The Outside Seat Podcast

Mike Tumalty

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The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty, featuring unfiltered conversations with CROs, VP Sales, PE operators, and the practitioners who actually run the commercial engine. No scripts. No sanitised answers. Just the conversations your buyers never have with you.

22h ago

Signals, Bluebird & Infinite Selling | Matt Webb, CEO Mentor Group

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 KPIsThe World Cup, the Signal article, and what leadership teams miss when they mistake an outcome for a strategyThe "bluebird" deal: what to ask before an unusually fast close gets baked into next year's forecastWhy sales is a team sport, not a relay race, between BDR, AE and CSForecasting a deal that hasn't landed yet, and the "mirage pipeline"Two signals leadership teams keep ignoring because it's inconvenient to look at themWhy a falling close rate is not always a training problemWriting Infinite Selling with James BartonRapid Fire: AI adoption, the cold-calling myth, and the most underrated person in Matt's networkAbout 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 Check out our Sponsor: https://info.helloflourish.com/hire-a-sales-exec/ New to the Outside Seat? Start Here - www.youtube.com/@theoutsideseat Follow us on Linkedin: https://www.linkedin.com/company/theoutsideseat/ Connect with our Host: https://www.linkedin.com/in/tumalty/ Follow us on TikTok: https://www.tiktok.com/@theoutsideseat Follow us on Twitter: https://www.x.com/@theoutsideseat Follow us on Instagram: https://www.instagram.com/theoutsideseat Check us out on Spotify: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb Check us out on Apple Podcasts: https://podcasts.apple.com/gb/podcast/the-outside-seat-podcast/id1896892470 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.
Aug 18

The Missed Signal That Cost England the World Cup Final | Mike Tumalty

England didn't lose their World Cup semi-final because they weren't good enough. They lost it to a decision made ten days earlier, in a different game, under completely different conditions. In this special solo episode, Mike Tumalty breaks down a leadership mistake that shows up everywhere, not just football: a good result gets recorded, the conditions behind it get thrown away, and what's left gets promoted to strategy. He traces it from Sir Alex Ferguson's approach to winning, through England's misread signal against Argentina, into the exact same failure mode Mike sees constantly inside B2B revenue teams: the seven-week deal mistaken for a repeatable motion, the webinar mistaken for a channel strategy, the save mistaken for a playbook. It closes with a simple three-question framework any GTM or sales leader can use before turning a result into a conclusion. Chapters: 0:00 The cold open 0:21 Welcome to The Outside Seat 1:33 Why this topic wouldn't leave me alone 3:58 Sir Alex Ferguson: "I planned to win every game" 6:25 The misread signal that cost England the final 8:53 Hollywood makes the same mistake, plus a word from Flourish 10:58 The same failure, inside your revenue engine 13:26 The three-question framework 15:49 Applying it: Mexico vs. the seven-week deal 18:08 Outro Drop your answer in the comments: what is the win your business is still taking the wrong lesson from? GTM strategy, B2B sales strategy, revenue leadership, commercial due diligence, mystery shop, sales leadership lessons, Alex Ferguson leadership Check out our Sponsor: https://info.helloflourish.com/hire-a-sales-exec/ New to the Outside Seat? Start Here - www.youtube.com/@TheOutsideSeat Follow us on Linkedin: https://www.linkedin.com/company/theoutsideseat/ Connect with our Host: https://www.linkedin.com/in/tumalty/ Follow us on TikTok: https://www.tiktok.com/@theoutsideseat Follow us on Twitter: https://www.x.com/@theoutsideseat Follow us on Instagram: https://www.instagram.com/theoutsideseat Check us out on Spotify: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb Check us out on Apple Podcasts: https://podcasts.apple.com/gb/podcast/the-outside-seat-podcast/id1896892470 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. #gtm #fifa #england #tuchel #lesson
Aug 11

