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 worlds 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:

Youre the most senior technical mind in the companya 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 productsyou know how to apply cryptography tokenization and key management correctly in real systemsand 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 3050% of the timewriting 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 leadershipdirection 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 managerkeeping 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 DataStealths 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 subsystemstokenization 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/ 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 jobnot 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 DataStealths application of AI and ML to security problemsdata 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 DataStealths defensive posture around AI-specific risks: prompt injection training data leakage model poisoning and adversarial MLaligned 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 GCPresilience 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 youdesign 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 managerthe 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 teamdirecting 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 Security Customer Success and executive leadership to translate the hardest 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 IC technical role at your organization (Chief Architect Distinguished Engineer Technical Fellow Principal Architect or equivalent)

Demonstrated hands-on coding at the most senior levelyou have shipped production code in a Chief Architect or Distinguished Engineer role not just approved designs. Expect to discuss specific systems you personally built and projects you personally de-risked through experimental development

Deep expertise in Java and JVM languages (required) plus at least two of TypeScript/ Golang or Rust with demonstrated ability to move fluently between them

Deep experience building security productsdata security tokenization encryption key management DLP CASB EDR or equivalent. You are a strong applier of cryptography: you know which primitives libraries and patterns to use have designed systems around key hierarchies and HSMs and have shipped systems under PCI-DSS SOC 2 or equivalent regulatory scrutiny. You do not need to be a cryptographer but you must know how to build secure systems with crypto correctly

Firsthand experience applying AI/ML to security problems in productionnot AI-adjacent not exploratory. You have designed and shipped at least one of: ML-based classification/detection LLM-based analyst augmentation agentic security automation or adversarial ML defense. You have clear opinions on the current state of AI in the security product landscape and where it is going

Proven ability to lead Principal and Distinguished Engineers through technical credibility rather than authorityRFCs design reviews exemplar code and technical vision documents

Comfort leading a small group of senior ICs as a technical lead in a shared-management modellight people-management load high technical-leadership load

Deep experience designing and operating distributed systems at production scaleresilience observability performance multi-region costincluding at least one major cloud provider at depth and working command of the others

Track record of de-risking the hardest projects through applied research prototyping and experimental development

Strong grasp of networking fundamentals (HTTP/S TLS SSH DNS TCP/IP) Linux systems and how they compose in distributed systems

Deliberate quality-driven use of agentic AI coding tools (Claude Code Copilot Cursor open-source agents) as an engineering force multiplierwith 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 (FPE) tokenization vaults and vaultless tokenization architectures as a consumer/integrator

Contributions to open-source in security data platforms or AI

Experience designing agentic AI systems in adversarial settingstool 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 presenceconference talks published papers standards work or technical writing that has influenced the field

Familiarity with configuration-as-code systems (we use Groovy) and infrastructure-as-code at depth

Cross-paradigm performance analysis experience (VisualVM/JProfiler pprof Chrome DevTools/V8 Profiler)you can profile and fix the hardest production performance problems yourself

Why DataStealth:

The most senior technical seat at a fast-growing patented-technology security scale-upreal scope real ownership real code

Solve hard problems that matter: your architecture and your code directly protect sensitive data for the worlds largest enterprises

Player-coach architect role: you lead the technical direction and you stay in the code

Lean shared-management model that keeps you deeply technicalPEs and DEs report to you for technical leadership while executive leadership absorbs the 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 multipliersnot crutches

Great Place to Work certified for five consecutive years with a team that is genuinely best-in-class

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; were open to flexible/remote arrangements for applicants located outside the region.

Additional Information:

This posting is for an existing vacancy. We use artificial intelligence (AI) 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!

Required Experience:

Chief