Head of Engineering (AI)

We are looking for a Head of Engineering (AI) to lead the design, development, and scaling of Pepper’s AI-native platform.This is a hands-on leadership role for someone who thrives at the intersection of engineering excellence, AI systems design, and people leadership. You will own the technical foundation behind Pepper’s multi-agent workflows, content intelligence systems, and platform reliability — while building and mentoring a high-performing engineering organization.You will work closely with Product, AI, Content, and Design leaders to translate Pepper’s vision into robust, scalable systems used daily by enterprise teams.What You’ll DoTechnical & Platform LeadershipOwn the end-to-end engineering architecture for Pepper’s AI-native platform, including agent orchestration, workflows, APIs, and core services.Design and scale production-grade AI systems, combining LLMs with deterministic logic, guardrails, evaluations, and human-in-the-loop workflows.Ensure systems are scalable, reliable, observable, and secure as usage grows across enterprise customers.Make principled decisions on build vs buy, architecture trade-offs, and long-term platform evolution.Hands-on EngineeringStay close to the code: participate in design reviews, code reviews, and critical implementations.Set engineering standards for code quality, testing, CI/CD, monitoring, and incident response.Drive best practices across backend systems, APIs, cloud infrastructure, and AI integrations.Team & Org LeadershipLead, mentor, and grow a team of engineers across backend, platform, and AI infrastructure.Own hiring, onboarding, and career development, building a strong engineering culture focused on ownership and quality.Foster a culture of systems thinking, fast iteration, and accountability.Cross-functional CollaborationPartner closely with Product and AI teams to turn evolving requirements into scalable technical solutions.Work with delivery and capability eaders to ensure AI systems align with real-world workflows and quality standards.Collaborate with leadership to shape Pepper’s long-term technology and AI roadmap.Skills & QualificationsMust-Have10+ years of professional experience in software engineering, with progressive leadership responsibilities.Strong experience building and scaling backend and platform systems (APIs, microservices, workflows).Proven track record of leading engineering teams in high-growth or product-focused environments.Deep understanding of system design, scalability, reliability, and performance.Hands-on experience with cloud platforms (AWS, GCP, or similar) and modern CI/CD practices.Excellent communication skills and the ability to work cross-functionally.Strong PlusExperience building AI- or ML-enabled products, especially LLM-powered or workflow-driven systems.Familiarity with agentic AI concepts, orchestration frameworks, or human-in-the-loop design.Experience integrating third-party tools, data sources, or external services at scale.Startup or scale-up experience where architecture had to evolve rapidly.What We’re Looking For (Mindset Fit)You think in systems, not just features.You’ve seen why AI pilots fail — and care deeply about making them work in production.You’re comfortable balancing speed with engineering rigor.You enjoy building teams as much as building technology.You believe AI works best when paired with strong guardrails and human judgment.Why Join PepperLead engineering at a company defining what AI-native growth and content systems should look like.Work on real-world, high-impact AI systems, not prototypes.Shape the technical foundation of a platform used by enterprise customers globally.Collaborate with experienced product, AI, and content leaders.Competitive compensation, meaningful ownership, and room to grow with the company.

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