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Pinkney Webster, Technical Support


Pinkney Webster is the Technical Support for MileStone Academy.

Pinkney did a few jobs before starting his work with MileStone Academy. As an adult, his career path started with 30 to 35 years of work in the IT industry. He was a business consultant and travelled a lot to engage with fortune 100 companies. During that time, Pinkney deployed software that ran important operations at many companies. He helped transform them into something greater and achieve their goals. After that, he shifted to real estate investment where he partnered with his wife Michele Hewitt-Webster. For the past eight years, they bought, renovated, and sold or rented properties.

Pinkney is more involved with MileStone Academy now than when it first began. He originally helped to consult with Michele when the school was just a startup. Their passion for the cause was already strong as our youngest child has learning differences. Family matters a lot to Pinkney as he knows it matters to others. His involvement began so he could help others as others have helped us in the past. He wanted to give back the effort that was given to their son when he struggled yet, was supported, during his time in the mainstream education system. MileStone has grown into having a supportive high school environment that Pinkney wish was available for his son at that time.

Pinkney got involved while still on the IT side of things. He helped develop and grow MileStone’s use of the Google platforms to engage with the kids. This was even before COVID’s first wave in 2020. The pandemic sent everyone including their small operation fully virtual. It gave them many opportunities to gain experience and adapt to new rules, mandates, and new opportunities for our students. They had a heavy reliance on technology as it kept them connected with our kids and with each other.

When everyone returned to in-person in the spring, Pinkney was still helping to run the tech elements of our school and new elements were added to my role. His role expanded into communication, engaging with kids on a person-to-person basis, and working with community leaders. He met with police officers, fire and medical personnel to help the school run smoothly and safely in person. Pinkney helped keep up to date with safe protocols and mandates regarding shifting rules…. and reminding students to pull up their masks!

Pinkney engages with our student population on a human level. He is a sounding board or just someone to talk to and have fun with. Sometimes it works well and other times less so as kids are not always psyched about my non-teacher authority. Other times it is important to just be a ‘comic relief’ of sorts.

For Pinkney, working at MileStone has been less of a job and more of a passion. Working at MileStone is his job, his passion, his inspiration, and a constant source of fun! Please consider getting involved and getting inspired yourself! Please feel free to contact Pinkney to learn more!

Contact Pinkney By Phone (215) 663-1160 or email.

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