Customer Engineer, AI & Integrations

About Bask Health

Bask Health is a software platform that enables entrepreneurs, doctors, and healthcare businesses to launch, manage, and grow direct-to-consumer telehealth businesses.

Our platform brings together patient experiences, clinical workflows, pharmacy operations, and commerce tools in one place.

We're an entrepreneurial, product-focused team that values ownership, technical excellence, and building software that solves real problems. Our teams work closely across product, engineering, customer success, sales, and company leadership to bring new capabilities to market and continuously improve the platform.

At Bask, we value engineers who enjoy working directly with customers, understand how different software systems connect, and take ownership of solving technical problems. Our customers include entrepreneurs and e-commerce operators building their own businesses, and our technical teams help them understand and use the platform's capabilities. We're looking for people who can combine strong technical judgment with practical, clear communication.

About the Role

We're looking for a Customer Engineer, AI & Integrations to help merchants implement, configure, troubleshoot, and adopt Bask Health's supported AI capabilities and third-party software integrations.

This is a customer-facing technical position that combines integration engineering, SaaS troubleshooting, technical onboarding, and customer enablement.

You'll work directly with customers and collaborate with Customer Success, Product, and Engineering to solve technical challenges involving connected software systems.

You'll help customers understand supported integration capabilities, investigate technical problems, and navigate implementation requirements.

Bask Health provides software that enables entrepreneurs, doctors, and healthcare businesses to launch, manage, and grow direct-to-consumer telehealth businesses.

Our platform connects merchant storefronts, patient questionnaires, checkout experiences, clinical workflows, pharmacy-related processes, and other business capabilities.

You'll develop a strong understanding of the platform's technical architecture and supported merchant-facing workflows.

You'll learn how customers connect Bask Health with other business tools and services.

You'll support technical onboarding for customers implementing approved integrations.

You'll help customers understand the technical requirements for connecting supported systems.

You'll review integration documentation and explain relevant configuration steps.

You'll work with customers to understand their technical goals and existing software environments.

You'll help translate customer requirements into supported integration configurations.

You'll identify potential technical limitations before implementation work begins.

You'll communicate integration requirements, dependencies, and constraints clearly.

You'll help customers understand what functionality is available and what requires additional engineering review.

You'll investigate technical issues affecting supported API connections.

You'll troubleshoot authentication, authorization, request formatting, and response-handling problems.

You'll analyze API requests and responses to identify integration failures.

You'll review HTTP status codes, error messages, and available diagnostic information.

You'll use approved tools to reproduce reported integration problems.

You'll investigate issues involving webhooks and event-driven integrations where supported.

You'll help identify problems involving data formatting, field mapping, or synchronization.

You'll document technical findings and recommended next steps.

You'll collaborate with Engineering when integration issues require changes to the platform.

You'll prepare detailed bug reports and escalation summaries.

You'll help distinguish between customer configuration problems, third-party limitations, and platform defects.

You'll communicate with external technical teams when appropriate.

You'll help customers understand integration testing and validation procedures.

You'll support approved integration testing before production use.

You'll help verify that supported integrations behave as expected.

You'll document implementation outcomes and unresolved technical risks.

You'll maintain organized technical implementation notes.

You'll work with Customer Success Managers to understand how integrations support customer goals.

You'll help identify integration-related obstacles affecting onboarding or platform adoption.

You'll participate in technical onboarding calls and implementation discussions.

You'll explain technical concepts to customers with different levels of engineering experience.

You'll communicate clearly with founders, operators, developers, and other stakeholders.

You'll avoid unnecessary jargon when explaining integration issues to non-technical customers.

You'll provide practical guidance based on approved product capabilities.

You'll avoid promising unsupported features or unapproved implementation timelines.

You'll support customer adoption of approved AI-enabled platform functionality.

You'll help customers understand how supported AI features are configured and used.

You'll explain documented AI feature capabilities and limitations.

You'll assist with troubleshooting AI-related workflow configuration issues.

You'll investigate reported failures involving supported AI integrations.

You'll help distinguish between configuration problems, integration failures, and unexpected AI behavior.

You'll document reproducible technical issues involving AI-enabled functionality.

You'll coordinate with Product and Engineering when AI behavior requires deeper investigation.

