Prioritizing Grit and Obsession in Sales Hiring and Management

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · January 09, 2026 · Listen to Original Episode →

Original Title: 20Sales: The Best Sales People Are F***** in the Head | The Unspoken Truths All Sales Leaders Need to Know in 2026 | Why Europe is a Nightmare for Recruiting | How to Improve Sales Team Performance in 24 Hours with Chad Peets

TL;DR

Hiring sales talent requires prioritizing "grit" and a demonstrated track record of closing net-new logos over domain expertise, as these foundational traits are unteachable and critical for startup success.
Sales leaders must be willing to "fire fast" and hold individuals accountable to performance metrics beyond quota, as retaining underperformers erodes the morale and productivity of top performers.
The ideal sales candidate exhibits an obsessive passion for their craft and a history of overcoming significant life challenges, indicating resilience and a drive for mastery beyond mere financial motivation.
Duration at a single large company can be a red flag, suggesting a lack of adaptability or accountability, whereas short stints with clear explanations of lessons learned are more indicative of valuable experience.
Effective sales compensation plans require careful design, bifurcating productivity metrics from compensation structures to ensure unit economics remain sound and incentivize desired behaviors like new logo acquisition.
While AI will automate many sales functions, particularly SDR/BDR roles, the core need for human enterprise sales professionals to navigate complex, high-stakes deals will persist due to the requirement for trust and human connection.
A company's ability to scale hardware successfully, as demonstrated by Nvidia and XAI, is a critical differentiator in the AI race, suggesting compute power will be the ultimate determinant of market leadership.

Deep Dive

Chad Peets emphasizes that exceptional sales talent is defined by an obsessive drive and a willingness to endure hardship, arguing that true high-performers are "a little bit messed up in the head" with an unwavering focus on their work. This perspective shapes his recruitment philosophy, prioritizing individuals who demonstrate profound dedication and a history of overcoming significant challenges over mere technical skills or domain expertise. The implication is that organizations seeking to build elite sales teams must look beyond conventional metrics and identify candidates whose intrinsic motivation and resilience align with an all-consuming pursuit of excellence, a trait he believes is becoming increasingly rare and difficult to cultivate, particularly in regions with different cultural norms around work.

Peets’ core argument centers on the scarcity of deeply committed sales professionals and the critical need for leaders to identify and foster this specific type of talent. He posits that while many can articulate a passion for sales, only a select few exhibit the relentless obsession required to excel, often evidenced by their internal drive to be the best, a desire for impact, and a history of facing adversity. This focus on "grit" and an almost pathological dedication means that traditional hiring criteria, such as specific industry experience or large deal sizes, are secondary to a candidate's demonstrated resilience and unwavering work ethic. The second-order implication is that companies that fail to identify and recruit these "messed up in the head" individuals will inevitably underperform, as they will be staffed by individuals who are merely going through the motions rather than embodying the drive necessary for true sales mastery. Furthermore, Peets highlights that this intense dedication is a prerequisite for success in high-stakes environments like XAI, where the mission transcends financial incentives and requires a profound personal commitment.

The practical application of Peets’ philosophy extends to his views on sales team management and performance. He advocates for rigorous performance measurement beyond just quota attainment, emphasizing the importance of tracking metrics such as new customer meetings and conversion ratios. This data-driven approach underpins his conviction that a certain level of attrition, specifically targeting the bottom 10% of performers, is not only acceptable but necessary to maintain a high-performing culture. The consequence of not rigorously managing performance and allowing underperformers to persist is the erosion of morale among top performers, leading to their eventual departure. This aggressive stance on performance management, while potentially controversial, is presented as crucial for cultivating an environment where A-players thrive and are incentivized to remain, ultimately driving organizational success. His experience, particularly with XAI, reinforces his belief that even in cutting-edge fields, the fundamental principles of relentless execution and uncompromising performance standards remain paramount.

Action Items

Audit hiring process: Implement weekly one-on-one cadence with direct reports for leaders to assess engagement and business understanding.
Design performance review framework: Establish criteria for identifying and addressing the bottom 10% of sales performers annually.
Develop talent assessment rubric: Define key indicators for grit, obsession, and a track record of closing net new logos for sales candidates.
Create a "fire fast" protocol: Document a process for quickly addressing and resolving hiring mistakes within 10-14 days.
Measure sales productivity: Track new ACV per rep and establish a minimum 3x OTE benchmark for unit economics.

