Visibility is no longer optional. It’s a leadership skill.

In this episode of She Wears the Pants, Ashley Deland is joined by Rebecca Cafiero, visibility strategist, PR expert, bestselling author, TEDx speaker, and Co-founder of PitchWell, a next-generation visibility platform helping founders earn credibility, get featured, and build authority with intention and structure.

Together, they explore what it truly means to be seen as a woman in leadership and why visibility is less about chasing attention and more about owning voice, credibility, and identity.

This conversation reframes PR as a discipline of leadership and positions earned media as a strategic asset for founders building legacy, not noise.

If you’re a woman building something meaningful and feeling the tension between being capable and being visible, this episode will recalibrate how you approach exposure, authority, and influence.

In this episode, you’ll learn how to:

Shift visibility from a hope into a repeatable leadership practice

Release outdated beliefs about PR that keep founders small and hidden

Build credibility that leads to real opportunity rather than vanity metrics

Strengthen your relationship with being seen as your leadership expands

Approach technology and platforms as tools for authority, not shortcuts to validation

By the end of this conversation, you’ll walk away with a clearer understanding of how to lead from your voice, position your expertise with confidence, and build visibility that supports the future you are creating.

Meet Rebecca

Rebecca Cafiero is a visibility strategist, PR expert, bestselling author, TEDx speaker, and Co-founder of PitchWell. Through her work, she helps founders, CEOs, and experts earn media, build authority, and establish credibility through systems that make visibility intentional, accessible, and sustainable.

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She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

Alright, welcome to She Wears The Pants. I’m your host, Ashley Deland. Today’s guest is Rebecca Cafiero, a visibility strategist, PR expert, bestselling author, TEDx speaker, and the co-founder of PitchWell—a next-generation visibility and media platform helping founders, CEOs, and experts earn credibility, get featured, and build authority without the guesswork.

Rebecca has spent years helping women unlock their voice, build media presence, and amplify influence in ways that move the needle in their businesses and their lives. She’s built systems that make high-level visibility and earned media accessible and actionable for founders ready to be seen—turning pitching from a hope into a habit, and replacing gatekeeping with strategy, structure, and self-led credibility.

Rebecca, thank you so much for being here today.

I’ll also say—because I’m an Enneagram Seven—I have a high tolerance for risk. I bought and remodeled an entire property without seeing it. I did it remotely and didn’t see it until the day furniture was installed, right before my first Airbnb renter arrived. My husband has adapted to that over the last 15 years.

How we decided to come here: my husband is technically Italian, though he was born in California. My father-in-law is from Milan and moved to the States in his thirties.

Before my husband and I were even engaged, I told him I’ve always liked dating men from other countries. Unfortunately, my husband doesn’t have an accent, and I joked, “Can you work on that?”

We went to an event through my father-in-law’s business, and one of his American coworkers shared that after they sold a company, he and his family spent a year in Italy on sabbatical with their young children. He said it was the most incredible experience—not just living in a different culture, but the closeness it created as a family unit. It changed their family’s trajectory. Twenty years later, they still talk about it. Even before having kids, I said, “I want that experience.”

This had always been something we talked about. My husband sold a startup five and a half years ago, and I said, “When you’re done with the golden handcuffs—your time commitment—let’s finally do the year in Italy, and let’s also get our citizenship.”

Dates changed. Where we were going to move changed. Originally I thought Florence. Then we talked about buying a boat and learning to drive it—my dad’s a captain. I loved the idea: driving a boat around for a year and homeschooling. Then I came back to reality. Neither of us had a boat license. We’d have to learn, then navigate ocean conditions.

We traveled together and spent time in hotel rooms, and I realized there was no way we would survive living in 250–300 square feet while navigating a foreign country, language, and everything else. So we decided to pick a place, build community, and have some structure.

