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March 31, 2025 59 mins

How do you balance a changing buying process, countless technologies to use, unrealistic expectations, and an extremely crowded market? That’s the challenge facing Chief Revenue Officers (CROs). Not to mention that there seems to be significant debate about what the role of CRO actually entails and where CROs should focus their attention. 

That’s why we’re talking with Jack Wilson, EVP of North America, at amplify5 leveraging his extensive experience in developing strategies, building high-performance teams, and delivering revenue and profitable growth. Jack is an accomplished senior executive, entrepreneur, and advisory board member with more than 25 years of successful executive leadership experience in various industries. He has experience in international market development, closing multi-million dollar deals, and building international sales teams. He’s been a part of six successful exits including an IPO with triple-digit growth with every venture. He’s also an avid runner who has participated in numerous marathons and Ultra Marathons including the Moab 240, and placed in the top 20 in the Ironman.

In this episode, Stephanie and Jack talk about when it’s time to hire your first sales leader, the role of a Chief Revenue Officer, what sales really wants from marketing, dealing with unattainable quotas, and so much more. and so much more. 

Key Takeaways:

  1. The CRO role is more than just sales. It should oversee all revenue functional areas including sales, marketing, and customer success. 
  2. Executives need to have more open and honest communication with each other. Executive team meetings should be a healthy debate each week to hold each other accountable and bring out the best ideas. 
  3. Never hire a sales leader until you have at least three sales reps consistently hitting their quota. A player/coach sales leader will never be successful.
  4. Companies need to invest significantly more in marketing. Bringing in an experienced sales leader won’t result in more sales if you have an existing pipeline problem. Invest in marketing and fix your pipeline problem first. 
  5. Prospects have become highly sophisticated in the buying process and want clear information from your company available to them. Start with your website and make it easy to understand. 
  6. Sales professionals are closers. They don’t want your leads. They want REAL opportunities that need to be worked. 
  7. Most sales quotas are spreadsheet exercises based on how much the company theoretically wants to grow rather than how much growth is realistic. Financial targets shouldn’t be created in a vacuum without significant input from your sales, marketing, and customer success leaders. 
  8. Don’t underestimate the impact of personal communication such as handwritten thank-you notes.
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