Enterprise Technical Lead

Caylent is an AI-first cloud services company that helps organizations turn ambitious ideas into meaningful business impact. As an AWS Premier Tier Services Partner and a charter member of Anthropic’s Claude Partner Network, we combine deep expertise in AWS, artificial intelligence, and Anthropic’s Claude platform to help customers modernize their technology, build intelligent products, and move AI from experimentation into production.

Our capabilities span generative and agentic AI, cloud migration and modernization, cloud-native application development, data and analytics, DevOps, managed services, security and compliance, and customer experience transformation. At Caylent, our people always come first.

We are a fully remote global company with employees in Canada, the United States and Latin America. We celebrate the culture of each of our team members and foster a community of technological curiosity. Come talk to us to learn more about what it means to be a Caylien!

The Mission 

We are seeking an exceptional Senior Engineering Manager to join our growing Cloud Native Applications team and lead delivery on Caylent's largest and most strategically important client engagements. The right candidate has deep expertise in designing and building applications, creating AI-first software solutions, and is energized by the scale, complexity, and stakes that come with our biggest accounts. 

Your mission will be to work alongside and lead Caylent’s Software Engineers, Architects, Sales, and Project Managers to deliver for our largest and most complex customers. You’ll be hands-on with the latest technologies, operate confidently amid the ambiguity and competing priorities that large enterprise environments bring, and serve as a steady, senior presence - both for your team and in front of client leadership - when the stakes are highest. 

Your Assignment

• Manage a team of 5-8 direct reports including software engineers and architects. 
• Perform people-leadership tasks including regular 1:1 meetings, performance reviews, performance management discussions, and career growth conversations to support the development and improvement of your direct reports.
• Lead software development project teams to deliver AI-first, production-ready solutions in environments with significant scale, technical complexity, and organizational complexity.
• Lead and own technical requirements gathering, technical decision making, backlog generation and refinement, and all architectural decisions- including where legacy systems, multiple integration points, or ambiguous requirements are in play.
• Lead discovery sessions with client stakeholders, including senior technical and business leadership to gather customer requirements and formulate them into a workable backlog.
• Build architecture diagrams to document, communicate, and defend your solution design to both engineering teams and client leadership.
• Apply your expertise in AI-first software development as a hands-on, contributing member of the technical team.
• Create, automate, and refine multiple levels of AI-driven testing.
• Coach and mentor teammates, provide guidance and assistance to software engineers and share practices for leading high-stakes engagements with peer Engineering Managers.
• Serve as the senior point of escalation on your engagement - identifying delivery risk, technical roadblocks, or relationship friction early, and stepping in to protect both the client relationship and the team.
• Own status reporting and communication with client leadership on your engagement, including presenting progress, risk, and roadmap in steering committees or business reviews.
• Collaborate with project managers, peers, and leaders to navigate client, technical, and team challenges with strong conflict resolution and leadership particularly across large, multi-stakeholder client organizations.
• Support pre-sales efforts through scope development discussions, contract document review, and client presentations when needed with particular focus on large or complex deals.

Your Qualifications 

Core Consulting Qualifications

Customer Experience

• Expertise in confidently addressing complex client questions, including from senior client stakeholders, and identifying gaps in requirements with proposed next steps.
• Focus on delivering clear, actionable solutions that meet client goals

Collaboration

• Facilitate alignment across a wide range of stakeholders, technical priorities, and deliverables, including in organizationally complex client environments.
• Navigate differing, and sometimes competing, perspectives with professionalism to ensure shared understanding and progress.

Communication

• Break down and communicate complex technical concepts for technical and non-technical audiences, including senior client stakeholders, in a clear, concise manner.
• Adapt communication style based on audience and context to improve clarity and decision-making.

Technical Qualifications 

• 8+ years of proven experience in software development and AWS cloud-native systems.
• 4+ years of previous experience managing a team of technical direct reports, including experience leading teams through large-scale or highly complex engagements.
• Experience managing professional services engagements and cross-functional projects, including engagements involving multiple stakeholders, legacy systems, or significant integration complexity.
• Strong background in established engineering practices and scalable architectures.
• Experience with more than one backend language such as Python, Node.js, C#, or TypeScript; and familiarity with frontend frameworks such as React, Vue, MVC, or .NET. Broad expertise is a plus, but proficiency across every technology listed is not required.
• Learning and building with AI both for productivity and for enhancing client solutions.
• Deep experience and expertise building with AWS.
• Knowledge of relational and NoSQL databases (DynamoDB, PostgreSQL, MySQL).
• Experience in API integrations across applications, vendors, and cloud environments.
• Understanding of modern application architectures including event-based systems, queues, microservices.
• Demonstrated ability to build credibility and trust with senior client stakeholders.
• Desire to integrate innovative technologies into development workflow.
• Proven ability to lead a workstream and support others while contributing individually, even under the added scale and visibility of large enterprise engagements.

Preferred Qualifications

• Degree in a computing-related field
• Experience with: UX/UI, LLMs, AgentCore, GenAI, automated testing, CI/CD, IaC
• Experience with large-scale system modernization or legacy migration
• Experience navigating enterprise IT governance processes (e.g., change advisory boards, security reviews, procurement cycles)

Benefits

• 100% remote work
• Flexible Time Off
• Competitive phantom equity
• Paid for exams and certifications
• Peer bonus awards
• State of the art laptop and tools
• Equipment & Office Stipend
• Individual professional development plan
• Annual stipend for Learning and Development
• Work with an amazing worldwide team and in an incredible corporate culture 

NOTE: We’re unable to provide visa sponsorship now or at any time in the future.

At Caylent, we are committed to fair, transparent, and inclusive hiring practices. As part of our recruitment process, we may use artificial intelligence (AI) tools or automated systems to assist with the screening and evaluation of applications to help match candidate qualifications with job requirements.

These tools are designed to support - not replace - human decision-making. Final hiring decisions are always made by our trained recruitment professionals.

If an AI or automated tool is used during your application process, it will only be in accordance with applicable laws and regulations, and your information will be handled in a secure and confidential manner.

If you have any questions, please contact [email protected] 

Caylent is a place where everyone belongs. We celebrate diversity and are committed to creating an inclusive environment for all employees. Our approach helps us to build a winning team that represents a variety of backgrounds, perspectives, and abilities. So, regardless of how your diversity expresses itself, you can find a home here at Caylent.  

We are proud to be an equal opportunity employer. We prohibit discrimination and harassment of any kind based on race, color, religion, national origin, sex (including pregnancy), sexual orientation, gender identity, gender expression, age, veteran status, genetic information, disability, or other applicable legally protected characteristics. If you would like to request an accommodation due to a disability, please contact us at [email protected].