support their growth. - Create best practices and improve the business and customer engagement model. Who you are Sales leader. You are an adept sales leader, capable of engaging in business-level and technical conversations at multiple levels of the organization. You see value in competitive situations and enjoy working on products that require both deep product understanding and technical knowledge, especially for AI industry users. People developer. You are a strong people leader who builds high-performing teams through coaching, accountability, and culture. You're as comfortable working with clients as with internal stakeholders (including executives) and are excited to become an expert and share your knowledge. You possess an organized, self-starter mindset and excellent communication skills, with a track record for improving the processes and organizations around you. AI enthusiast. You have deep context in the AI industry and are energized by keeping up with new developments in the space. You bring a user-first mindset— you approach every customer interaction as a consultative partner rather than a transactional seller. Technically curious. You understand APIs, webhooks, and modern developer tools—and you can hold credible conversations with engineering leaders about how Stripe's infrastructure fits into their stack. Minimum requirements - 8+ years of sales leadership experience, launching and growing high-functioning sales teams/products. - 10+ years of experience in hyper-growth SaaS or technology environments across the AMER region. - Demonstrated success managing existing/growth customer portfolios and driving revenue expansion. - Proven ability to be a self-starter, capable of driving business results without significant supervision. - Ability to understand complex technical requirements and craft solutions across multiple stakeholders. - Deep understanding of AI industry dynamics, business models, and monetization strategies (usage-based pricing, API-first distribution, agentic commerce). - Strong product acumen—ability to learn and articulate complex product capabilities, understand how they work technically, and connect them to user needs. - Excellent verbal and written communication skills, including strong presentation skills for in-person meetings with multiple stakeholders. - An enthusiastic "roll up your sleeves" mentality. - Proven ability to lead complex negotiations involving bespoke agreements with commercial and enterprise businesses. Preferred qualifications - Industry experience in payments, financial infrastructure, developer tools, or AI/ML platforms. - Existing relationships within the AI ecosystem (AI labs, AI-native SaaS companies, developer platforms). - Experience selling complex platform solutions involving multiple products. - Prior experience at a growth-stage software company or a leading payments/fintech company. - Familiarity with Stripe's product suite and how AI companies leverage financial infrastructure to scale.
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