Senior Software Engineer (Data Connectors & Integration Platform)

Location: Remote / Americas (South / Central / North)

Why Chiri

We help teams work smarter via the Chiri platform, leveraging our technology and playbooks, by integrating AI into the way work actually happens. Think of us as AI sherpas, guides who meet clients where they are, map the terrain, and help them reach the next ridge safely and sustainably.

Role Overview

We're seeking a skilled Software Engineer with a few years of hands-on experience to play a pivotal role in both client-facing AI audits and internal platform development. This position is perfect for someone who excels at building MVPs quickly in familiar tech stacks, while collaborating empathetically with teams to drive AI adoption. You'll split your time between assessing clients' AI readiness through structured audits and creating robust internal tools that empower our team to deliver streamlined, ROI-focused insights to clients. Expect a dynamic environment where rapid iteration, independent feature development, and adherence to agile task management are key to success.

Key Responsibilities

Client-Facing AI Audits (50% of role): Engage directly with engineering teams at client organizations to conduct comprehensive AI audits. Using our provided questionnaires and frameworks, evaluate their AI readiness, adoption capacity, and potential barriers (e.g., integration challenges or cultural resistance). Provide actionable insights on workflow acceleration, compliance in regulated sectors, and sustainable AI embedding—all while building trust through empathetic, conversational interactions.
Internal Tooling & Platform Development (50% of role): Design, prototype, and implement internal tools for our client intelligence platform. This includes building features for sharing ROI metrics on AI adoption, integrating AI workflow builders, and creating streamlined automations to enhance client servicing. Focus on rapid MVP development in TypeScript/Vite with AWS infrastructure, ensuring scalability and user-friendly interfaces for tracking productivity gains like cost savings or faster deployments.
Collaborate cross-functionally with our consulting team to align tools with client needs, such as tailoring solutions for HR (e.g., talent management), Finance (e.g., risk analysis), or Engineering (e.g., automated testing).
Independently develop and iterate on features, adhering to project direction and using task management tools like Linear or JIRA for efficient tracking and delivery.
Leverage AI tooling (provided by us) to boost your productivity, such as Cursor, Claude Code, or OpenAI's Codex CLI, while prototyping solutions that deliver short-term wins and long-term impact.

Required Qualifications

Bachelor's degree in Computer Science, Software Engineering, or a related field.
2-4 years of professional software engineering experience, with proven ability to build and deploy MVPs rapidly in tech stacks you're comfortable with.
Proficiency in TypeScript, Vite, and AWS (e.g., for building scalable web applications and cloud infrastructure).
Experience with AI-assisted development tools like Cursor, Claude Code, or OpenAI's Codex CLI—demonstrating how you've used them to accelerate coding workflows.
Strong English proficiency both written and verbale at CEFR C1 Level for non-native speakers for clear communication in client interactions, documentation, and team collaboration.
Ability to work independently on feature development while following structured task management in tools like Linear or JIRA.
Passion for AI's role in driving measurable outcomes, such as workflow efficiency and cultural adoption.

What We Offer

A fast-paced global remote team environment where your contributions directly impact high-growth clients in tech-forward industries.
Opportunities to grow with us as we evolve product innovation, with access to cutting-edge AI tools and training.
The chance to "summit" AI challenges alongside inspired colleagues, delivering real ROI like 50% faster processes or enhanced compliance.

If this role and Chiri's mission excite you and aligns with your expertise, we'd love to hear from you!

The Opportunity

We are a premier AI Services firm seeking a Senior Software Engineer to build and own the data connector layer powering a critical transformation program for a Fortune 500 Health Insurance client.

This is not a standard backend role. We need a pragmatic systems engineer who can translate cross-functional requirements into secure, scalable, stateless integrations—bridging Cybersecurity Awareness (Proofpoint), LMS platforms (SumTotal / future: Cornerstone or Workday Learning), and Workday HCM. You will work closely with the HR Lead, HR Consultant (functional architect), and Technology Lead to ensure the platform turns security awareness activity into auditable HR risk and compliance data.

Project Context

The client is building a “future-ready” integration that standardizes data from Proofpoint (Security Awareness) through the current LMS (SumTotal) and into Workday. The design goal is a stateless middleware / abstraction layer that decouples vendor-specific mappings so the same pattern can support future LMS platforms (specifically Cornerstone or Workday Learning) with minimal rework.

