Ryan Leonard
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Ryan Leonard Email & Phone Number

Strategic HR Generalist | Employee Relations Professional | Driving Employee Engagement and Organizational Success at KAYAK
Location: Greater Boston, United States 7 work roles 2 schools
1 work email found @kayak.com 9 phones found area 781, 860, 617, and 201 LinkedIn matched
✓ Verified August 2026 4 data sources Profile completeness 100%

Contact Signals · 1 work email · 9 phones

Work email r****@kayak.com
Direct phone (781) ***-****
LinkedIn Profile matched
3 free lookups remaining · No credit card
Current company
Role
Strategic HR Generalist | Employee Relations Professional | Driving Employee Engagement and Organizational Success
Location
Greater Boston, United States
Company size

Who is Ryan Leonard? Overview

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Quick answer

Ryan Leonard is listed as Strategic HR Generalist | Employee Relations Professional | Driving Employee Engagement and Organizational Success at KAYAK, a with 882 employees, based in Greater Boston, United States. AeroLeads shows a work email signal at kayak.com, phone signal with area code 781, 860, 617, 201, and a matched LinkedIn profile for Ryan Leonard.

Ryan Leonard previously worked as HR Generalist - Technology, Product, & Legal at Kayak and Human Resources Specialist, Healthcare at Home, MGB Medical Group, & ERAP at Mass General Brigham. Ryan Leonard holds Bachelor'S Degree, Business Management & Leadership from Western New England University.

Company email context

Email format at KAYAK

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{first}@kayak.com
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Profile bio

About Ryan Leonard

🎯 Strategic HR Generalist | 💼 Employee Relations Professional | 🚀 Driving Engagement & SuccessHi there! I’m a passionate HR Generalist with a knack for transforming workplaces and enhancing employee experiences. Currently, at Kayak, I play a crucial role in driving strategic HR initiatives and fostering a positive employee relations environment. My focus is on enhancing engagement, resolving workplace issues, and implementing effective HR policies that align with organizational goals. My data-driven insights have been key in making informed decisions that boost organizational effectiveness.In my previous role at Mass General Brigham, I supported the Healthcare at Home & MGB Medical Group by coaching leaders, streamlining communication, and ensuring our compensation practices were top-notch. I mentored and uplifted our onboarding team as a Senior Talent Operations Coordinator, leveraging tech to create seamless workflows. My time at Hornblower Group was all about managing high-volume onboarding and automating HRIS functionalities for maximum efficiency. At Cataldo Ambulance Service, I crafted a comprehensive field training program and guided a fantastic team of 40 field training officers, ensuring stellar training for our new hires.🎓 I hold a Bachelor’s in Business Administration from Western New England University and am currently pursuing an MBA in Human Resources at Fitchburg State University. My tech toolkit includes UltiPro HRIS, PeopleSoft, and Microsoft Suite, among others. I’m all about fostering vibrant workplace cultures and driving employee engagement. Let’s make great things happen together!

Listed skills include Customer Service, Team Leadership, Project Management, Team Management, and 11 others.

Current workplace

Ryan Leonard's current company

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KAYAK
Kayak
Strategic HR Generalist | Employee Relations Professional | Driving Employee Engagement and Organizational Success
stamford, connecticut, united states
Website
Employees
882
AeroLeads page
7 roles

Ryan Leonard work experience

A career timeline built from the work history available for this profile.

Hr Generalist - Technology, Product, & Legal

Current

Cambridge, Massachusetts, United States

– Directly supports executives at the director level down, providing strategic HR guidance and solutions to address organizational needs.–Collaborates with regional partners to support a global workforce, ensuring adherence to international labor laws and fostering a cohesive company culture.– Consults with management on international workforce strategies, delivering insights to optimize talent management and improve organizational effectiveness across regions.– Partners with management to identify and resolve workforce challenges, including talent acquisition, retention, and succession planning.– Develops and implements standardized processes and documentation to enhance HR operations and maintain organizational consistency.– Oversees reduction in force (RIF) and workforce realignment initiatives, aligning them with business goals, legal requirements, and effective communication to support organizational resilience and growth.– Acts as a trusted advisor to executives, offering expert guidance on complex HR matters and contributing to high-level decision-making.– Leads cross-functional teams to execute major HR projects, ensuring alignment with corporate strategy and achieving targeted outcomes.

