"Avoiding the No Is the Game"

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"Avoiding the No Is the Game"

With Tom Castley, Chief Sales Officer at Sedna

Jul 29, 2025

Quick recap

Tom Castley, a veteran in sales, discussed the evolution of technology purchases and the importance of understanding buyer archetypes to scale sales processes effectively. He emphasized the need for salespeople to create compelling cases for their products and shared insights on improving win rates through a reverse demo process. Castley also highlighted the significance of maintaining momentum during the sales process and structuring post-sales efforts as project management to ensure successful deal closures.

Summary

Understanding Technology Buyer Archetypes

Tom Castley, a veteran in sales with experience bringing American software companies to Europe, discussed the evolution of sales and technology purchases. He identified three main categories of technology buyers: "world on fire" solutions, which are urgent and necessary; "next big thing" innovations, often associated with AI and new technologies; and "shiny new toys," which include speculative investments like Bitcoin.

Tom emphasized that while technology sales can be complex, understanding these buyer archetypes can help companies scale their sales processes more effectively.

Enhancing Sales Win Rate Strategies

Tom discussed the challenges in sales, emphasizing the importance of understanding and improving win rates by breaking down problems into smaller, manageable chunks. He highlighted the difference between inspiring change and closing deals, advocating for a new definition of win rate that focuses on the number of companies that decide to make a change, rather than just the number that choose the company's solution.

Tom also stressed the need for salespeople to create compelling, emotionally resonant cases for their products in a world saturated with information and options, comparing it to the depth of analysis required in medical decisions.

Reverse Demo Process Success Story

Tom shared his experience with a reverse demo process inspired by Matt Borniac and Goddard Abel, which has led to an 85% conversion rate. He emphasized the importance of genuine curiosity and spending time understanding the customer's business before demonstrating the solution.

Tom also discussed the need for a tailored approach and the use of tools like Demo Monkey to create a more personalized demo experience. The process has been successful in building emotional commitment and momentum, leading to higher close rates.

Sales Process Engagement Strategies

Tom discussed the importance of maintaining momentum and engagement during the sales process, emphasizing the need to navigate deliberate hurdles and compartmentalized information within large organizations. He highlighted the significance of the emotional stage in securing a deal, which typically takes no more than six weeks, compared to the extended rational stage that often follows.

Tom advised structuring the post-sales process as a project management effort, ensuring clarity on next steps and maintaining communication to prevent potential deal breakdowns. He also stressed the importance of disqualifying early if necessary and involving key stakeholders at the right stages to ensure a smooth process.

Title: A Legend, Maybe Not a Legend
Timestamp: 0:17
The guest opens with humility and humour after being introduced as a legend in the sales community.
Title: Started Selling SaaS Before SaaS
Timestamp: 0:52
A reflection on a long sales career that began before “SaaS” was even a recognised term.
Title: Nothing Happens Without an Email
Timestamp: 1:14
Explains how email still powers global shipping and why infrastructure matters in high-stakes industries.
Title: World on Fire, Shiny Toys, Hard Facts
Timestamp: 2:40
Breaks down three types of buyers: urgent, trendy, and practical. Most lasting value sits in the third.
Title: You Need a Decision Before a Deal
Timestamp: 4:00
Outlines why deals don’t really start until the buyer commits to making a change in the first place.
Title: Win Rate vs. Close Rate
Timestamp: 5:30
Unpacks the importance of measuring both how many buyers decide to act and how many actually buy from you.
Title: You’re the BDR for Competitors
Timestamp: 7:00
A warning for sellers who generate interest but fail to close, leaving competitors to pick up the benefit.
Title: Reverse Demos Build Emotional Buy-In
Timestamp: 10:00
Explains a method where buyers show their current process first, revealing pain points that create urgency.
Title: Only One Yes in Sales
Timestamp: 13:30
Highlights the importance of getting a buyer to say “I’m changing.” That’s the only real yes in the process.
Title: Buyers Don’t Know How to Buy
Timestamp: 17:00
Reframes the buyer journey by reminding sellers that most buyers lack experience and confidence in navigating internal processes.
Title: Selling Is About Inertia, Not Momentum
Timestamp: 23:00
Suggests that what pushes deals through complexity isn't just momentum but sustained internal pressure.
Title: From Win to Close Is a Desert
Timestamp: 24:00
Describes the silent stretch between verbal yes and signed contract and how many deals die there.
Title: Disqualify Early, Post-Close Too
Timestamp: 29:00
Argues that qualification doesn’t stop at discovery. Deal viability must be reassessed even after the yes.
Title: The Deal They're Most Proud Of
Timestamp: 33:00
Leaves the next guest with a thoughtful challenge: share the one deal that meant the most and why.

Title: A Legend, Maybe Not a Legend
Timestamp: 0:17
The guest opens with humility and humour after being introduced as a legend in the sales community.
Title: Started Selling SaaS Before SaaS
Timestamp: 0:52
A reflection on a long sales career that began before “SaaS” was even a recognised term.
Title: Nothing Happens Without an Email
Timestamp: 1:14
Explains how email still powers global shipping and why infrastructure matters in high-stakes industries.
Title: World on Fire, Shiny Toys, Hard Facts
Timestamp: 2:40
Breaks down three types of buyers: urgent, trendy, and practical. Most lasting value sits in the third.
Title: You Need a Decision Before a Deal
Timestamp: 4:00
Outlines why deals don’t really start until the buyer commits to making a change in the first place.
Title: Win Rate vs. Close Rate
Timestamp: 5:30
Unpacks the importance of measuring both how many buyers decide to act and how many actually buy from you.
Title: You’re the BDR for Competitors
Timestamp: 7:00
A warning for sellers who generate interest but fail to close, leaving competitors to pick up the benefit.
Title: Reverse Demos Build Emotional Buy-In
Timestamp: 10:00
Explains a method where buyers show their current process first, revealing pain points that create urgency.
Title: Only One Yes in Sales
Timestamp: 13:30
Highlights the importance of getting a buyer to say “I’m changing.” That’s the only real yes in the process.
Title: Buyers Don’t Know How to Buy
Timestamp: 17:00
Reframes the buyer journey by reminding sellers that most buyers lack experience and confidence in navigating internal processes.
Title: Selling Is About Inertia, Not Momentum
Timestamp: 23:00
Suggests that what pushes deals through complexity isn't just momentum but sustained internal pressure.
Title: From Win to Close Is a Desert
Timestamp: 24:00
Describes the silent stretch between verbal yes and signed contract and how many deals die there.
Title: Disqualify Early, Post-Close Too
Timestamp: 29:00
Argues that qualification doesn’t stop at discovery. Deal viability must be reassessed even after the yes.
Title: The Deal They're Most Proud Of
Timestamp: 33:00
Leaves the next guest with a thoughtful challenge: share the one deal that meant the most and why.