Katie Winland
Pittsburgh,PA
Summary
Dynamic Senior Instructional Designer and L&D Program Manager specializing in scalable learning solutions that yield significant business impact. Proven track record in developing multi-tiered leadership programs and achieving high engagement rates, aligning training with organizational goals to elevate performance across global teams.
Overview
1
1
Certification
14
14
years of professional experience
Work History
Senior Instructional Designer
Dialpad
10.2021 - Current
- Architected a scalable, multi-tiered leadership development program structure that enables consistent, high-quality experiences across leadership levels — building the framework, curriculum, facilitation guides, and measurement strategy entirely from scratch.
- Designed cohort-based learning experiences, live workshops, asynchronous modules, and manager toolkits that build practical leadership skills grounded in Dialpad's values and business context.
- Drove 76% monthly attendance across program, demonstrating strong engagement and relevance of learning journeys for leaders.
- Partnered with senior executives and People leadership to align program strategy with organizational priorities, performance expectations, and career development frameworks.
- Established success metrics and feedback loops using participant surveys, engagement data, and manager performance indicators to refine and improve program continuously.
- Expanded the program each year based on stakeholder feedback and demonstrated impact, growing from a single track for frontline managers to a three-track ecosystem serving leaders at every stage.
- Led global sales readiness for the Agentic AI product launch, designing enablement that improved seller confidence and supported successful adoption across GTM teams.
- Built the company's AI Academy, creating a role-based curriculum that improved AI fluency and increased sales effectiveness across global segments.
- Designed simulations, activities, and assessments that enhanced learner engagement and facilitated application of skills in real-world scenarios.
- Partnered with GTM executives and subject matter experts to ensure AI enablement content stayed aligned with product roadmaps and go-to-market strategy.
Instructional Designer
Expedia Group
03.2019 - 10.2021
- Design Lead & Program Manager for the global Pathways learning program supporting 8,000 employees across multiple functions.
- Designed comprehensive learning programs across tools, product, analytics, soft skills, and strategy, enhancing productivity and partner satisfaction.
- Developed campaign training content achieving 84% win rate, contributing to $460M in incremental revenue (+17% YoY).
- Partnered with product and marketing teams to deliver product launch enablement that improved adoption and contributed to increased revenue.
- Collaborated with SMEs, leaders, and cross-functional teams to ensure content accuracy and alignment with business objectives.
Learning & Development Specialist
Expedia Group
09.2018 - 03.2019
- Designed and facilitated global learning programs — including workshops and e-learning modules — in collaboration with subject matter experts to ensure content relevance for diverse audiences.
- Expanded regional leadership initiatives to reinforce talent development strategy.
- Conducted needs assessments to identify learning opportunities across departments.
- Developed e-learning modules using innovative digital tools and platforms.
Partner Success Lead
HomeAway/Vrbo
02.2017 - 09.2018
- Led a team of 10, delivering coaching and feedback to enhance performance and customer experience.
- Conducted training sessions for sales representatives on best practices and platform utilization, improving their effectiveness.
- Cultivated team relationships to enhance collaboration and support growth initiatives.
- Oversaw daily operations and resolved escalations to ensure high sales team satisfaction.
Account Manager
HomeAway/Vrbo
03.2015 - 02.2017
- Managed client relationships to ensure satisfaction and retention.
- Managed accounts to enhance ROI through effective contract negotiations and streamlined renewal processes.
- Collaborated with cross-functional teams to resolve client issues efficiently.
- Provided training and support to junior account managers on best practices.
Account Manager
Acquirent, LLC
12.2012 - 06.2014
- Managed client accounts and maintained strong customer relationships for HomeAway/Vrbo.
- Drove territory growth by developing outbound sales processes for key clients.
- Analyzed market trends to identify potential business opportunities for clients.
- Collaborated with teams to develop marketing strategies and promotional campaigns.
- Conducted training sessions for new team members to improve onboarding and skill development.
Education
Bachelor of Fine Arts -
Kent State University
Kent, OH01-2010
Skills
- Curriculum design
- E-learning development
- Learning management systems
- Sales training design
- Training evaluation
- Learning analytics
- Needs assessment
- Program management
- Stakeholder management
- Stakeholder engagement
- Organizational learning strategies
- Coaching and mentoring
- AI training development
Certification
- Project Manager Certification, ATD, 01/01/21
- Storyline Certification, 01/01/23
Awards
- Spotlight Award, Expedia Group, 04/01/21
- Culture Superstar Award, Expedia Group, 03/01/19
- Circle of Excellence, HomeAway, 01/01/16
Timeline
Senior Instructional Designer
Dialpad
10.2021 - Current
Instructional Designer
Expedia Group
03.2019 - 10.2021
Learning & Development Specialist
Expedia Group
09.2018 - 03.2019
Partner Success Lead
HomeAway/Vrbo
02.2017 - 09.2018
Account Manager
HomeAway/Vrbo
03.2015 - 02.2017
Account Manager
Acquirent, LLC
12.2012 - 06.2014
Bachelor of Fine Arts -
Kent State University