Introduction to Caleb Whittle

Today we have joining us Caleb Whittle. Caleb is currently the Chief Marketing Officer at PrivateAuto. He’s been called the Tom Cruise of Utah, since he spends his free time on movie sets and his run form is comparable to Tom’s.

Caleb has been in marketing for over 10 years and has been a part of the digital revolution happening in several industries, ranging from outdoor sporting goods to guitars.

In 2022 and 2023, Caleb was the host of a podcast called Everyday Intrapreneurs. It had over 60 episodes and focused on leaders within companies that run their teams as if it were their own business.

Table of Contents

• Who is Caleb Whittle?
• Current Projects that Excite Caleb
• Tactical and Strategic Marketing Advice from Caleb
• Where Does Caleb See the Future of Marketing Going?
• How to Get in Contact with Caleb
• Additional Insights from Caleb’s Journey
• Advice for Aspiring Marketers
• Advice to His Younger Self
• Books, Podcasts, Leaders
• Conclusion

Who is Caleb Whittle?

Early Aspirations and Education

Caleb wanted to be a fighter pilot when he grew up. He lived next to the Air Force Academy in Colorado and would see fighter jets flying over all the time. His parents weren’t in the military but he was in the Air Force Junior Reserve Officer Training Corps (AFJROTC) in high school.

But his dreams of joining the Air Force were squashed by asthma and poor eyesight in his right eye. So he looked into aerospace engineering as an alternative way to work with fighter jets.

The Pivot to Marketing

Caleb’s journey into marketing was unplanned. He took a marketing class as an elective his sophomore year of college and enjoyed it more than his engineering classes. So he changed his major.

Because of the technical nature of his previous major, switching to a business major would have meant repeating two years of college. Instead, Caleb used his two years of living in a Spanish speaking country to major in Spanish and would pursue an MBA for formal business education later.

First Steps in the Marketing World

During his senior year of college, Caleb landed an internship at Armor Sports, an outdoor sporting goods company, in their in-store marketing department. This internship turned into a full-time job before he graduated, marking the beginning of his marketing career.

Lessons from Early Experiences

Caleb’s early experiences taught him valuable lessons:

1. The importance of being curious and trying different things
2. The value of pivoting when something isn’t working
3. The necessity of failing and learning from those failures

These lessons have been crucial in his marketing career, where testing and adapting strategies is key to success.

Parental Influence

While Caleb’s parents didn’t directly create an environment focused on failure and learning, they provided him with the freedom to explore various interests. This allowed him to experiment with different activities, from sports to music lessons, fostering a natural inclination towards trying new things and learning from experiences.

Current Projects that Excite Caleb

PrivateAuto: Revolutionizing Private Car Sales

Caleb is currently excited about his work at PrivateAuto, where they’re changing the way people buy and sell cars privately. Some of the projects he’s particularly enthusiastic about include:

1. Launching new influencer programs
2. Developing a new product feature set to launch in the current quarter, which Caleb believes will give them a significant edge over the competition

The Pressure and Excitement of Startup Life

Working in a startup environment brings both pressure and excitement for Caleb. He notes that in a business like PrivateAuto, the company’s success largely depends on two factors:

1. Having a great product (which Caleb believes they have, thanks to their product team)
2. Effective marketing (which falls primarily on Caleb and his small team of two)

This responsibility creates pressure but also drives Caleb’s enthusiasm for his work.

Tactical and Strategic Marketing Advice from Caleb

Content Strategy Matters

Caleb says content is key to everything you do online, whether written, video or photo. Good content is how you get found online and how you connect with your audience.

Long-Tail Keywords

Caleb recommends creating content around long-tail keywords. These are more specific, less competitive phrases that may have lower search volumes but are highly relevant to your business. For example PrivateAuto creates content around license plates which while not directly related to their core business of buying and selling cars is still within the automotive industry and drives traffic to their site.

Repurpose Content

Caleb says repurpose content across different formats to get more out of it. A blog post can be turned into a video or an infographic. This makes content creation more doable for small teams and new business owners.

Leveraging Social Media

TikTok Experimentation

Caleb shared his experience experimenting with TikTok, where he grew an account to over 12,000 followers. His key learnings include:

1. You can’t force virality – it’s unpredictable what will resonate with the audience.
2. Niching down can lead to a more engaged audience, even if overall reach is smaller.
3. Content should either entertain, educate, or inspire to be effective.
4. Quick, spontaneous content often performs better than heavily produced videos.

Business Use of TikTok

For businesses looking to use TikTok, Caleb suggests:

1. Don’t spend too much time on individual videos – quick, authentic content often performs better.
2. Consider using TikTok for lead generation rather than direct conversions.
3. Ensure your profile link is up-to-date and relevant, especially if you gain followers quickly.

Influencer Marketing

Caleb’s approach to influencer marketing focuses on natural integration of the product or service into the influencer’s content. He advises against obvious ad spots that interrupt the viewer’s experience, as these are often skipped or ignored.

Instead, he recommends finding ways to incorporate the product or service naturally into the influencer’s content, making it feel like a genuine part of their story or experience.

Networking and Relationship Building

Caleb emphasizes the importance of networking and building relationships without an immediate agenda. He credits much of his career success to connections he’s made and maintained over time. His advice includes:

1. Attend industry events and engage with people in person.
2. Be active on professional networking platforms like LinkedIn.
3. Focus on building genuine relationships rather than immediately trying to sell or gain something.

Where Does Caleb See the Future of Marketing Going?

