Jenn Shemtob Starkie taught her last class at Gladwyne Elementary School in the Lower Merion School District on March 13, 2020, a Friday that she assumed was just the start of a normal weekend. She had a student teacher beside her, a lesson plan for the following Monday, and no idea she’d never walk back into that classroom. Jenn had been tutoring nights, weekends, and summers for a full decade before she ever considered leaving teaching. She was slowly building the case to herself that families needed more individualized support than a single classroom teacher could offer. Teachers do everything they possibly can, but with classrooms of 20+ students it is next to impossible to meet each one’s specific needs. 

Today, as founder of Teacher Time To Go, she leads a team of 120 tutors serving roughly 400 families across the Main Line and western suburbs. She does all this while raising two young children with her husband and staying deeply rooted in the community where she grew up.

Jenn Starkie is a 2026 Main Line Parent Women of Influence Award Winner

Main Line Parent’s Women of Influence Awards celebrate exceptional women making significant impacts in our community. Jenn was nominated by a friend and fellow business owner, Sarah DiSanto, and selected based on her achievements and dedication to creating positive change. Each Women of Influence Award Winner has committed to support Family Focus Media’s core values. Together, we are fostering a sense of belonging and empowerment for all families. All backgrounds, races, genders, and sexual orientations are welcome and safe with us.

Beyond the awards, our Women of Influence Luncheon and Speed Networking Night attendees come together as our Women of Influence Network, a community fostering connections, collaboration, and mutual support.

A Slow Build, Then a Leap

Jenn had always planned to open a physical tutoring space. In January 2020, she was actively searching for a location when her mother suggested something different: a travel-to-you model, meeting families in their own homes instead of asking them to drive to her. Jennifer wanted the professionalism of a storefront and pushed back. Two months later, COVID hit, and the location she never signed a lease on turned out to be a blessing in disguise.

The scarier part wasn’t the pandemic. It was doing it without a safety net. Jenn wasn’t married yet, had no business plan, and was walking away from full benefits at one of the best school districts in the country. “I didn’t have a business plan,” she said. “People are always like, ‘What was your framework?’ The reality was, I didn’t have one.” What she did have was a decade of proof that families needed what she was offering, and role models close to home. Her mother built her own law firm, and her father left a large company to launch his own financial services business. Watching them take that risk gave her the confidence to take hers.

From 75% Incomplete to 100% Turned In

Ask Jenn for a story that captures what Teacher Time To Go actually does, and she doesn’t point to a test score. She points to a habit. 

She’s worked with a student, who’s now heading into his senior year at Harriton High School, since ninth grade, focused entirely on Executive Functioning and Organization. The problem was never the academic material. He was completing the work; he just wasn’t turning it in. He was lost in the maze of different platforms and expectations across his teachers. It took a few months to build a system that stuck and worked for him. They used a shared google doc where every assignment and its submission method gets logged, with standing check-ins every Monday after school to plan the week and every Thursday to make sure nothing slipped through. By the second semester of his freshman-year, his assignments went from 75% incomplete to 100% submitted.

“It’s really just finding a system that works for each kid,” Jenn said. 

For the student’s parents, it meant getting to be parents again instead of homework enforcers. “I don’t want to hurt our relationship by constantly being on top of him,” one mother told her. 

“We assume the role of the middleman,” Jenn said. “We take that on for families and let parents be parents to their kids, and enjoy the fun things.”

That same philosophy of meeting kids where they are when tutoring, shows up in smaller moments too. When a student told Jenn she was falling behind on her summer reading because she couldn’t get through the pages, Jenn suggested the audiobook instead. The student asked if that was even allowed. “The process is different, but the product is the same,” Jenn told her. “You’re still retaining the same information, it just looks different.”

Building the Business Behind the Business

What started as one woman tutoring on nights and weekends is now a company with three full-time staff. Sarah, the Client Relations Manager, has been with Jenn since the company’s earliest days. Rachel is the Director of Recruitment and Andrea is the Head of Operations.  Jenn highlights, “Our Admin team is the heart and soul of everything we do. Each member has their roles which they execute flawlessly, but we are consistently coming together as a team on our daily calls.” From running client intakes, performing background checks, and matching with a reported 98% success rate between families and tutors, the team has perfected the process and our approach.  “We pride ourselves on matching families with tutors within 24 to 48 hours of their first consultation. Families want support for their children ASAP and we want to be able to deliver that” says Jenn.

Every tutor, drawn from local classroom teachers, graduate students, retired educators, and subject specialists, is personally interviewed by Jenn and trained in her method before ever meeting a family. 

The growth has been almost entirely word of mouth. “Ninety percent of the families we work with come from a referral or a Facebook recommendation! We are so honored that clients trust us and our services and pass us along to their friends and family.

Giving Back Close to Home

Jenn has stayed rooted in the community she grew up in. She loves giving back to the community and showing up where and when it matters most.  Her team is currently sponsoring the Healthy Kids Running Series in Wissahickon this year by donating bags and tutoring sessions after previous years supporting the series in Lower Merion and West Chester. It’s a natural extension of her own belief in staying active; she starts most weekdays at a 6 a.m. workout class before coming home to get her kids ready for school.  

Advice for the Woman Ready to Leap

Jenn’s advice for anyone sitting on an idea of their own is characteristically direct: take the leap, and don’t treat other business owners as competition. We are all in this together!

“I like competition personally, but there are more than enough kids to go around,” she said. “At the end of the day, we’re all in this to help.” She’s especially encouraging toward teachers curious about tutoring full-time. She offers staff development workshops on topics like Growth Mindset and Executive Functioning strategies to anyone who joins her team.

What’s Next

Jenn has been asked more than once whether she’ll franchise, expand into new states, or build Teacher Time To Go into something bigger and less personal. Her answer is consistently no. “I love the personal touch of knowing the local school district administrators, the siblings of our students, the referrals,” she said. Instead, she’s channeling her energy into a new project: an Executive Functioning Children’s Book Series, with the first book already written and in the process of finding a publisher.

Between early mornings, family dinners together every night, and an inbox she deliberately keeps under five emails (an essential skill her father taught her) Jenn has built something rare. She grew a business that scaled without losing the personal relationships that started it.

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Follow Teacher Time To Go on Instagram @teachertimetogo. Connect with Jenn on LinkedIn.

Help us honor Jenn by sharing what her contributions mean to you in the comments below.