We are seeking a seasoned and visionary Head of Engineering to lead and scale our technology organization at Crimson. You will own the full engineering charter from architecture and delivery to team building and cultural excellence. Working directly with the CEO and cross-functional leadership, you will be the technical backbone of Enago and Crimson's product ecosystem, ensuring that our platform remains world-class in quality, scalability, and innovation.

This is a highly impactful senior leadership role for someone who combines deep technical credibility with strong people leadership and a product-centric mindset.

KEY RESPONSIBILITIES:

Engineering Leadership & Strategy

Define and drive the engineering vision, strategy, and multi-year technology roadmap in alignment with business goals
Partner closely with the CEO, Product, and business stakeholders to shape product direction and execution priorities
Build and sustain a high-performance engineering culture rooted in ownership, quality, and continuous learning
Represent engineering in leadership forums; act as a key decision-maker for technology investments and trade-offs

Architecture & Technical Governance

Own and govern end-to-end architecture across product, platform, and infrastructure portfolios
Drive technology modernization initiatives — including cloud-native migration, microservices evolution, and tech debt reduction
Establish architectural standards, design review processes, and engineering best practices across teams
Ensure scalability, resilience, performance, and security are first-class concerns in all technical decisions

Delivery & Execution

Manage end-to-end delivery of engineering projects against commitments, milestones, and quality benchmarks
Introduce and enforce robust engineering metrics, delivery governance, and incident management frameworks
Align Agile/Scrum execution across multiple teams for consistent, high-velocity delivery
Provide hands-on technical guidance and unblock teams through architectural and design decision-making

REQUIRED SKILLS & EXPERIENCE:

Experience

14+ years of progressive software engineering experience, with at least 3–5 years in a senior engineering leadership role (Head of Engineering, Director of Engineering, or equivalent)
Proven track record of leading and scaling engineering organizations of 25+ people
Experience building and shipping large-scale SaaS products used globally.

Technical Depth

Strong hands-on background in backend systems — microservices architecture, REST & WebSocket APIs, distributed systems
Proficiency in cloud platforms, especially AWS (EC2, RDS, Lambda, S3, CloudFront) and/or GCP; deep understanding of cloud-native architecture and cost optimization
Solid understanding of front-end technologies — Angular or React; experience with browser plugins, desktop plugins, or Word add-ins is a strong plus
Experience in back end technologies like .NET, Java, or
Strong grasp of data structures, algorithms, system design, and object-oriented & functional programming principles
Knowledge of both relational databases (PostgreSQL, MySQL) and NoSQL stores (MongoDB, DynamoDB, Redis)
Experience with high-data-volume systems and optimizing for throughput and latency at scale

Leadership & Management

Demonstrated ability to hire, mentor, and retain engineering talent across diverse seniority levels
Strong stakeholder management skills — able to communicate complex technical concepts clearly to non-technical audiences
Experience defining engineering KPIs, OKRs, and delivery governance frameworks
Product-centric mindset with strong empathy for end users and design sensibility

Head Of Engineering