Will Beats Skill, Always | Simon Edmunds, Director of International Sales Development, BeyondTrust

Simon Edmunds leads international sales development at BeyondTrust, the cybersecurity company specialising in privileged access and identity security. He manages 28 SDRs and BDRs across hubs in Manchester, Frankfurt, Dubai, and Singapore, covering every market outside the United States. In this episode, Simon and Mike cover what separates the BDRs who progress into AE roles from those who plateau, why the hierarchy myth is one of the most damaging beliefs in B2B GTM, how to hire for will over skill at the top of the funnel, and what a well-designed BDR compensation plan actually looks like. They also get into AI use in the SDR workflow, partner BDRs, and why Simon's Monday morning metric is a Claude project pulling intent signals, not a CRM dashboard. In this Episode: SDR versus BDR: the structural difference and why it mattersPartner BDRs: using intent data to build brand inside strategic partner organisationsHiring for will over skill, and how coachability is tested without asking about it directlyThe 70/15/15 compensation framework and the short/medium/long logic behind itIncentives at scale: how to regionalise motivation across four continentsCareer progression: why your number opens the door but your brand with the AEs around you gets you through itAI in the SDR stack: ZoomInfo, Sixth Sense, Outreach, Gong, and Claude in practiceRapid Fire: Outreach, the hierarchy myth, a Claude intent project, The Multiplier Effect, Problem Prospecting, and Maury Haber About Simon Edmunds Simon Edmunds is Senior Manager, International Markets at BeyondTrust, leading a 28-person sales development function across four global hubs. He began his career in graduate recruitment before moving into sales development leadership and has spent over a decade building and coaching the next generation of B2B sales talent in the cybersecurity sector. Links: YouTube Channel: https://www.youtube.com/@TheOutsideSeat Spotify Channel: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb?si=dcc0e644f79f4f77 Apple Podcast: https://podcasts.apple.com/gb/podcast/the-outside-seat-podcast/id1896892470 TikTok: https://www.tiktok.com/@theoutsideseat Simon's Linkedin: https://www.linkedin.com/in/simon-edmunds/ The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week. Episode 11 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/ InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io
Aug 4

What does RevOps Own? | William Taylor, Head of RevOps, Shopware

William Taylor has been in Revenue Operations for nearly 15 years. He came from finance, not sales, which means he sees the commercial engine differently from most people in the function. In this episode, Mike sits down with William to work through what RevOps actually is versus what most organisations think it is, what breaks first in a hyper-scale environment, and why the function is so consistently misunderstood, underfunded, and hired too late. They also get into the CRO and RevOps relationship, hiring for the function, AI in RevOps, and the question that follows every RevOps leader around: how do you know if it is working? William's answer involves a toolbox. Nobody thinks about the toolbox when fixing a car. But you would not have your tools without it. In this episode: Why RevOps is the toolbox, not the tool, and what that means for how you hire and resource the functionChannel conflict: why marketing and sales will always disagree until someone reframes the objectiveWhat breaks first in a hyper-scale environment, and why outbound is always the first thing abandonedThe CRO and RevOps relationship: what it looks like when it works and where it becomes dysfunctionalHiring for RevOps: why attitude and aptitude beat technical skills every timeAI in RevOps: why rubbish in still means rubbish out, and why CRM remains the foundation most teams do not have rightThe cost of doing nothing, and why the CFO budget argument is easier to win than most people thinkRapid Fire: the tool William cannot live without (not AI), the GTM myth he wants to kill, and why MEDDIC is not a methodology About William Taylor William Taylor is a Revenue Operations leader with nearly 15 years of experience scaling RevOps functions across high-growth B2B SaaS businesses. He came to RevOps from a finance background, giving him a cross-functional perspective on the commercial engine that most RevOps practitioners do not have. Links YouTube Channel: https://www.youtube.com/@TheOutsideSeat Spotify Channel: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb?si=dcc0e644f79f4f77 Apple Podcast: https://podcasts.apple.com/gb/podcast/the-outside-seat-podcast/id1896892470 TikTok: https://www.tiktok.com/@theoutsideseat William's Linkedin: https://www.linkedin.com/in/williamdavidtaylor/ The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week. Episode 10 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/ InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io
Jul 28

