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#1 vs. #2

Updated: Sep 19

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 Typically C-Level

#2 at a larger company Often VP / Head Of

Sales

CRO / Head of Sales

Enterprise Sales SMB Sales

Sales Development Sales Engineering

Marketing

CMO

Demand Gen

Product Marketing Brand

Customer Success

CCO / VP of CS

Enterprise CS Scale (tech-touch) CS Professional Services

Support Account management (sometimes in sales)

RevOps

VP of RevOps

SOPS GTM Systems

Sales Strategy Post-Sale (CS) Operations

MOPS

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)

Other Considerations


  • Sometimes you can create a role by talking to a C-Level leader. You will have much higher chance of success when targeting a #2 role

  • When thinking about taking a #1 role, some reasons that can help increase the success include:

    • You have worked with someone in the C-Suite before

    • You know the industry well


Want more inspiration... ?

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