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Building go-to-market teams

Aug 17, 2021


5 not-so-obvious hiring red flags 🚩


What is more critical to a fast growth technology company than effective hiring? 

When I’m building go-to-market teams, at least 50% of my time is spent on a variety of hiring related tasks. Once you get to a certain point, which is not long after Product Market Fit, nothing is more important than hiring in my opinion.

To me, hiring should be an “always on” motion. The best leaders NEVER stop thinking about hiring, and are always networking with their potential future hires.

Regardless, even with this level of commitment it’s still so easy to get hiring wrong. It’s really tough, especially when it comes to hiring go-to-market teams, who by nature are great at selling themselves.


Here are 5 not-so-obvious red flags to help you make the right hires:


  1. Screen for functional expertise over industry expertise

    This is perhaps the most common mistake I see. The precise mistake I observe is the failure to correctly screen for functional expertise of building and closing pipeline, at or above industry standards conversion rates.

    If someone can prove they are a functional expert in the trade of B2B technology sales at your stage of company with your $ACV (annual contract value), and they can clearly outline their scientific process to build and close pipeline at or above industry standards, I would hire that candidate every day ahead of the industry expert who struggles to clearly outline their pipeline build and close process.
    Obviously, if you are able to find the candidate who can illustrate both functional and industry expertise this candidate will naturally rise to the top of the pile.

  2. Don’t be wowed by the candidate’s rolodex (contacts)

    When companies are going through fast growth, it is easy to understand why a founder would be wowed by someone’s contacts. They appear to offer a fast route to conversations that will lead to deals, given the candidate has pre-existing trusted relationships.

    The sales person that offers longevity, offers far more than their contact list, and frankly the best sales people would feel demeaned if they were being hired primarily for their contact list, and will be wary of their perceived value diminishing once the contact list has been worked. The best candidates will shy away from leaning heavily on their contact list as a reason for hiring them.
    In short a candidate’s rolodex (contact list) should not be a primary driver for hiring someone, and if a candidate over indexes on their contacts as a reason to hire them, solid red flag, pass there and then.

  3. Screen for an $ACV (annual contract value) that is reflective of your own

    This one is simple, but often overlooked. The motions involved with high value, low volume sales (Enterprise) are very different to the motions involved in low value, high volume product/marketing led sales in the SMB.
    Hire the candidate that can prove they have sold the $ACV you are selling to, in order to maximize your chance of success.

    If a candidate has done both enterprise and SMB, establish where have they been most successful, and where their real passion lies, it should be obvious. Are they able to clearly articulate why they prefer the differences in each sales motion? If they can’t convince you, red flag, pass.

  4. Screen for someone who has been successful in an environment with similar resources to your own

    If you are evolving from founder led sales in a boot-strapped start-up, then it should be obvious that hiring someone out of Oracle or Salesforce is a bad move.
    It’s amazing how frequently I see this mistake being made. The candidate moves for the title and glamour, lack of red tape and the lure of no glass ceilings; and the founder makes the move because that person is a “safe bet” as they are clearly “proven”.

    Sadly, 9 times out of 10, the candidate learns they cannot function in a relative resource poor environment with little to no brand recognition, and the founder discovers the candidate cannot function effectively without an army of resources and brand awareness.

  5. Screen for real-world experience

    Don’t be fooled by the text book warrior.  For those that have never entered the field of battle, but want to lead a go-to-market team this is a “sorry, not sorry” moment.  You need to have experienced the field of battle first hand, to be credible in front or alongside of your future team.   There are hundreds of outstanding sales and management books out there. Some of my favorites are: “How to Win Friends and Influence People” by Dale Carnegie; “High Output Management” by Andy Grove; “Proactive Selling” by Skip Miller and “The New Strategic Selling” by Miller and Heiman.

    Absolutely none of these excellent scripts are a substitute for the hard yards of wisdom learned from engaging successfully and unsuccessfully with prospects and customers at every stage of the sales cycle.

    You and your go-to-market team need to be able to look into the whites of the eyes of this future colleague and trust they have what it takes to succeed in the unforgiving field of battle that is sales. In an interview process, one way I screen for this is by getting deep into a few of the deals they have done throughout their career to date.  I typically use the exercise stage of an interview process get into this kind of detail.


This is not an exhaustive list, please feel free to add your own suggestions in the comments, I’d love to hear them. 

Good luck!