You'll help customers understand approved testing and validation procedures for AI-enabled workflows.

You'll support appropriate human review and escalation requirements for sensitive use cases.

You'll avoid representing AI-generated output as guaranteed accurate or clinically authoritative.

You'll recognize when an AI-related issue may create privacy, security, or compliance concerns.

You'll escalate sensitive AI issues through established procedures.

You'll work with Engineering to understand the technical dependencies of supported AI features.

You'll become familiar with relevant AI APIs and integration patterns used by the platform.

You'll help document common AI integration questions and configuration issues.

You'll contribute to internal technical documentation for supported AI functionality.

You'll help identify opportunities to improve technical onboarding resources.

You'll develop and maintain approved integration troubleshooting guides.

You'll contribute to API documentation and implementation instructions.

You'll help identify recurring integration failures and common configuration mistakes.

You'll share technical feedback with Product and Engineering.

You'll help prioritize recurring technical problems based on customer impact and established team processes.

You'll participate in discussions about improving integration reliability and usability.

You'll assist with validating fixes for reported technical issues.

You'll help test supported integration workflows in approved environments.

You'll document test results and communicate unexpected behavior.

You'll follow established engineering change management procedures.

You'll avoid making unauthorized changes to production systems.

You'll use approved methods for handling API credentials, authentication tokens, and sensitive configuration data.

You'll never request or store customer secrets through unapproved channels.

You'll follow applicable security and access control requirements.

You'll use only authorized diagnostic tools and environments.

You'll recognize when technical issues may involve protected or otherwise sensitive information.

You'll escalate privacy and security concerns to the appropriate teams.

You'll understand the boundaries between software integration support and clinical operations.

You'll never provide medical advice or make clinical decisions.

You'll never independently approve prescriptions, pharmacy fulfillment, or regulated healthcare activities.

You'll recognize when customer requests involve clinical, pharmacy, or compliance matters.

You'll direct those requests to qualified or authorized professionals.

You'll help ensure AI-enabled workflows are supported within approved product and operational boundaries.

You'll work closely with Customer Success to provide a consistent customer experience.

You'll collaborate with Product to communicate technical feedback and feature requests.

You'll partner with Engineering on complex integration investigations.

You'll communicate proactively when technical issues are blocked by external dependencies.

You'll help customers understand what information is needed to continue an investigation.

You'll maintain clear records of assigned technical cases and implementation tasks.

You'll take ownership of technical follow-up responsibilities.

You'll manage multiple customer implementation and troubleshooting requests.

You'll prioritize work based on customer impact and established team guidelines.

You'll identify potential implementation risks and communicate them early.

You'll remain professional when helping customers resolve frustrating technical issues.

You'll be comfortable investigating unfamiliar APIs and third-party software systems.

You'll read technical documentation independently and ask questions when clarification is needed.

You'll use a structured approach to diagnosing complex problems.

You'll develop a strong understanding of the relationship between integrations, merchant workflows, and customer outcomes.

You'll help customers make effective use of supported technical capabilities.

You'll contribute to a team environment that values ownership, technical accuracy, and continuous improvement.

We're looking for someone with hands-on experience troubleshooting APIs, supporting SaaS integrations, and communicating directly with customers.

You should be comfortable reading technical documentation, investigating web application behavior, and explaining complex problems clearly.

Experience with e-commerce platforms, merchant-facing software, AI APIs, or automation workflows would be particularly valuable.

You don't need to be a machine learning researcher, but you should understand how AI-enabled software features interact with APIs, application workflows, and customer configurations.

Success in this role means helping customers complete supported integrations, resolving technical obstacles, improving implementation documentation, and providing reliable technical guidance while following security and compliance requirements.

