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, technical support plays an important role in helping customers operate their businesses with confidence. We value strong technical judgment, clear communication, thoughtful troubleshooting, and people who take ownership of difficult problems through resolution. About the Role We're looking for a Senior Technical Support Engineer to investigate and resolve complex technical issues affecting customers using Bask Health's software platform. This role is responsible for advanced troubleshooting, technical escalations, issue investigation, and helping improve the reliability of the customer support experience. You'll work with customer success managers, customer success engineers, product managers, software engineers, and other internal stakeholders to resolve technical problems efficiently and accurately. Bask Health enables entrepreneurs, doctors, and healthcare businesses to launch and operate direct-to-consumer telehealth businesses. Our platform supports merchant storefronts, patient questionnaires, checkout experiences, clinical workflows, pharmacy-related processes, and other business-critical capabilities. You'll develop a detailed understanding of how these systems interact and how technical issues can affect customer operations. You'll serve as an escalation point for complex customer-reported problems that require deeper technical investigation. You'll troubleshoot application behavior, configuration issues, integrations, and unexpected platform errors. You'll investigate issues affecting storefront functionality, questionnaire behavior, checkout flows, and supported platform workflows. You'll use available technical tools, logs, browser debugging capabilities, and internal documentation to gather evidence and identify likely causes. You'll reproduce reported issues whenever possible and document the conditions under which they occur. You'll distinguish between user configuration errors, integration problems, product defects, and broader platform incidents. You'll work closely with software engineers when an issue requires code-level investigation, infrastructure expertise, or a product fix. You'll provide engineering teams with clear reproduction steps, technical evidence, customer impact details, and relevant troubleshooting history. You'll coordinate with product managers when reported issues involve product behavior, functionality gaps, or unclear requirements. You'll communicate technical findings and resolution updates to customer-facing teams and, when appropriate, directly to customers. You'll help ensure that customers receive accurate information about known issues, workarounds, and next steps. You'll take ownership of assigned technical escalations and maintain clear accountability until they are resolved or appropriately transferred. You'll prioritize issues based on severity, customer impact, business disruption, and established internal escalation procedures. You'll participate in incident investigations involving customer-facing platform functionality. You'll help document incident timelines, observed symptoms, customer impact, and resolution steps. You'll support follow-up reviews to identify recurring issues and opportunities to prevent similar problems. You'll help build and maintain technical troubleshooting guides, internal knowledge base articles, and escalation procedures. You'll identify gaps in existing support documentation and recommend clearer, more effective troubleshooting workflows. You'll assist with improving how technical issues are categorized, investigated, and routed to the appropriate teams. You'll collaborate with customer success engineers on integration-related issues that require deeper investigation. You'll work with customer success managers to understand the business impact of technical problems affecting important accounts. You'll help support customers through technical changes, configuration updates, and issue resolution when appropriate. You'll also help validate that customer-reported problems have been addressed after engineering releases a fix. You'll monitor patterns in support tickets and technical escalations to identify recurring product problems. You'll share technical findings with product and engineering teams to help inform reliability and usability improvements. Because Bask Health operates in healthcare-related environments, you'll need to handle customer information carefully and follow applicable internal security and privacy requirements. You'll recognize when an issue involves clinical, pharmacy, compliance, or patient-related decisions that must be handled by the appropriate authorized team. You'll avoid making clinical or pharmacy decisions while providing technical support for the software workflows involved. As a senior team member, you'll help establish effective troubleshooting practices and may provide technical guidance to less-experienced support engineers. You'll be expected to work independently on complex investigations while knowing when to involve engineering or other specialists. This is a senior individual-contributor role focused on technical support execution and problem resolution, not formal people management. We're looking for someone with substantial experience supporting SaaS applications, strong debugging skills, and the ability to communicate clearly under pressure. You should be comfortable investigating ambiguous technical issues, organizing evidence, and working across teams to drive resolution. Experience supporting e-commerce platforms, payment workflows, or other transaction-heavy software environments is particularly valuable. Success in this role means resolving difficult technical issues, improving escalation quality, reducing recurring support problems, and helping customers operate reliably on Bask Health. What You'll Do
- Serve as a senior escalation point for complex customer-facing technical issues.
- Investigate advanced software application and platform problems.
