Chief Software Engineering Architect

About DataStealth:

DataStealth is a single, unified data security platform (DSP) that discovers, classifies, and protects sensitive data across your entire environment, from on-premise to legacy cloud to cloud; wherever your data lives or flows, we protect it using the latest technologies and AI. We do this without requiring complex integrations or changes to your existing applications, ensuring security that enables, rather than hinders, your business. By seamlessly applying data protection strategies, such as tokenization, we ensure that even if your perimeter is breached, your data remains unusable if it falls into the wrong hands.

Recognized for the fifth consecutive year as a Great Place to Work , we are one of the world's leading and fastest growing cybersecurity software companies. Our team is the best in the business. Our patented technology provides our large enterprise customers with the ability to solve complex data security problems with a paradigm shifting technology that can actually solve problems.

About You:

You're the most senior technical mind in the company—a hands-on architect who still writes code, still ships, and still de-risks the hardest problems personally. You set the technical direction for the entire platform, own the architecture roadmap end-to-end, and lead our team of Principal and Distinguished Engineers through technical credibility rather than authority. You think in decades of system evolution, but you prove your ideas in weeks of working code. You have deep experience building security products—you know how to apply cryptography, tokenization, and key management correctly in real systems—and you have firsthand experience applying AI and ML to hard security problems, not as a buzzword, but as engineering. You are comfortable being the final technical escalation point for anything the team cannot solve, and equally comfortable pairing with a senior engineer at a keyboard to unblock a nasty distributed systems bug.

Role Overview:

The Chief Software Engineering Architect is the most senior technical role at DataStealth. You own the overall technical strategy, architecture, and engineering standards for the entire DSP platform, and you lead the technical direction of our most senior engineering cohort. Crucially, this is not a non-coding architect role. You are expected to be hands-on in code roughly 30–50% of the time—writing our most difficult components, leading applied research and experimental development to de-risk our riskiest projects, and prototyping the designs you propose before asking anyone else to commit to them.

Our Principal and Distinguished Engineers report to you for technical leadership—direction, design review, unblocking, architectural calls, and the growth of their craft. Management is a shared function. The executive team retains ownership of performance reviews, compensation, career progression decisions, and the bulk of day-to-day people management. Your reports are self-motivated senior ICs, and the expectation is that you lead them more like a principal technical lead than a traditional engineering manager—keeping the management overhead light so you can stay deeply technical.

Based in Mississauga with a hybrid schedule (4 days in-office per week), you will work directly with the CTO and executive team on multi-year technical strategy, and directly with our Principal and Distinguished Engineers on the code that matters most. This role defines what "done right" means at DataStealth.

What You Will Do:

Technical Strategy & Architecture Leadership

Own the multi-year technical roadmap and architecture vision for the DataStealth DSP across discovery, classification, tokenization, encryption, and key management

Define and evolve engineering standards, platform RFCs, technology selection, and "paved paths" that Principal and Distinguished Engineers build on

Partner with the CTO, product, and security leadership on build-vs-buy, platform bets, and competitive technical strategy

Represent DataStealth's architecture externally to enterprise customers, design partners, auditors (PCI-DSS, SOC 2), and the broader security community

Hands-On Deep Technical Work

Write production code in our hardest, highest-risk subsystems—tokenization engine internals, high-throughput data-path services, security-critical platform components, and cross-cutting platform libraries

Lead applied research and experimental development to de-risk our most ambitious projects: timeboxed prototypes, spikes, and reference implementations that the broader team then productionizes

Set the quality bar through exemplar code, design reviews, and technical mentorship of Principal and Distinguished Engineers

Work across the stack using the right language for the job: Java (primary), TypeScript/Node.js, Golang, and Rust

Security Architecture & Threat Leadership

Own end-to-end security architecture for the platform: threat models, trust boundaries, applied cryptographic design, key hierarchies, HSM integration, and compliance boundaries for PCI-DSS, SOC 2, GDPR, and related frameworks

Apply the right cryptographic tools for the job—not invent them. You know which primitives to use, which libraries to trust, how to design key hierarchies and rotation, where HSM boundaries belong, and how to structure systems so compliance and operational reality both hold

Act as the final technical escalation point for novel security questions, adversarial scenarios, and high-stakes architectural trade-offs

Drive secure-by-design engineering culture: threat modeling as a first-class engineering artifact, not an afterthought

AI in Security Products

Define and lead DataStealth's application of AI and ML to security problems—data classification, anomaly and sensitivity detection, analyst augmentation, and agentic automation

Own the technical strategy for combining classical detection (regex, structured matchers, tokenization) with ML-based classification (transformer classifiers, embedding-based similarity, small distilled models) and LLM-based augmentation where appropriate

Establish DataStealth's defensive posture around AI-specific risks: prompt injection, training data leakage, model poisoning, and adversarial ML—aligned to NIST AI RMF, OWASP LLM/ML Top 10, and MITRE ATLAS

Evaluate and prototype emerging patterns (agentic security workflows, RAG over telemetry, privacy-preserving inference) and make clear recommendations on what DataStealth adopts, builds, or rejects

Cloud, Platform & Operational Excellence

Set architectural direction for cloud-native deployment across AWS, Azure, and GCP—resilience, observability, cost, multi-region, and regulated-workload patterns

Define standards for CI/CD, container orchestration (Kubernetes/Docker), observability (Prometheus, Grafana, OpenTelemetry, ELK), and infrastructure-as-code (Terraform, Pulumi)

Lead architectural decisions on event-driven backbones, data stores across paradigms, and high-throughput processing systems

Engineering Leadership & Culture

Provide technical leadership to the Principal and Distinguished Engineer cohort who report to you—design review, architectural direction, unblocking, and craft development through RFCs, architecture guilds, and direct technical mentorship

Work as a principal technical lead, not a traditional line manager—the executive team handles performance reviews, compensation, and the bulk of people-management load so you can stay deeply technical

Drive AI-augmented engineering practices across the team—directing agentic AI coding tools (Claude Code, Copilot, Cursor, open-source agents) as disciplined engineering partners, setting the bar on review, testing, and production quality for AI-generated code

Help hire, grow, and retain our most senior technical talent; raise the technical bar through mentorship, documentation, and visible engineering excellence

Work cross-functionally with Product,