When I chose where we would live, I thought about where we live normally: Carmel-by-the-Sea in Northern California. It’s walkable, village-like, artistic, idyllic. With the contrast of living here, Carmel feels like a heart hug. Everything is beautiful. Everyone feels like they’re on vacation. It’s an easy place to live.

I said, “I want the place in Italy that feels most like Carmel.” Walkable, a village, great weather most of the year, close to the water—we’re five blocks from the beach in California and do daily walks. I didn’t want to be landlocked.

I also wanted a place without a lot of Americans, because I wanted to learn Italian. If we moved to Rome or Florence where many people speak English, the moment they hear an American accent, they respond in English. Here, the teachers at my kids’ school don’t speak English beyond maybe “hello.” It’s an Italian public school. That’s forced us to be fully immersed, learn the language, and become resilient.

From what I’ve read about you and what I know about you, we’re similar. You used to create lists of a hundred goals—ten in each category. I can’t help thinking how different that version of you must be from who you are now. You’re still high-achieving and high-integrity, but it feels like a more surrendered kind of control—almost “release control to gain control.” What was the switch? What was the moment?

Always having a million things I want to do and create comes from two places. One: as an Enneagram Seven, we want novelty and choices. A lot of options feels like freedom. Two: I’m fascinated by human potential—personal growth, what we can learn, what we can experience, how we design our lives, who we become, how we show up, the families we create.

It’s also a trauma response. Planning is trying to create certainty for the future when you have a hard time living in the present. I still love planning, but for me, it came from parts of my life where the present felt uncertain and scary, and I didn’t feel in control.

So it was always, “Someday, when I do X, Y, Z.” That started young. No one taught it to me—it was just what I did. I’d lose myself in books, in visualizing, in designing a life—escaping something uncomfortable when I didn’t have the autonomy to change it yet.

My husband is a Three—the achiever. The Seven is the enthusiast or visionary. He used to say, “We’re the same person,” because our behavior looked similar: high-achieving, always doing things. But our motivations are completely different.

He sees a goal, hits the goal, and that’s alignment. I can accomplish a lot when it feels fun and free, but I’m not doing it to win. Even doing a TEDx or writing a book wasn’t about proving something; it was, “That’s a cool experience—what would it feel like to do it?” Once I did it, I didn’t need to do it again, even though I always have a stack of book ideas.

My mom is a CPA, my stepdad is a water well driller, and my dad is a commercial fisherman. I grew up with two homes—blue-collar, ruled by seasons and legislation. In the days of answering machines with tapes, it felt like our life revolved around that machine. Holidays were built around weather and seasons. There were feast seasons and famine seasons. I didn’t want to be ruled by all of that.

I’ve always loved writing and communication. I’m curious. I ask questions. I want to understand things—especially when there’s injustice. I want the full picture, in order.

I did journalism and yearbook in middle school and high school. In high school, I was yearbook editor as a sophomore and as a junior, I taught the class. I finished my credits early. My senior year, I worked at a college newspaper and student-taught at another high school, teaching yearbook. I loved it because it’s about telling the human experience—and choosing the lens you tell it through.

I went to college for journalism and wrote for a daily paper while in school. I bartended, did makeup—everything—because I put myself through school.

After college, I realized if I stayed in journalism, I’d need to keep bartending to pay for my journalism job. We were making less than minimum wage. I loved it, but I wanted stability. My mom was a single mom until I was eight, and there was a lot of financial stress growing up.

So I went into real estate sales on the developer side for two publicly traded companies—Fortune 150-level. It was exciting because you meet new people every day. I didn’t think I’d like sales, but it’s really learning about someone, learning about a product, seeing if it’s a fit, and qualifying.

I moved up quickly. My managers said I had the rare combination of being able to sell and manage. My approach was partnership: “I’m here to support you in achieving your goals and the company goals.”

I stayed in that career for 13 years. The last seven, I was VP of Sales and Marketing, and the broker for California. Our final year, I oversaw $400 million in sales with a team of 43.

