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, customer reliability means helping merchants depend on the software they use to operate their businesses. We value careful technical investigation, clear communication, strong follow-through, and people who look beyond immediate fixes to understand and prevent recurring problems. About the Role We're looking for a Customer Reliability Engineer to help improve the reliability of customer-facing workflows and resolve technical issues that affect merchants using Bask Health. This role combines technical troubleshooting, customer-impact analysis, incident investigation, and proactive identification of recurring software problems. You'll work closely with customer success, technical support, product, and engineering teams to understand where customers experience technical difficulties and help coordinate lasting solutions. Our customers include entrepreneurs, e-commerce operators, online business owners, and healthcare businesses using Bask Health to operate direct-to-consumer telehealth services. These customers rely on our platform to support important parts of their business operations. Bask Health brings together merchant storefronts, patient questionnaires, checkout experiences, clinical workflows, pharmacy-related processes, and other business capabilities. You'll develop a detailed understanding of how these systems interact and where technical problems can disrupt customer workflows. You'll investigate customer-reported software issues and determine how they affect the customer's ability to use the platform. You'll help identify patterns in recurring errors, configuration problems, integration failures, and unexpected application behavior. You'll use available technical evidence, logs, browser diagnostics, and support records to understand reported issues. You'll reproduce problems when possible and document the conditions under which they occur. You'll distinguish between customer configuration errors, third-party integration issues, application defects, and broader platform incidents. You'll evaluate the scope and impact of customer-facing problems to help internal teams prioritize investigation and resolution. You'll work with technical support teams to understand escalated issues and identify opportunities to prevent repeated customer contacts. You'll collaborate with customer success managers to understand the business impact of technical problems affecting merchant accounts. You'll work with customer success engineers to investigate implementation or integration issues that continue after onboarding. You'll coordinate with software engineers when issues require code-level investigation, infrastructure expertise, or product fixes. You'll provide clear reproduction steps, technical evidence, customer impact details, and relevant troubleshooting history. You'll collaborate with product managers when recurring problems reveal product usability issues or functionality gaps. You'll help investigate incidents affecting customer-facing platform functionality. You'll support the documentation of incident symptoms, affected workflows, customer impact, and resolution steps. You'll participate in follow-up reviews to understand why problems occurred and how similar issues might be prevented. You'll help identify whether temporary workarounds are being repeatedly used instead of addressing underlying problems. You'll recommend opportunities to improve troubleshooting procedures, customer documentation, or product behavior. You'll support validation of customer-facing fixes after engineering releases changes. You'll help confirm that reported issues are resolved under the relevant conditions. You'll identify potential regression risks when recurring problems involve critical customer workflows. You'll coordinate with appropriate technical teams when additional testing or investigation is needed. You'll monitor available support trends, recurring ticket categories, and customer-reported errors to identify patterns. You'll help organize technical findings so product and engineering teams can prioritize improvements. You'll contribute to internal knowledge bases, troubleshooting guides, and incident documentation. You'll help improve the quality of technical escalation records and reduce repeated investigation of known problems. You'll communicate technical findings clearly to both technical and nontechnical stakeholders. You'll help customer-facing teams understand what is known about an issue, what remains under investigation, and which next steps are appropriate. You'll avoid making unsupported promises about resolution times, product changes, or platform capabilities. You'll maintain accurate records of investigations, technical findings, and outstanding follow-up activities. You'll help improve internal coordination when customer-impacting issues involve multiple teams. You'll contribute to discussions about customer-facing reliability, support quality, and recurring operational challenges. You'll identify opportunities to make customer workflows more dependable through better documentation, configuration guidance, and preventive improvements. You'll work with engineering teams to understand available monitoring and diagnostic capabilities. You'll use approved tools and access levels rather than independently making unapproved production or infrastructure changes. You'll recognize when an issue involves a security or privacy concern and follow established internal escalation procedures. Because Bask Health supports healthcare-related businesses, you'll need to handle customer information carefully and follow applicable internal privacy and security requirements. You'll also recognize when technical issues involve clinical, pharmacy, or compliance responsibilities that require authorized specialist involvement. You'll provide technical guidance about software behavior without making clinical or pharmacy decisions. You'll work in a remote, cross-functional environment where analytical thinking, clear communication, and accountability are important. We're looking for someone who enjoys investigating difficult software problems and identifying why they keep happening. You should be comfortable working with customer-facing teams, software engineers, and business stakeholders. You'll need to be organized, technically curious, and capable of managing several investigations simultaneously. Experience supporting e-commerce platforms, payment workflows, merchant-facing SaaS products, or other transaction-heavy applications is particularly valuable. Success in this role means reducing recurring customer-facing problems, improving technical investigation quality, supporting faster issue resolution, and helping merchants operate more reliably on Bask Health. What You'll Do
- Investigate technical issues affecting customer-facing platform workflows.
