Job descriptionAbout DataStealth
DataStealth is a unified data security platform (DSP) that discovers, classifies, and protects sensitive data across your entire environment, from on‑premise to legacy cloud to cloud. The platform protects data without requiring complex integrations or changes to existing applications, ensuring security that enables, rather than hinders, your business. About You
You're the most senior technical mind in the company—a hands‑on architect who writes code, ships, and de‑risks the hardest problems personally. You set technical direction for the entire platform, own the architecture roadmap, and lead our cohort of Principal and Distinguished Engineers through technical credibility rather than authority. Role Overview
The Chief Software Engineering Architect is the most senior technical role at DataStealth, owning technical strategy, architecture, and engineering standards for the DSP platform. You are expected to be hands‑on in code roughly 30–50% of the time, writing difficult components, leading research, and prototyping before wider adoption. What You Will Do
Technical Strategy & Architecture Leadership
Own the multi‑year technical roadmap and architecture vision for the DSP across discovery, classification, tokenization, encryption, and key management. Define and evolve engineering standards, platform RFCs, technology selection, and paved paths for Principal and Distinguished Engineers. Partner with the CTO, product, and security leadership on build‑vs‑buy decisions, 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 most risky 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 ambitious projects: timeboxed prototypes, spikes, and reference implementations. Set the quality bar through exemplar code, design reviews, and technical mentorship of senior engineers. Work across the stack using Java (primary), TypeScript/Node.js, Golang, and Rust. Security Architecture & Threat Leadership
Own end‑to‑end security architecture: 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, choosing appropriate primitives, trusted libraries, key hierarchy design, and HSM placement. 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. 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 strategy for combining classical detection with ML‑based classification and LLM‑based augmentation. Establish defensive posture around AI‑specific risks: prompt injection, training data leakage, model poisoning, and adversarial ML. Evaluate and prototype emerging patterns—agentic security workflows, RAG over telemetry, privacy‑preserving inference—and recommend adoption or rejection. 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, and high‑throughput processing systems. Engineering Leadership & Culture
Provide technical leadership to Principal and Distinguished Engineers—design review, architectural direction, unblocking, and craft development through RFCs and architecture guilds. Work as a principal technical lead, not a traditional line manager; executive team handles performance reviews and people‑management load. Drive AI‑augmented engineering practices—directing agentic AI coding tools, setting standards for review, testing, and production quality. Help hire, grow, and retain senior technical talent; raise the technical bar through mentorship, documentation, and visible engineering excellence. Work cross‑functionally with Product, Security, Customer Success, and executive leadership to translate customer problems into coherent technical strategy. What You Bring
Required
15+ years of professional software engineering experience, with at least the last 5 in the most senior individual‑contributor technical role. Hands‑on coding experience at this level—shipped production code in a leading technical role, not just approved designs. Deep expertise in Java and JVM languages (required) plus at least two of TypeScript/Node.js, Golang, or Rust. Deep experience building security products—tokenization, encryption, key management, DLP, CASB, or equivalent, with proven cryptographic design and compliance compliance. Firsthand experience applying AI/ML to security problems in production—at least one of ML‑based classification/detection, LLM‑based analyst augmentation, agentic security automation, or adversarial ML defense. Proven ability to lead senior engineers through technical credibility—RFCs, design reviews, exemplar code, technical vision. Comfort leading a small group of senior ICs with a shared‑management model—light people‑management load, high technical load. Deep experience designing and operating distributed systems at production scale—resilience, observability, performance, multi‑region, and major cloud provider depth. Track record of de‑risking hard projects through applied research, prototyping, and experimental development. Strong grasp of networking fundamentals, Linux systems, and how they compose in distributed systems. Deliberate, quality‑driven use of agentic AI coding tools—rigorous review, testing, and validation of all AI‑generated code before production. Comfort working in a hybrid environment (Mississauga office, 4 days/week). Nice to Have
Experience as a technical founder or early technical leader at a security scale‑up. Experience with format‑preserving encryption, tokenization vaults, or vaultless tokenization architectures. Contributions to open‑source in security, data platforms, or AI. Experience designing agentic AI systems in adversarial settings—tool use, multi‑agent coordination, human‑in‑the‑loop gating, prompt injection hardening. Deep experience with event‑driven architectures (Kafka, NATS) at scale. Familiarity with MITRE ATLAS, NIST AI RMF, OWASP LLM/ML Top 10, and how they apply to security product architecture. Public technical presence—conference talks, published papers, standards work, or technical writing that has influenced the field. Familiarity with configuration‑as‑code systems (Groovy) and infrastructure‑as‑code at depth. Cross‑paradigm performance analysis experience—VisualVM, pprof, Chrome DevTools, enabling you to profile and fix hard production performance problems. Why DataStealth
The most senior technical seat at a fast‑growing, patented‑technology security scale‑up—real scope, real ownership, real code. Solve hard problems that matter: your architecture and code directly protect sensitive data for the world’s largest enterprises. Player‑coach architect role: you lead the technical direction and stay in the code. Lean, shared‑management model that keeps you deeply technical—principal engineers report to you for technical leadership, while executive leadership absorbs performance‑management load. Polyglot engineering culture: choose the right tool for the job, not the only tool you know. AI‑forward engineering team that treats AI tools as force multipliers—not crutches. Great Place to Work certified for five consecutive years with a genuinely best‑in‑class team. Direct partnership with the CTO and executive team on multi‑year technical strategy. This role follows a hybrid schedule (4 days/week in‑office) for those based in the GTA; we’re open to flexible or remote arrangements for applicants located outside the region. Additional Information
This posting is for an existing vacancy. We use artificial intelligence to screen, assess, and select applicants. DataStealth is an equal opportunity employer. We encourage applications from candidates of all backgrounds and experiences. We look forward to reviewing your application.
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