Rebuilding a company for the AI era.
At Teachable, we power hundreds of millions of dollars a year in creator sales, and we are in the middle of rebuilding how this company goes to market; from the ground up, with AI in the stack from day one.
That means the sales motion you are joining is being written right now. We are instrumenting the funnel from zero, building signal-driven prospecting on top of AI tooling, and replacing manual research and hand-typed email with systems.
You would be one of a small number of people whose fingerprints end up on all of it.
Most sellers never get this shot. You either join a startup with no product and no customers, or a large company where the playbook was frozen five years before you arrived.
This is the rare third thing: a real business at real scale, with a product people already love, being rebuilt in public.
The opportunity you would own: Payments
Teachable Payments is a merchant-of-record checkout built for creators. We handle sales tax across every US state and 18 countries, support 35+ payment methods, run affiliate payouts and the tax back office, and we migrate accounts for the customer instead of handing them a help doc. Your job is to go get it.
What you would actually do
Own a book of high-volume creators
and businesses already on Teachable, and move their checkout and payment processing onto Teachable Payments.
Hunt.
Build your own pipeline against real buying signals: competitor pricing changes, processing volume, launches, overage.
Run full cycle:
Prospect, discover, build the business case (total cost of processing, tax exposure, migration risk), negotiate, close.
Sell a migration, not a feature.
These are conversations about money movement, tax liability, and operational risk. You will get deep on checkout economics, and you will be expected to out-detail the customer's own finance person.
Close enterprise and education accounts
where the platform and the payments decision are the same decision.
Feed field insights directly into product:
Sit in the same room as the people building the machine, feeding what you learn in the field straight into product, pricing, and the playbook.
What success looks like
90 days:
You know the payments product cold, you have built your own target list, you are generating first meetings without anyone handing you leads, and you have closed something.
6 months:
You are at or over quota consistently, your pipeline is self-generated and predictable, and the accounts you closed have actually gone live. A signed deal that never activates is not a deal here.
12 months:
You are the person this company points at when it wants to know how payments get sold, and the first person we ask when we hire the next two.
Who this is for
Track record:
You have carried a number and beaten it, repeatedly, and you can walk us through exactly how.
High motivation:
You are highly motivated, drive outcomes, and thrive in an environment where speed and ownership matter.
Proactive hunter:
You prospect. Not "open to prospecting"—you have built a pipeline out of nothing and you liked it.
Relentless follow-up:
These deals need persistence across finance, ops, and the creator primary stakeholder.
Fintech interest:
Payments, fintech, checkout, billing, or commerce infrastructure genuinely interests you. You want to understand merchant of record, tax nexus, interchange, and chargebacks, not just recite features.
Outcome-driven:
You measure yourself in outcomes, not hours. Nobody here will count your time; everybody here will count your results.
Ownership mindset:
You want ownership more than you want process. You will be handed a market and asked to figure it out; with support, without hand-holding.
AI-native:
Building your own workflow with AI tools excites you rather than threatens you.
Who this is not for
People who need a mature playbook, a full pipeline handed to them, and three layers of enablement before they dial.
People who want to manage an existing book and grow it 10%.
People who would rather be right than close.
What you will bring
2+ years closing B2B SaaS, fintech, or payments
, full cycle, with a track record you can defend number by number.
Proven self-sourcing:
Real experience self-sourcing a meaningful share of your own pipeline.
Structured methodology:
A structured methodology you actually run (MEDDPICC, SPIN, Challenger; we care that you have one).
CRM discipline:
Clean CRM habits. If it is not in the system, it does not exist.
Nice to have:
Experience working at or selling against payments/fintech target companies (e.g., Paddle, FastSpring, SamCart, Whop, Toast, Block/Square, Shopify/Shop Pay, Stripe, Finix, Recurly, Chargebee, Recharge) or experience selling to creators/owner-operators.
Working model
Full Remote
(with candidate sourcing focused on Austin, Houston, and Dallas, TX).
What is Teachable?
Teachable is the platform for experts and businesses who take education seriously. In a world where anyone can ask AI for information, we are the home for people who educate with purpose and humanity; through courses, coaching, and digital products that students actually finish. We are part of the Hotmart Company portfolio, whose platforms have helped creators and businesses earn more than $10 billion.
Teachable encourages individuals from a broad diversity of backgrounds to apply. We are an equal opportunity employer, committed to a fair and consistent interview process. Please tell us in your application if you require an accommodation to apply for a job or to perform your job.