- Identify recurring software problems and technical failure patterns.
- Analyze the customer impact of reported platform issues.
- Troubleshoot merchant storefront, questionnaire, and checkout functionality.
- Investigate REST API, webhook, and integration-related failures.
- Analyze HTTP requests, responses, logs, and technical error messages.
- Use browser developer tools and available diagnostic systems.
- Reproduce customer-reported software issues and document findings.
- Distinguish configuration errors from integration problems and product defects.
- Support investigation of customer-impacting platform incidents.
- Document incident symptoms, affected workflows, and relevant technical evidence.
- Help identify underlying causes of recurring customer problems.
- Collaborate with engineering teams on technical investigations and fixes.
- Provide clear reproduction steps and customer impact information.
- Coordinate with product teams on recurring reliability and usability issues.
- Work with technical support teams on complex customer escalations.
- Collaborate with customer success managers on account-impacting technical issues.
- Support customer success engineers with recurring implementation problems.
- Help validate customer-facing fixes following engineering releases.
- Identify potential regression risks in important customer workflows.
- Review recurring support tickets and technical escalation patterns.
- Recommend improvements to technical troubleshooting and escalation procedures.
- Create and maintain technical knowledge base articles.
- Document known issues, approved workarounds, and resolution steps.
- Help improve the quality of technical incident and escalation records.
- Communicate technical findings to customer-facing and engineering teams.
- Track investigation progress and maintain accurate follow-up records.
- Identify opportunities to reduce repeated customer support contacts.
- Follow approved security, privacy, and production-access procedures.
- Escalate clinical, pharmacy, and compliance concerns to authorized teams.
- Contribute to customer-facing reliability and support quality improvements.
- Take ownership of assigned investigations through resolution or appropriate handoff.
Requirements
- 3+ years of experience in technical support engineering, customer engineering, application support, production support, or a closely related customer-facing technical role.
- Demonstrated experience investigating complex technical issues affecting SaaS applications.
- Strong understanding of web-based software behavior and common failure patterns.
- Experience troubleshooting customer-facing software workflows.
- Working knowledge of REST APIs, HTTP methods, status codes, and JSON.
- Familiarity with webhooks, authentication, and common integration patterns.
- Experience analyzing application logs, error messages, and diagnostic information.
- Ability to use browser developer tools to investigate software problems.
- Experience reproducing software defects and documenting investigation steps.
- Ability to distinguish configuration issues from application defects.
- Familiarity with technical escalation and incident investigation processes.
- Experience working with software engineering teams to resolve technical problems.
- Ability to provide clear technical evidence and reproduction steps.
- Experience identifying recurring issues and recommending preventive improvements.
- Ability to understand and communicate the customer impact of technical problems.
- Strong analytical thinking and structured problem-solving skills.
- Strong written and verbal communication skills.
- Ability to explain technical findings to nontechnical stakeholders.
- Experience using technical support or ticketing systems.
- Strong organizational skills and attention to detail.
- Ability to manage multiple technical investigations simultaneously.
- Experience maintaining accurate troubleshooting and incident documentation.
- Comfortable learning complex software platforms and technical workflows.
- Ability to work independently on ambiguous technical problems.
- Comfortable collaborating across customer success, product, and engineering teams.
- Availability to collaborate during required U.S. Eastern Time working hours.
- Strong ownership mentality and commitment to improving customer-facing reliability.
Nice to Have
- Experience supporting e-commerce SaaS or merchant-facing software.
- Experience working with Shopify, BigCommerce, or other storefront platforms.
- Familiarity with direct-to-consumer business models.
- Experience troubleshooting checkout and payment-related software issues.
- 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 troubleshooting third-party integrations.
- Familiarity with OAuth and API authentication.
- Experience working with application monitoring or observability tools.
- Familiarity with Datadog, Sentry, New Relic, or similar platforms.
- Experience participating in incident reviews or root cause analysis.
- Understanding of software reliability and regression testing principles.
- Familiarity with cloud-hosted SaaS environments.
- Experience supporting transaction-heavy applications.
- Experience creating technical troubleshooting guides or incident documentation.
- Experience identifying recurring issues through support ticket analysis.
- Familiarity with healthcare technology or telehealth platforms.
- Experience improving technical support or customer reliability processes.
