Braun Board

Head of Product Sales, Payouts

Stripe · Nyc, NY

Base
Not disclosed
OTE
Not disclosed
Posted
Yesterday

Still open · checked 1h agoon Stripe's careers page

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay
No pay listed at all.
Transparency
Shares 1 of 5: quota, attainment, deal size, territory, sales cycle.
Pipeline
Doesn't say where pipeline comes from. Ask.
Time on market
Brand new.
Company hiring
80 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. Flags 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 Stripe's global Payouts go-to-market, building and managing a team across AMER, EMEA and APAC that sells money-movement products to platforms, marketplaces, enterprises and fintechs. Also engages directly on the largest deals.

Mixed

Selling motion

Mixed

Who you're selling to

Buyer:
Platforms, marketplaces, enterprises and fintechsIn their words: “Build repeatable sales motions that address the needs of platforms, marketplaces, enterprises, fintechs, and other businesses moving money to third parties.”

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
  • 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 investing in building out its Payouts product sales team to help prospects and customers move money globally with greater speed, flexibility, and control. Our growing footprint of Payouts products (Instant, Next day, Global payouts, FX, MCS solutions) enable businesses to send funds to sellers, service providers, contractors, creators, claimants, customers, and other third-party recipients around the world. You will represent Stripe across our global markets externally while helping develop and strengthen our culture internally. You know what it takes to build and scale a business structurally and methodically. You have a strong understanding of technical and financial concepts and enjoy working closely with Product and Engineering teams, as well as broader Sales and go-to-market organizations. As the Head of Product Sales, Payouts, you will be a critical member of the go-to-market leadership team. You will drive the strategy and execution of Stripe’s Payouts GTM, accelerating adoption and revenue growth across Payouts, platform and marketplace payout capabilities, cross-border payouts, FX/MCS solutions, payout methods, and recipient experiences. What you’ll do - Own and drive the global go-to-market strategy for Payouts. - Recruit, inspire, and lead a high-performing global team responsible for delivering ambitious adoption and revenue targets across Stripe’s Payouts portfolio. - Partner with Product, Engineering, Sales, Product Marketing, Finance, and other cross-functional teams to align the Payouts GTM strategy and product roadmap with customer needs. - Establish Stripe as a strategic partner to businesses seeking to modernize how they move money to customers, sellers, service providers, and other recipients. - Operate effectively at the highest levels of a matrixed organization, bringing together multiple functions to deliver against shared customer and revenue goals. - Serve as the voice of the customer, translating market feedback into actionable insights that inform product strategy, prioritization, and execution. - Scale Payouts business to fastest growing part of Money Management Responsibilities We are looking for a seasoned leaderwith a proven track record of building teams, delivering outstanding results, and maintaining a long-term, user-first mindset. This leader will thrive amid ambiguity, operate effectively in a high-growth environment, and bring structure to complex problems. Ideal candidates will have deep sales management and leadership experience, domain experience in payments, solid product knowledge, including bringing new products to market, developing go-to-market strategies, scaling technology sales teams, and building trusted relationships with senior customers and internal stakeholders. - Recruit, develop, and lead a global team focused on the Payouts business across AMER, EMEA, APAC. - Coach the team in developing consultative, solution-oriented sales skills across every stage of the sales cycle. - Create structure and focus for new GTM ideas, use cases, and product sales campaigns. Drive execution, measure results, and make timely recommendations based on performance. - Manage day-to-day operations, with a focus on performance against key adoption, pipeline, and revenue metrics. - Drive revenue growth, increase product adoption and attach rates, and acquire new users. - Partner with regional and account sales leaders to embed Payouts into Stripe’s broader customer strategy. - Engage directly in the largest and most strategic opportunities, developing executive relationships and helping the team win and grow complex customers. - Develop a deep understanding of customers’ funds flows, operational requirements, and regulatory considerations, and translate those needs into compelling Stripe solutions. - Lead with clarity and context, developing a compelling plan aligned with Stripe’s overall direction. - Build repeatable sales motions that address the needs of platforms, marketplaces, enterprises, fintechs, and other businesses moving money to third parties. - Continuously improve programs and operating mechanisms by introducing new ideas, sharing best practices, and strengthening Stripe’s customer engagement model. 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. Preferred qualifications are a bonus, not a requirement. Minimum requirements - 15+ years of technology sales experience. - 10+ years of people leadership experience. - 5+ years of experience in payments, financial services, or money movement. - Demonstrated experience building and scaling global teams that consistently deliver against ambitious goals. - Experience bringing new products to market and building repeatable go-to-market motions. - A builder’s mindset, with the ability to drive immediate results while establishing the foundations for long-term growth. - Deep understanding of payments, payouts, treasury, or financial infrastructure and the complex funds flows that support global businesses. - Excellent relationship-building skills, with experience engaging senior executives and customers at all levels. - Ability to explain complex technical, operational, and financial concepts in clear, accessible language. - Strong cross-functional leadership skills and experience influencing Product, Engineering, Marketing, Finance, and regional Sales organizations. - Highly analytical, with a deep understanding of how to use data to guide decisions and improve the performance of revenue teams. - Detail-oriented and willing to help a growing team navigate the operational aspects of scaling a global business. - Ability to think globally, act regionally, and thrive in a multicultural, fast-moving environment. - Experience representing an organization publicly and communicating effectively with customers, partners, regulators, the press, and internal employees. - High energy, a strong work ethic, disciplined execution skills, and a willingness to do what it takes to deliver results. - A true team player who puts Stripe and its users first.
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