Influential Woman · Corporate Training and Leadership Development
Jen Silva Boucher
Leadership Communication Coach, Consultant, and Speaker, For The Middle Academy
Watertown, CT 06795
Her Story
About Jen
Jen Silva Boucher Boucher is a leadership communication strategist, keynote speaker, and founder of For The Middle Academy, where she helps organizations empower middle managers to lead with clarity, confidence, and connection. With more than 20 years of experience in corporate America, primarily in marketing, communications, and public relations within the financial industry, Jen has built a career centered on people, communication, and leadership development. Her work is driven by a passion for helping organizations close what she calls “the promotion gap” — the challenge of promoting high-performing employees into leadership roles without giving them the training and support needed to effectively lead others. Throughout her corporate career, Jen held leadership roles with organizations including Torrington Savings Bank, Webster Bank, and Resorts World Catskills, where she led strategic marketing, communications, branding, and community engagement initiatives. In 2023, she was recognized with the Connecticut Bankers Association’s New Leader in Banking Award for her impact and leadership within the industry. Drawing from her own experiences working under both supportive and ineffective leaders, Jen developed a deep understanding of how communication, trust, and leadership directly influence workplace culture, employee engagement, and team performance.
Today, Jen combines her corporate expertise with her entrepreneurial mission through For The Middle Academy, offering keynote speaking, leadership training, coaching, webinars, and consulting designed specifically for middle managers. She is passionate about bringing humanity back into the workplace by teaching practical communication and people leadership skills that help managers build trust, create clarity, and support the growth of their teams. Through her work, Jen continues to advocate for stronger leadership development at every level, helping organizations create healthier cultures and more confident, capable leaders.
Her Interview
Ten minutes with Jen
01What do you attribute your success to?
I attribute my success to never wanting to stop, always wanting to take it a step further, even when I didn't know where that path led. I believe the most successful people keep trying, and if it doesn't work out, they try something new. That's honestly the secret to success. As I get older, you realize that all these people that are successful didn't have it figured out from the get-go, and they don't. They're just brave enough to try and fail, and then try again.
02What’s the best career advice you’ve ever received?
The best career advice I ever received probably came from my mother. Funnily enough, we weren't talking about careers - she was asking me when I was going to have a baby. I was like, well, you know, we're still starting out in our careers, we're not ready. And she said, 'You're never ready.' I realized I was never 100% ready. We're never ready, right? When we get promoted, we're never ready to really take on the challenges, but we do it anyway. So I would say, if you're not ready to take something on, that's the exact time to take something on.
03What advice would you give to young women entering your industry?
I would say, raise your hand but use your voice. Because sometimes as women, we tend not to. But always be open to hear somebody's side of things. I think sometimes, too, earlier in our careers, we are so quick to listen to reply. But we especially earlier on - there's so much information that we need to learn, that its critical to listeni to understand, as opposed to just listening to reply.
04What are the biggest challenges or opportunities in your field right now?
One challenge right now is there's a lot of noise, and people tend to have a lot of priorities. That's when communication breaks down. That is why, also, I opened my business, because it's really about the opportunity to communicate to connect - with the people you work with, the people you work for, the ones that work for you. If we take sometimes an extra 2 to 5 minutes, it makes such an impact. Making that impact is the real opportunity here, by bringing the humanity back into the workforce, starting with communication.
05What values are most important to you in your work and personal life?
The values that matter most to me in both my work and personal life are trust, loyalty, and transparent communication. These are the foundations of relationship building and meaningful leaders value genuine connection.
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