Revenue Diaries Entry 8

There’s always something on the to-do list we’re dodging. And boy, was I dodging a couple of major things this week. It wrecked me. My sleep was affected. My attitude shifted from “highly productive 40.5-year-old” to “whiny, self-indulgent 6-year-old.” 

No offense to the six-year-olds out there.

You know what I’m talking about: the big project that feels overwhelming or the workout you keep promising to "start tomorrow… or in January." It’s not fun to admit, but the magic of moving forward usually hides in the stuff we’re avoiding. I’m not big on gimmicky motivational quotes, but I heard one in Andrew Huberman’s conversation with Dr. Layne Norton, and it hit hard.

Easy to type, harder to do. 

Tackling those hard things doesn’t mean diving headfirst into everything you’ve been avoiding. Don’t be crazy. Start small. It’s something I learned from Tim Kopp, ex-CMO at ExactTarget and one of the sharpest leaders I’ve worked with: If you’re stuck or dodging something, start small. Knock out something easy. Build momentum, and you’ll find your way forward.

So, start small and progress. 

❤️ Kyle

On Balancing Creativity & Ambition

We all remember the pandemic. Many of us were working at home, having been ripped out of offices and thrown into a home office (if lucky) or the kitchen counter. 

During this time, I craved conversations that were unrelated to work. Revenue Diaries (the podcast of the same name) became my outlet to the world. It became a place for raw, unfiltered, and meaningful conversations with peers.

This past week, I rebooted the Revenue Diaries podcast (Spotify & YouTube) and couldn’t be more thrilled with my conversations over the past month. We are keeping the same format… an unfiltered look into the personal lives of many different types of leaders. 

CRO. CMO. Heads of Engineering. Directors. From mental health and parenting to aging parents and suicide, no topic is off-limits. The catch? Guests don’t see the questions ahead of time.

The first episode features Margaret Kelsey a mother, artist, podcaster, and brilliant marketing leader. In our conversation, Margaret reminded me that ambition, creativity, and balance can coexist if you connect them to your core values. She shared her values of curiosity, creativity, balance, and audacity that help guide her decisions and keep her grounded. She regularly revisits them to ask:

• Am I staying true to my values?

• Are my actions moving me closer to the future I want to create?

• What do I want to be known for—even seven generations from now?

This episode is a solid reminder to focus on what matters, be deliberate with your energy, and build systems that help your values stick as you grow. Whether you’re dealing with burnout, a demanding boss, or just trying to make it through the day, this episode lays out a practical way to find clarity and purpose in the chaos.

I hope you enjoy this conversation as much as I did. 

On the $750M Content Marketing Playbook (Part 2) 

Last week, I wrote about the four types of content marketing to set the stage for the playbook I’ve been writing over the past year. Finally, I “did the work I’ve been avoiding” and started building the framework.

Successful content marketing requires a structured and repeatable process. Whether producing global content campaigns for a $300 million software company or weekly newsletters for a leading venture capital firm, the fundamentals remain the same.

Through these experiences, I’ve simplified the content marketing process into six key steps: Craft, Research, Execute, Amplify, Track, and Evolve. 

And I wouldn’t be a true marketer without forcing the process into an acronym, right? 😆

I’m pleased to introduce the CREATE framework.

This framework helps you and your team approach content creation with purpose, from defining the story to measuring its impact. By following CREATE, you can build campaigns that align with business goals and engage your audience effectively.

I’ll introduce each part over the next six weeks. For this week, we will be focusing on Crafting the Story.

Every content marketing strategy starts with a clear, focused story. Begin by crafting a one-sentence main story that puts the prospect first and highlights the outcome they care about.

So how do you get there? Start small. Pick a value prop and expand to a one-sentence description. Ask the following questions (I’m going to use myself (CMO) as the example: 

Who do you help? Start with the persona.

• Example: "We help marketing leaders..."

How do you help?

• Example:  “drive revenue growth”

What’s the outcome?

• Example:  “by aligning marketing campaigns with sales goals.”

Let’s write it out. We help marketing leaders drive revenue growth by aligning marketing campaigns with sales goals.

Let’s come up with a few additional examples to help you on your journey. 

• Ecommerce: “We help growth marketers increase average order value with hyper-personalized recommendations.”

• Healthcare: “We help hospitals improve patient outcomes by streamlining care coordination.”

• Education: “We help teachers create engaging lesson plans faster with ready-to-use templates.”

• Financial Services: “We help financial advisors build stronger client relationships with personalized reporting.”

Expanding to the Sub-Stories: Relational & Operational

Great! We have the start of a value prop, ultimately, the main story you want to tell. Here’s where the fun begins. From there, they expand into sub-stories that tackle the relational and operational aspects of the prospect’s (or customer’s) lives and jobs. Effective communication and engagement depend on addressing their needs and motivations. 

