CX Tooling Engineer

The CX Tooling Engineer will design, build, and operate the systems that power Spring Health’s customer experience and support operations at scale.

This role sits within Technology in the Care Division’s Engineering Department and supports production systems across Zendesk, Zendesk Contact Center built on Amazon Connect, Tray.ai, Talkdesk, Decagon and approved operational AI integrations. You will combine platform configuration, workflow automation, systems integration, and technical problem-solving to improve reliability, reduce manual work, and create durable solutions for teams operating in a regulated environment.

You will work closely with Operations, Product, Engineering, Data, Security, Legal, Compliance, and external implementation partners to translate business needs into scalable technical solutions.

This is a full-time, remote position reporting to the Senior Manager of Tooling Management. No regular travel is required; occasional travel for team and company onsites may be requested.

What you’ll do

• Design, configure, test, and maintain Zendesk architecture and extensibility, including forms, fields, triggers, automations, service-level agreements, skills, queues, views, permissions, applications, routing logic, custom data structures, integrations, and workflow automation.
• Build and operate contact-center infrastructure using Zendesk Contact Center and Amazon Connect, including contact flows, queues, routing profiles, phone numbers, recording, voicemail, after-hours behavior, overflow, crisis routing, and escalation paths.
• Design, build, and maintain cross-system workflows in Tray.ai using APIs, webhooks, authentication, conditional logic, data transformation, document-processing services, and controlled system writeback.
• Support approved AI-enabled chat, voice, email, and agent-assist workflows by implementing eligibility rules, intent capture, verification, ticket creation, escalation, human handoff, fallback behavior, access controls, data-minimization or redaction controls where required, auditability, and operational safeguards.
• Design solutions with clear system boundaries, dependencies, data flows, and failure modes, considering scalability, reliability, security, maintainability, accessibility, and approved privacy and regulatory requirements, including requirements related to PHI, PII, recording, retention, and regional regulations.
• Monitor platform and workflow health, investigate routing defects, hidden or stale work, status conflicts, integration failures, and reporting gaps, and use operational data and root-cause analysis to implement durable corrective actions.
• Build scalable tooling, permissions, routing, integrations, and service-transition controls that support global launches, specialized teams, outsourced support partners, and round-the-clock operations, replacing brittle or duplicative configurations with standardized and reusable patterns where practical.
• Support centralized tooling intake and partner with Product, Engineering, Data, Security, Legal, Compliance, and operational stakeholders to clarify business impact, translate requests into technical requirements, identify dependencies and risks, estimate effort, define acceptance criteria, and validate outcomes.
• Coordinate with platform vendors and implementation partners on technical requirements, sequencing, dependencies, testing, issue escalation, and delivery quality, while communicating technical decisions, risks, and tradeoffs clearly to technical and nontechnical stakeholders.
• Deliver production changes with appropriate testing, monitoring, logging, alerting, validation, rollback, and recovery procedures, and maintain architecture diagrams, workflow inventories, test plans, change records, release communications, runbooks, and platform standards.

What success looks like in this role

• Assigned routing, telephony, automation, and integration workflows consistently meet established reliability and successful-execution targets.
• Platform enhancements are delivered against agreed scope, acceptance criteria, testing requirements, and delivery expectations, with risks and dependencies raised early.
• Routing defects, silent failures, stale work, and recurring configuration issues decline from established baselines through monitoring, root-cause remediation, and reusable solutions.
• Eligible repeatable work is increasingly handled through automation or standardized platform patterns, with reductions in manual effort measured.
• AI-enabled workflows demonstrate reliable eligibility, escalation, human-handoff, and fallback behavior within approved use cases.
• Tooling improvements contribute to measurable gains in routing accuracy, first-reply time, resolution time, support capacity, platform reliability, or cost per interaction.
• Material production changes include documented testing, monitoring, ownership, validation, rollback, and recovery procedures.

What you’ll bring

• 3+ years of experience administering, engineering, or operating customer experience, contact-center, workflow, automation, and integration platforms in a production environment.
• Hands-on experience with Zendesk configuration and architecture, including business rules, forms, fields, routing, permissions, applications, integrations, or comparable platform capabilities.
• Experience with an enterprise contact-center platform such as Amazon Connect, Zendesk Contact Center, Talkdesk, Genesys Cloud, Five9, Twilio Flex, or a comparable platform.
• Experience configuring interactive voice response or contact flows, queues, routing logic, phone numbers, recording, voicemail, overflow, after-hours, or escalation behavior.
• Working knowledge of REST APIs, webhooks, JSON, authentication, data transformation, and API-testing tools.
• Experience building or maintaining production workflows using an integration, automation, or orchestration platform such as Tray.ai, Workato, or a comparable platform.
• Experience troubleshooting production issues and identifying underlying technical or process causes.
• Understanding of monitoring, error handling, retry behavior, fallback design, recovery procedures, and production change management.
• Ability to translate operational needs into clear technical requirements and maintainable solutions.
• Strong written and verbal communication skills, including technical documentation and communication with technical and nontechnical stakeholders.
• Ability to independently manage assigned work, make progress through ambiguity, and raise risks or dependencies early.
• Sound judgment regarding platform governance, standardization, access controls, and the maintenance impact of technical decisions.

Nice to Have

• Experience with advanced Zendesk development and extensibility capabilities such as the Zendesk Apps Framework (ZAF), custom objects, events and profiles, custom actions or action flows, Zendesk Copilot, intelligent triage, custom agents or procedures, or comparable platform capabilities.
• Experience with Tray.ai, Workato or another enterprise integration and orchestration platform.
• Experience integrating AI-enabled support platforms, conversational AI tools, or large language model services, such as Decagon, OpenAI, Anthropic Claude, Zendesk AI/Copilot, or comparable technologies into operational workflows.
• Experience supporting contact-center infrastructure across multiple countries, outsourced support teams, or round-the-clock operations.
• Familiarity with call-recording consent, privacy, retention, data residency, accessibility, or regional telecommunications requirements.
• Experience with DocuSign, document processing, fax automation, customer relationship management integrations, or similar operational systems.
• Experience working in healthcare, financial services, insurance, or another regulated environment.
• Familiarity with infrastructure as code, automated testing, structured deployment practices, or configuration version control.
• Experience with incident response, root-cause analysis, production observability, or reliability engineering practices.

The target base salary range for this position is $105,000 - $115,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay. 

Benefits provided by Spring Health:

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals. 
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub,  which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.