#1 vs. #2

We see hundreds of career focus statements from top executives each week.  Inevitably, executives want to be the leader of their function.   

But in many cases, a better move is to pursue a #2 role at a larger, breakout company. 

“Taking a #2 role is a strategic move, not a step down. The right #2 role will allow you to learn from a great leader, build your skills, and accelerate your path to a top leadership position.”  Whispered member

Instead of taking a C-Level role at a smaller company, here are alternatives you can take at larger companies:

	#1 at a smaller company	#2 at a larger company
Sales	CRO / Head of Sales	VP of Enterprise Sales Head of Sales Development
Marketing	CMO	VP of Demand Gen VP of Product Marketing
Customer Success	CCO / VP of CS	Head of Professional Services Director of Mid-Market CS Head of Support
RevOps	VP of RevOps	Director of GTM Systems Sr. Director of Sales Strategy Director of MOPS VP, GTM Enablement

The tradeoffs between #1 and #2 roles

If you have all of the following, definitely stay focused on getting the top role in your function:

• Strong enterprise logos

• Experience leading entire function

But if you are still in the middle of your career or hearing feedback like:

• “You haven’t operated at this size before”

• “You don’t have all the skills we need”

Then consider targeting larger companies where you can get a role working for a great senior leader.  Here are some of the considerations and tradeoffs:

	#1 at a smaller company	#2 at a larger company
Air Cover	Limited since you report to to C-Level	You have someone who understands your function and is immersed at C-level
Mentorship	Your manager isn’t deep in your function so can’t provide much guidance	Your manager is an expert in your function and can guide your success
Growth Potential	You are at senior level, little growth potential at company	You can take on more responsibility in your function
Brand Recognition	Limited to what you’ve led before	Can get much bigger logo
Company GTM	May still be figuring out PMF	Has PMF and scaling
Support	You need to do it yourself	You have strong enablement, RevOps….

If you are strong but don’t have the resume to prove it, consider coming in as a #2 for a great leader and crush your role.  You will often find rapid promotion, opportunity to add skill sets, and that you are getting recruiter calls to hire you for #1 roles.

Determining whether to take this step down involves a lot of considerations. Below is a great podcast on this topic from a great executive.

"I think you are way more likely to be successful when someone is stretching up into the role because they are going to have a chip on their shoulder..... they might feel like the role isn't big enough for them... they will want to hire a team that is bigger than it needs to be. With that said, I've seen plenty (times when this works well) but then you really have to test for humility." Eeke de Milliano, Head of Product at Stripe (see podcast.. at 32:20)

Want more inspiration... ?

See this amazing reflection from an executive