What is "Senior Sales Leadership" for a Startup?

A couple of early-stage CEO clients have recently asked me if they should be hiring sales leaders with "big company experience" or from a more entrepreneurial environment.  I've been thinking a lot about this important make-or-break question. 

As a startup CEO, one of the most critical decisions you will make is hiring a senior sales leader to drive revenue growth for your company.  

The right sales leader can be the key to accelerating your business's success and achieving your goals. The wrong hire can set you back years, easily cost 6 or 7 figures in wasted expenses, damage or fray important relationships, and undermine confidence among the rest of the team.  

When it comes to hiring a senior sales leader, there are two main types of candidates to consider: those with big company experience and those with entrepreneurial experience. Each has its pros and cons, and the decision criteria for choosing the right candidate for your business will depend on several factors. 

Big Company Experience 

Senior sales leaders with big company experience often come from well-established organizations with proven sales processes and infrastructure. They have experience managing large sales teams, working with complex sales processes, and navigating bureaucratic decision-making. 

If your business is looking to scale rapidly and needs to establish a solid foundation for sales operations, a senior sales leader with big company experience can be an excellent choice. They bring a wealth of knowledge about sales processes and best practices, as well as established networks and relationships within the industry. 

However, big company experience can also come with downsides. Senior sales leaders with big company experience may be more risk-averse and less adaptable to change. They may be used to working within the confines of well-established sales processes and may struggle to innovate or adapt quickly to new market conditions. 

Entrepreneurial Experience 

On the other hand, senior sales leaders with entrepreneurial experience bring a different set of skills and strengths to the table. They are used to working in fast-paced, dynamic environments where they need to be adaptable and innovative to succeed. 

Entrepreneurial sales leaders are comfortable taking risks and finding creative solutions to problems. They are skilled at building relationships from scratch and have a strong sense of ownership over their work. They are also used to working with limited resources and can be more cost-effective than candidates with big company experience. 

However, those with overarching entrepreneurial experience may struggle to scale sales operations and build sustainable sales processes. They may not have the same level of knowledge or experience with complex sales structures and may struggle to manage large teams effectively. 

Decision Criteria 

When deciding between a senior sales leader with big company experience and one with entrepreneurial experience, it's essential to consider several factors.  

First, consider the stage of your business. If you're in the early stages of your business and need to establish a solid sales process, a candidate with big company experience may be the best choice.  

However, if you're in a fast-paced, dynamic industry, a candidate with entrepreneurial experience may be a better fit. 

You should also consider your goals for revenue growth and your timeline for achieving those goals. A candidate with big company experience may be better equipped to help you achieve rapid growth, while a candidate with entrepreneurial experience may be better suited to building sustainable, long-term revenue streams. 

Ultimately, the decision criteria for hiring a senior sales leader will depend on the unique needs and goals of your business -- and the strengths of each type of candidate. Choose the one that is best suited to help you achieve your goals. Either way, this question and its answers get to the core DNA of company culture, leadership, priorities, and the likelihood of growth outcomes. 

Contact me if you want to discuss the topic for your own business.