Dee Barrett Grosso, Head of HR on Influential Women

Influential Woman · Human services, Pharma, BioTech, Financial Services

Dee Barrett Grosso

Head of HR, Big Brothers Big Sisters Independence

Philadephia, PR

Her Story

About Dee

I’ve learned that leadership doesn’t always look the way people expect it to.

For me, it’s never been about being the loudest voice in the room or having all the answers right away. It’s been about listening first, understanding the full picture, and staying steady when things are complex or uncertain.

I tend to lead in moments where clarity isn’t obvious — when people, systems, and emotions are all in motion at once. I’m comfortable holding multiple perspectives, even when they conflict, and finding a path forward that is thoughtful and humane. That hasn’t come from theory; it’s come from experience — from navigating change, pressure, and responsibility over time.

I care deeply about people. That shows up in how I make decisions, especially difficult ones. I don’t separate outcomes from impact, and I don’t treat individuals as numbers or problems to solve. I believe leadership means carrying the weight of decisions responsibly, even when they’re uncomfortable, and doing so with integrity.

I don’t lead by force or performance. I lead through consistency, preparation, and presence. I speak when it matters, and I’m intentional about when I don’t. Over time, I’ve learned that influence doesn’t require constant visibility — it comes from trust, follow-through, and showing up when it counts.

Complexity doesn’t intimidate me, but I respect it. I know that sustainable leadership isn’t about reacting quickly or proving something — it’s about discernment, balance, and knowing when to lean in and when to step back. I’ve learned to value steadiness over urgency and clarity over control.

At this stage in my life and career, I’m grounded in who I am. I don’t lead to be seen, and I don’t need validation to stay aligned with my values. I lead because it matters — to the people involved, to the work itself, and to doing things the right way.

That quiet, steady approach may not always draw attention in the moment, but it leaves things stronger than they were before. And for me, that’s what leadership is meant to do.

Her Interview

Ten minutes with Dee

01What do you attribute your success to?

When I think about what I attribute my success to, it isn’t a single achievement or title. It’s a set of choices I’ve made consistently over time.

I attribute my success to listening more than I speak and taking the time to understand before acting. I’ve learned that good decisions come from context, not urgency, and that patience often creates better outcomes than speed.

I attribute it to doing the work even when it’s unseen — preparing thoroughly, following through, and staying accountable to what I commit to. I’ve never relied on shortcuts or optics. I’ve trusted that steady effort and integrity compound, even when recognition is delayed or absent.

I attribute it to learning from complexity instead of resisting it. I’ve faced situations where the path forward wasn’t clear, where people’s needs conflicted, and where the stakes were high. Rather than looking for simple answers, I’ve learned to sit with ambiguity and move forward thoughtfully.

I also attribute my success to the people who’ve trusted me — mentors who offered guidance, colleagues who challenged my thinking, and teams who showed up with resilience and honesty. I don’t believe success is individual; it’s built through relationships and shared effort.

I attribute it to resilience shaped by experience. Life has taught me how to recover, recalibrate, and continue without losing perspective or compassion. Those lessons have influenced how I lead and how I define progress.

And finally, I attribute my success to staying aligned with my values, even when it would have been easier not to. I’ve learned that long-term fulfillment and credibility come from consistency between what you believe and how you act.

Success, for me, has never been about visibility or validation. It’s been about creating stability, clarity, and forward movement — and leaving people and systems better than I found them.

02What’s the best career advice you’ve ever received?

The best career advice I ever received was this: pay attention to how something feels to sustain, not just how it feels to achieve.

Early on, I was taught to focus less on titles and momentum and more on whether the work, the environment, and the leadership style were things I could live with day after day. Not just at my best — but when things were hard, unclear, or demanding.

I was also advised to let my reputation speak before I did. To prepare thoroughly, follow through consistently, and resist the urge to explain or prove myself. Over time, I learned that trust is built quietly, and credibility travels faster than self-promotion ever could.

Another piece of advice that stayed with me was to choose integrity over immediacy. Short-term wins can be tempting, but they rarely outweigh the cost of compromising your values or your sense of self. I learned that walking away from the wrong opportunity can be just as important as saying yes to the right one.

