Matt Webb has sent and received thousands of emails as CEO of MentorGroup. In three and a half years, he has had roughly 3,000 cold emails land in his inbox, and four phone calls. He took every one of the four. That single stat sets up a wider conversation about signals: the ones revenue leaders read correctly, and the ones they mistake for a repeatable motion when they were actually a one-off.

Mike sits down with Matt Webb, CEO of MentorGroup, for a conversation that runs from the World Cup semi-final and the Signal article through to the bluebird deal, the mirage pipeline, and why a falling close rate is so often misdiagnosed as a skills problem when the real issue is upstream in pipeline quality. Matt also talks through the genesis of his and James Barton's book, Infinite Selling, and where AI has genuinely changed his own working week.

What's covered:

• What MentorGroup does and why customer experience sits ahead of KPIs
• The World Cup, the Signal article, and what leadership teams miss when they mistake an outcome for a strategy
• The "bluebird" deal: what to ask before an unusually fast close gets baked into next year's forecast
• Why sales is a team sport, not a relay race, between BDR, AE and CS
• Forecasting a deal that hasn't landed yet, and the "mirage pipeline"
• Two signals leadership teams keep ignoring because it's inconvenient to look at them
• Why a falling close rate is not always a training problem
• Writing Infinite Selling with James Barton
• Rapid Fire: AI adoption, the cold-calling myth, and the most underrated person in Matt's network

About Matt Webb: Matt Webb is CEO of MentorGroup, a UK-based sales performance consultancy helping CROs and enablement leaders build sustainable selling motions and predictable revenue growth. He has spent close to 20 years at MentorGroup following 13 years at Vodafone in sales and sales leadership roles. He is co-author, with James Barton, of Infinite Selling.

Chapters:
00:00 Cold open: the outside seat, and today's show
01:15 Welcome and guest introduction
03:43 What MentorGroup does and why customer experience comes first
08:27 The World Cup, the Signal, and the Liverpool vs Man United thread
15:35 The bluebird deal: what a fast close is really telling you
22:43 Sales as a team sport, not a relay race
26:38 Forecasting the bluebird and the mirage pipeline
31:20 Two signals leadership teams keep misreading
33:41 When a falling close rate isn't a skills problem
36:10 Why nobody comes to work to fail: getting the North Star right
40:56 Writing Infinite Selling with James Barton
45:42 Rapid Fire
47:46 Close: sign-off and how to get involved

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So what is The Outside Seat?

Most revenue leaders have never sat where their buyers sit. The Outside Seat is the podcast that fixes that, bringing GTM leaders and the unsung heroes behind them into conversations they'd never normally have with each other. Real talk on sales, revenue operations and what actually works from the buyer's side of the table, not the vendor's.

Hosted by Mike Tumalty, 25 years into B2B SaaS GTM, from ServiceNow to founding InsideNow. New episodes every Tuesday.