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Teachable is a platform for experts and businesses who take education seriously, helping them scale impact through courses, coaching, and digital downloads. Part of the Hotmart Company portfolio (whose platforms have helped creators earn over $10 billion), Teachable is a market-leading product prioritizing student outcomes and business growth.
You will own Teachable Payments, a merchant-of-record checkout built for creators. The product handles sales tax across every US state and 18 countries, supports 35+ payment methods, runs affiliate payouts and tax back office operations, and migrates accounts for customers rather than handing them documentation.
In this role, you will:
- Own a book of high-volume creators and businesses already on Teachable, moving their checkout and payment processing to Teachable Payments
- Hunt and build your own pipeline against real buying signals (competitor pricing changes, processing volume, launches, overages)
- Run full-cycle sales: prospect, discover, build business cases around total cost of processing, tax exposure, and migration risk; negotiate and close
- Sell migrations, not features—these are deep conversations about money movement, tax liability, and operational risk. You will be expected to out-detail the customer's own finance person on checkout economics
- Close enterprise and education accounts where the platform and payments decision are intertwined
- Sit with product builders and feed field learnings directly into product, pricing, and playbook development
Success milestones:
- 90 days: Know the payments product cold, build your own target list, generate first meetings independently, close your first deal
- 6 months: Hit or exceed quota consistently with self-generated, predictable pipeline; closed accounts actually go live (signed deals that don't activate don't count)
- 12 months: Become the company's go-to expert on how payments get sold; first person consulted when hiring the next sales reps
This role is for someone who has carried a number and beaten it repeatedly with a clear methodology (MEDDPICC, SPIN, Challenger, or equivalent). You prospect actively—not just "open to it," but have built pipelines from nothing and enjoyed it. You are relentless on follow-up across finance, ops, and decision-makers. Payments, fintech, checkout, billing, or commerce infrastructure genuinely interests you; you want to understand merchant-of-record models, tax nexus, interchange, and chargebacks, not just recite features. You measure yourself in outcomes, not hours, and welcome ownership over process. You are comfortable building workflows with AI tools.
This is not for people who need a mature playbook handed to them, want to manage an existing book with 10% growth, or prioritize being right over closing deals.
The company operates as remote-first but holds in-person events throughout the year for bonding, strategic alignment, and celebrations. A NY office is available for local employees.
REQUIREMENTS:
- 2+ years closing B2B SaaS, fintech, or payments deals (full cycle) with a defensible track record
- Real experience self-sourcing a meaningful share of your own pipeline
- A structured sales methodology you actually run (MEDDPICC, SPIN, Challenger, or equivalent)
- Clean CRM habits (if it's not in the system, it doesn't exist)
- Nice to have: payments or fintech background; experience selling to creators or owner-operators
