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 Fortune 2000 clients
• Strong understanding of Agile project delivery

Benefits

• Medical Insurance for you and eligible dependents
• 401k plan with company match up to 4% and immediate vesting
• Competitive phantom equity
• Company issued laptop
• Dental and Vision insurance
• Term Disability Insurance
• Term Life Insurance
• Flexible Spending Account
• Equipment & Office Stipend
• Annual stipend for Learning and Development
• Unlimited Paid Time Off
• 10 Paid Holidays

NOTE: We are unable to provide sponsorship for this position.

Base Salary Range: The expected base salary range for this position is $185.000 - $235.000 per year, commensurate with experience and qualifications.
Additional Compensation Components: In addition to the base salary, the compensation package may include bonuses, commissions, equity, and other incentives. The specific components will vary depending on the role and individual and/or company performance.

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 talent@caylent.com

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 hr@caylent.com.