Principal Change Strategist
Caylent is a cloud native services company that helps organizations bring the best out of their people and technology using Amazon Web Services (AWS). We provide a full-range of AWS services including workload migrations and modernization, cloud native application development, DevOps, data engineering, security and compliance, and everything in between.
At Caylent, our people always come first. We are a global company and operate fully remote 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!
About the Job
We are seeking a Principal Change Strategist to join our strategic customer portfolio, embedding you with our most important enterprise clients—working alongside executives, business leaders, and frontline teams to drive adoption of strategic initiatives, technology implementations, and organizational transformations.
This is not a traditional change management role. You will serve as a trusted advisor and implementation partner who architects and executes change programs that deliver measurable business value and sustainable behavioral change across complex, global organizations.
You will bring deep expertise, strong executive presence, and the leadership to guide clients through ambiguity—translating strategic priorities into actionable roadmaps and embedding human-centered change practices in technology-driven environments, including those shaped by Generative AI.
Your Assignment
Change Strategy & Stakeholder Leadership
- Architect change strategies for complex global initiatives, translating priorities into multi-horizon roadmaps that inform decisions on pacing, investment, and organizational readiness.
- Serve as a trusted advisor to C-suite leaders, providing coaching on change sponsorship, diagnostic insights, and solutions that simplify complexity and drive cross-organizational alignment.
- Lead stakeholder engagement and impact assessments, developing communication, training, and reinforcement plans while surfacing risks and building shared context.
- Sequence and balance initiatives to manage prioritization, cognitive load, and change fatigue—protecting adoption capacity and maximizing program success.
Adoption & Outcomes Management
- Define and monitor adoption metrics in partnership with Analytics and Product teams, linking behavior change to business outcomes and ROI through quantitative, qualitative, and AI-enabled insights.
- Drive continuous improvement by tracking readiness, surfacing risks, and adapting strategies based on data-driven findings and post-launch learnings.
- Develop change management frameworks that facilitate smooth transitions, employee engagement, and sustained adoption of new behaviors and processes.
AI-Enabled Transformation & Innovation
- Lead enterprise reinvention efforts where work, workforce models, and human experiences are shaped by data, automation, and Generative AI—helping clients sustain change as roles and skills evolve rapidly.
- Partner with clients to enable GenAI adoption, addressing readiness, skills shifts, workforce impacts, and responsible use while reinforcing human accountability and governance.
- Apply AI and AI agents strategically to enhance productivity, delivery quality, and program effectiveness—including accelerating content development without sacrificing quality or impact.
- Design future-ready operating models using human-centered design principles to co-create scalable change solutions and personalized journeys where humans and digital tools work seamlessly together.
Delivery Excellence
- Direct and mentor consulting teams, fostering a culture of excellence, continuous learning, and performance improvement while coaching others in effective delivery practices.
- Cultivate strong client relationships that position Caylent as a partner of choice, ensuring exceptional service delivery and identifying opportunities to convert into long-term partnerships.
- Contribute to thought leadership and growth by leading proposal development, delivering compelling presentations to prospective clients, supporting business development effort and influencing Caylent's evolving change practice.
Requirements
Experience
- 7 - 10 years of progressive experience in organizational design, transformation and change enablement within top-tier consulting or professional services environments.
- Senior leadership experience (management or director level) leading high-impact, large-scale transformation initiatives.
- Proven success with technology-enabled transformations, including digital, product, or engineering initiatives (GenAI experience preferred).
- Strong client management capabilities with a track record of building trusted advisor relationships and converting opportunities into long-term partnerships.
Skills & Capabilities
- Exceptional leadership with ability to inspire and lead high-performing teams through complex, ambiguous change environments.
- Strategic thinking with outstanding analytical and problem-solving abilities across large-scale, multi-faceted initiatives.
- Executive communication skills—capable of building relationships and influencing at all levels, from frontline teams to C-suite.
- Expert facilitator of workshops and strategy sessions with excellent storytelling and executive presentation skills.
- Fluency in AI, automation, and Generative AI, including understanding of workforce and organizational implications.
- Business development acumen with proven ability to identify and convert opportunities into partnerships.
Flexibility
- Willingness to travel as needed to meet client and project requirements.
Preferred Qualifications
- AWS certifications or data governance certifications
- Experience working across regulated industries (financial services, insurance, healthcare, higher education)
- Background partnering with data architects and engineers to translate strategy into technical execution
- Experience building or scaling a data strategy practice within a consulting organization
Benefits
- 100% remote work
- Medical Insurance for you and eligible dependents
- Generous holidays and flexible PTO
- Competitive phantom equity
- Paid for exams and certifications
- Peer bonus awards
- State of the art laptop and tools
- Equipment & Office Stipend
- Individual professional development plan
- Annual stipend for Learning and Development
- Work with an amazing worldwide team and in an incredible corporate culture
This role may require up to 25% travel, depending on business needs.
Base Salary Range: The expected base salary range for this position is CAD $215,000 - $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.Create a Job Alert
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