Principal Strategist

USAPosted 8 weeks ago

Role Overview

Caylent is hiring a Principal Strategist. This is a full-time role in USA. Part of Caylent's Lifecycle hiring. Full responsibilities, required qualifications, and the apply link are listed in the description below.

Salary Context

Salary is not disclosed in this posting. Market median for Principal-level Lifecycle roles is $185k-$283k (based on 43 comparable listings). Many employers share specifics during the interview process or after an initial screen.

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Job description

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.

About Caylent

Caylent

caylent.com

LifecycleOn-site

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Frequently Asked Questions

How do I apply for the Principal Strategist position at Caylent?

Use the Apply button above to submit your application directly to Caylent. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.

Where is the Principal Strategist position at Caylent located?

This position is based in USA. Caylent has not indicated remote or hybrid options for this role, so candidates should plan for on-site work.

What does a Principal Strategist at Caylent earn?

Caylent has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.

When was the Principal Strategist role at Caylent posted?

This role was posted on May 22, 2026 (60 days ago). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.