Jul 2024 - Present

Human Resources Specialist, Healthcare At Home, Mgb Medical Group, & Erap

Boston, Massachusetts, United States

Supporting over 6,000 employees in the Community Division including the Healthcare at Home, Mass General Brigham Medical Group, and ERAP (emergency medicine, radiology, anesthesiology and pathology)-Provides coaching to executives and line managers across the group on issues of employee relations, compensation, benefits, wage and hour, training, staffing, workforce planning/job re-leveling, performance management, and skill assessment.-Facilitates effective communication between management and staff by conducting regular presentations and training on HR policies, procedures, and initiatives, resulting in increased awareness and adherence across all levels of the organization.-Collaborates closely with MGB Compensation team to conduct thorough benchmarking and market analysis, ensuring alignment of compensation practices with industry standards and organizational objectives.-Leverages relationships with departmental stakeholders to optimize talent acquisition strategies, including participation in recruitment events and partnerships to attract top talent and meet business unit needs.-Responsible for conducting detailed investigations of complex employee relations issues and recommending solutions that are in alignment with the MGB's core values.-Supports managers with Reduction in Force actions including guidance with developing and writing business cases and supporting documentation, and conducting notification meetings.-Proactively monitors and analyzes HR metrics and trends to identify areas for improvement and drive data-informed decision-making, providing regular reports and recommendations to senior leadership for strategic planning purposes.

Sep 2023 - Jul 2024

Senior Talent Operations Coordinator, Brigham & Women’S Hospital

Boston, Massachusetts, United States

-Mentored and guided junior onboarding coordinators, providing training, support, and feedback to build their skills and expertise, while also serving as a role model for exemplary onboarding practices and professionalism within the team.-Conducted regular evaluations and feedback sessions with stakeholders and new hires to gather insights, identify pain points, and implement iterative improvements to the onboarding experience, enhancing overall effectiveness and satisfaction-Leveraged technology platforms such as HRIS (Human Resources Information Systems) and LMS (Learning Management Systems) to automate onboarding workflows, enhance efficiency, and maintain accurate records.-Spearheaded the development and implementation of comprehensive onboarding programs tailored to various job roles and levels within the organization, ensuring alignment with company goals, values, and culture.

Jun 2023 - Sep 2023

Talent Operations Coordinator, Mass General & Brigham And Women’S Hospitals

Boston, Massachusetts, United States

-Acted as a primary point of contact for new hires, offering guidance, answering questions, and providing resources to facilitate a smooth transition into the organization.-Assisted in the development and maintenance of onboarding materials, including welcome packets, handbooks, and training guides, ensuring accuracy, relevance, and accessibility for new hires.-Stayed abreast of industry best practices and trends in onboarding and employee engagement, seeking opportunities for professional development and incorporating new ideas and strategies into the onboarding process.-Ensured compliance with legal and regulatory requirements throughout the onboarding process, including EEOC guidelines, background checks, and privacy regulations, maintaining accurate records and documentation to mitigate legal risks.-Managed high-volume onboarding workflows while maintaining meticulous records, tracking progress, and promptly resolving any issues or discrepancies to ensure a positive experience for new employees.-Collaborate with cross-functional teams, including HR, hiring managers, IT, and facilities, to streamline onboarding processes, optimize resource utilization, and enhance the overall onboarding experience for new hires.

Aug 2022 - Jun 2023

Hr Onboarding Specialist

Boston, Massachusetts, United States

-Oversaw the candidate pipeline from initial application to final offer stage, tracking progress, and ensuring timely communication and follow-up to keep candidates engaged and informed.-Coordinated interview schedules and logistics, liaising with hiring managers and candidates to schedule interviews, coordinate travel arrangements (if applicable), and provide necessary information and support throughout the process.-Orchestrated the onboarding process for a high volume of new hires, managing logistics, coordinating orientation sessions, and ensuring all required documentation and training were completed accurately and on time.-Collaborated with senior leadership to assess existing HRIS (UltiPro) functionalities and identify opportunities for optimization and automation to streamline onboarding processes and improve data accuracy and accessibility.-Led the redevelopment and implementation of automated workflows, customized reports, and communication templates within UltiPro HRIS, enhancing efficiency, visibility, and transparency throughout the onboarding lifecycle.-Provided training and support to HR and hiring managers on utilizing new features and functionalities within UltiPro HRIS, ensuring seamless integration and adoption across the organization.