The Human Is Now The Exception | Daniel Gray, SVP North America GTM, Acolad

Daniel Gray has spent 25 years in localisation. He now leads the go-to-market function for North America at Acolad, one of the leading localisation, interpretation, and data services businesses in the market. This conversation is about what happens to a GTM motion when the category itself gets turned upside down by AI. What we cover: How AI has flipped the human-to-machine ratio in localisation — and what that means for how you sell, price, and hireThe stakeholder evolution: why the CFO and CTO are now in localisation deals that used to be managed entirely by programme managersAbove and below the algo: the framework from *Reshuffle* that every GTM leader in a tech-adjacent category should understandSocial selling and micro-events: what is actually working in North American outbound right nowThe tight localisation buyer community and why competitors share war stories across the dinner tableWhy the modern localisation sales rep needs to be as comfortable talking infrastructure as they are talking contentSales velocity as the Monday morning metricAbout Daniel Gray: Daniel Gray leads the go-to-market function for North America at ACLAD, a full-breadth localisation business offering translation, interpretation, multimedia, and data services. He has spent 25 years in the localisation industry and operates at the intersection of technology, commercial transformation, and AI-powered GTM. Links YouTube Channel: https://www.youtube.com/@TheOutsideSeat Spotify Channel: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb?si=dcc0e644f79f4f77 Apple Channel: https://podcasts.apple.com/gb/podcast/the-outside-seat-podcast/id1896892470 TikTok: https://www.tiktok.com/@theoutsideseat Daniel's Linkedin: https://www.linkedin.com/in/danielgray/ The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week. Episode 9 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/ InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io
Jul 21

Good At Fighting Fires? You're Probably Lighting Them Too | Ted Ruscitti, CCO at MoveMedical

Ted Ruscitti is Chief Customer Officer at Movemedical, a SaaS platform serving the medical device and healthcare supply chain industry. After 25 years leading customer success across HR, pharma, hospitality and now medical devices, Ted has landed somewhere unusual: 20 accounts, each worth millions, where the job is almost unrecognisable from running CS for thousands of low-value customers. In this episode, Mike Tumalty and Ted talk about what changes when every account is a board-level conversation, how Movemedical's FIM (Field Inventory Management) assessment quantifies a client's ROI before the contract is even signed, and why Ted believes the people who are best at fighting fires are often the same people lighting them. What's covered: The difference between managing 20 high-value accounts and 2,000 lower-value onesThe FIM assessment: quantifying ROI before the sale closesWhy a single customer health score hides more than it revealsThe five components of a genuinely useful health scoreWhy "land and expand sells itself" is a mythWhat changes when you scale customer success internationallyWhy the goal of good CS is to be boringGuest bio: Ted Ruscitti is Chief Customer Officer at Movemedical, where he leads customer success for the company's enterprise medical device and healthcare supply chain clients. He brings over 25 years of experience building and scaling customer success and support organisations across multiple industries, including HR technology, pharmaceutical clinical trials, hospitality, and enterprise SaaS. Links YouTube Channel: https://www.youtube.com/@TheOutsideSeat Spotify Channel: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb?si=dcc0e644f79f4f77 TikTok: https://www.tiktok.com/@theoutsideseat Ted's Linkedin: https://www.linkedin.com/in/tedrus/ The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week. Episode 8 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/ InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io
Jul 14

If AI Can Replace Your CSM, They Were Never a Good CSM | Revital Guetta, Customer Success & Growth

