Sales Talk for CEOs: Innovating from the Top: How a Former CMO Revitalized a Company as CEO (Ep107)

Feb 13, 2024 | Sales Talk for CEOs Podcast

Imagine taking over the CEO role of a company just as COVID hit. Alice Heiman sat down with Andee Harris, the dynamic CEO of Challenger Inc., who did just that. Harris shared her riveting journey of steering the company through the COVID-19 pandemic and moving from 100% in-person training to 100% online training basically overnight, revealing not only the challenges faced but also the exact strategies she implemented to drive rapid growth and adapt to a rapidly changing business landscape.

The Catalyst for Change: Pivoting in a Pandemic

Harris’s tenure at Challenger began amidst the pandemic. She was met with the daunting task of revitalizing a company that was “dead in the water” due to the pandemic-induced halt in its traditional training services. Recognizing the urgent need to pivot, Harris spearheaded the transition to virtual and e-learning platforms, ensuring that the high demand for Challenger’s training could be met despite the constraints of the global crisis.

One of the most striking revelations from Harris was the absence of a demand generation and marketing strategy within Challenger. The company had previously relied heavily on leads from Gartner and engagements with legacy customers. Leveraging her background as a Chief Marketing Officer (CMO), Harris embarked on building a robust demand generation engine. This included optimizing the company’s website for SEO, engaging in social selling, and rebranding Challenger as an innovative tech company, thereby widening its appeal to include SMB and mid-market customers alongside its enterprise clientele.

Strategic Sales Team Restructuring

Harris didn’t stop at marketing transformations. She meticulously restructured the sales team to better align with customer segments, differentiating between new logo acquisition and existing account management. This strategic segmentation enabled Challenger to tailor its approach to various customer needs more effectively, showcasing Harris’s keen understanding of the nuances in customer buying processes.

Key Takeaways for CEOs:

Andee Harris’s journey with Challenger Sales Training Company offers invaluable lessons for CEOs navigating their businesses through uncertainty:

  1. Embrace Agility: The swift pivot to virtual and e-learning platforms was a testament to the importance of agility in business. CEOs should be ready to adapt their product delivery to meet customer needs, regardless of external pressures.
  2. Demand Generation is Key: Harris’s focus on building a demand generation engine highlights the critical role of marketing in driving growth. CEOs should ensure their companies have robust strategies for lead generation and brand positioning.
  3. Strategic Sales Team Structure: Tailoring sales strategies to customer segments can significantly enhance effectiveness. CEOs should consider how their sales teams are structured to best meet the diverse needs of their clientele.
  4. Customer-Centric Approach: Above all, Harris’s strategies were rooted in a deep understanding of customer needs and buying behaviors. CEOs should maintain a laser focus on serving their customers in the manner they prefer, ensuring success and satisfaction.

Andee Harris’s CEO journey, is a compelling case study on leading with resilience, innovation, and an unwavering focus on customer needs. Her success in transforming Challenger amidst unprecedented challenges offers inspiration and practical advice for CEOs looking to navigate their companies through turbulent times.

For a deeper dive into her strategies, challenges, and the innovative steps she took to transform Challenger, watch the full episode and subscribe to our channel!

Watch below or on our YouTube channel


[02:55] ‘Andee’s decision to become CEO of Challenger after selling High Ground’

[06:17] ‘Transition of Challenger’s founders and how opportunity came Andee’s way’

[08:43] ‘Overcoming the absence of demand generation and marketing at Challenger’

[10:42] ‘Andee’s strategy for developing lead generation and hiring new sales talent’

[13:19] ‘Fastest path to lead generation and impact on sales processes’

[16:25] ‘Upscaling sales talent and adapting to remote selling during Covid’

[17:08] ‘Recruiting the right salespeople and providing sales training under unique circumstances’

[18:52] ‘Segmenting the sales team according to customer needs and buying processes’

[21:06] ‘Finding the right sellers to handle segmented customer groups’

[22:47] ‘Aligning the structure of the sales team with customer acquisition and growth strategies’

[23:17] ‘Adapting to customer buying preferences and servicing key accounts’

[25:03] ‘Ongoing growth and hiring for the sales team at Challenger’

[26:01] ‘Training focus for sellers on understanding and addressing customer indecision’

[27:24] ‘Real-world impact of Challenger selling philosophy beyond sales’

[28:20] ‘Looking forward and recognizing the power of partnerships and integrations’

[32:33] ‘How the new Salesforce app will enhance the sales process with Challenger methodology cues’

About Guest

Andee Harris is the CEO of Challenger. A proven leader, Harris brings more than two decades of experience in growing and scaling service and technology businesses. She has previously led multiple companies, both as CEO and Senior Vice President, through periods of rapid revenue growth, critical fundraising and successful acquisition.

She is an unstoppable, successful business builder, right brain thinker in a left-brain world. She is known for clearing pathways by connecting data and people. Andee is an Adjunct Professor at Kellogg School of Management, sharing her entrepreneurial wisdom in the course, Launching and Leading Startups. She is a highly regarded technology thought leader with broad expertise in market share growth, business development, multi-channel marketing and revenue management.

Andee is a member of YPO Chicago and a board member to Bonfire, Chicago Ideas Week, Lyft Community Board and The Lurie Children’s Hospital Strategic Founders. She lives in Lincoln Square with her husband, two teenagers and black lab. She is an avid traveler and loves to cook and be outdoors.

Social Links

You can learn more about and connect with Andee Harris in the links below.


The Challenger Sale | Sales, Marketing, & CS Approach (

Winning The Challenger Sale podcast:

Winning the Challenger Sale – Sales Podcast | Challenger Inc

Andee on LinkedIn:

(99+) Andee (Weissman) Harris | LinkedIn

You can learn more about and connect with Alice Heiman in the links below.

Connect with Alice on LinkedIn:

(99+) Alice Heiman | LinkedIn

Check out Alice’s website:

Alice Heiman | Sales Consultant and Strategist for CEOs


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