- Troubleshoot merchant storefronts, questionnaires, checkout flows, and supported workflows.
- Diagnose configuration errors, integration failures, and unexpected application behavior.
- Reproduce customer-reported bugs and document technical findings.
- Use browser developer tools, logs, and available diagnostic systems.
- Investigate REST API, webhook, and authentication-related problems.
- Analyze HTTP requests, responses, and relevant error messages.
- Distinguish product defects from configuration and integration issues.
- Prioritize technical issues according to customer impact and severity.
- Own assigned escalations and coordinate them through resolution.
- Work with engineering teams on issues requiring code-level investigation.
- Provide detailed reproduction steps and technical evidence to engineers.
- Collaborate with product managers on product behavior and functionality concerns.
- Coordinate with customer success teams on high-impact account issues.
- Communicate technical updates and recommended next steps clearly.
- Identify and document supported workarounds when appropriate.
- Help validate customer-facing fixes following engineering releases.
- Participate in investigations of customer-impacting platform incidents.
- Document incident symptoms, timelines, and resolution information.
- Identify recurring technical issues and recommend preventive improvements.
- Create and maintain internal technical troubleshooting documentation.
- Improve technical escalation procedures and support workflows.
- Help develop consistent issue categorization and triage practices.
- Review technical support trends and recurring customer complaints.
- Support internal training on troubleshooting tools and procedures.
- Provide technical guidance to junior support engineers when needed.
- Maintain accurate support ticket records and investigation notes.
- Follow security and privacy procedures during technical investigations.
- Escalate clinical, pharmacy, or compliance concerns to authorized stakeholders.
- Collaborate with engineering on platform reliability improvements.
- Take ownership of complex technical problems and follow through on commitments.
Requirements
- 5+ years of experience in technical support engineering, application support, production support, or a closely related technical role.
- Strong experience supporting customer-facing SaaS applications.
- Demonstrated ability to investigate and resolve complex software issues.
- Experience troubleshooting web applications and browser-based platforms.
- Working knowledge of REST APIs, HTTP methods, status codes, and common integration patterns.
- Familiarity with JSON, webhooks, and API authentication.
- Experience using browser developer tools for technical investigation.
- Ability to analyze logs, error messages, and application behavior.
- Experience reproducing software defects and documenting reproduction steps.
- Ability to distinguish configuration problems from application defects.
- Experience working directly with software engineering teams.
- Familiarity with technical ticketing and escalation management systems.
- Experience prioritizing issues based on severity and customer impact.
- Strong technical documentation skills.
- Ability to communicate complex technical findings clearly.
- Experience coordinating investigations across multiple internal teams.
- Strong problem-solving and analytical thinking skills.
- Ability to manage several technical investigations simultaneously.
- Understanding of software incident management and escalation procedures.
- Familiarity with application security and appropriate data-handling practices.
- Ability to work independently on ambiguous technical problems.
- Strong organizational skills and attention to detail.
- Ability to maintain clear and accurate technical records.
- Comfortable collaborating with customer success and product teams.
- Comfortable working in a remote, cross-functional environment.
- Availability to collaborate during required U.S. Eastern Time working hours.
- Ability to take ownership of technical escalations through resolution.
Nice to Have
- Experience supporting e-commerce SaaS or merchant-facing software.
- Familiarity with Shopify, BigCommerce, or other online storefront platforms.
- Experience troubleshooting payment and checkout workflows.
- Familiarity with Stripe or similar payment processing integrations.
- Working knowledge of JavaScript, HTML, and CSS.
- Experience using Postman or similar API testing tools.
- Familiarity with SQL and database query fundamentals.
- Experience with application monitoring or observability platforms.
- Familiarity with tools such as Datadog, Sentry, New Relic, or similar systems.
- Understanding of cloud infrastructure and hosted SaaS environments.
- Experience supporting webhooks and asynchronous processing systems.
- Familiarity with OAuth, access tokens, and authentication flows.
- Experience supporting transaction-heavy applications.
- Experience participating in incident response and post-incident reviews.
- Familiarity with software release processes and regression testing.
- Experience building technical support knowledge bases.
- Experience improving escalation workflows and support processes.
- Experience mentoring junior technical support professionals.
- Familiarity with healthcare technology or telehealth platforms.
- Understanding of HIPAA-related technical considerations.
