life coach for women, midlife, empty nest, coach, next act, coaching for women

Let’s Hear from an Expert: Diane Flynn, ReBoot Career Accelerator


dianes-headshotWhat is the need you were trying to fill when you launched ReBoot?

When I returned to work after a 15-year pause, I felt confident about many hard and soft skills that don’t diminish over time. I had a background in management consulting and technology marketing, but I felt ill-equipped with current workplace technology skills that “passed me by” during my pause—LinkedIn, Social Media, Collaborative Tools (Google Suite), Presentation Graphics, Video Technologies (Zoom, Google Hangouts, Skype, WebEx) and commonly used communication software like Slack. This recognition, along with the overwhelming interest from peers in returning to work, made me think there’s an opportunity to help women interested in reentering the workforce.



Tell us more about how ReBoot helps women.

ReBoot helps women become currentconnected and confident to re-start careers, start new businesses, or pursue new goals.  Accelerators offer an intensive experience to get you ready for reinvention through hands-on learning of current tech, workplace, and career skills. Club ReBoot, a monthly membership club available in cities throughout the US, offers twice monthly speakers, workshops, and networking with like-minded women.

ReBoot taps into a huge and growing pool of talent that has been largely overlooked. According to a study published by the Center for Talent Innovation in 2010, 43% of women pause their career and 90% want to opt back in. That’s 3.3mm women per year in the US alone, and all indications suggest this is an international trend. ReBoot is unique in providing 30 hours of curriculum that gets women current with today’s workplace technologies and helps them develop a growth mindset. We also provide a safe, supportive community for women.

ReBoot Career Accelerator for Women is now offered in Silicon Valley, Chicago, Seattle, and NY, with Club ReBoot programs opening in 7 cities this fall. Five hundred women have participated in our program. ReBoot was recently featured on The Today Show, WSJ, Forbes, ABC Business News, and PRI’s The TakeAway, all indications of the growing interest in tapping into this new and exciting talent pool. Key sponsors include IBM, Expedia, and Frontier Communications; training partners include Google, Apple, LinkedIn, and Enjoy.



What unique challenges and opportunities do you see for women in midlife seeking to return to work?

The main challenge is that these women, who have so much to offer, have very low self-confidence. What they don’t realize is that their experience (whether paid or unpaid), connections, and soft skills are immensely valuable to employers. They are able to work autonomously, are energized, and know how to “get things done.” Women are often victims of the Imposter Syndrome, in which they undermine their capabilities and resist applying for jobs unless they feel 100% qualified. We encourage women to take a risk, apply for the job, and sell themselves with the valuable skills they offer.


Can you give us an example of a woman who ReBoot helped return to work in midlife?  

82% of our ReBoot alumnae seeking work find meaningful engagement. Whether they start their own businesses, work in part-time project work, or assume full-time positions, we help catalyze their careers. One of my favorite ReBoot success stories is a woman Engineer/MBA who took a 16-year pause to raise her children, and then went through Reboot. She was one of nine finalists for an Office Manager position with Jet Blue Technology Ventures, and secured the job because of her maturity, judgment, and exceptional workplace skill set. She has been in her role over one year, and is a valued, thriving team member. We hear more and more of these success stories. Each week, we receive calls from companies specifically seeking this demographic to fill both part-time and full-time roles.

The Reboot team

The Reboot team


What resources do you recommend?

I would start by subscribing to our weekly ReBoot newsletter, offering many tips, articles, and jobs for returners.

We have 5-day Accelerators running March 6-10 in Silicon Valley and Seattle, and March 13-16 in LA. We have an 8-week Accelerator in Seattle running March 29-May 24. We also recommend our partners who have great job boards, including Après, Maybrooks, Manera Solutions, Business Talent Group, Talent ReConnect, MomCorps, Werk and

For books, I’d suggest:

Work Pause Thrive: How to Pause for Parenthood Without Killing Your Career by Lisen Stromberg

Nail the Interview, Land the Job: A Step-by-Step Guide for What to Do Before, During and After the Interview by Michelle Tillis Lederman

Twist: How Fresh Perspectives Build Breakthrough Brands by Julie Cottineau


Contact Diane Flynn at






Diane Flynn is Chief Marketing Officer of GSVlabs, a leading Silicon Valley accelerator for individuals, startups and corporations seeking growth and innovation. She is also Co-founder of ReBoot Career Accelerator for women returning to the workforce after taking a work pause.  ReBoot gets women current, connected, and confident to return by teaching essential workplace tech skills and providing a community of like-minded returners.  

Diane is passionate about helping women reinvent themselves and find their purpose. She also chairs the marketing committees for several non-profit boards. She holds a BA in Economics from Stanford and an MBA from Harvard.  

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