20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

McMahon explains how sales has evolved from perpetual licenses to subscription to consumption-based models, fundamentally changing value realization timelines. He discusses how the art of sales (dealing with people) remains constant, but the science and discipline around sales processes has become more formalized. The shift to consumption models means companies now have weeks instead of years to prove value.

• •Sales process discipline has become more regimented with formal playbooks, ideal customer profiles, and messaging frameworks
• •Consumption/PLG models compress value realization from years to weeks, making net dollar retention critical
• •The art of sales (adapting to different personality types) hasn't changed, but execution speed requirements have accelerated
• •Smaller initial ACVs in consumption models require different sales org structures and investment strategies

McMahon reveals his approach to separating signal from noise in deals using frameworks like MEDDIC. He emphasizes that if a rep has been in an account for six months claiming to have a champion but hasn't met the economic buyer, they don't actually have a champion and won't get the deal. The key is understanding exactly where reps are in the sales process versus where they think they are.

• •Use qualifying questions to determine where reps actually are in the sales process, not where they think they are
• •The most revealing question: 'Have you met the economic buyer?' - if not after 6 months, you don't have a champion
• •Sales process is like GPS - you need to know your exact location to get accurate directions to close
• •Most lost deals result from skipping steps in the sales process, particularly around champion development

McMahon explains how to win deals by locking down decision criteria through champions who understand your differentiators solve their pain. He reveals the critical technique of implicating pain by asking 'who suffers and what suffers' if problems aren't solved. This creates genuine urgency that can't be manufactured through discounting.

• •Lock down decision criteria by aligning your differentiators to quantified pains in the customer's process
• •Ask 'who suffers and what suffers' if pain isn't solved - this implicates pain and drives real urgency
• •Control in sales belongs to either the customer, you, or your competition - champions help you take control
• •Never discount to drive urgency - only discount at quarter-end for deals you're getting anyway
• •Prepare champions for internal meetings by predicting objections and ensuring they can defend your solution

McMahon strongly advocates for hiring 'athletes' with intelligence and PhD (Persistence, Heart, Desire) over domain experts. At PTC, they specifically avoided hiring anyone who had sold mechanical CAD software before. He looks for people who are coachable and adaptable, noting that many reps are coachable but fail to actually adapt their behavior.

• •Hire for intelligence and PhD (Persistence, Heart, Desire) over domain knowledge - smart people learn quickly
• •Domain experts bring baggage and preconceptions; athletes bring adaptability and drive
• •Coachability is necessary but insufficient - reps must actually adapt and change their skill sets
• •The best reps adapt as products, markets, and competition evolve; many hit walls when they can't change

McMahon identifies listening as the single most important skill for sales success and the hardest to develop. He teaches reps to 'listen with the intent to understand, not the intent to reply' and to ask five or six follow-up questions before talking about their product. Great reps like Carlo Carpinelli used genuine curiosity and security to disarm customers.

• •Listen with intent to understand, not intent to reply - ask multiple follow-up questions before presenting
• •Most sales reps are horrible listeners who talk too much about their product too early
• •John Kaplan's principle: 'Customers don't care how much you know until they know how much you care'
• •The best salespeople are secure enough to be genuinely curious and ask 'why?' without defensiveness

McMahon describes his rigorous onboarding process requiring reps to learn prerequisites before training, then testing them on day one. If they fail, it reflects poorly on both the rep and their hiring manager. He puts new reps on calls immediately but focuses training on skill development, not just knowledge transfer, recognizing that skills take much longer to develop.

• •Send prerequisites (product differentiators, competition, ICP, case studies) before training starts
• •Test reps on day one - failure indicates either lack of preparation or poor hiring manager oversight
• •Put reps on customer calls immediately (listening/shadowing), let them lead relatively quickly
• •Focus on skill development (how to execute) not just knowledge (what to do) - skills require repetition like throwing darts 1000 times

McMahon reveals he can't remember the last time he missed a number, attributing this to rigorous planning with CEOs around ramp times and hiring schedules. He explains how first-time CROs get trapped by agreeing to double revenue without accounting for six-month ramp times, leading to rushed hiring of B and C players, bad culture, and missed numbers.

• •Plan hiring six months ahead of when you need the revenue, accounting for ramp time
• •Example: To do $20M next year vs $10M this year with 6-month ramp, start hiring in June, not January
• •Rushed hiring to hit aggressive targets leads to B/C players, managers taking quotas, bad culture, and discounting
• •Better to hire 8 great reps slowly than 20 mediocre reps quickly - protect culture and predictability

McMahon shares the story of keeping a rep who went 13 months without a deal because he saw incremental skill improvements in every sales call and internal meeting. He contrasts this with managers who can't articulate specific skill gaps and give vague answers like 'lack of grit.' The key is identifying the exact step in the sales process where reps get stuck.

• •Don't fire based on time alone - look for incremental improvements in knowledge and skills
• •Example: Kept a rep for 13 months without a sale who then closed two $1M+ deals because he showed progress
• •Managers must identify specific skill gaps (e.g., 'can't develop champions' or 'struggles with metrics') not vague generalizations
• •Use the hockey line analogy - demote underperformers to lower lines publicly so they know what to improve

McMahon discusses the limitations of remote selling, particularly the loss of intuition and gut feel that comes from reading a room in person. He also warns about the 'PLG trap' where companies build cost models around PLG, then struggle to transition to enterprise sales requiring $300K OTE reps and different go-to-market motions.

• •Remote work enables access to higher-level executives but eliminates gut feel and intuition from reading rooms
• •In-person meetings allow you to identify gatekeepers, champions, and enemies by observing body language and handshakes
• •Not all products can be sold through PLG - complex solutions requiring multiple stakeholders need traditional sales
• •Companies that start PLG-only often hit walls when trying to move upmarket due to incompatible cost structures and cultures

McMahon shares his personal story of growing up poor with a father who never went to junior high school and lived in a chicken coop as a teenager. This background drove his extreme persistence and discipline, including waking at 4:50 AM every day regardless of time zone. He has a rule: if he lays in bed for four days in a row after the alarm, he quits the job.

• •Wake at 4:50 AM daily to work out before family time - non-negotiable for mental clarity and patience
• •If you lay in bed 4 days in a row when alarm goes off, quit the job - it means something is fundamentally wrong
• •Persistence, heart, and desire (PhD) matter more than raw intelligence - willingness to outwork everyone
• •Balance work intensity with family by getting up early, not sacrificing weekends to golf with colleagues
• •Childhood hardship and father's suffering created unshakeable drive to succeed and prove himself