Matthew Dixon, author of The Challenger Sale, said it best when discussing the difficulty of closing complex, high value sales when he commented, “Buyers don’t have time for their own best friends today!”

The environment to win new business is particularly challenging today given the need for extensive client collaboration in architecting built-to-suit solutions.

One of the most important sales strategy decisions is determining the right level of experience to invest in for your client-facing sales executives. In this article, we are focusing on the sales executive/buyer dynamics on deals with an average deal size of $1M+ per year.

These are two critical circumstances in the marketplace to consider when deciding what is the right sales executive profile to sell complex, high contract value solutions today:

  1. Buyers need built-to-suit solutions that can only get architected through collaborative, guards-down meetings with potential providers;
  2. Buyers don’t have time for these meetings or to meet new people!

This is worth repeating: VP buyers don’t have the time to have the meetings they need to truly understand how a particular vendor can leverage their assets and capabilities for optimal value-added solutions.

Given these circumstances, you must have individual contributors with equal or greater executive presence than their peers on the prospective client side. This factor, combined with deep industry experience, leads to relevant, content-rich conversations that offer the potential to engage on a more strategic level.

Hiring a sales executive with a strong “rolodex” is one way to acquire the guards-down dynamic required to architect built-to-suit deals. However, this profile must simultaneously have strong domain expertise and the rights soft skills required for ongoing success.

What does a modern sales executive look like that is capable of getting meetings and closing business with time-pressed, value-driven executives?

  • Strong executive presence for a peer-to-peer dynamic with prospects – the basis for unguarded discussions and getting to solutions that create the most value for clients;
  • Natural sales executive who gets their adrenaline from the deal, yet is simultaneously measured, analytical, empathetic and disciplined;
  • Deep domain knowledge;
  • Reflexively comfortable with change;
  • Charm comes less from personality and more from engaging in highly relevant conversations and out-preparing others;
  • Excitement about technology and how software can drive efficiencies for clients;
  • Hands-on approach to owning meeting preparation and executive summaries.

Sales organization design that was effective and differentiated four years ago does not work today; and what is effective and differentiated today will not be effective in four years. As you contemplate individual contributor talent in your sales organization, look for someone who understands the demanding work of selling on value to each prospective client. Finally, consider investing in top-heavy individual contributors if that is the only realistic way to produce a peer-to-peer environment with your prospective clients. Doing so might be the only way to execute strategic, built-to-suit deals that benefit both parties.

About Kit Cooper

Kit Cooper has spent much of his career founding and running two successful business services companies, both of which relied on highly adaptive sales organizations selling multi-million deals to Fortune 1000 companies. As Managing Director for Taylor Winfield, Kit works with private-equity and high growth companies to build enterprise value through world-class management teams.