This episode of Sell With Authority is another part of our very special series on trust — and distrust — in the agency sales process.

You've been hearing from agency leaders who are leaning into this issue head-on. These conversations are not only timely — they're also forming the research foundation for my next book, The Trust Architecture, and a new series of Field Guides we'll soon be sharing with our community.

As we've seen time and again from our work alongside agency owners and their teams — trust, or the lack of it — is one of the biggest obstacles to having a sales pipeline that flows with right-fit prospects.

When trust is present — awesome — the pipeline flows.

When trust is absent — not awesome — friction sets in, uncertainty creeps up, and momentum stalls.

Which makes today's conversation another rock solid awesome fit for this series.

Our special guest expert is Maddy Osman, Founder of The Blogsmith, a content marketing agency trusted by top B2B technology brands. Maddy's perspective is such a valuable addition to this series because agencies know that the quality of content can either build or break credibility.

A missed deadline, an inconsistent voice, or a sloppy process erodes trust instantly.

But content that's consistent, well-structured, and scalable doesn't just demonstrate credibility — it earns it.

You'll hear how Maddy defines trust in agency-client relationships, how content and thought leadership can build trust at scale, how her team ensures quality and credibility through strong operations, and how to balance efficiency — maybe even AI — with human creativity to keep trust at the center of it all.

Content can transform your agency's credibility into trust — THEN turn that trust into growth.

Maddy shares her proven processes, mistakes to avoid, and her hard-won lessons on turning trust into lasting growth.

• Why trust — or lack of it — is the single biggest friction in your agency's sales pipeline
• Maddy's playbook for building trust from the very first client touchpoint
• The secret behind "the trust cookie"
• How to leverage operational discipline so your clients see you as the safest pair of hands they've used — ever
• Candid examples of when it's time to say "no" for the sake of integrity — and how that builds referral gold
• A balanced approach to leveraging AI, building human connections, and never losing your voice in the noise

• Website: https://www.theblogsmith.com/
• LinkedIn Personal: https://www.linkedin.com/in/madelineosman/
• LinkedIn Business: https://www.linkedin.com/company/theblogsmith/
• X: https://x.com/maddyosman
• Writing for Humans and Robots: The New Rules of Content Style: https://www.amazon.com/dp/B09X4NJ9H8

This episode of Sell With Authority is part of our special series exploring one of the most vital dynamics inside every agency's sales process: trust and distrust.

You've been hearing from agency leaders who are leaning into this issue head-on. These conversations are not only timely — they're also forming the research foundation for my next book, The Trust Architecture, and a new series of Field Guides we'll be sharing with our community.

As we've seen time and again from our work alongside agency owners and their teams — trust, or the lack of it, is often the biggest obstacle to having a sales pipeline that feels like a steady stream of right-fit prospects flowing into your agency.

Which makes today's conversation a perfect fit for this series.

Our special guest expert is Jerry Gennaria, President and CEO of TOKY.

Jerry brings more than 30 years of experience helping professional service firms tell their story more effectively, build stronger businesses, and reach their full potential. He's also the host of The Intangible Brand podcast — where he explores what brand really means beyond the surface-level tactics.

Here's why Jerry's perspective matters so much for this series…

In a recent LinkedIn post, he made an incredibly sharp observation — when Southwest Airlines cut away the very things customers loved most about their experience, it wasn't just a rebrand.

A brand isn't just graphics or identity — it's about who you are internally and how customers experience you externally. When you change that alignment — you break trust.

That ties directly to what we saw in the 2025 Edelman Trust Barometer — when trust erodes, grievance and frustration take over — but when trust grows, optimism and loyalty follow.

That's exactly the kind of work Jerry and his team at TOKY do every day — helping clients align their brand and their actions so that trust is reinforced at every single touchpoint.

When your agency's brand and your actions are aligned — trust isn't an abstract idea. It's felt — in every interaction, every proposal, every conversation.

When trust is felt at every touchpoint — selling more of what you do stops being about persuasion — and starts being about consistency.

That's why we wanted Jerry's perspective to be part of this series.

When I say we — I mean Hannah Roth, our Director of Strategy and Mad Scientist, is here with me for this conversation to bring her data-driven perspective into this discussion with Jerry — because when you combine brand alignment with real-world strategy — that's when trust becomes measurable and scalable.

• How to make prospects feel seen — and why that matters for conversion
• Jerry's "brand is a promise delivered" philosophy for agencies
• The art and science of pushing back — and how it earns deep respect from right-fit clients
• Why authentic storytelling aligned with your brand delivers exponential results
• Ways to boldly show your expertise without being self-aggrandizing
• Why trust is not built in the big gestures

• Website: toky.com
• LinkedIn Personal: https://www.linkedin.com/in/gennaria/
• The Intangible Brand: https://www.linkedin.com/company/the-intangible-brand/
• TOKY: https://www.linkedin.com/company/toky-branding/
• The Intangible Brand Podcast: www.theintangiblebrand.com

Today's episode is part of our special series exploring one of the most vital dynamics inside every agency's sales process: trust and distrust.

Over the coming weeks, you'll hear from agency leaders who are leaning into this issue head-on. These conversations are not only timely — they're also forming the research foundation for my next book, The Trust Architecture, and a new series of Field Guides we'll be sharing with our community.

Here at Predictive ROI, we help agencies sell more of what they do. And time and again, from our work alongside agency owners and their teams, we've seen that trust — or the lack of it — is the biggest variable determining whether your pipeline flows like a steady stream of right-fit prospects… or grinds to a halt.

When trust is present — momentum builds.

When trust is absent — friction takes over.

Which makes today's conversation a perfect fit for this series. Our special guest expert is Darren Magarro, Founder and President of DSM. Since launching DSM in 2007, Darren has led his agency through the ups, downs, twists, and turns that every agency owner knows too well.

But what truly sets him apart is how he leads. Darren's people-first, community-centered approach is at the heart of how DSM builds trust. He works tirelessly to put others on a path to success — and that shows up in every corner of his business.

When trust increases — optimism replaces grievance — and people shift from frustration to future-focused hope.

Darren's leadership embodies that shift.

• The rock solid data that proves why "people-first" and community-centered leadership is now the must-have ingredient for agencies that want to build real trust
• How Darren's approach to leadership at DSM turns transparency and empathy into a competitive business advantage
• Why budget qualification must happen early
• The three-step biz dev process that weeds out bad fits so you can focus on dream clients
• Why client stories, tough conversations, and owning mistakes can translate directly into agency resilience and reputation
• Candid advice for agency owners who want their team and clients to be truly optimistic about the future
• Why your LinkedIn content should be more helpful

• Website: https://thedsmgroup.com/
• LinkedIn Personal: https://www.linkedin.com/in/darrenmagarro/
• LinkedIn Business: https://www.linkedin.com/company/the-dsm-group/
• Facebook: https://www.facebook.com/TheDSMGroup
• Instagram: https://www.instagram.com/thedsmgroup