At 26, when I was “killing it,” I hired my first life coach—20 years ago, before coaching was mainstream. In my first session, I launched into a LinkedIn-style rundown: top sales, big goals, CEO by 40.

She looked at me and said, “What do you really want?”

I started crying. I was caught up in what everyone around me wanted. I was achieving the things, and I was miserable, because I wasn’t feeding my creative soul. At first it was a challenge, and I loved learning—but once I wasn’t learning anymore, I didn’t want it.

It took me another nine years to change, but I left and went into entrepreneurship. I realized I was already coaching—coaching salespeople is business coaching, with a lot of personal development.

I left and started coaching. I’d had a multimillion-dollar marketing budget in corporate, and we did some PR, mostly marketing. But when I left, I went from recruiters reaching out to… silence. Everyone thought I was insane.

I coached business owners on business and personal development. The personal side was influenced by losing my boyfriend to cancer at 31.

I didn’t have a single dark night of the soul—I had about four years of it. The stress crushed my immune system and adrenals and affected my heart. It gave me discernment, and it showed me that when life becomes lighter, you pursue joy and fulfillment more than money, validation, or external success.

When things improved, I met my husband—my soulmate. We’ve been together 15 years. I wanted kids, and I didn’t want to have children while working corporate. I’d seen the stress of returning to work after weeks.

When I started coaching, about two years in, I plateaued. I was making good money—six figures—but I didn’t see a growth curve. I asked, “How do I differentiate?”

My journalist brain went to PR. I interviewed three PR agencies: goals, expertise, strategies. They all promised visibility, but when I asked how it converts—sales calls, rates, program sales, list growth—they couldn’t answer. They wanted $30K with no conversion path. It felt like spending money and hoping.

So I did it myself. Within a year, I landed about 20 publications and speaking opportunities. I got resourceful. I asked. I found opportunities.

A client asked, “How are you getting all this media? Will you teach me?” I hesitated because I hadn’t studied PR—only journalism. She pushed: “You’re getting results.”

She was actually my former national VP of sales. She was strong in curriculum development. I walked her through my process. She got even better results: speaking engagements, Forbes, Today, podcasts.

Thousands of women have gone through my trainings, and hundreds have become clients.

Here’s what I’ll say: visibility and PR help you get eyes on your work, build credibility, justify higher rates, attract elite clients, and convert to profitability—which usually means greater impact.

Yet the deeper transformation is our core need to be seen, heard, and valued. When you work alone or with a small team, it’s easy to doubt your brilliance and impact. Media doesn’t make you better, and I don’t want people using it as a confidence crutch. Still, when an outside source says, “You’re an expert,” it helps quiet the noise and helps you pull your seat up to the table.

It also becomes market feedback—when you pitch different ideas, you learn what’s needed right now.

First: your transformation began when you stopped chasing success and validation and started putting your health, needs, and mindset first.

Second: you leaned into the ask. You started asking for opportunities—podcasts, features—giving yourself permission to step forward.

Third: so many women hesitate to ask. They choose work and worth over everything. It took me a long time to learn that I have to pour from a full cup.

You asked earlier when the switch happened. There was a moment: I was sitting in the driveway. I was 26, custom-building a house, top salesperson in the nation, getting married (not to my husband now), sitting in a nice car. Everything was “working,” and all I wanted was to run away and travel.

I wasn’t happy. People looked at my life and said, “Wow,” and I was daydreaming about being somewhere else. I wasn’t present in my life.

That’s when I realized the be–do–have pattern. Most people say, “When I have this, I can do this, so I can feel this.” When I have a multiple six-figure business, then I can hire help, take the trip, feel the feeling.

We’re putting it in the wrong order—creating restrictions around feeling how we want to feel. We get the outcome, it feels good for a moment, then it fades.

Instead: how do I want to feel? Who do I want to be? How do I want to show up? Then—how can I do that now?

Understanding something intellectually is different than integrating it into habits, beliefs, patterns, and relationships.

