How should founders diagnose and decide the fate of an underperforming head of sales?

Chris Degnan · Nov 10, 2023

Founders should put an experienced sales leader on their board or in an advisor role, because that person can diagnose whether the current sales leader can scale and give them the direct feedback needed.

CEOs and founders tend to point the finger at sales first; John McMahon's blunt feedback on Snowflake's board told Chris exactly what he had to do to keep his job, and he acted on it.

Scope: the key test is whether the sales leader acts on the feedback

43:37 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Chad Peets · Aug 23, 2024

Founders aren't to blame for not knowing what to look for in a sales hire — the failure is that they lack investors and board members who can tell them what to hire for

You can't make the right hire until you know what you're looking for, and most CEOs he consults with have no idea and no one to ask

60:11 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

Chad Peets · Jan 9, 2026

Founders are bad at hiring CROs and heads of sales — roughly 48 out of 50 CEOs he speaks to are not workable for him

He can tell from LinkedIn alone that the CRO they hired only worked at large companies and is wrong for them, and most founders aren't prepared to fire the CRO and half the reps

Scope: 'not right for me to work with' doesn't mean they aren't great founders

19:49 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Chad Peets · May 23, 2026

He will only engage with a company if the founder commits upfront to replacing a chief revenue officer he judges unworkable — it's black and white

Being polarizing up front is a good qualifier: founders who recoil shouldn't work with him, and those who want it get what the org needs

Scope: only when he has assessed the existing CRO as someone he can't work with

29:50 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

John McMahon · Nov 28, 2025

When a sales team misses its number, the root cause is usually that the CEO failed to plan hiring around ramp time, not that the head of sales failed to execute

If a CEO asks a CRO in November to double revenue with the same headcount and a six-month ramp, the hiring should have started in June; instead the CRO is told to hire late and then blamed

38:16 Ceo hiring plan not the sales leader is the root cause

Carles Reina · Feb 14, 2026 · hedged

When a sales team's numbers are down, the problem may well be the leader who doesn't understand the sales process, the product or the team's pain points

Sales leaders who only lead and never sell don't know the pain their team is suffering

34:00 Leader who never sells is the first suspect

David Schneider · Sep 11, 2024

When an internal go-to-market leader has the energy, intelligence, willpower and fear of failure, you should ride that horse and coach the gaps rather than replace them with an outside hire

Frank backed him at Data Domain after he missed his first-year number, and growth blew through the doubts before they could act; the good outweighed the bad by a long shot

18:56 Back the leader with innate drive and coach the gaps rather than replace

Chris Degnan · Nov 10, 2023

There is no single answer on whether founders fire heads of sales too fast or too slow — it's situational, and often the underlying problem is the founders not listening to customers or building the right product rather than the sales leader.

He has seen boards call a sales leader bad when the real issue was product-market fit, marketing lead generation, or product-sales communication; Frank's view is there is no playbook, it's situational.

44:41 Situational and often the real cause is product not sales