We had quite the subscriber jump this week. It’s a pleasure to have you! Welcome to the Revenue Diaries. Thanks for subscribing and agreeing to share a small part of your Sunday evening. 

And a quick reminder: this newsletter is a snapshot of my week, which can include everything from what I’m reading to the challenges of running marketing a high-growth startup. The content will vary, depending on what’s in my head. And my head is an interesting place, I think. :)

❤️ Kyle

 Without further ado, here’s what’s in today’s newsletter. 

• No Easy Outs: Building True Alignment & Accountability

• Part 4 of the $750M Content Marketing Framework: Amplify

• Podcast: Fitness, Family, and Resilience in the Face of Suicide

• Why You Aren’t Getting Promoted

On No Easy Outs: Building True Alignment & Accountability

I’ve written about my conversations with Andrew Lau, my boss and CEO of Jellyfish, many times over the past 2 ½ years. He’s a wealth of knowledge and we don’t want to keep knowledge hidden behind the walls of Jellyfish. 🙂 

Hide it under a bushel? No! (Sunday school recovery crew, that one’s for you.)

Recently, we dove into the importance of buy-in and alignment for a strategic initiative we’ve been working on. Andrew shared a perspective that stuck with me… why alignment done right means having no easy way out. It’s uncomfortable, but it’s what it takes to build real accountability.

Let me try to do his thoughts justice. Here’s the truth: alignment isn’t just about everyone nodding along in agreement. It’s about ensuring there’s no easy way out when things don’t go as planned. 

I think you know the scenario. The room looks like this 🤷.

Too often, teams unknowingly build backstops into their strategies. Not because they’re lazy or shifting blame but because they haven’t spent the time arguing over the tough questions—prioritizing, defining ownership, and aligning on deliverables. It’s easier to leave things vague; before you know it, the 🤷 appear.

If the product launch flops, sales might say, “I didn’t have enough deals to work.” If sales miss quota, marketing might say, “We generated the leads; it’s not on us.”

It’s the god-forsaken squishy middle where accountability goes to suffocate and die. 

How’s that for a visual? Ha.

Real alignment only happens when every team owns the outcome, when sales and marketing define the goals together and take shared responsibility for achieving them, and when every team looks beyond their silos to align on clear priorities and stick to them, even when difficult.

So, the next time you’re tempted not to prioritize and avoid a difficult conversation, stop and ask yourself: Does this encourage shared accountability? Or does it give someone an easy way out? Because without accountability, alignment is just a LinkedIn Bro buzzword.

On Amplifying: Part 4 of the $750M Content Marketing Framework

In the first three parts of our Content Marketing Framework, CREATE, we covered how (and the teams I’ve had the pleasure of serving) built the foundation of content marketing that created and/or influenced over $750 million in the pipeline for various companies. It all started with Crafting the Story, where we nailed down the one-sentence statement that connects with the audience’s needs. 

This involved focusing on operational themes (the functional benefits and solutions) and relational themes (the emotional connection and human value). 

Next, we dove into Researching with Customers, validating the story by digging into what our audience cares about and including them in the process. Then, we tackled Executing with Your Team, where we took everything we learned and researched and produced great content through the team.

What’s better than researching an building the content? Amplifying it.

Without an audience, even the best content falls flat. Amplification is how we get our message in front of the right people at the right time, marking sure the effort we’ve put into crafting, researching, and executing doesn’t go to waste.

And you know amplification matters. Do we really need to cover this? Non-caffeinated Kyle says, “Yes.”

Amplification (or distribution, but it didn’t fit the acronym well 😄) is the bridge between creating content and driving the business (pipeline and bookings). It’s safe to say we don’t have long attention spans, and it’s rare that content is discovered by chance. Amplifying ensures that what you create finds the audience it was made for and drives demand.

Points to Remember!

1. Find the Right Channels: Different channels work better for different types of content. Blog posts do well with SEO and email, while videos work on social media or paid ads.

2. Repurpose for Reach: Don’t limit your content to one format. A blog post can become a social media carousel, a webinar can become a series of video clips, and a customer success story can become an infographic. Repurposing helps your message reach more people, making creating more content from one long-form piece easier. Some examples:

   • Turn a long-form blog post into a series of LinkedIn posts targeted at different audience segments.

   • Clip highlights from a webinar and share them as short videos on Instagram or YouTube.

   • Create an infographic based on data in your content and share it on Twitter to drive traffic back to the original piece.

3. Balance Paid and Organic: It’s very important to balance organic search production and paid ad strategy to amplify content. I haven’t found a marketer who will say the opposite.

4. Involve Your Customers and Prospects: Remember the customers you researched and spoke with in the Crafting and Research portion of the CREATE Framework? You included them in the content production, right? Use them to help distribute the content.

5. Timing is Key: It’s not just about where you post but when. Use data to figure out when your audience is most active and schedule your content to hit at those times.

We could dive into each of these points with essays on balancing paid/organic and the right timing, but for the sake of our sanity and eyes, let’s focus on finding the right channels to amplify the content.

