Head of Engineering

About the Role

At Spekit, we’re building the future of intelligent enablement, a contextual AI platform that helps revenue teams learn, adapt, and perform at the speed of change. We’re entering a defining stage of growth where our success depends on innovation velocity, technical precision, and bold architectural thinking.

We’re seeking a Head of Engineering who thrives in fast-moving environments and is ready to architect, scale, and lead the next generation of AI systems transforming how people learn and work. Reporting directly to the CEO, you’ll lead a distributed, high-performing organization across backend, frontend, ML, and integrations — designing the intelligent backbone that powers Spekit’s AI and agentic workflow platform.

This role is for a deep systems thinker and hands-on innovator — someone who lives at the edge of technology, holds an unrelenting bar for quality, and drives 10x innovation through architecture, design, and culture.

What we need

An experienced leader for a multi-national engineering team to partner with our Head of Product and CEO to build the next generation AI-powered revenue automation platform.

You will:

Drive category-leading innovation to out-compete AI-first startups and legacy incumbents.

Dramatically increase velocity by attracting and developing top engineering talent, building a scalable organization, adopting modern AI-assisted coding practices, while maintaining quality and stability.

Work with the Product team to help align product vision with technical constraints and identify architectural competitive advantages we can leverage in the market.

Drive material business outcomes for our customers by empowering major shifts in sales team performance.

About Spekit

Spekit is the modern, AI-powered enablement platform built around context — redefining how revenue teams learn, act, and sell.

We believe the future of effective AI systems depends on governed, dynamic content — knowledge that’s structured, explainable, and always in context. That’s why Spekit unifies content management, enablement, and personalized guidance into one intelligent system that understands a company’s GTM data model, sales process, and the relationships between content, workflow, and outcomes.

At the core is AI Sidekick, the Just-in-Time Sales Assistant™, which leverages signals from CRM, call intelligence, and communication tools to deliver real-time recommendations, adaptive guidance, and automated workflows — directly within a rep’s flow of work. Sidekick’s contextual AI agents continuously learn from governed content and rep activity, turning static documentation into living, actionable intelligence that drives consistent execution at scale.

Backed by leading investors including Craft Ventures and Felicis, Spekit has raised over $60M and is trusted by world-class organizations like GitLab, ZoomInfo, Southwest Airlines, Equifax, and more to power their enablement in the flow of work.

• You’re a seasoned technical leader (8+ years in leadership, 3+ at VP/Senior Director level) who’s scaled engineering orgs in high-growth SaaS or AI-native companies.
• You move fast and want to build with others who do. You thrive in an environment where speed, curiosity, and bold decisions are celebrated, not slowed down.
• You’re deeply inspired by our vision. You see the massive opportunity to redefine enablement and sales productivity in the age of AI, and you want to be part of shaping that future.
• You live at the edge of technology. You’re obsessed with understanding and experimenting with the latest AI and systems innovations – not just following trends, but pushing them forward. You’re someone our entire company will learn from.
• You’re a deep systems thinker. You’ve architected and scaled secure, intelligent data systems for the enterprise — designing the connective tissue between applications, data, and outcomes. You understand how to model complex relationships through knowledge graphs, data orchestration layers, interoperability frameworks, and real-time event pipelines that keep systems cohesive, governed, and extensible.
• You have depth in modern AI architecture. You’ve built or led teams building context-aware AI pipelines — from RAG frameworks and vector retrieval systems to agent runtimes and model-context protocols (MCP) — and you know how to operationalize them safely in production. You think beyond experimentation, designing the infrastructure, feedback loops, and governance required to make AI accurate, explainable, and enterprise-ready.
• A passion for context, governance, and action. You believe AI’s future lies in systems that are explainable, governed, and integrated into real workflows — not disconnected copilots.
• You demand excellence. You hold yourself and your team to the highest standards for design, architecture, and collaboration, and you’re hands-on enough to dive into code reviews yourself. 
• You build world-class engineering organizations. You’ve done it before – attracting and inspiring top-tier talent, creating cultures of craftsmanship, and delivering products that set a new bar for innovation and impact.

• Partner with our CEO, COO, CMO, Head of Product, and GTM leaders to translate business vision and customer needs into a forward-thinking engineering roadmap. 
• Build and scale a world-class engineering organization that attracts top-tier technical talent. A team that moves fast, collaborates deeply, and executes with precision.
• Create clarity and alignment across time zones while driving accountability and speed.
• Establish a culture of ownership, simplicity, and continuous improvement where learning and innovation are constant.
• Push the boundaries of what’s possible with AI-native enablement, inspiring your team and peers to think bigger and build smarter.

• Bring rigor to scaling distributed systems and data pipelines, ensuring performance and resilience at every layer.
• Stay fluent in the latest technologies for building AI applications, including application frameworks (e.g.,LangChain), architectural patterns (e.g. RAG), data platforms (e.g. Databricks) and cloud infrastructure (e.g., AWS, GCP).Maintain hands-on engagement with the codebase and architecture, performing reviews, mentoring engineers, and ensuring technical decisions match the bar of excellence you set.
• Lead experimentation and innovation cycles that transform emerging AI technologies into real customer value.
• Partner closely with Product and Data to design AI-native capabilities that leverage embeddings, retrieval-augmented generation (RAG), and context modeling.
• Make bold, forward-looking technical bets that keep Spekit at the forefront of applied AI.
• Cultivate a culture of curiosity and technical mastery where engineers are encouraged to learn fast, ship fast, and think in systems.

• Translate ambitious vision into scalable, well-sequenced execution plans.
• Drive operational excellence through CI/CD, observability, reliability, and testing automation.
• Balance velocity and stability, delivering innovation without sacrificing quality or maintainability.
• Ensure predictability and excellence across all releases, fostering trust between engineering, product, and go-to-market teams.