Hello, I'm
Jenn Wilson
Digital Strategy & Operations Leader


I’m a digital strategy and operations leader with 20+ years of experience across web, creative, content, and digital delivery. I started my career as a hands-on designer and web professional, and that foundation still shapes how I lead today.
I build the systems behind great digital work. Throughout my career, I’ve led multidisciplinary teams, scaled creative and web operations, built new digital programs from the ground up, and created the processes, tools, and operating models that turn complex work into something clear, measurable, and scalable.
What I bring is a combination of creative judgment and operational discipline. I understand both how the work gets made and what teams need to deliver it successfully. I’m at my best when there’s an ambitious idea, a complicated problem, or an undefined program that needs structure, strategy, and a path forward.
My career spans creative, web, digital strategy, and operations. These four areas represent the strongest and most consistent threads across 20+ years of experience.
Career-long foundation
Teams up to 31
Strategy, UX & delivery
Process, programs & systems
I lead at the intersection of strategy, creativity, and operations. My experience includes building multidisciplinary teams, designing scalable workflows, managing complex digital portfolios, and creating the structure and visibility organizations need to turn strategy into execution.
The tools have changed throughout my career, but the goal hasn’t: creating better, more efficient ways to turn ideas into execution.
My career has evolved from hands-on web and creative work to leading global teams, digital programs, and operations. Along the way, I’ve built brands, developed teams, improved delivery systems, and created structure around complex work. Each role has added a new layer to how I approach strategy, leadership, and execution.
Leading project management strategy and operations across digital programs, with a focus on defining team responsibilities, strengthening delivery processes, and creating greater consistency across project execution. Building the frameworks, reporting, and cross-functional partnerships needed to improve visibility, accountability, and the client experience as the organization evolves.
Selected to build the operational framework for a newly launched website product within Kaseya MSP Success. Established end-to-end delivery processes, project management infrastructure, QA standards, reporting, and KPIs while coordinating work across internal teams and external partners. Built the systems supporting growth from zero to 284 active website projects and 31 successful launches in eight months.
Led creative operations supporting 11 global brands and approximately 100 creative and content assets each month. Strengthened delivery through centralized intake, standardized workflows, approval structures, and reporting in Wrike, helping reduce delivery SLAs by 20%. Served as a Wrike Champion supporting adoption, workflow architecture, documentation, and training across the global marketing organization.
Led a multidisciplinary global creative and web organization that grew from 22 to 31 people at peak, spanning UX, web design and development, web production, design, and production. Directed brand governance across 11 global properties and led creative for major user conferences including DattoCon and Kaseya Connect, while building scalable brand systems and improving global creative and event production.
Led creative strategy and execution across digital, print, web, and marketing initiatives during a period of organizational growth. Managed multidisciplinary creative talent and production workflows while partnering with marketing and business stakeholders to translate campaign and brand objectives into scalable creative systems, mentor designers, and provide art direction across departments.
Joined Kaseya as a Senior UX Designer, creating internal dashboards, landing pages, and user flows before moving into implementation leadership. The role combined my hands-on background in design and web with growing responsibility for teams and delivery, ultimately leading to my promotion to Creative Director within my first year.
Led an approximately 10-person multidisciplinary implementation organization spanning web design, production, and technical integrations. Partnered with Implementation Specialists on custom requirements involving APIs and third-party systems while developing standardized scope-of-work templates and processes for evaluating, documenting, approving, and delivering non-standard implementations.
Designed and developed responsive websites and reusable templates for SMB clients, translating brand and marketing requirements into digital experiences while building deeper expertise in front-end design and web production.
Produced and maintained high-volume client and corporate websites through Yodle’s proprietary platform, building the hands-on web production foundation that would later inform my approach to design, implementation, operations, and leadership.
My education in multimedia and visual communication gave me a foundation in design, technology, and visual storytelling that has shaped more than 20 years of professional growth. What began as a creative discipline has evolved into a career spanning web, digital strategy, operations, and leadership.
Advanced study in multimedia design with an emphasis on digital animation production, graphic design, and color theory, expanding my foundation in visual communication and digital media. The program broadened my understanding of how design, technology, and storytelling come together to create engaging digital experiences.
Foundational study in visual communication and digital design, with hands-on training in Adobe Photoshop, Illustrator, QuarkXPress, typography, layout, and design principles. Served as a student tutor supporting peers in Photoshop, Illustrator, and QuarkXPress.
A selection of work spanning creative direction, brand, web, digital experiences, and operations. Each project reflects a different part of my career and the thinking, collaboration, and execution behind the work.
I’m always open to connecting with people who are building interesting things, solving complex problems, or simply want to exchange ideas. Feel free to reach out and start a conversation.
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