API Integration Specialist

About Osano: Osano is an innovative B-Corporation built around a simple belief: privacy is a fundamental right. Since day one, we’ve been focused on giving modern enterprises the ability to innovate quickly, stay competitive, and earn customer trust by respecting data privacy and complying with consent guidelines. Our products help organizations operate confidently in a rapidly evolving regulatory and technological landscape. About the Role: We're looking for an API Integration Specialist to join our team and own the connective tissue between our billing, CRM, and product systems. This role is all about making data move accurately and automatically between Stripe, HubSpot, and the Osano platform: making sure that every contract change, upgrade, downgrade, and cancellation is reflected everywhere it needs to be, without anyone patching it by hand. You'll spend your time in and around the APIs and integrations that link subscription billing to the CRM, configuring and maintaining the Stripe-to-HubSpot sync, mapping objects and fields between systems, monitoring webhooks and failed syncs, and building the automation that replaces manual provisioning steps. When something drifts or breaks, you're the person who traces it through the integration layer and fixes the root cause rather than the symptom. Sitting at the intersection of RevOps, Finance, Customer Success, and Product, you'll be the person who keeps our data clean and our systems in sync. When a deal closes or a contract changes, you make it real, provisioning accounts in the product, updating records in HubSpot, and reconciling billing in Stripe so nothing slips through the cracks. Importantly, this is post-sale operational and integration work, not customer support. You won't be fielding help tickets or troubleshooting product questions. Instead, you'll focus on the systems, integrations, and provisioning tasks that keep the business running smoothly behind the scenes. This is an ideal role for someone who is system-oriented, detail-obsessed, loves clean data, and takes pride in building repeatable, automated processes. Responsibilities: Billing & Subscription to CRM Integration *Own the day-to-day operation of the integrations connecting Stripe (subscription billing), HubSpot (CRM), and the Osano product. *Configure and maintain object and field mappings, sync rules, and automations so subscriptions, invoices, entitlements, and deal records stay aligned across every system. *Monitor webhooks, sync logs, and API errors, diagnosing failures and resolving them at the source instead of correcting records by hand. *Build and maintain integrations using native connectors, iPaaS tooling (Zapier, Make, Workato, Tray, or similar), and direct REST API calls where native options fall short. *Partner with Product & Engineering on new packaging, pricing, and entitlement models, translating them into integration and data requirements before launch. *Document integration architecture, data flows, and runbooks so the setup stays maintainable by someone other than you. Contract Changes & Account Provisioning *Process contract changes end to end, ensuring each one is accurately recorded across HubSpot, the Osano product, and Stripe. *Create and configure new customer accounts, provision licenses, and manage user access as deals close. *Execute account upgrades and downgrades, updating entitlements, licenses, and billing to match the new contract terms. *Handle cancellations cleanly, deprovisioning accounts and access and reconciling billing so records stay accurate. *Identify the manual steps in this workflow that can be automated through the integration layer, and automate them. Account Maintenance & Onboarding Support *Perform ongoing operational administration of customer accounts throughout the customer lifecycle. *Support onboarding by standing up new accounts and access so customers can get started quickly and smoothly. *Manage licenses and access changes as customer teams grow, shrink, or restructure. Data Integrity & System Audits *Maintain data integrity, ensuring entitlements and usage records are accurate and consistent in Stripe and Hubspot, working closely with the Product & Engineering teams on new product and package offerings. *Run regular system audits to catch and correct discrepancies across HubSpot, the product, and Stripe before they become problems. *Complete system updates and reconcile data between platforms so every source of truth agrees. *Document processes and flag recurring issues, recommending improvements that make provisioning faster and more reliable. About You: *You're detail-oriented and organized. Small discrepancies bother you, and you catch them before anyone else does. *You're comfortable in an API: reading documentation, interpreting a JSON payload, testing an endpoint, and reading a webhook log to find out what actually happened. *You're self-directed and dependable. Given a process and a queue of work, you run with it and follow through. *You enjoy clean systems and repeatable processes, and you're motivated to keep data accurate and tidy. When you find yourself doing something manually for the third time, you look for a way to automate it. *You're comfortable navigating multiple tools at once and moving information reliably between them. *You're excited about privacy, responsible AI, and building trustworthy technology. Must-Haves: *Hands-on experience integrating billing or subscription software with a CRM: connecting the two systems, mapping data between them, and keeping them in sync. Stripe and HubSpot strongly preferred; comparable stacks (Chargebee, Recurly, Zuora, NetSuite, Salesforce, Dynamics) considered. *Practical working knowledge of REST APIs and webhooks: reading API documentation, interpreting JSON, testing endpoints with Postman or similar, and troubleshooting failed calls, retries, and sync errors. *Experience with integration and automation tooling, whether native connectors, iPaaS platforms (Zapier, Make, Workato, Tray.io), or lightweight scripting, used to eliminate manual data movement. 1–3 years of experience in operations, account administration, billing/revenue operations, order management, integration/systems administration, or a similar detail-driven role. *Strong attention to detail and a track record of accurate, error-free work. *Comfort working across multiple business systems (CRM, billing, and product admin tools). *Strong organizational skills and the ability to manage a steady queue of tasks and deadlines independently. *Clear written communication and the ability to collaborate cross-functionally with Sales, Finance, Customer Success, and Product. Nice-to-Haves: *Direct experience with the Stripe API (subscriptions, invoices, webhooks, usage records) and the *HubSpot API (deals, companies, custom objects, workflows). *Experience building or maintaining a Stripe-to-HubSpot sync specifically, whether native, through a third-party connector, or custom-built. *Scripting ability (Python, JavaScript/Node, or similar) for one-off reconciliations, data migrations, and small automations. *Familiarity with SaaS provisioning, license management, or user lifecycle processes. *Experience with usage-based or entitlement-based billing models. *Experience in privacy, legal tech, compliance, SaaS, or a regulated industry (industry knowledge can be taught — B2B SaaS experience is not required). *Familiarity with Notion, spreadsheets, or other documentation and data-hygiene tools.