Caitland Pearson
Lake Stevens,WA
Summary
I'm a passionate Senior Product Manager who thrives on fostering alignment and clear communication across teams, stakeholders, and clients. I specialize in making product-led decisions grounded in user data and behaviors, ensuring every feature and roadmap prioritization is designed to solve real customer problems. With a knack for turning complex challenges into actionable strategies, I’ve successfully led cross-functional teams to build a new client portal from scratch, transforming the user experience, and launched innovative AI-driven solutions like chatbots and phone reference tools. My strength lies in bringing people together, simplifying the complex, and driving impactful results through thoughtful planning and collaboration.
Overview
12
12
years of professional experience
Work History
Senior Product Manager
Certn
07.2021 - 01.2025
- Spearheaded competitive analysis initiatives, leveraging insights to inform data-driven decisions that enhanced user experience and shaped long-term product strategies.
- Designed, implemented, and launched AI-driven solutions, including a chatbot and AI-powered phone reference tools, improving operational efficiency and client satisfaction.
- Managed end-to-end product delivery across multiple engineering teams, ensuring the successful and timely delivery of high-quality solutions for complex mandates such as U.S. background screening, client portals, enterprise client management, ATS integrations, API enhancements, and global criminal screening products.
- Directed cross-functional teams, aligning stakeholders and resources to strategic product priorities, effectively navigating competing demands and maximizing impact.
- Led enterprise client crisis management efforts, leveraging strong communication skills to resolve critical issues, prevent account loss, and maintain key client relationships reliant on product enhancements.
- Conceptualized and launched a new MVP for client experience, driving measurable improvements in user satisfaction and engagement through alignment with client needs and organizational goals.
PRODUCT MANAGER
STERLING TALENT SOLUTIONS
03.2018 - 07.2021
- Managed product roadmap deliverables and drove platform enhancements across multiple products, including Form I-9/E-Verify, New Hire Forms, and Partner Integrations, in collaboration with cross-functional software engineering teams.
- Ensured compliance with all legal requirements for the Form I-9 and E-Verify product line, as well as Federal and State tax forms, maintaining adherence to evolving regulatory standards.
- Drove partner enablement and relationship management, facilitating smooth API integrations and enhancing collaboration to expand partner ecosystem and drive business growth.
- Led end-to-end product development cycles from concept to launch, ensuring alignment with market needs and delivering solutions that met customer expectations and regulatory demands.
PRODUCT ANALYST
STERLING TALENT SOLUTIONS
05.2017 - 03.2018
- Managed projects for the Form I-9/E-Verify and New Hire Forms product teams, ensuring timely execution of platform enhancements and alignment with business goals.
- Collaborated closely with software engineers to define product requirements and drive the successful progression of platform improvements.
- Ensured compliance with all legal requirements for the product lines, including necessary legal enhancements to meet regulatory standards.
- Partnered with internal and external legal counsel to identify and mitigate potential product risks, ensuring compliance and protecting the product’s integrity.
MANAGER, PROFESSIONAL SERVICES
STERLING TALENT SOLUTIONS
12.2016 - 05.2017
- Directed a team of eight professionals across onsite, remote, and international locations, ensuring workload balance, career development, and overall success.
- Oversaw team hiring, onboarding, and performance management while ensuring the successful delivery of client implementation projects.
- Acted as the primary escalation point for client and internal issues, resolving challenges efficiently and contributing as a subject matter expert for enterprise-level implementations.
- Designed and standardized the implementation process, developing deployment tools to enhance consistency and efficiency across teams.
- Led the development and execution of the new employee training program, ensuring seamless onboarding and alignment with organizational goals.
DEPLOYMENT MANAGER
TALENTWISE, INC. NOW STERLING TALENT SOLUTIONS
12.2014 - 12.2016
- As a Deployment Manager I worked daily with new clients, managing their account implementation and onboarding experience from contract finalization to go live on the platform
- This work included technical account configuration in addition to project management
- I worked with many internal teams to ensure the success of each client’s implementation, from small to enterprise level businesses
- Additional duties included partnering with the small and medium business sales team to drive revenue and adoption, as well as create and implement a new employee training program for the Professional Services department
CLIENT SERVICES TEAM LEAD
TALENTWISE, INC. NOW STERLING TALENT SOLUTIONS
08.2012 - 12.2014
- Provided technical support to clients and their candidates via inbound calls, emails, and the CRM platform, ensuring prompt issue resolution and a high standard of service.
- Managed daily work assignments and workloads for a team of seven, optimizing team efficiency and productivity.
- Maintained and strengthened vendor relationships to ensure seamless collaboration and service delivery.
- Identified training opportunities for team members and implemented tailored solutions to enhance skills and performance.
Education
Undergraduate Certificate - Project Management
City University of Seattle
03.2021
High School Diploma - undefined
Summit K-12
06.2007
Skills
- Product Strategy & Roadmapping
- Product Development & Lifecycle Management
- Customer Research & Design Thinking
- Data-Driven Decision Making & Product Metrics
- Stakeholder & Cross-Functional Team Management
- Competitive Market Analysis & Strategic Planning
- Product Launches & Go-to-Market Execution
- Project Management & SCRUM Methodology
- Vendor & Business Relationship Management
- Customer Support, Service, & Retention Strategies
Timeline
Senior Product Manager
Certn
07.2021 - 01.2025
PRODUCT MANAGER
STERLING TALENT SOLUTIONS
03.2018 - 07.2021
PRODUCT ANALYST
STERLING TALENT SOLUTIONS
05.2017 - 03.2018
MANAGER, PROFESSIONAL SERVICES
STERLING TALENT SOLUTIONS
12.2016 - 05.2017
DEPLOYMENT MANAGER
TALENTWISE, INC. NOW STERLING TALENT SOLUTIONS
12.2014 - 12.2016
CLIENT SERVICES TEAM LEAD
TALENTWISE, INC. NOW STERLING TALENT SOLUTIONS
08.2012 - 12.2014
High School Diploma - undefined
Summit K-12
Undergraduate Certificate - Project Management
City University of Seattle
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