Last year, my word was integrity. Integrity in every area. If I say something matters, I show up for it. If I want clear communication, I have the hard conversations. It felt good—even when it was hard—because you do the hard thing upfront and you don’t slowly suffer over time.

That became part of my identity. This year, my word is consistency. It’s not sexy—especially for a Seven—but true freedom comes from consistency.

Reinvention and transformation are consistent parts of entrepreneurship. We’re conditioned to follow a path and then wonder why we’re unhappy. We have a choice to recreate ourselves—through movement or through stillness. The fear and the “I don’t know what I’m doing” moment is part of the plan.

We both share that: building a tech platform without prior tech experience. I hear this all the time as a business advisor: “I’m not sure what I’m doing,” “I don’t know how I’ll accomplish it.” I want to pour permission into the ears of women listening.

First: becoming comfortable with being uncomfortable.

Second: the importance of being around people with a bigger vision than you—the upward spiral.

Third: the balance between confidence and humility.

Now: what is PitchWell, and why do I see it as the legacy I’ll leave?

First—being comfortable with being uncomfortable. We all hit moments where we don’t know how to do something, it feels uncomfortable, or it feels risky. Many people stop there.

When I left corporate, I noticed that every time I put myself in a growth situation—learning something new, stepping into a new experience—I felt discomfort. But as I moved through it imperfectly, my worst fears never happened. Most of the time, something positive came out of it, even if it wasn’t what I expected.

I started to recognize that sensation: fear and discomfort became a signal. It meant I was close to what I wanted—on the other side of that edge.

Second—the upward spiral. You’ve heard, “You become the sum of the five people you spend time around.” It’s true.

When I started in Las Vegas real estate, I asked my boss, “Is it possible to make $100K a year here?” He said, “If you only make $100K, you’ll be fired.” That became normal.

Then I met my husband. He had a different upbringing and a different reference point for what’s possible. He went to Wharton and Stanford. His father, who moved from Italy, is a prolific entrepreneur and engineer—sold multiple startups to Cisco.

Being around that level of possibility expanded my view. It wasn’t hustle.

If I only have one precious life on this earth, how am I going to use my time and my talents? How am I going to serve? That question has become central for me.

In entrepreneurship, it’s the same. And this isn’t about “upcycling” your friends all the time. I believe deeply in honoring relationships, and also recognizing when a relationship is no longer a growth relationship.

This year, I’m in a mastermind with multiple seven-figure entrepreneurs. Sometimes I’m amazed by what they do daily. It isn’t glorified to them. It’s normal. And that normalizes what’s possible. It moves from “I’ll put that on my vision board” to “Tell me how you did this. How did you grow this company to $30 million in this space?” Being able to ask real questions changes everything.

The more time you spend with people who have built incredible things—and who are open about how they did it—the more expansive your thinking becomes. And that only works when you’re also bringing value to those relationships.

That’s why we’re such advocates of not gatekeeping. When you share information, you also share the energy behind it. Saying, “Here’s how I did it, and I’ll show you,” is still rare in women’s entrepreneurship.

I’ve been fortunate to have mentors, coaches, bosses, friends, and colleagues who have shared resources, support, and access with me. I’m always asking, “How can I pass this forward?” We aren’t competing with each other—we’re only competing with our own limitations.

I’ve always loved teaching visibility. What we teach isn’t just PR. It’s visibility aligned to the actual impact you want your business to have. Your goals matter. Your mission matters.

For me, I won’t sell something just to sell it. I care about transformation. I’m fed by results. I’m fed when someone says, “This changed my business,” or “This changed my life.”

That’s why I knew the results couldn’t be dependent on me continuously supporting someone. I love high-touch containers, yet I wanted people to graduate and continue creating results independently—both in business and in visibility.

First: where in Italy we were going to live.

Second: what I was going to do with all this intellectual property—processes, systems, media pathways.

