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