Revital Guetta has spent more than 22 years in post-sale, customer-facing organisations, from support through to Chief Customer Officer. She now advises companies on CS strategy and growth as an independent consultant. In this conversation, Mike and Revital go deep on what genuinely great Customer Success looks like when it is built as a revenue function rather than a support function, how the function has evolved from GRR to NRR accountability, and what the best CSMs do that no AI model can replicate. What is covered: How CS evolved from reactive support to active revenue contributor, and what that means for hiringWhy the CSM skill set is not a single profile, and how hiring strategy has to match the product and the customerThe commercial cost of treating CS as a support function, and what it takes to shift leadership thinkingOverselling as one of the most predictive indicators of churn, and how to catch it before it damages the relationshipWhat AI genuinely adds to a CS operation, and what it cannot replaceWhy cutting CS headcount in exchange for AI tools is the wrong calculationThe handoff between sales and CS, and why embedding a CSM in the late stages of an enterprise deal mattersThe pandemic licensing decision that cost nothing and returned revenue About Revital Guetta Revital Guetta is a Customer Success and Growth Advisor based in Israel, with over 22 years of experience in post-sale, customer-facing roles spanning support, CS, customer marketing, customer education, and CCO-level commercial leadership. She has worked across SMB and enterprise, in both early-stage and scaling businesses. She now works independently, advising organisations on CS strategy, growth, and the gap between commercial intent and operational execution. Links YouTube Channel: https://www.youtube.com/@TheOutsideSeat Spotify Channel: https://open.spotify.com/show/033ujY7VMYJiHa40HlycUb?si=dcc0e644f79f4f77TikTok: https://www.tiktok.com/@theoutsideseat Revital’s website: www.revitalguetta.comThe Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week. Episode 7 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/ InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io
Jul 7

The BDR Skill Most AEs Abandon | Andy Bailer, Director Strategic Accounts at Tanium

Andy Bailer started as employee number 1,200 at ServiceNow in 2012, just after the IPO. He spent 11 years inside the business, 44 or 45 quarters, as Mike points out, moving through BDR, BDR management, partners and alliances, inside sales, and solution sales before leaving for CDW and eventually Atlassian. He is now Director of Strategic Accounts at Tanium, covering enterprise cybersecurity in the Northeast US. This conversation covers the full arc: what a decade-plus inside one of the world's fastest-growing enterprise software companies actually teaches you, why the BDR skillset never leaves the best sellers even when they are running seven-figure accounts, and what enterprise buyers in cybersecurity are actually thinking when they go quiet on you. What's covered: Why staying at one company through three distinct growth phases gives you something job-hopping cannotThe hardest career transition Andy made — and why it was IC to manager, not any of the othersWhat strategic account management actually means at Tanium versus what the title impliesHow CISOs buy: not on fear, but on trust and proofWhy silence from a buyer is not progress — and what to do about itMulti-threading as a discipline, not a tacticThe BDR habit Andy still uses every Monday morning, 12 years onPipeline coverage as a vanity metric: why 3X unqualified beats 1.5X quality every time (it does not)The Challenger Sale, the Enneagram, and what Andy learned about his own selling style About Andy Bailer: Andy Bailer is Director of Strategic Accounts at Tanium, where he covers enterprise cybersecurity accounts across the Northeast US. He spent 11 years at ServiceNow across BDR, management, partners and alliances, inside sales, and solution sales roles, before positions at CDW and Atlassian. He is based in the US. Links: The Outside Seat website: theoutsideseat.com InsideNow: insidenow.io Andy Bailer on LinkedIn: https://www.linkedin.com/in/andrewbailer/ The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week. Episode 6 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/ InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io

The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty, featuring unfiltered conversations with CROs, VP Sales, PE operators, and the practitioners who actually run the commercial engine. No scripts. No sanitised answers. Just the conversations your buyers never have with you.

Creator

Mike Tumalty
Years Active

2026
Episodes

13
Rating

Explicit
Copyright

© 2026 The Outside Seat Podcast
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The Outside Seat Podcast