Courses didn’t feel right anymore. Technology has changed. People don’t need more information. They need integration and implementation.

I sat with that. Then I co-hosted an innovation event at my house and realized I was playing small.

I’ve lived in Silicon Valley for 12 years, surrounded by some of the most educated people on the planet. And many of them didn’t know how to do a podcast interview. That’s when it clicked.

I asked: How do I take what I’ve taught and make it easier than ever? How do I help more people—not just deep, but wide?

AI is changing everything. And I don’t believe in using AI to replace the human voice. Especially for personal brands. Humanity matters. Imperfection matters.

I’m a proponent of using AI to expand us, not replace us.

After that event, I spent six hours in the car over two days mapping out the concept of PitchWell. I didn’t want another custom chatbot. I wanted an operating system.

I asked: how do I help founders who aren’t ready for a PR agency yet? Founders who are bootstrapping, or whose investors don’t yet see the value of PR?

How do I connect journalists directly with credible sources—efficiently, intelligently, and with integrity?

PitchWell is about helping people go from being a “best-kept secret” to being findable, searchable, confident, and accessible.

Exactly.

The idea came in May. I sat on it for a week, which is rare for me. I pitched it to three people I deeply respect: a close founder friend, a Silicon Valley business attorney, and my husband.

I already had the business plan, the total addressable market, the differentiator, and the vision for how the platform would deliver maximum value in minimal time.

I built it through the lens of having been a journalist, a PR agency owner, a founder who needed PR, and a visibility coach. I wanted to solve the problem from every side.

We framed the platform in June and began development in July. I tried a bit of no-code, then realized this needed to be built properly. We brought on a full-time developer—who happens to be my nephew. His first job ever.

I love that.

He used to fillet fish for my dad in the summers. We launched in August. By January, we had hundreds of users. We’re pacing toward thousands by March, and we’ll be at South by Southwest.

I’m so excited. You’ve shared so many powerful insights. Before we wrap, where can people learn more about PitchWell?

You can visit www.gopitchwell.com.

You can create a free account, though the capabilities are limited. If you go to the pricing page and enter the code REBECCA7, you’ll receive a seven-day free trial.

Onboarding takes about five minutes. You’ll upload your bio, topics, and a non-AI writing sample so the platform captures your voice.

In about one hour a week, you can create personalized podcast pitches, media pitches, LinkedIn content, and more. We have over 3.8 million media and podcast contacts, with thousands added monthly.

This isn’t about volume. It’s about high-quality authority-building visibility.

If you want to follow the journey of building a tech startup from Sicily, you can find me on Instagram at @rebeccacafiero.

Perfect. Our signature question: looking back on your journey, what message do you want to leave future generations of women in business?

Don’t wait until you feel ready. Readiness is a myth.

If you feel completely ready, you’re either late—or overly confident.

Action creates readiness. Taking the step is the initiation. When you finally feel prepared, that’s your cue that it’s time for the next level.

There’s a balance between confidence and humility. I see brilliant women who hesitate, and I see loud confidence without substance. Your idea is not you. If an idea lands with you, it’s your responsibility to bring it to life.

And finally: none of us get anywhere alone. Once a week, intentionally help someone else. Make an introduction. Share a resource. Open a door.

The ripple effect would change business entirely.

I couldn’t agree more. Pass it forward.

Thank you, Ashley. For your presence, your honesty, your leadership.

Thank you so much for tuning into another episode of She Wears the Pants. I hope today’s conversation expanded how you think about leadership, visibility, and the role your voice plays in the future you are building.

If this episode resonated, I’d love for you to share it with a woman who needs to hear it, and don’t forget to follow, rate, and review the show so these conversations can reach more women around the world.

For daily leadership insight and behind-the-scenes perspective, you can connect with me on Instagram at @ashleydeland.

And for deeper strategy, resources, and ways to work together, visit ashleydeland.com.

Until next time — keep rising into the woman your calling requires.