Here's why both sides are critical:

Relational stories build empathy and trust by addressing the human, such as collaboration, empathy-based leadership, or stress management. They show that you understand their aspirations and daily struggles because you are a partner rather than just a vendor.

Operational stories demonstrate expertise and results. They focus on measurable outcomes like tracking ROI, improving efficiency, or meeting performance goals. These stories provide the proof prospects need to justify decisions and highlight the real value you deliver.

Here is why you must focus on both: Using only relational stories can make your content feel too abstract, personal, and disconnected from your day-to-day job (or measurable goals). Relying solely on operational stories (which most marketers do) can make your brand seem transactional and impersonal. 

Speak to the person behind the role and the outcomes they’re working toward. Balancing both will help you connect on a human level, build stronger relationships, and create content that drives real results for your brand.

Finding Relational Stories

Digging into a customer's or prospect's relational stories means tapping into their emotional, interpersonal, and aspirational sides. Here are some steps I’ve used to uncover the relational side of a content marketing strategy. 

Start with Empathy

Step into their shoes. What pressures, challenges, or goals are they juggling daily? Think about how their role impacts their team, workplace relationships, and personal sense of fulfillment.

Tip: Ask yourself, “How does this role juggle their work responsibilities with the challenges of collaboration and team building?”

Listen to Them (novel idea)

Leverage tools like Gong or Chorus to dive into sales and customer calls. Or let genAI tools help you search the web for interviews, blogs, podcasts, or webinars where they’ve shared personal stories or insights.

You could also check LinkedIn for personal posts or comments about their role or industry challenges. Sometimes, their most candid thoughts are shared on social media.

Ask Open-Ended Questions During Calls

Use interviews or surveys to understand their experiences deeply. Focus on understanding the “why” and “how” behind their decisions and struggles, not just the “what.”

Tip: Try questions like, “What motivates you most in your role?” or “What’s the biggest challenge you face when working with your team?” to spark meaningful conversations.

Relational stories are about connection. When you understand the pressures and mental stress a prospect faces, you build trust. These stories show you’re focused on both their outcomes and the journey. Adding them to your content positions yourself as a partner in their success. Now that we’ve covered relational stories let’s look at how to pair them with operational stories to create a balanced approach.

Finding Operational Stories

Finding operational stories means focusing on the measurable aspects of your prospect's role. Ultimately, how they get results and track success, you should already know what they’re measuring, but if not, here are a few suggestions to get you started.

Focus on Business Goals & Metrics

As part of your persona work, you should have already mapped how your prospect views goals and KPIs. However, if you still need to, start here. Most operational stories revolve around measurable goals. 

• Consider standard metrics for their role, like ROI, lead conversion rates, customer acquisition cost (CAC), or retention rates.

• Find industry reports or benchmarks highlighting what "success" looks like for someone in their position.

Start by understanding the key performance indicators (KPIs) or metrics that matter most in their role. Operational stories revolve around these measurable goals.

Talk to Your Sales & Customer Success Teams

Talking to the customer is primary, but if anything is secondary, it’s talking to the “boots on the ground” team. They have direct insight into the operational challenges prospects and customers share.

• My favorite is using the call analysis features within Gong to surface operational pain points.

• Ask sales what questions or objections prospects bring up most frequently.

• Gather feedback from customer success about what tools or solutions your customers value most for solving operational pain points.

Your sales and customer success teams are on the front lines, hearing directly from prospects and customers. Tapping into their insights helps you uncover the most resonating operational challenges and build stories grounded in real-world needs.

Use Customer Data & Feedback (Talk to them!) 

Track and review how existing customers use your product or service to achieve a measurable outcome. Their successes can reveal operational stories that resonate with similar prospects. 

• Review case studies or testimonials.

• Analyze usage data to see where your product is driving the most value.

• TALK TO YOUR CUSTOMER

Customer data and feedback provide concrete proof points for operational stories. Highlighting real successes builds credibility and shows prospects exactly how your solution can help them achieve similar results.

Bonus! Key Questions to Ask

• What measurable outcomes do they care about most?

• Where are they currently wasting time, resources, or budget?

• What tools or processes are critical to their day-to-day success?

• What specific goals are they struggling to achieve?

Finding operational stories means understanding your prospects' measures and tying your content to their goals. By focusing on key metrics, using insights from sales and customer success, and talking directly to customers, you can create stories that address real challenges and show how your solution drives results.

Whew. Take a quick breath. I know it’s a lot to take in. The relational and operational stories will help build future themes for your content product.

Remember, the CREATE framework is designed to help you build a content marketing strategy that grows your brand and drives pipeline toward revenue growth.

Crafting the Story is the foundation for creating content that aligns with your audience’s priorities and builds credibility. With a strong story in place, the next step is bringing it to life through research and execution.

Stay tuned for the following two parts of the CREATE framework: Research and Execution.