Michelle Tresemer and Brett Schklar | Fractional CMOs & The 90-Day Win

This video features a discussion between Michelle Tresemer and Brett Schklar on the topic of fractional Chief Marketing Officers (CMOs) and their strategies for achieving significant results within the first 90 days of a new engagement. The conversation is hosted by Dean Waye and covers various aspects of the role of fractional CMOs, including common challenges, early wins, and key considerations for effective marketing leadership.


Fractional CMOs play a crucial role in driving early wins and establishing effective marketing strategies within the first 90 days of engagement. Their focus on understanding the company’s goals, identifying allies and potential obstacles, and creating a solid marketing foundation are essential for achieving success.

Key points

🎯 Identifying Allies: Michelle emphasizes the importance of identifying key players who will support or hinder marketing efforts early on.

🚧 People Problems: Both Michelle and Brett highlight that issues often arise from people within the organization who resist change or lack faith in marketing.

πŸ” Assessment and Benchmarking: Conducting thorough assessments and benchmarking against industry standards is crucial for understanding the current state and setting realistic goals.

🍏 Early Wins: Securing early wins through alignment with the CEO’s vision and gap analysis is vital for gaining momentum.

πŸ“Š Marketing Cadence: Consistent and repetitive marketing efforts, rather than grand gestures, are essential for sustained success.

🧠 Strategic Thinking: Fractional CMOs must be high-level strategic thinkers rather than just executors of tasks.

πŸš€ Leveraging AI: Embracing AI and generative technologies is becoming increasingly important in modern marketing strategies.

πŸ“ˆ Aligning Sales and Marketing: Effective collaboration between sales and marketing is crucial, especially when hiring a fractional head of sales.

πŸ› οΈ Building Foundations: Marketing leaders need to build a solid foundation that sales teams can leverage for better results.

🧩 Leadership Qualities: True leadership and alignment within the organization are key to overcoming obstacles and achieving marketing success.


  1. Introduction: Dean Waye introduces the podcast and the topic of fractional CMOs and their role in achieving early wins in client engagements. [0-3]
  2. Identifying Allies: Michelle discusses the importance of identifying key players who will either support or hinder the marketing efforts early in the engagement. [38-85]
  3. People Problems: Brett agrees with Michelle, highlighting that people-related issues are often the biggest challenges in new engagements. [107-146]
  4. Assessment and Benchmarking: Brett outlines the steps of gaining access, conducting assessments, and benchmarking against industry standards. [230-287]
  5. Early Wins: Michelle emphasizes the importance of aligning with the CEO’s vision and securing early wins through gap analysis. [293-350]
  6. Leveraging AI: The discussion touches on the use of AI and generative technologies in creating marketing strategies. [361-381]
  7. Strategic Thinking: Michelle explains that CMOs are strategic thinkers who should not be bogged down with execution-level tasks. [418-455]
  8. Aligning Sales and Marketing: Michelle and Brett discuss the importance of having a collaborative relationship between sales and marketing teams. [930-986]
  9. Leadership Qualities: The importance of true leadership in supporting marketing efforts and ensuring organizational alignment is highlighted. [1051-1113]
  10. Client Red Flags: The panel identifies red flags that indicate a client may not be ready for a fractional CMO, such as lack of appreciation for marketing and unrealistic expectations. [1181-1325]


  1. 0:00 – “How do fractional CMOS hit the ground running? Hi, I’m Dean Waye, welcome to the podcast, Fractional CMOS and the 90-Day Win.”
  2. 0:30 – “You just started a new engagement. You’re the fractional CMO. What problems do you typically see or what problems do you normally look for on day one of a new engagement?”
  3. 0:52 – “When I kick off an engagement, the first thing I look for is allies. I want to get a sense of who the players are that are going to help or hinder the marketing efforts.”
  4. 1:30 – “It’s amazing who can derail a project. Sometimes it’s an admin assistant, someone in sales, IT, or even someone else on the C-suite team.”
  5. 2:27 – “The problems are people problems. Companies often lose confidence or faith in marketing, and they don’t understand the value of a solid marketing strategy.”
  6. 3:53 – “Benchmarking against industry standards and the goals of the CEO or president is crucial for understanding the current state and setting realistic goals.”
  7. 4:30 – “One of the most important things in the first 90 days is finding alignment and understanding where things are today versus where they can be.”
  8. 5:15 – “Getting alignment with the founder or CEO on what they want for their company is key. The plan we build will be different based on their long-term vision.”
  9. 7:00 – “CMOs are strategic thinkers. It’s not all about execution. They’re meant to be high-level, providing a strategic framework for consistent results.”
  10. 9:10 – “Companies need to be learning organizations. Little 1% wins all over the place add up and shift the organization’s learning and growth.”
  11. 11:20 – “One of the key functions of marketing is to build a foundation that the salespeople can leverage. Without this foundation, sales efforts can fail.”
  12. 13:32 – “A true leader can build excitement and have a roadmap that gets everyone on board. Leadership qualities are essential for overcoming obstacles and achieving success.”
  13. 15:30 – “If a CEO doesn’t have the passion for the product but appreciates the value of marketing, they can still achieve success by trusting their team and allowing them to execute effectively.”
  14. 16:45 – “The difference between a leader and a manager impacts the success of the marketing function. True leaders understand and support the strategic role of marketing.”
  15. 18:12 – “Marketing is one of the first places where AI truly transforms the discipline. If you are not well-versed in AI, you are falling behind in marketing.”
  16. 20:45 – “When hiring a fractional CMO, CEOs should not just look for cost savings. They should seek strategic value and experience that can significantly impact the company’s success.”
  17. 22:15 – “Understanding the transformative impact of generative AI is crucial. If a potential client doesn’t get excited about this, they may not be a good fit for a fractional CMO.”
  18. 24:00 – “Operational CEOs from private equity-backed companies may not have the same passion as founder CEOs, but they need to understand the strategic role of marketing for success.”
  19. 25:30 – “Fractional CMOs need to find clients who appreciate and understand the strategic value of marketing, even if they are not passionate about the product themselves.”
  20. 27:00 – “True leadership qualities in CEOs, such as excitement and support for the marketing strategy, are essential for achieving long-term success.”
  21. 29:12 – “You can find me on LinkedIn, Brett Schklar, or visit my website Grow Powerful. Also, feel free to reach out via carrier pigeon if necessary!”
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