Q: Where were you born and raised … what led you to Silicon Valley?
DF: I was born and raised in Minnesota. I came to Silicon Valley to attend Stanford, then spent time in Chicago and Boston for work and graduate school, and returned when I got married in 1988.

Q: Tell us about some of your past positions you’ve held.
DF: I was an associate consultant at BCG (The Boston Consulting Group) before attending Harvard Business School. After getting my MBA, I joined Electronic Arts and spent over 10 years in marketing and business development, and helped launch our educational software division with Cap Cities ABC and Disney.

I then started a family and when my girls were toddlers, my husband traveled all the time. I did what I never thought I’d do. I paused my career. That pause turned into 16 years and a third child. When I decided to resume my career in 2014, I found that while I thought I had much to offer an employer, my workplace tech skills were definitely rusty. It was this recognition, along with the fact that so many of my friends were interested in resuming careers, that led to the start of ReBoot Accel. While my 4 co-founders and I initially thought we were running a local program to help our friends, it quickly mushroomed into a national movement to help train and place “returners”. I can think of nothing more gratifying than helping this accomplished talent pool re-engage in meaningful paid work. What I’m doing now does not feel like work. It feels like my calling.

Q: Can you define ReBoot Accel and your current position there?
DF: ReBoot Accel helps source mid to senior level hires from those who’ve paused their careers. We also have online and in-person programs to get women current, connected, and confident to return to the workplace.

This talent pool is increasingly being recognized by small and large companies alike.   Visa, Apple, GM, J&J, Ford, Fidelity, and Bloomberg are just a few of the companies that are currently running return to work programs to attract this talent.

I am co-founder and CEO, along with a talented group of 4 other cofounders.

Q: How do you support the women who come to Reboot?
DF: ReBoot Accel offers a suite of programs to get women current, connected, and confident to return to the workforce or pursue new goals. ReBoot Accel has served over 1000 women in Silicon Valley and has programs in 6 additional cities, including Chicago, Boston, Atlanta, LA, Detroit, and Houston.  A recent survey of our alumnae found that 82% of those who were seeking have found meaningful work, either part-time, full-time, or as entrepreneurs. We have a program called ReBoot Connect that offers semi-monthly workshops and a supportive community for women interested in reentering the workforce.

Q: What are the biggest changes you see in the job market now from when you left your career before ReBoot?
DF: The biggest change is today’s workplace technologies. Most people who paused careers years ago are not familiar with collaborative workplace tools (G-suite, for ex.), new communication tools (Slack, Telegram, for ex.) and video technologies (Zoom, Google Hangouts, for ex.) They may also lack a LinkedIn profile and the requisite 500 connections.

Today’s workplace requires individuals to CONSTANTLY be upskilling, so a growth mindset and desire to learn are critical to career success.

Q: Where are the biggest opportunities for women returning to the workplace today? And what traits do they have that make them successful?
DF: This talent pool of “returners” has tremendous potential to fill key roles in HR, FP&A, Sales, Marketing, Legal, and Office Management, along with technical roles, because they approach reentry with maturity, experience, wisdom, and stability.  Most have over a decade of work experience and 65% have Master’s Degrees.  They typically don’t require relocation, and generally won’t go out on leave for an extended period.

Q: What advice do you have for women seeking to re-enter the job market?
DF: Many women who’ve paused careers don’t have the confidence they need to even apply for the job. Our workshops help develop this confidence by demystifying today’s workplace technologies and providing a safe, supportive community for their return. We strongly suggest a well-crafted LinkedIn profile, resume, 30-second “elevator pitch” and solid answers to common interview questions, including how to explain the “gap”. ReBoot Accel helps candidates develop these, which in turn helps them land the job.

We also recommend that women try to keep a foot in the professional world during their pause, even if it’s unpaid. Being on a board, volunteering with an organization, and maintaining professional connections can greatly help the reentry process, even it if’s years later.

Q: What are the biggest challenges that you’ve had at ReBoot and how have you dealt with them?
DF: We have grown rapidly in the past year, and launching operations in 7 cities require tight standards of our brand and practices. While we want each city to be entrepreneurial and develop new ideas, we also want to maintain the quality and consistency of our brand nationwide. This has proven to be one of our largest challenges.

Q: Any predictions for the next two or three years?
Where do you see ReBoot’s role growing to be in the near future?
DF: I am very bullish about our business over the next 5 years. The willingness to hire candidates with non-traditional backgrounds has increased markedly in recent years, given that employment is at a high and that those hiring returners have had such a positive experience. Hiring Managers are starting to recognize that those who’ve paused their careers have a great deal to offer in the workplace, and even continue to expand skillsets during their years of volunteerism. There seems to be less of a stigma around the resume “gap” and an expanded awareness of the soft skills these individuals bring to the role. I’m hoping we get to the point where careers are fluid, filled with “ins” and “outs” and so full of flexibility that a pause will no longer be a factor.

Five Things About Diane Flynn

1. If you could talk to one person from history, who would it be and why?
Jesus Christ. I have tons of questions I’d like answered, especially why so many bad things happen to good people.

2. What’s the best advice anyone’s ever given to you? 
If it can be done in 2 mins, just do it. Using this strategy, I accomplish a great deal more each day.


3. Do you have a favorite movie?
Embarrassingly, the remake of Parent Trap. Was addicted to The Good Wife and haven’t found a series that comes close.


4. Where is your dream vacation?
Carmel, though most anywhere as long as my family is with me.


5. Do you enjoy working out? If so, can you share some of your strategies for integrating workouts into your business schedule?
I love working out. I try to work out on the treadmill every morning for 30 mins while reading 2 the Merc News and the WSJ (I still read those in paper format!) I also try to go for a walk each day, by myself, to think, regroup, and “defrag” my brain.

ReBoot Career Accelerator for Women
https://rebootaccel.com/
585 Broadway, Redwood City, CA 94063
(650) 387-3743