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Employee Spotlight: Sheila Holiday

Skyward Digital Media Group
Skyward Digital Media Group - Putting Faces to Names


If you have ever been involved in the implementation of Skyward technology, odds are you have come into contact with one or more of our project managers. These are the pros who coordinate your consultation, training, data migrations, IT/hardware recommendations, and more to ensure a smooth transition and effective launch. When we made the decision to bring back our Employee Spotlight series, the project management team was the first place we turned, due to their visibility and the multitude of areas they touch for every install.

Our project managers are subject to a thorough review and advancement process based on experience, outcomes, and knowledge base. Our new hires start out as a "Pro-0" and immediately set their sights on specific goals to achieve the next level of occupational mastery. When we turned to Tim Casey, one of the Project Management department leaders, to determine who would be the best candidate for recognition, his response was immediate – we needed to talk to the only "Pro-4" project manager in the department, someone whose experience was matched only by her enthusiasm and track record of success. We are proud to introduce our first Employee Spotlight subject of 2015:


Sheila Holiday

Project Manager
Corporate Office

Hi, Sheila! You are officially in the spotlight. Let's start things off on a serious note and work our way down from there...

First up – can you tell us a little bit about your experience with Skyward?

I have been here for a little over 17 years. At last count, I've worked with approximately 427 districts on both Finance and Student implementations – more if you count add-on features for existing customers. 

Wow! Over the years, what would you say has been the most rewarding part of your job?

Having a customer say after a few months of being on Skyward that they are glad they chose us, the software is working great for them, and it has made their job a little easier.

What is your advice to someone just getting started in a new career?

Don't be afraid to ask questions! The more you ask, the more you will learn and understand.

Last work-related question; what's the most important tip you can share for a successful large-scale implementation project? 

I'll actually give you two.

1) Trust your project manager. We have years of experience handling implementations with many different kinds of scenarios. We can offer some good advice on what will and won't work.

2) Assign one key person within your organization to serve as the main point of contact, coordinate schedules, and keep staff on task. It makes such a difference when you have a project manager on both sides of the fence.

What can you tell us about your life outside of the work? 

I am happiest hanging around home: doing stuff with my husband, working in my garden, taking care of my roses, detailing my cars, or just hanging with family and friends on our patio. You can't go wrong grilling out and sitting by a fire. 

Now that summer is finally coming into view, what are you most looking forward to?

I have a love for classic cars. I have a 1967 Mustang Fastback, 1968 Camaro SS, and a 1981 Camaro Berlinetta. In the summer, my husband and I organize car cruises with a local establishment which run every other week. 

Sheila's impressive, shiny lineup of classic cars

If you could go anywhere in the world, where would you find yourself?

Bora Bora, French Polynesian Islands. If I won the lottery I would buy a private island in the Caribbean.

If you could star in a movie, what would be your first choice?

Isn't it obvious? Gone in Sixty Seconds.

I should have guessed. In keeping with the entertainment theme, what would happen if you had a dance-off with Cliff King (Skyward's CEO)?

It wouldn't be a dance-off, it would be a drag race! I'd like to see what Cliff can do with that Mustang of his. 

Fast Facts about Sheila

  • Favorite Vacation Spot: Negril, Jamaica (where she was married)
  • Favorite Movie(s): Anything with a lot of action. Fast & Furious; The Expendables (1, 2, and 3); The Dark Knight; Iron Man... You get the picture. 
  • TV Show I'm Afraid to Admit I Love: Millionaire Matchmaker
  • Favorite Food: Sushi
  • Favorite Sport(s): Golf & Yoga
  • Phobia: Snakes! (Why does it always have to be snakes?)

Ok, last question. In the past five years, what's the most important thing you have learned?

I've learned that you can't please everyone. Be true to yourself and who you are.

Excellent advice. Thank you, Sheila! 

Have you worked with any Skyward employees that you'd like us to feature in this section? Send us an email at content@skyward.com and we'll see what we can do to make it happen.




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