Key Quotes

"I need people just to be blunt that are a little messed up in the head like I am. That's what I need. When I wake up at 3 o'clock in the morning, the moment I become conscious of being awake, I'm thinking about my work. I can't help it, I'm obsessed. I wake up at 3 o'clock in the morning, 6 o'clock in the morning, 10 o'clock at night, and I can't help it. I'm obsessed with making sure we are doing things correctly, and I need people that are a little bit messed up in the head like that."

Chad Peets explains that he seeks individuals who possess an intense, almost obsessive dedication to their work, mirroring his own drive. He believes this level of commitment, characterized by constant focus on tasks and improvement, is crucial for success in high-performance environments. Peets emphasizes that this "messed up in the head" quality is not a flaw but a necessary trait for achieving excellence.

"I have to feel like I'm adding value with whoever I'm working with. I simply cannot be the guy that sits in the room and is sitting back and kind of hanging out. I'm just not capable of doing that. Number two, I have to find people that I want to work with that value not only what I bring to the table, but they've got to be able to put up with my approach, and you either love my approach or you hate it, and I would say more people hate it than love it. And then number three, I have to feel like I'm continuing to learn. It's so critical for me to work with people that I respect and can learn from."

Chad Peets outlines his criteria for choosing his work engagements, highlighting three core principles. Peets states he must feel he is contributing value, find colleagues who appreciate his direct approach (even if polarizing), and continuously engage in learning. These conditions are essential for him to remain motivated and productive in his professional endeavors.

"The number one thing is pipeline generation and landing new accounts. So when I say, 'Tell me about the deals that you've closed,' I don't care if you said, 'Well, look, I inherited this customer and I went and up-sold them.' Don't give a crap. Okay, that's not a value to me at a startup because at a startup, I'm going to give you 50 accounts that have never heard of us. So I want to know how many net new logos did you bring in? And if you can't tell me that you brought in net new logos, the interview is over super, super quickly, right? So that's the one thing that you have to have first and foremost is a demonstrated track record of closing new accounts."

Chad Peets emphasizes the critical importance of pipeline generation and acquiring new clients for startups. Peets explains that he prioritizes candidates who can demonstrate a history of bringing in net new logos, as this directly aligns with the needs of a startup environment where new business acquisition is paramount. He considers the ability to close new accounts a non-negotiable requirement for potential hires.

"The hardest working bunch of individuals I've ever seen. It's not about money, it's about missions, it's about purpose, it's about doing things correctly, and I love that. Love it."

Chad Peets describes the intense dedication of the team at XAI, highlighting their focus beyond financial gain. Peets notes that the team is driven by a sense of mission, purpose, and a commitment to executing tasks correctly. This collective drive and shared values create an environment he finds highly motivating and fulfilling.

"If you have A players in your company and they're surrounded by a bunch of B players and you're not holding those B players accountable, your A players will quit. I'm busting my butt. I'm an A player. I'm killing myself. I'm a shareholder in the company, and I've got three reps next to me that don't work hard, don't do the stuff I do, and you do nothing to them. Forget that. I'm not, I'm not going to put up with that. I'll quit."

Chad Peets argues that maintaining a high-performing sales team requires holding all members accountable, especially underperformers. Peets explains that A-players will leave if they perceive a lack of accountability for B-players, as it devalues their own hard work and commitment. He asserts that a culture of accountability is essential for retaining top talent and fostering a winning environment.

"Listen, we are all going to make hiring mistakes, as I just said to somebody yesterday in a, it was a bit of a tense conversation. We're all going to mess up. The difference between you and me is when I mess up, I own my mess-ups and I fix them quickly. You like to pretend like you didn't mess up and you want to give it more time and claim that you didn't make a mistake, which allows the problem to fester and get bigger. So will I fire fast? Yes, I will fire fast."

Chad Peets advocates for swift action when hiring mistakes are made, emphasizing accountability and rapid problem-solving. Peets distinguishes his approach by stating he owns and rectifies errors quickly, contrasting it with those who delay or deny mistakes, allowing issues to escalate. He confirms his commitment to firing quickly when necessary to address hiring missteps.

Resources

External Resources

Books

Videos & Documentaries

Research & Studies

Tools & Software

GRC - Mentioned as a tool for enabling sales people technically.

