Principal Strategist

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 a talented Principal Strategist to join our growing Customer Strategy team. Your role will be to support Caylent's go-to-market motion for mid-market clients undergoing active transformation, working closely with our Sales and Service Delivery teams to ensure successful solution delivery and customer satisfaction. You will be expected to deliver strategic engagements for our customers in a billable capacity. Finally, you will act as Caylent's expert on the project, developing the value case for data modernization, AI strategy, and leading strategic customer engagements across the transformation lifecycle. Your Assignment Support Caylent's Mid Market Go-To-Market Motion Partner with Sales on our GTM strategy, ensuring alignment with our organizational structure and objectives. Collaborate with sellers to effectively bring the GTM strategy to AWS and our clients, targeting the acquisition of new strategic customers. Maintain alignment with Technical Practices to ensure a holistic approach that addresses both market positioning and technical capabilities. Deliver Strategic Engagements Lead strategic engagements for key clients, providing expert insights at critical points to guide strategy and maximize success. Support other delivery resources and Engagement Leaders in navigating the unique challenges of mid-market businesses undergoing transformation. Industry Expertise - Syndication and Enablement Enable internal teams, including Account Executives, Customer Success Associates, Principal Consultants, and Delivery personnel with mid-market knowledge, in collaboration with AWS. Populate libraries with value case and ROI-specific materials that align with Caylent's frameworks. Capture and disseminate wins and success stories to foster a culture of learning and achievement. KPIs New Logo Acquisition Growth in Bookings and Revenue across engagements Billable Utilization (50% target) Your Qualifications 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 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 that demonstrate financial cost savings and/or ROI of initiatives in support of prioritization and strategic planning. Proven ability to lead strategic engagements with key clients, building and maintaining high-value relationships. Experience in guiding organizations through significant digital and platform transformations. Highly collaborative, adaptable to a fast-paced changing environment. Expertise in public cloud infrastructure and services, preferably AWS. Willingness to travel for customer and AWS meetings. Preferred Qualifications AWS or other Cloud Certifications Experience in competitive Cloud ecosystems to AWS Experience in AWS consulting with Fo…