What You'll Do

• Support technical onboarding for customers implementing Bask Health integrations.
• Help customers configure and troubleshoot supported third-party software connections.
• Investigate API authentication, authorization, and request-handling issues.
• Analyze API responses, error messages, and integration failures.
• Troubleshoot supported webhook and event-driven workflows.
• Investigate data mapping, formatting, and synchronization problems.
• Review technical requirements and identify implementation dependencies.
• Explain integration capabilities and limitations to customers.
• Participate in customer technical onboarding and implementation calls.
• Support approved testing and validation of integrations.
• Document technical implementation outcomes and outstanding issues.
• Prepare detailed engineering escalations and reproducible bug reports.
• Collaborate with Engineering on complex integration problems.
• Support customer adoption of approved AI-enabled platform features.
• Help customers understand AI configuration requirements and documented limitations.
• Investigate technical problems involving supported AI APIs and workflows.
• Document unexpected AI behavior and escalate sensitive issues appropriately.
• Coordinate with Product and Engineering on AI-related technical investigations.
• Contribute to API documentation and integration troubleshooting guides.
• Create internal resources for common configuration and implementation questions.
• Identify recurring integration issues and opportunities for improvement.
• Communicate technical findings clearly to customers and internal teams.
• Coordinate with Customer Success Managers on customer-impacting technical issues.
• Assist with validating fixes in approved testing environments.
• Follow established engineering change management and escalation procedures.
• Handle API credentials and sensitive configuration information securely.
• Follow privacy, security, and access control requirements.
• Escalate clinical, pharmacy, and compliance matters to authorized teams.
• Maintain accurate technical case records and implementation notes.
• Manage multiple customer-facing technical projects and follow-up tasks.
• Identify implementation risks and communicate them proactively.
• Take ownership of technical investigations and customer integration outcomes.

Requirements

• 3+ years of relevant experience in Customer Engineering, Solutions Engineering, Integration Engineering, Technical Support Engineering, or a related technical SaaS role.
• Hands-on experience supporting or troubleshooting software integrations.
• Strong understanding of REST APIs and HTTP fundamentals.
• Experience investigating API authentication and authorization issues.
• Ability to read and interpret JSON payloads and API responses.
• Experience using Postman, Insomnia, curl, or similar API testing tools.
• Familiarity with webhooks and event-driven integration concepts.
• Ability to troubleshoot software configuration and integration problems.
• Strong understanding of common web application behavior and error handling.
• Comfortable reading technical documentation and investigating unfamiliar systems.
• Ability to document technical problems clearly and accurately.
• Experience preparing reproducible bug reports and engineering escalations.
• Strong written and verbal communication skills.
• Ability to explain technical concepts to non-technical customers.
• Experience working directly with customers or external technical stakeholders.
• Ability to gather technical requirements and identify implementation dependencies.
• Strong problem-solving skills and attention to detail.
• Ability to manage multiple technical investigations and implementation tasks.
• Comfortable collaborating with Customer Success, Product, and Engineering teams.
• Understanding of secure API credential handling and access control principles.
• Willingness to learn AI-enabled software functionality and integration patterns.
• Ability to recognize technical limitations and communicate them accurately.
• Understanding of the importance of privacy and secure information handling.
• Ability to follow established escalation and engineering change procedures.
• Availability to collaborate during required U.S. Eastern Time working hours.
• Strong initiative, accountability, and willingness to take ownership of technical problems.
• Comfortable working in a growing software company with evolving technical requirements.

Nice to Have

• Bachelor's degree in Computer Science, Software Engineering, Information Systems, or a related field.
• Experience supporting AI-enabled SaaS products or AI API integrations.
• Familiarity with large language model APIs and related application workflows.
• Experience integrating with OpenAI, Anthropic, or other AI service APIs.
• Understanding of AI output limitations, testing, and evaluation concepts.
• Experience using JavaScript, TypeScript, Python, or similar languages for troubleshooting and scripting.
• Experience working with Shopify, BigCommerce, WooCommerce, or other e-commerce platforms.
• Familiarity with merchant storefronts, checkout flows, and subscription businesses.
• Experience supporting payment, CRM, or marketing automation integrations.
• Familiarity with OAuth and common API authentication patterns.
• Experience troubleshooting webhook delivery and event-processing failures.
• Basic SQL knowledge for investigating application data.
• Experience using Git or GitHub.
• Familiarity with logging, monitoring, and observability tools.
• Experience using Jira, Linear, Zendesk, or similar tools.
• Experience creating API documentation or technical onboarding guides.
• Experience supporting enterprise or complex SaaS implementations.
• Familiarity with data privacy and security requirements in regulated environments.
• Experience working with healthcare technology or telehealth software.
• Experience collaborating with distributed engineering and customer-facing teams.