On the latest episode of ⁠⁠⁠⁠⁠⁠⁠Digital Doorways⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, we had the privilege of welcoming Holly Rollo, an iconic Chief Marketing Officer with a remarkable career spanning over 30 years in business transformation and growth in the B2B technology sector to the podcast. With a track record of driving results for organizations facing major market disruptions, turnarounds, and pre/post-equity events, Holly has been at the forefront of innovation in cybersecurity, SaaS, martech, and more. As the former CMO at RSA Security, Fortinet, and SumTotal Systems, with leadership roles at esteemed companies like FireEye, SuccessFactors, and Cisco, Holly brings a wealth of experience and expertise to the table. Her groundbreaking book, “Power of Surge,” provides a clear blueprint for transforming marketing strategies to unleash hidden value, especially in the lead-up to transaction or exit events. Listen below as we delve into Holly’s illustrious career and explore the transformative insights outlined in her book.

⁠⁠⁠⁠⁠⁠Digital Doorways⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ is Hosted by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jason Siegel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Founder of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Bluetext⁠⁠.


  1. Can you share some pivotal moments from your career that have shaped your approach to marketing and business transformation?
  2. Your book, “Power of Surge,” outlines a strategic approach to marketing using SURGE―Strategy, Unity, Reputation, Gains, and Efficiency. Can you elaborate on these concepts and how they can be applied in the B2B technology sector?
  3. As a seasoned executive leader, what advice do you have for CEOs and investors in small to midsize B2B software companies looking to transform their marketing strategies?
  4. You’ve held leadership roles at prominent companies like RSA Security, Fortinet, and SumTotal Systems. How did your experiences at these organizations influence your perspective on marketing and growth strategies?
  5. Can you discuss the common disconnects between CEOs and CMOs that undermine execution, as mentioned in your book, and how they can be addressed?
  6. Achieving radical alignment across sales, marketing, and customer success is crucial for success. What strategies do you recommend for fostering this alignment within organizations?
  7. Your expertise spans cybersecurity, SaaS, martech, and more. How do you tailor marketing strategies to effectively target audiences in these diverse sectors?
  8. Building a compelling competitive market position and brand reputation is essential. Can you share some strategies for establishing and strengthening brand reputation with customers?
  9. In your experience, what are some key steps for unlocking hidden revenue streams in B2B technology companies?
  10. How do you approach developing a customer-centric strategy tailored to the unique business situation of each organization?
  11. The competitive talent market can pose challenges in finding and keeping the right marketing leader. What advice do you have for CEOs in navigating this landscape?
  12. How can CEOs and CMOs work together to drive growth, lower customer acquisition costs, and boost valuation, as outlined in your book?
  13. Shortening sales cycles is a key objective for many organizations. What strategies have you found effective in achieving this goal?
  14. Can you share some insights on driving growth and ROI through modern marketing engines in B2B technology companies?
  15. What role does organizational change management play in implementing marketing transformations, and how do you approach this aspect of leadership?
  16. With your extensive experience, what future trends do you foresee shaping the marketing landscape in the B2B technology sector?
  17. How do you balance the need for innovation with the necessity of maintaining brand consistency and integrity?
  18. As a frequent speaker and contributor to publications, how do you stay informed about the latest developments in cybersecurity, digital transformation, and transformational leadership?
  19. Can you discuss your role as a board member for MYOB and Santa Clara University Leavey School of Business, and how these experiences inform your perspective on business transformation?
  20. What motivates and inspires you to continue driving transformational change in the B2B technology industry, and what legacy do you hope to leave behind in your career?