Articles & Papers

People

Chad Peets - Guest, CRO sales leader.
Harry Stabbings - Host of 20Sales.
Mike Palmer - CEO of Sigma Computing.
Brad Gishner - Mentioned as someone the speaker works with at Allmeter.
Apoorv - Mentioned as someone the speaker works with at Allmeter.
Mike Speiser - Mentioned as a mentor.
John McMan - Mentioned as a mentor.
Elon - Mentioned in relation to how he builds companies.
Chris Degnan - Mentioned as a friend and former colleague at Snowflake.
Shridhar Ramaswami - CEO of Snowflake.
Jeremy Duggan - Mentioned as a European sales leader.
Dolly Rojek - Chief Operating Officer at Wiz.
Scott Deaton - Mentioned for advice on parenting.

Organizations & Institutions

20Sales - Monthly show featuring sales leaders.
RokS - Company pioneering revenue agents.
Airwallets - Company providing an intelligent financial operating system.
Daily Body Coach - Service for founders and executives focused on health.
Sigma Computing - Company the speaker sits on the board of.
Allmeter - Company the speaker works with.
Augment Code - SaaS company the speaker sits on the board of.
Parloa - European-based company focused on AI for customer service.
XAI - Company the speaker is involved with, focused on AI and robotics.
Canva - Business mentioned as a client of Airwallets.
McLaren - Business mentioned as a client of Airwallets.
Deal - Business mentioned as a client of Airwallets.
Snowflake - Company where the speaker previously helped find efficiencies.
11 Labs - Company mentioned for its rapid scaling.
OpenAI - Company the speaker had a conversation with.
Anthropic - AI company mentioned as a leader in enterprise.
Nvidia - Company mentioned for its hardware at scale.
MongoDB - Company mentioned for its sales training and development.

Courses & Educational Resources

Websites & Online Resources

roks.com - Website for RokS.
airwallets.com - Website for Airwallets.
dailybodycoach.com - Website for Daily Body Coach.