Key Responsibilities

As the Senior Software Engineer, you will partner with the Technology Lead and collaborate daily with the HR Lead and Senior HR Consultant across three pillars:

1. Connector Architecture & Data Standardization

Design Connector Patterns: Build a reusable connector framework for vendor ingestion (Proofpoint/LMS) and downstream publishing (Workday), including versioning and schema evolution.
Canonical Data Model: Implement the canonical event/data structures (e.g., training activity, completion, assignment, competency/risk signals) aligned to the HR Consultant’s data dictionary and mapping strategy and Shareable Content Object Reference Model (SCORM standards).
Mapping & Transformation Layer: Develop configurable transformation rules so mappings can be updated without re-deploying core services (where feasible).
Data Quality Controls: Implement validation, deduplication, idempotency, reconciliation reports, and error quarantining.

2. Secure Integration Engineering & Future-Readiness

API + File-Based Integrations: Build and maintain integrations using REST/SOAP APIs, webhooks, and/or SFTP extracts depending on vendor capabilities (Workday/LMS constraints).
Privacy-by-Design Implementation: Enforce strict privacy requirements (minimal PII, no PHI) through field-level controls, tokenization/pseudonymization where appropriate, and secure storage/transport.
Reliability & Scale: Engineer for retries, backoff, rate limits, pagination, async processing, and throughput scaling for enterprise volumes.
Extensibility Playbooks: Co-develop “Future LMS” technical onboarding patterns and connector runbooks to accelerate migrating from SumTotal to Cornerstone or other platforms.
Testing & Validation: Own automated tests (unit/integration/contract), test harnesses with representative payloads, and support HR-functional PoC test cycles.

3. Delivery Execution, Governance, and Cross-Functional Partnership

Partner with HR Leads: Translate HR reporting needs and competency/risk definitions into implementable fields, events, and Workday-compatible constructs.
Operational Readiness: Produce runbooks, monitoring dashboards, and incident response workflows; support go-live and hypercare.
Audit & Evidence Support: Ensure the integration produces traceable, reproducible evidence (timestamps, source-of-truth identifiers, processing logs) aligned with compliance and retention policies.
Cross-Functional Design Sessions: Represent engineering in sessions with IT, Security, Legal, and HR to align on security posture, data retention, and approval workflows.

Required Qualifications

Experience: 5-7+ years building production integrations, backend systems, or data platforms in enterprise environments.
Integration Expertise: Proven experience integrating with HRIS/LMS systems or similar enterprise SaaS platforms via APIs, webhooks, and/or SFTP feeds.
Data Engineering Fundamentals: Strong skills in transformation pipelines, schema management, data validation, and canonical modeling.
Security & Compliance: Practical experience building systems under strict privacy/security constraints (PII handling, least privilege, encryption, audit logging).
Regulated Industry Background: Prior experience in Healthcare or highly regulated industries (Biotech, Pharma, Finance) with sensitivity to PII/PHI boundaries.

Preferred Qualifications

Experience integrating with Workday (RaaS, EIB, Studio, APIs) and/or LMS platforms like Cornerstone or SumTotal.
Familiarity with Proofpoint Security Awareness (or similar platforms) and security awareness telemetry patterns.
Experience building stateless middleware, data abstraction layers, or connector frameworks intended to support multiple vendors over time.
Consulting experience delivering to Fortune 500 clients with stakeholder-heavy governance.

Deliverables You Will Own

Connector Framework supporting Proofpoint ingestion and LMS/Workday publishing patterns.
Canonical Data Schemas + Transformation Rules aligned to the HR data dictionary and competency/risk model.
Security Controls & Compliance Evidence (audit logging, retention alignment, field-level governance).
Test Harness + Validation Reports for PoC and production readiness.
Operational Runbooks + Monitoring Dashboards for ongoing reliability and support.
“Future LMS” Technical Playbook (connector onboarding, mapping approach, and integration checklist).

How You’ll Work (Cross-Functional Operating Model)

HR Lead: Align on outcomes, adoption needs, and what must be visible in Workday.
Senior HR Consultant: Implement the data dictionary, mapping requirements, and validation criteria for HR/compliance/audit use cases.
Technology Lead: Align on architecture, environment constraints, deployment strategy, and engineering standards.

To Apply

Please submit your resume highlighting relevant experience with enterprise integrations, HRIS/LMS systems, and building secure data connectors suitable for regulated environments. Include examples of connector frameworks, canonical models, or multi-vendor integration work where possible.

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