Integration of Commerce and Social Media

Caleb predicts that more transactions will happen where people are spending their time online. He points to developments like TikTok Shop as examples of this trend. While acknowledging that TikTok Shop may have initially overdone its push, Caleb believes the seamless purchasing experience it offers (allowing users to buy products without leaving the app) is indicative of future e-commerce trends.

Peer-to-Peer Payments in Social Media

Caleb mentions the potential introduction of peer-to-peer payments on platforms like X (formerly Twitter), further integrating financial transactions into social media experiences.

Virtual and Augmented Reality

While Caleb believes VR and AR experiences will continue to increase in marketing and e-commerce, he doesn’t expect mass adoption in the immediate future. He sees these technologies becoming a part of the purchase journey but not the primary method for some time.

Evolution of Influencer Marketing

Caleb anticipates that influencer marketing will continue to grow, but with a shift towards more natural, integrated content rather than obvious sponsored posts. He emphasizes the importance of authentic integration of products or services into influencers’ content to avoid viewer fatigue with traditional ad formats.

How to Get in Contact with Caleb

For those interested in connecting with Caleb or learning more about his work:

1. LinkedIn: Caleb Whittle

Additional Insights from Caleb’s Journey

The Value of Internships

Caleb’s career trajectory highlights the importance of internships in launching a successful career. His internship at Armor Sports not only provided him with practical experience but also opened the door to his first full-time position in marketing.

Internal Networking

During his time at Armor Sports, Caleb emphasizes the value of internal networking. By connecting with colleagues across different departments and brands within the company, he was able to:

1. Learn about different aspects of the business
2. Understand how his role impacted others
3. Identify potential career growth opportunities within the organization

This approach ultimately led to his progression through five different positions over about four years with the company.

Adapting to Digital Transformation

Caleb’s experience at Armor Sports also involved participating in the company’s digital transformation. This included:

1. Shifting from in-store marketing to digital and direct-to-consumer strategies
2. Developing digital experiences for customers
3. Adapting marketing strategies to align with new digital initiatives

This experience proved valuable in his subsequent role at Gibson, where he was tasked with helping the company develop its direct-to-consumer capabilities.

Balancing Growth and Existing Relationships

At Gibson, Caleb faced the challenge of introducing direct-to-consumer sales without alienating existing retail partners. His approach focused on communicating how this new strategy could benefit all parties, emphasizing that “a rising tide lifts all boats.”

The Importance of Continuous Learning

Throughout his career, Caleb has demonstrated a commitment to continuous learning. This includes:

1. Taking on new challenges and roles within organizations
2. Experimenting with new marketing platforms and strategies
3. Reading extensively about business and marketing (though he notes the importance of balancing learning with application)

Work-Life Balance in Marketing

Caleb touches on the importance of maintaining work-life balance, especially in high-pressure startup environments. He mentions shifting some of his personal media consumption towards entertainment rather than purely educational content as a way to relax and recharge.

Advice for Aspiring Marketers

Here are the takeaways from Caleb’s experiences:

1. Be curious and try stuff: Experiment and pivot when needed.
2. Use failure as a learning opportunity: Don’t be afraid to fail; use those experiences to improve and grow.
3. Build relationships: Network within your company and industry without an agenda.
4. Be adaptable: Be prepared to adjust as technology and consumer behavior changes.
5. Have a content strategy: Create content that can be repurposed across platforms.
6. Understand social media: Try TikTok but focus on authentic, engaging content not advertising.
7. Keep learning: Stay up to date with industry trends but apply what you learn.
8. Balance data with creativity: Use data to inform but don’t let it stifle creative thinking.
9. Think long term: Focus on building sustainable strategies not short term viral success.
10. Maintain work-life balance: Remember to recharge and pursue interests outside of work to stay creative and avoid burnout.

Advice to His Younger Self

If Caleb could go back in time and give advice to his younger self he would say:

“You can do more than you think you can”

Caleb says he’s struggled with self confidence his whole life. He would tell his younger self to “just go for it” and believe in himself, you can probably do about 95% of what you think you can do.

Books, Podcasts, Leaders

Caleb’s sources of inspiration change often but he mentioned a few:

1. Brad Parker, founder of PrivateAuto: Caleb says he’s an amazing, friendly and down to earth guy who has a lot to teach.
2. Gary Vaynerchuk (Gary V): Caleb is a fan of Gary V because of his pulse on social media. He’s looking forward to his new book coming out this year.
3. Fiction Books: Caleb has switched to more fiction for entertainment rather than business books. He got burnt out after reading 70 business books in 2022-2023 and realized he wasn’t applying much of what he was learning.
4. Entertainment Podcasts: Caleb has switched to listening to more fun, entertainment focused podcasts rather than educational ones.

He says he’s focused on entertainment right now because so much of his day is spent in the startup world. He needs to relax with his books and podcasts.

Conclusion

Caleb Whittle’s journey from aspiring fighter pilot to Chief Marketing Officer offers valuable insights into the evolving world of digital marketing. His experiences highlight the importance of adaptability, continuous learning, and relationship-building in navigating the rapidly changing landscape of modern marketing.

As the lines between social media, e-commerce, and traditional marketing continue to blur, marketers must stay agile and open to new approaches. Caleb’s emphasis on authentic content, strategic experimentation, and natural integration of products into influencer partnerships provides a roadmap for effective marketing in the digital age.

Whether you’re a seasoned marketing professional or just starting your career, Caleb’s insights offer valuable guidance for navigating the challenges and opportunities in today’s digital marketing landscape. By focusing on building genuine connections, creating valuable content, and staying open to new technologies and platforms, marketers can position themselves for success in an increasingly digital world.