Jan 2022 - Aug 2022

Onboarding Program Lead

Somerville, Massachusetts, United States

-Led the design and implementation of a comprehensive field training program tailored to the specific needs and requirements of new employees, encompassing both theoretical knowledge and hands-on practical skills.-Collaborated with subject matter experts and department heads to identify key learning objectives, curriculum content, and assessment criteria, ensuring alignment with organizational goals and industry best practices.-Established standardized processes and procedures for field training delivery, including training materials development, scheduling, evaluation methodologies, and feedback mechanisms to ensure consistency and effectiveness across training sessions.-Oversaw a team of 40 field training officers (FTOs), providing leadership, guidance, and support to ensure the delivery of high-quality training experiences for new employees.-Conducted regular performance evaluations and provided constructive feedback to FTOs, identifying areas for improvement and implementing professional development initiatives to enhance training effectiveness and instructor competencies.-Facilitated mentorship opportunities and career advancement pathways for FTOs, providing coaching and resources to support their professional growth and progression within the organization.-Led investigations into allegations of employee misconduct, harassment, or policy violations, conducting interviews, gathering evidence, and analyzing relevant documentation to ascertain facts and determine appropriate actions.-Prepared detailed investigative reports outlining findings, conclusions, and recommendations for management review and decision-making, ensuring accuracy, objectivity, and compliance with legal and regulatory requirements.

Sep 2020 - Jan 2022

Emergency Medical Technician

Somerville, Massachusetts, United States

Cataldo Ambulance Service, Inc., has continually distinguished itself as a leader in providing routine and emergency medical services. As the needs of the community and patients change, we continue to introduce innovative programs to ensure the highest level of care is available to everyone we serve. Cataldo Ambulance Service deploys Over 200 late model custom designed ambulances packed with the latest healthcare technology. We also staff an Incident Support and Fire Rehab Unit capable of remote communications, and a fully equipped Mass Casualty Incident Support Unit!

Aug 2019 - Jan 2022
Team & coworkers

Colleagues at KAYAK

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2 education records

Ryan Leonard education

Bachelor'S Degree, Business Management & Leadership

Activities and Societies: Resident Representative in Student SenateMinor in Human Resources

Master Of Business Administration - Mba, Human Resources Management/Personnel Administration, General

Two year program expected In 2025

FAQ

Frequently asked questions about Ryan Leonard

Quick answers generated from the profile data available on this page.

What company does Ryan Leonard work for?

Ryan Leonard works for KAYAK.

What is Ryan Leonard's role at KAYAK?

Ryan Leonard is listed as Strategic HR Generalist | Employee Relations Professional | Driving Employee Engagement and Organizational Success at KAYAK.

What is Ryan Leonard's email address?

AeroLeads has found 1 work email signal at @kayak.com for Ryan Leonard at KAYAK.

What is Ryan Leonard's phone number?

AeroLeads has found 9 phone signal(s) with area code 781, 860, 617, 201 for Ryan Leonard at KAYAK.

Where is Ryan Leonard based?

Ryan Leonard is based in Greater Boston, United States while working with KAYAK.

What companies has Ryan Leonard worked for?

Ryan Leonard has worked for Kayak, Mass General Brigham, City Experiences, and Cataldo Ambulance Service Inc..

Who are Ryan Leonard's colleagues at KAYAK?

Ryan Leonard's colleagues at KAYAK include Lydia Hall, Bella Lin, Ąžuolas Krušna, Euna Chae, and Lars Hartmann.

How can I contact Ryan Leonard?

You can use AeroLeads to view verified contact signals for Ryan Leonard at KAYAK, including work email, phone, and LinkedIn data when available.

What schools did Ryan Leonard attend?

Ryan Leonard holds Bachelor'S Degree, Business Management & Leadership from Western New England University.

What skills is Ryan Leonard known for?

Ryan Leonard is listed with skills including Customer Service, Team Leadership, Project Management, Team Management, Project Coordination, Website Development, Web Design, and Project Planning.

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