Serving Over Selling will Perfect Your Sales Conversion with Gwen Tinsley

I’m thrilled to introduce you to someone who’s made a profound impact on my business already: my sales coach, Gwen Tinsley.

This is the first time I’ve publicly shared that I’ve hired a sales coach, and it feels surreal to say that out loud. I met Gwen through the brand designer who led me through my visual rebrand earlier this year. Her sales process left such a strong impression on me. It was seamless, intentional, and made me feel fully supported. When she mentioned Gwen during her interview on this podcast, I immediately knew I needed to connect with her. And here we are.

Gwen is the founder of Grit and Tenacity Consulting, and the name is more than just clever wordplay on her own name. It encapsulates the values that have shaped her personal and professional journey.

Grit, Growth, and Gwen’s Story

Gwen’s story is one of resilience from the start. Raised amid family complexities, from divorced parents to learning about a half-brother she didn’t know existed until she was 10. She was forced to develop grit at a young age. That grit extended into her academic journey as well, where she was misdiagnosed with a learning disability. Later, it was correctly identified as ADHD, a reminder of how far education systems have come and how critical self-awareness can be.

Rather than letting those labels define her, Gwen leaned into her strengths and pursued higher education. She earned her MBA, though she lovingly refers to it as an “MBA in heart,” because what truly fuels her work is the human side of business- understanding what drives and motivates people.

Gwen admitted that she avoided sales for years, seeing it as slimy and manipulative. The stereotypical “used car salesman” vibe. But after years of personal growth and working in career development (during the 2008 economic crisis no less), she realized that everyone, regardless of title or income, shares the same basic humanity. That became the foundation of how she approaches sales today: with empathy, authenticity, and connection.

Saying Yes to the Journey

Gwen’s career shift was catalyzed by her former colleague Victoria (the same Victoria who introduced her to me). When Victoria left corporate to start her own business, Gwen witnessed firsthand how one person’s courage to say “yes” can spark change for others. That chain reaction eventually led Gwen to start Grit and Tenacity Consulting, where she now helps female entrepreneurs build confidence in their sales processes by embracing their authentic selves.

Gwen focuses on helping women develop repeatable, sustainable, and genuine sales methods. It’s about selling from a place of connection rather than coercion. And that’s what drew me to her.

Selling with Confidence: The Real Struggle

One word stood out during our conversation: confidence.

It’s something I’ve personally struggled with. Not just in business, but throughout my life. I shared with Gwen that even as a high school freshman on the varsity soccer team, my coach constantly pushed me to “find my confidence.” I had the skill, but I lacked the inner certainty to perform at my best. That theme has followed me into entrepreneurship, especially in sales.

When I asked Gwen what holds most women (realtors, business owners, creatives, etc) back from selling with confidence, she answered without hesitation: the “what ifs.”

What if it goes wrong? What if they think I’m pushy? What if I fail?

These questions can paralyze us. Gwen calls it “analysis paralysis,” where we get stuck imagining worst-case scenarios instead of simply jumping in and learning as we go. The key, she says, is to trust ourselves enough to know we can figure it out even if we fall flat at first.

And here’s the hard truth: no one else is going to hand you the life you want. It’s up to you to take ownership of your goals, your income, and your outcomes. Gwen learned that when she left her corporate job in June, choosing to bet on herself and her mission was a move that required both grit and tenacity.

The Fear of Failing Fast

Many entrepreneurs fear failing fast. We often admire the idea of “failing forward,” but in practice, it’s terrifying.

Gwen pointed out that confidence doesn’t mean having it all figured out. It means believing that, no matter the outcome, you’ll find your way through. I resonated deeply with this, especially as someone who prefers certainty and calculated risks. I’m not naturally a risk-taker, so I prepare myself by visualizing the worst-case scenario in advance. It helps me feel more in control, as if I’ve already built a safety net for the unknown.

But even then, embracing uncertainty is still hard.

Why Women Struggle with Valuing Themselves in Business

One one of the most critical barriers holding women back in business is a lack of self-valuation.

While women have made remarkable strides in corporate spaces, fighting for fair pay and recognition, there’s still a psychological gap when transitioning into entrepreneurship. In corporate settings, women can attach their value to a job title, a salary, or performance feedback from a boss. In the home, they might measure their worth based on their role as a partner or parent.

But when stepping into business ownership, those external validators disappear. You are the boss. You set the prices. And for many women, Gwen explained, that independence feels more unsettling than empowering at first.

The Emotional “Ick” Around Selling

Gwen illuminated the internal tension many women feel about charging for their services. We’re naturally wired to nurture, to help, to give. But entrepreneurship requires something that can feel at odds with that instinct: asking to be paid. This friction can create a mental block when it comes to confidently selling.

Instead of owning their value, many women overdeliver and undercharge. They might throw in extra services to justify their price or discount too quickly, hoping to make the sale. The result? Burnout, underpaid expertise, and often a shaky foundation for long-term business success.

I personally resonated with this, having shifted from a product-based wedding industry role into a more intangible service offering with my agency, Brand & Market. It’s much easier for someone to justify a price when they’re receiving a tangible deliverable, like a photo album, than when they’re paying for a strategy or experience. But Gwen reminded me: the key lies in communicating the value, not just the features.

Selling Intangible Services with Clarity

In service-based industries, whether you’re a brand strategist, photographer, coach, or creative, how you articulate your offer matters deeply. Gwen encouraged simplifying your language: “If a sixth grader can’t understand your pitch, your ideal client might not either.”

