In general do you think it's easier to sell to a new leader or a more tenured leader? Who do you prefer to target?

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Director of Sales2 months ago
Definitely selling to a new leader, they are open to change and new ideas before they get established. They are looking for a quick win to prove the ROI.
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CSO2 months ago
Each is easy. Each is difficult. We sell to the individual so first do your research then tailor your presentation accordingly. Selling is:

“Persuading someone of the merits of …”.

And the dictionary definition of merit is
“The quality of being particularly good or worthy, especially so as to deserve praise or reward”

Around these definitions we can build our whole story and actions by asking
“What are we good at and how can we influence the leader to agree with our value proposition?”

We now decide to whom we wish to communicate and what will be our brand/sales promise.

Depending on whether the leader is new or tenured will influence the approach and presentation.

Factors to take into account will be selling to the leader's dominant communication and behavioural style - Researcher, Expressive, Amiable, Director. All the time LOQ-on to the leader - Listen, Observe, Question.

When you embrace that selling is persuading someone of the merits of … it becomes a "pull" not a "push"

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Founder in Services (non-Government)2 months ago
People new to the role may be better positioned and lean more toward considering innovative products and services. They tend to be less attached to the status-quo and more open to considering new ways of doing things. On the other-hand, a more tenured leader may better able to relate to the pain points you can discuss and how your solution provides relief from the problems this person has been dealing with for too long already.
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Founder in IT Services2 months ago
People who are new are more likely to want to shake things up or take bold action.  However, their ability to get budget and close the deal may be more tenuous.   Also their ability to fully understand the needs and how to execute within their company may be limited.   Best bet if you're selling to a new leader is to make sure you have others involved in the sales process who have been around longer so don't take a risk of having a rogue/ineffective new leader who is unable to get the deal closed or to support a successful rollout. 
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Define lower level customers? Are you referring to non c level audience I.e. managers? Or enterprise c level vs small businesses?
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