Principal Strategist

Caylent, Inc.

Job Overview

Location

CANADA

Job Type

Full-time

Full Job Description

📋 Description

• As a Principal Strategist at Caylent, you will play a pivotal role in driving the company’s go-to-market strategy for mid-market clients undergoing digital transformation, directly contributing to revenue growth and customer success by aligning sales, service delivery, and technical expertise.
• Your day-to-day responsibilities include partnering with sales teams to refine and execute GTM strategies, leading high-impact strategic engagements for key clients, enabling internal teams with mid-market expertise, developing value cases and ROI materials, and tracking KPIs such as new logo acquisition, bookings growth, and billable utilization (targeting 50%).
• Caylent is a fully remote, cloud-native services company specializing in AWS-powered solutions, with a global team across Canada, the U.S., and Latin America. The company prioritizes people-first culture, technological curiosity, and inclusive collaboration, operating as a trusted partner in cloud modernization, data engineering, DevOps, and AI strategy.
• In this role, you will deepen your expertise in enterprise GTM strategy, cloud transformation consulting, and value-based selling while building executive-level relationships with mid-market clients. You’ll have the opportunity to shape internal enablement programs, influence Caylent’s market positioning, and grow as a trusted advisor in AWS-centric digital transformation initiatives.

🎯 Requirements

• 10+ years of consulting experience in cloud and digital transformation, or leadership roles focused on mid-market or PE-backed companies
• Demonstrated experience in developing and implementing go-to-market (GTM) strategies
• Deep understanding of market dynamics, customer segmentation, and competitive analysis in mid-sized businesses
• Ability to build robust business cases with quantitative value cases demonstrating financial ROI or cost savings
• Proven ability to lead strategic engagements with key clients and maintain high-value relationships
• Experience guiding organizations through significant digital and platform transformations
• Highly collaborative and adaptable to fast-paced, changing environments
• Expertise in public cloud infrastructure and services, preferably AWS
• Willingness to travel for customer and AWS meetings

🏖️ Benefits

• 100% remote work with global team collaboration across Canada, the U.S., and Latin America
• Comprehensive health benefits including 100% premium coverage for employee and dependents via Equitable Life Hybrid Plan
• Competitive phantom equity, 4% employer pension match, long-term disability, and unlimited vacation policy
• Paid holidays, sick leave, parental leave, and stipends for learning, development, exams, and certifications
• Peer bonus awards, state-of-the-art laptop and tools, equipment/office stipend, and individual professional development plans
• Annual learning and development stipend, and the opportunity to work with an amazing worldwide team in an inclusive, innovative culture

Skills & Technologies

AWS

Senior

Remote

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Caylent, Inc.

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About Caylent, Inc.

Caylent provides cloud-native engineering services and DevOps consulting, helping enterprises design, migrate, and manage workloads on Amazon Web Services. The company delivers containerization, infrastructure automation, CI/CD pipelines, and data platform modernization through dedicated engineering teams. Serving mid-market to Fortune 500 clients, Caylent focuses on accelerating cloud adoption, cost optimization, and security compliance across regulated industries including healthcare, fintech, and SaaS.

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