The Toughest Role You'll Hire in 2022

Over the 20 years of business working with Founders, CEOs, and their Heads of Talent, we've played an active role in the early stage decisions that need to be made to stand up functions like Product Management, Marketing, and Sales.

While hiring the first functional leaders for each team is a thrilling process, there is a role that most leaders will admit is the toughest you will ever be asked to hire for: THE LEADER WHO CAN DELIVER SCALE.

The functional leader who can step into a business (with revenues exceeding $50-100M) and transform their function, whether sales, marketing, engineering, or product. Technically, these businesses are no longer considered startups by anyone except the Founding team, for whom the company will always be their startup.

The leader who can enable global scale is the toughest role any leader will make. Why? 

  1. The Founder will need to let go 
  2. The hire will disrupt

Letting Go

A lot has already been written about Founders who struggle to let go, but we're not here to focus on Founder psychology

Today we're highlighting the moment (we’ve had many front-row seats to) when a Founder makes the bold move to hire a leader who is "better than they are." And in most cases, it works out great.

When it comes to attracting and recruiting, the humility and wisdom of a Founder are valued qualities that will help them attract the talent they need. Senior-level executives can sense when a Founder is resisting changes recommended by the Board, and the best-of-the-best want no part in that gong show. 


In the world of tech startups, the word "disrupt" has shed its negative connotations and is instead worn as a badge of honour among tech Founders. We've had the privilege of partnering with Founders who are disrupting:

Disruption also occurs when any business decides to hire leaders to enable scale. And this disruption of the company can take many forms:

  • Organizational Structure 
    • Reporting structures
    • Hiring practices and speed to hire 
    • Newly built-out teams
  • GTM Strategies
    • Addition of BDRs or Lead Gen into sales cycles
    • Opening up or closing of channel partners 
    • Shifts from geography-focused reps to vertical-focused selling
    • Territory carve ups 
    • International expansion
  • Process Reengineering
    • Agile transformations  
    • Spotify Squad model implementation
    • Sales team processes and hand off points
  • Technology Transformation
    • MarTech substitutions or additions 
    • Trello/Asana
    • Tech for tech; the options are endless, and every leader has their preferences.

When new leadership joins with a mandate to scale, you can be assured not only will the tools and team change, the processes to help enable that scale will change as well.

All of this creates a natural disruption as well as a culture shift. Which can be an extremely tough pill for a Founder to swallow, but needs to be done if scale and growth are to happen. 

When hiring a leader with the mandate to scale, it is crucial to be in a position of readiness to accept the changes that come along with the hire. It is also important to be in the best possible position to find that hire. 

Whether through an introduction via your rockstar investor or a specialized recruitment agency, ensuring you have the best partners to help you find leaders who have done this before and can trust will help give you the confidence to let go and embrace disruption.


Unhappy with the results of your current search processes? As a disruptor in your industry, you need to partner with a recruiting disruptor to find the right talent for your organization.