Podcasts & Audio

Other Resources

Applied AI Talent - Mentioned in relation to RokS.
Revenue Agents - Mentioned as a product of RokS.
Global 2000 - Mentioned in relation to RokS.
Data Warehouse - Mentioned in relation to RokS.
CRM - Mentioned in relation to RokS and Airwallets.
Board Level ROI - Mentioned as a deliverable of RokS.
Sales and Revenue Agents - Mentioned as a product of RokS.
GTM Stack - Mentioned in relation to RokS.
Knowledge Graph - Mentioned in relation to RokS.
AE Productivity - Mentioned in relation to RokS.
Growth Tax - Mentioned in relation to Airwallets.
Payments and Finance Stack - Mentioned in relation to Airwallets.
Banking Portals - Mentioned in relation to Airwallets.
Manual Reconciliation and Reporting - Mentioned in relation to Airwallets.
Operational Drag - Mentioned in relation to Airwallets.
Intelligent Financial Operating System - Mentioned as a product of Airwallets.
Banking, Treasury, Payments, and Spend - Mentioned as functions managed by Airwallets.
Generative Finance - Mentioned as an investment area for Airwallets.
High Touch Service - Mentioned in relation to Daily Body Coach.
Personalized Nutrition and Training - Mentioned in relation to Daily Body Coach.
Psychology Based Coaching - Mentioned in relation to Daily Body Coach.
Systems, Habits, and Mindset - Mentioned in relation to Daily Body Coach.
DEXA Scans and Blood Work - Mentioned in relation to Daily Body Coach.
SaaS - Mentioned in relation to Augment Code.
Cursor Competitor - Mentioned in relation to Augment Code.
AI for Customer Service - Mentioned as a use case for Parloa.
Customer Support - Mentioned in relation to Parloa.
AI - Mentioned in various contexts throughout the episode.
LLMs - Mentioned in relation to AI and sales.
Enterprise Sales - A primary theme of the discussion.
Sales Reps - Mentioned throughout the episode.
CRO (Chief Revenue Officer) - Mentioned in relation to hiring.
Head of Sales - Mentioned in relation to hiring.
Immigrants - Mentioned as a demographic for hiring.
Eastern Europeans - Mentioned as a demographic for hiring.
Passion - Mentioned as an interview topic.
Grit - Mentioned as a trait to measure in candidates.
Pipeline Generation - Mentioned as a key sales function.
Net New Logos - Mentioned as a key sales metric.
Deal Size - Mentioned in relation to sales experience.
Domain Expertise - Mentioned as a trainable skill.
Integrity - Mentioned as an untrainable skill.
Ramp Time - Mentioned in relation to hiring and enablement.
Sales Organization - Mentioned in relation to company quality.
C Players - Mentioned in relation to hiring from competitors.
B Players - Mentioned in relation to hiring for talent.
A Players - Mentioned in relation to company culture.
Productivity Model - Mentioned in relation to sales forecasting.
Attrition Rates - Mentioned in relation to sales team performance.
Involuntary Attrition - Mentioned in relation to firing.
Over Hiring - Mentioned as a strategy for managing attrition.
Culture of Fear - Mentioned as a potential outcome of firing fast.
Apprenticeship Businesses - Mentioned in relation to in-person work.
Hero to Zero - Saying about switching between work and home personas.
Full Time Mom - Mentioned in relation to family support.
Mission Focused - Mentioned in relation to XAI employees.
Compute - Mentioned as a critical factor in AI.
Hardware at Scale - Mentioned in relation to XAI's advantage.
Sales Morale - Mentioned in relation to XAI.
APIs - Mentioned in relation to XAI and enterprise sales.
Enterprise Hardware Robotics - Mentioned as a frontier for XAI.
New Hiring Red Flag - Mentioned as a new concern for leaders.
One on Ones - Mentioned as a crucial meeting cadence.
Shitty Product - Mentioned as a factor that can lead to failure.
Sales Execution - Mentioned as a critical factor in sales.
New ACV (Annual Contract Value) - Mentioned in relation to comp plans.
Expansion ACV - Mentioned in relation to comp plans.
Net Dollar Retention (NDR) - Mentioned in relation to expansion ACV.
Accelerators - Mentioned in relation to comp plans.
Comp Plans - Mentioned in relation to sales motivation.
Productivity - Mentioned in relation to measuring business health.
Quota - Mentioned as a measure of compensation.
Unit Economics - Mentioned in relation to sales compensation.
OTE (On-Target Earnings) - Mentioned in relation to sales compensation.
Emerging Market - Mentioned in relation to comp plan grace.
Established Business - Mentioned in relation to comp plan expectations.
Salesforce - Company mentioned in relation to hiring.
New Logo Gate - Mentioned in relation to comp plans.
Chinese Style Work - Mentioned in relation to work hours.
Balance and Presence - Mentioned in relation to work-life integration.
Respect - Mentioned as a requirement for sales leaders.
Conflict - Mentioned as a necessary part of leadership.
Country Club Days - Mentioned in relation to past work culture.
HR Complaints - Mentioned as a reaction to direct feedback.
Apprenticeship - Mentioned in relation to sales learning.
Hero to Zero Drive - Mentioned in relation to context switching.
Grit - Mentioned in relation to teaching children.
National Geographic and Discovery Channel - Mentioned as parenting resources.
Mission - Mentioned as a driver for XAI employees.
AI Driven Robots - Mentioned as a future of enterprise.
Compute - Mentioned as a key differentiator for XAI.
Hardware at Scale - Mentioned as a key differentiator for XAI.
Sales Morale - Mentioned as a positive aspect of XAI.
APIs - Mentioned as a product offering for XAI.
Enterprise Software - Mentioned in relation to Anthropic.
Consumer and Chat GPT - Mentioned in relation to OpenAI.
Enterprise Hardware Robotics Frontier - Mentioned in relation to XAI.
Rate of Change - Mentioned in relation to XAI's model.
Trillion Dollar Deals - Mentioned in relation to compute.
Sales Teams - Mentioned throughout the episode.
SDRs (Sales Development Representatives) - Mentioned as a role likely to be replaced by AI.
BDRs (Business Development Representatives) - Mentioned as a role likely to be replaced by AI.
Pre Sales Engineer - Mentioned as a changing role due to AI.
Forward Deployed Engineer - Mentioned as a role in post-sales.
Sales Engineer - Mentioned as a role.
Demos - Mentioned in relation to sales reps performing them.
Post Sales - Mentioned in relation to forward deployed engineers.
World Class Go to Market Function - Mentioned as a focus for hiring.
Training and Development - Mentioned in relation to MongoDB's sales organization.
Personality Clash - Mentioned in relation to a conversation with OpenAI.
Enterprise Software - Mentioned in relation to Anthropic.
Consumer and Chat GPT - Mentioned in relation to OpenAI.
Enterprise Hardware Robotics Frontier - Mention