Finding the Right Channels

1. Get In Your Prospect’s Head!

   • Where does your audience spend their time online? Use tools like Google Analytics, SimilarWeb, or customer surveys to identify platforms they frequent.

   • Segment your audience based on demographics or behavior to focus your content marketing strategy. For example, tech-savvy professionals might be active on LinkedIn, while younger audiences may prefer TikTok or Instagram.

   • Don’t be a boomer. ;)

2. Prioritize Fans, Followers, and Subscribers

   • Invest in platforms that allow you to control the connection to your audience, like email and your website/blog. These are long-term assets that won’t be affected by algorithm changes. As we used to say at ExactTarget, Subscribers Rule!

3. Observe Competitors and Industry Trends

   • Watch what your competitors are doing and what’s gaining traction in your industry. Tools like BuzzSumo or social media listening platforms can help.

4. Consider Context and Timing

   • What’s the purpose of your content? For product launches, paid search or display ads might be ideal. For thought leadership, focus on LinkedIn or industry forums.

   • Align your channel selection with the goal of your content, whether it’s awareness, engagement, or conversion. More of tracking and measurement in next week’s entry!

Amplifying content is about making sure your hard work reaches its full potential. It’s the step that turns good content into great results. Now, get out there and start amplifying! When done well, marketing the content will get your story heard, your message connects, and your audience takes action.

And we all want our audience to take action.

On Fitness, Family, and Resilience in the Face of Suicide

And we are back to the Revenue Diaries podcast. You know the drill: five questions about everything other than work. Only one caveat, the guests do not get the questions ahead of time. Each episode is an unfiltered look at the challenges, learnings, and wins lessons that define us as humans.

This week’s episode features Dave Sims, Chief Marketing Officer of Austin Fitness Group, and a dedicated triathlete, about how fitness, family, and resilience have shaped his life. Dave’s story is raw and deeply personal, but it’s also a testament to the strength we can find in the hardest moments.

We talked about how fitness became more than a hobby for both of us, and 100% his saving grace. From triathlons to daily workouts at OrangeTheory, he’s found consistency and balance through sweating (which I also firmly believe in). It’s given him a sense of control, especially during chaotic periods of life. 

We dove into his family’s journey through trauma, including his ex-wife’s struggles with borderline and narcissistic personality disorders, their difficult divorce, and the devastating impact it had on his daughters. 

Dave opened up about the pain of estrangement, the long path to reconnecting with his kids, and how therapy played a critical role in helping them rebuild their lives. He also shared the heartbreaking reality of his ex-wife’s suicide and the lasting impact it has had on his family. 

And like the standup guy he is, he didn’t shy away from the complexity of grief, trauma, and healing. He showed me how sharing these stories through his podcast Over the Borderline and conversations like this one can help others feel less alone.

We also touched on:

• The challenges of navigating mental health conversations at work.

• How storytelling can be a tool for healing and connection.

• The importance of therapy and finding the right support, even when it’s hard.

This isn’t just a conversation about fitness or family—it’s about resilience. It’s about what it means to show up for yourself and your loved ones when life feels impossible. 

On Why You Aren’t Getting Promoted

This thread is absolute 🔥 I had to share it here. In 15+ years at Amazon, Ethan Evans helped influence over 30 promotions to the Director level. He’s seen firsthand why some people climb the corporate ladder while others, often people performing at a high level, get stuck.

Here’s a synopsis of what he shared about getting promoted and why you are being blocked. Here’s what he shared about breaking through promotion roadblocks:

The Two Barriers to Promotion

1. Being Overlooked

2. Being Considered but Passed Over

These are fundamentally different problems, and the strategies to overcome them aren’t the same.

If You’re Overlooked

You may feel like you’re working hard and going unnoticed. Here’s why:

• You’re waiting to be discovered.
  The higher you go, the less likely someone will randomly notice your hard work. You need to advocate for yourself.

• You lack the right relationships.
  People promote those they trust. Even if your work is exceptional, you need strong relationships to back you.

Ethan’s advice? Build relationships and make sure your contributions are recognized. This isn’t about playing politics, it’s about being intentional. You need to own your career. 

If You’re Considered but Passed Over

Getting close but not getting the promotion 100% feels worse. Here are some reasons it happens:

• You’re stuck in your current role: Promotions often require “next-level” work. If you’re doing only what’s required of your current role, it’s harder to showcase readiness for the next.

• You’re not as strong as you think: Tough love: Conduct a 360-degree feedback review. Include your manager, peers, and even critics. Honest feedback is invaluable.

• You have a fixable flaw: This could be communication, temperament, or a skill gap. Seek feedback, identify the issue, and address it head-on.

• You lack key qualifications: For example, if the next level requires financial skills and you lack them, start acquiring them. Look at others in your desired role and ask your manager about gaps to fill.

If No Promotion, Should You Leave Your Job?

Before you jump ship, do the hard work of identifying the real reason for your stagnation. If it’s something within your control (like relationships or skill gaps) address it first. If you’ve done everything you can and unconscious bias or structural issues remain, it’s time to consider moving on.

This breakdown is a valuable reminder that promotions are rarely just about performance. They’re about visibility, relationships, timing, and self-awareness.