Most importantly, I was reminded that a career is not a race. It’s a long arc shaped by learning, relationships, and resilience. The advice wasn’t to avoid ambition — it was to anchor it in purpose and perspective.

That guidance helped me make decisions that weren’t always obvious in the moment, but proved to be right over time. And it’s advice I continue to return to, especially when the path forward isn’t clear.

03What advice would you give to young women entering your industry?

The best career advice I can give is this: build a career you can sustain, not one you have to survive.

Titles, speed, and recognition come and go. What lasts is credibility, relationships, and your ability to stay grounded while navigating change. Learn how to do the work well, but just as importantly, learn how to work with people — especially when things are difficult.

Don’t rush clarity. Most meaningful careers aren’t linear, and growth often happens in seasons that don’t look impressive on paper. Pay attention to what you’re learning, not just what you’re earning. Experience compounds, even when it’s uncomfortable.

Be known for your integrity and follow-through. Say less, do more. Prepare well. Keep your commitments. People remember how you handle pressure, not how loudly you speak when things are easy.

Seek mentors, but also listen to your own discernment. Advice is helpful; alignment is essential. If something costs you your values, your health, or your sense of self, it’s too expensive — no matter how good it looks from the outside.

And finally, remember this: your career is part of your life, not the other way around. Choose paths that allow you to grow, contribute, and still be whole. Success that requires you to abandon yourself isn’t success.

04What are the biggest challenges or opportunities in your field right now?

Here are the top 3 biggest challenges in the HR field right now, based on current industry reports and trend analyses:

1) Attracting, Developing & Retaining Talent

Finding and keeping the right people remains HR’s number one core challenge. Many organizations struggle to recruit qualified candidates, fill key roles quickly, and retain high performers — especially as job markets evolve and employee expectations change. Competitive pay and benefits help, but employees increasingly seek meaningful work, career growth, and supportive workplace culture, not just compensation.

Why this matters: Without strong talent pipelines and retention strategies, organizations face performance gaps, internal disruption, and higher turnover costs.


2) Adapting to Technology & AI (Including Skills Gaps)

Technology — particularly AI — is reshaping HR and the workforce at a rapid pace. HR leaders must not only integrate new tools into recruitment, performance, and workforce planning but also manage the human side: trust, bias, training, adoption, and ethical use. Many HR teams report uncertainty with AI deployment and a lack of confidence in using it effectively.

At the same time, skills gaps are widening — employees need upskilling and reskilling to remain productive in shifting roles.

Why this matters: HR must balance innovation with strategy, ensuring technology improves outcomes without eroding trust or belonging.


3) Compliance, Regulation & Work Model Complexity

The regulatory environment is increasingly complicated — from AI governance and pay transparency laws to expanded leave policies. Complying with varying requirements across jurisdictions adds pressure on HR teams.

Plus, managing hybrid and flexible work models continues to challenge HR in terms of:

  • culture and engagement
  • performance expectations
  • onboarding and mentoring
  • policies that fit multiple work environments

Why this matters: Compliance missteps can lead to legal risk, while poorly designed work models can erode employee experience and productivity.

05What values are most important to you in your work and personal life?

Here are my top three values,

Integrity is the foundation of how I live and work. I believe in doing the right thing even when it’s uncomfortable, inconvenient, or unseen. I don’t separate who I am personally from how I show up professionally — the same values guide both. Credibility, trust, and honesty matter more to me than speed, titles, or recognition.

Responsibility to people is central to every decision I make. I take seriously the impact my choices have on others, whether I’m leading a team, supporting a colleague, or showing up for the people in my life. I believe leadership is stewardship — protecting dignity, being thoughtful with authority, and never losing sight of the human side of decisions.

Alignment and sustainability guide the paths I choose. I value work and relationships that I can sustain without compromising my values, my health, or my sense of self. I’m intentional about building a life and career that are coherent and grounded, not impressive at the expense of well-being. Success, to me, is something that can last.


Join Influential Women and start making an impact. Register now.