Braun Board

Forward Deployed AI Accelerator, Sales Development

Stripe · Remote · Canada

Base
Not disclosed
OTE
Not disclosed
Quota attainment
Not disclosed
Posted
3mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 3h agoon Stripe's careers page

What Stripe sells

Takes payments and pays people around the world

A business that sells online has to collect payments from customers, then pay the sellers, contractors, and creators it works with around the world. Stripe helps businesses accept those payments and send money to those people across the globe. Money moves with greater speed, flexibility, and control.

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

More Finance & payments companies →

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 104 days. Ask why it's been hard to fill.
Company hiring
77 sales roles open, hiring at a steady pace. Ask how many reps they hired last year and how many are still there.

Red flags

None spotted.

Worth asking about

  • Open 90+ days. This role has been posted for three months or more. Ask why it's been hard to fill, and whether anyone left it.

Green flags

  • Pays accelerators. Higher commission rates once you pass quota. Overperformance actually pays.

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.

    This role has been open a while. What's made it hard to fill?

    The answer tells you what candidates saw that made them walk.

  2. 2.

    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.

  3. 3.

    What percentage of reps on the team have been here more than 18 months?

    Tenure shows whether people stay long enough to get paid.

  4. 4.

    Has the comp plan changed in the last 12 to 18 months? What changed?

    A plan that changes every year means the goalposts keep moving.

  5. 5.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  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.

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The role

Internal, non-quota role building AI tools and automations embedded with Stripe's Sales Development team. Not a sales role; it does not describe selling to customers.

Selling motion

Not stated in the posting.

Who you're selling to

Buyer:
Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”

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 The Stripe Marketing organization is undergoing a fundamental transformation in how it works. We're building a team of Forward Deployed AI Accelerators (FDAs) embedded directly with marketing cohorts to make AI the default mode for all work — not an occasional tool, but the foundation of how every marketer at Stripe executes. Today, marketers are already achieving remarkable results — building their own data dashboards, creating agents that compress multi-day processes, and authoring tools that accelerate workflows. The FDA team exists to take what's working and systematically scale it across the entire marketing organization. What you'll do As a Forward Deployed AI Accelerator for Sales Development, you'll be embedded with the Sales Development (SD) team. You'll work directly with SD reps, managers, and leadership to understand how the team works, and you'll build the AI tools and automations that make that work faster and better. Your measure of success is the improvement in the speed and quality of the SD team’s work that your builds drive. Responsibilities - Identify the highest-leverage workflows in SD's day-to-day work by deeply understanding the processes, inputs, and outputs behind them - Build custom tools, agents, automations, and skills tailored to how SD works - Work with SD leaders to prioritize what to build, and be clear about what is and isn't worth building - Ship quickly, put working versions in front of users, and improve them based on how the team uses them - Make what you build reliable: understandable, documented, and maintainable as data, systems, and processes change - Measure the effect of what you ship, using before-and-after evidence on time saved, quality, or work made possible - Partner with engineering, analytics, and operations teams when a tool needs production systems, sensitive data, or long-term ownership - Share results with SD leadership and the wider FDA team Who you are We're looking for people who have already used AI to change how real work gets done. - You are a deep AI practitioner. You build agents, automations, and tools fluently. You've built things that other people used, or that ran in production systems, and that measurably improved the speed or quality of their work. - You spot transformation opportunities and execute on them. You look at a team's workflows and see where AI changes the economics: where existing work can be done in a fraction of the time, or where entirely new work becomes viable. - You learn the work quickly. You may have direct experience in sales development, sales operations, or marketing, or you quickly learn the workflows, deliverables, tools, and pressures of a new team. You know that understanding someone's work is a prerequisite to transforming it. - You are a pattern recognizer. When you build something that works for one person, you immediately see how it applies to others. You think in systems, not one-off solutions. - You are a strong communicator. You explain technical concepts clearly to non-technical audiences and make progress visible to leadership and stakeholders. - You bias toward action and speed. You'd rather show someone a working proof-of-concept on their own deliverable today than present a polished deck about what's theoretically possible next week. - You are comfortable with ambiguity and evolution. This is a new team building a new operating model. The playbook will be rewritten as we learn. You thrive in that environment. Minimum requirements - 3+ years of professional experience in a role requiring diagnostic thinking, problem-solving, and cross-functional collaboration - Hands-on experience building and deploying AI-powered agents, tools, automations, or workflows that other people used or that ran as part of production systems, and that measurably improved the speed or quality of the work - Proficiency with AI development tools and platforms (e.g., Claude Code, Codex, custom agent frameworks, API integrations, workflow automation tools) - Strong written and verbal communication skills, with the ability to explain technical concepts to non-technical audiences - Comfort working across multiple workstreams and relationships simultaneously Preferred qualifications - Experience in a formal AI transformation or automation role where the job was substantially about identifying opportunities for workflow transformation and executing on them with hands-on builds - Experience in sales development, sales operations, revenue operations, marketing operations, or a closely adjacent function - Experience taking a prototype to something reliable, such as monitoring, documentation, or handoff to an engineering owner
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