We often forget that industry terms like “branding” or “consulting” can feel vague to someone outside our world. But when we reframe those services in terms of outcomes it becomes easier for clients to see the value. As Gwen put it: people are buying confidence, not just a logo.

The Sales Process Starts Sooner Than You Think

One of the biggest mindset shifts Gwen introduced to me was this: the sales process doesn’t start when you get on a discovery call. It starts the moment someone fills out your inquiry form or sends a DM.

In fact, your very first touchpoint is shaping a potential client’s perception of you. That includes everything from the questions on your contact form to how you structure your follow-up. Gwen immediately picked up on my need to improve my follow-up process, which I hadn’t even realized was a gap.

She also emphasized a major misconception: marketing is not sales.

The Difference Between Marketing and Sales

Gwen gave a powerful breakdown between the two:

• Marketing is about awareness. It’s public relations. It’s sharing your work, your expertise, and your perspective to a broader audience. It attracts attention and builds authority. But it’s not a direct conversation.
• Sales, on the other hand, is personal. It happens in the DMs, the emails, the inquiry responses, and the calls. It’s intentional and rooted in connection.

Marketing might get someone interested. Sales helps them decide.

But the danger, Gwen noted, is when we blur the two. For example, she’s not a fan of asking for a client’s budget on an inquiry form. That immediately shifts the conversation into price, before value has even been established.

When you ask someone for their budget too early, you inadvertently hand over the control. You’re letting the client define your worth without them even understanding what you bring to the table. Gwen’s philosophy? If someone really knew how to do what you do, they wouldn’t be reaching out in the first place.

Clarity in the Sales Journey

Another lightbulb moment from our conversation: people often think they know what they need, but they’re wrong.

Gwen explained that clients often self-diagnose inaccurately. Thinking they need a social media audit, for example, when what they truly need is brand positioning. It’s our job as service providers to gently guide them toward the right solution, and that starts with asking the right questions and truly listening during the sales conversation.

As Gwen said, sales is about perception and precision.

A Better Way to Build Your Sales Process

From inquiry to conversion, every moment a potential client interacts with your brand is part of your sales experience. And while platforms like Instagram are great for visibility, don’t mistake posting for pitching. Sales is active. It’s intentional. It’s direct.

Gwen emphasized that the goal isn’t just to land clients. It’s to lead them. To show up confidently. To speak clearly. To create an experience that earns both trust and payment.

And that starts well before the call.

Selling Is Serving: A Mindset Shift That Changes Everything

One of my favorite moments in the conversation was when Gwen shared her take on the phrase “selling is serving.” It’s not just a feel-good quote. It’s the heart of her approach.

She recounted her early experience with Mary Kay, where she rose quickly to become a national leader not by selling in the traditional sense, but by sharing. She shared the impact the company had on her life, the opportunities it gave her, and how excited she was about it. That passion resonated more deeply than any pitch.

Gwen explained it this way: when you view your offer as a gift, selling becomes an act of generosity. Whether someone accepts it or not is up to them. But not offering it at all would be a disservice.

This perspective transforms the sales experience from something transactional and intimidating into something warm, relational, and authentic.

The Human Element: Authenticity, Curiosity, and Confidence

Gwen’s sales formula is simple, but powerful:
Authenticity + Curiosity + a Desire to Help = Confident Selling

By approaching sales with genuine curiosity about how you can help, telling real stories of past client success, and being your true self, you naturally become more confident. You’re not pushing — you’re connecting.

But confidence doesn’t always come easily. Even Gwen admitted to having moments of self-doubt, especially after time away. After taking a vacation, she spiraled into the fear that her clients might be unhappy or questioning her value, despite having communicated clearly beforehand. This kind of post-break guilt is something many of us as entrepreneurs can relate to.

Her reminder? People have lives. They’re not always watching your every move. And often, the narrative we create in our head is far more critical than reality.

Grace Over Assumption: Trust the Relationship

One of the most powerful takeaways from this episode was Gwen’s story about a prospective client who missed a scheduled call and didn’t respond for two weeks. Rather than writing her off or spiraling, Gwen followed up with kindness, and sure enough, the woman eventually reached out with an apology and eagerness to reconnect.

The lesson? Give people grace. Don’t assume the worst. Life happens. Silence doesn’t always mean rejection. It often just means “not right now.”

And as Gwen so clearly put it: If someone doesn’t want what you’re offering, they’ll tell you. Until then, it’s your responsibility to follow up and believe in the value of what you’re sharing.

The Biggest Sales Misconception? Thinking You’re Bugging People

I asked Gwen what she believes is the most common sales misconception among female entrepreneurs. Her answer?

Thinking you’re annoying people.

Too many women worry that following up is bothersome or pushy. But in truth, most people need the follow-up. Gwen shared a striking statistic from her “Fortune Is in the Follow-Up” class:

80% of people say yes between the 5th and 12th follow-up.

Read that again. Following up isn’t being pushy. It’s being persistent in service of your potential client’s transformation. It’s about staying top of mind, continuing the conversation, and offering value until they’re ready.

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Gwen Tinsley is helping reframe what selling can and should look like for female entrepreneurs. It’s not about manipulation, pressure, or perfectly crafted pitches. It’s about human connection. It’s about clarity. It’s about service.

From recognizing the emotional “ick” around charging for your services to understanding that your sales process extends into every client interaction, this conversation was packed with honest insight, real-life stories, and empowering mindset shifts.

And if there’s one message to walk away with, it’s this:

You’re not bugging people. You’re showing up with a solution they need.
Keep showing up. Keep serving. Keep selling, with heart.

Want to sell with more confidence?