Job Overview
Location
CANADA
Job Type
Full-time
Category
Product Management
Date Posted
April 21, 2026
Full Job Description
đź“‹ 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
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.
Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.
Newsletter
Weekly remote jobs and featured talent.
No spam. Only curated remote roles and product updates. You can unsubscribe anytime.
Similar Opportunities
Extend Your Team, LLC
3 months ago
Affirm Holdings, Inc.
2 months ago
