The Exit Five Podcast

Latest Episodes:

How to Get 10X More Traffic From Content You Already Have (with Ross Simmonds, Foundation Marketing) Oct 05, 2026

Show notes

#398 | Dasha chats with Ross Simmonds, founder of Foundation Marketing and Distribution.ai, live at Drive. They talk about why most marketing content fails: it gets created once and then left to collect dust. Ross breaks down his full distribution playbook for a single blog post - from social and email to Reddit, shorts, carousels, and reposting on a schedule. Then, Ross shares the receipts: 10X traffic and a three-year-old asset that now gets cited in AI answers and still generates leads. He explains his rule to create ridiculously good content once and distribute it forever, the four E's that separate great content from slop, and the two blog posts that changed his career. Plus, how to hire people that runs without you, why spamming Reddit with self-promotion is ineffective, and Ross’s bet on in-person events in 2027.

Show notes:

14 books to get a job in advertising: https://rosssimmonds.com/blog/20-books-read-job-advertising/

Timestamps:

(00:00) - Recording Live at Drive

(02:36) - Why Most Great Content Just Collects Dust

(03:43) - How AI Made Distribution Noisier and Cheaper

(04:56) - Distributing One Blog Post Across Every Channel to Maximize Reach

(06:55) - 10X Traffic and Playing the Long Game with Content

(09:19) - The Four E's of Great Content

(11:01) - The Blog Posts That Changed His Career

(14:30) - His Biggest Win: A Team That Runs Without Him

(17:30) - Reddit Done Right: White-Hat, Not Spam

(18:58) - His Bet for 2027: In-Person Events Come Back

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

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Brought to you by:

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Convertiv - A B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy, specializing in AEO. Podcast listeners get a free AI search review showing how you stack up against competitors. Learn more at convertiv.com/exitfive.

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Compound Growth Marketing- A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive.

Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.

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Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

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[Best of B2B] April Dunford - Positioning, Differentiation, Lessons from 200+ Sales Pitches, and How To Do It Right Oct 02, 2026

Show notes

#397 | One of our most popular episodes ever, inducted into our Best of B2B series: April Dunford is a B2B positioning expert and author of Obviously Awesome and Sales Pitch. Sales Pitch guides you through an eight-step sales pitch structure the helps you stand out and win business. Building on the concepts of the bestselling book, Obviously Awesome, Sales Pitch will give your sales reps a story that makes your product shine. We talk about her new book, lessons from her first book, and covered:

- Positioning vs. Category Creation vs. Strategic Narrative
- Lessons from 200+ B2B sales pitches
- Why differentiation is everything and how to do it
- Why positioning has to be a cross-functional activity - not just for the marketing
- A structure anyone can use to turn positioning into a strong sales pitch
- Why she set out to write a follow up book to her 2019 hit Obviously Awesome called Sales Pitch (and go through the pain of writing a book all over again)

Timestamps

(00:00) - Why timeless marketing lessons still matter
(01:21) - How April does positioning in one week
(07:22) - Why marketing never wins a battle of opinions
(08:38) - Who you really compete with
(11:49) - Positioning vs. strategic narrative vs. category creation
(19:40) - No decision, FOMO, and the race to the bottom
(22:44) - Finding differentiation when you think you have none
(27:58) - Selling what's on the truck vs. the vision
(34:18) - Why April wrote Sales Pitch
(41:00) - The sales pitch structure, with a Help Scout example

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

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Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

Dave & Dasha Live from Drive: Beating Brain Rot, Burnout, and Boredom After 15 Years in B2B Oct 01, 2026

Show notes

#396 | Dave and Dasha recorded this episode live during Drive 2026 - our biggest event yet. Dave explains how Drive nearly moved to Boston, and why he thinks keeping it in Vermont matters. They also went deep into how Dave wrote this year's keynote. He shares his struggle of building an outline with Claude that had no soul, and asking Harry Dry for help. Eventually, the talk became about one idea: connection. Dave also covers how that experience changed the way he gives feedback to his team, his biggest wins of 2026, and what he's betting on for 2027.

Timestamps

(00:00) - Interviewing Dave IRL at Drive about His Career and Keynote Writing Process

(03:49) - How the Drive Event Started

(09:08) - Why This Year's Keynote Matters and How Dave Wrote It

(11:49) - Moving Past the Writer’s Block: "AI Rotted My Brain"

(13:47) - Getting Harsh Feedback from Harry Dry

(16:00) - The Angle: a Story About Human In-Person Connection

(20:13) - Bringing Harry's Feedback Style to the Team

(25:41) - How to Build an Outstanding Team and Why This is Your Biggest Lever

(31:43) - The Canadian Snack Taste Test

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

Is the MQL dead? (with Freya Ward, Headley Media) Sep 28, 2026

Show notes

#395 | Dasha sits down with Freya Ward, Associate Managing Director at Headley Media, to talk about why MQLs get a bad rap and what to do about it. Freya explains why the problem is usually the framing rather than the tactic, how renaming MQLs changes how sales handles them, and what you should rename them to. They also get into how to run a workshop that aligns the team on what counts as a qualified lead, and three specific fixes you can make today for better sales and marketing alignment.

Show notes

Gareth James at Hallam on getting brand investment signed off by finance directors: https://hallam.agency/blog/investment-for-brand-how-to-get-sign-off-from-finance-directors/

Timestamps:

(00:00) - Why Freya quit marketing to join the sales team

(09:02) - Is the MQL actually dead?

(10:02) - Rename the MQL to qualified outbound leads

(11:22) - Why every marketer has speak the sales, finance, and other department’s languages

(16:47) - Three rituals that keep sales and marketing aligned

(20:47) - Build your MQL definition from deals that closed

(24:43) - Why Dasha's BDs report into marketing

(26:26) - Fix #1: make lead rejection a required CRM field

(31:46) - Fix #2: assign someone to nurture dead leads

(38:00) - Fix #3: pilot alignment with one SDR

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

Dave Goes UNBOUND: 5 Things B2B Marketing Leaders Are Doubling Down On Sep 25, 2026

Show notes

#394 | Dave takes his phone to the conference floor at HubSpot's UNBOUND in Boston and asks 5 B2B marketing leaders two questions: what are you doubling down on at work, and what are you doubling down on in your personal life? He opens with thoughts on why strategy and positioning matter more than tactics now that AI makes everyone sound the same. Then you'll hear from Jonathan Hunt of HubSpot on treating brands as live experiences, Palmer Houchins of G2 on balancing AI efficiency with effectiveness, Sangram Vajre of GTM Partners on the power of one-on-one conversations, Jess Cook of Vector on personally rebuilding her company's website with Claude Code, and Amit Sharan of Tatari on the importance of exploring new channels and how they're creating video content built to be found by AI search.

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

Navigating a Rebrand: Why SurveyMonkey Went Back to the Monkey (With Katie Miserany, CCO & Global Head of Marketing) Sep 24, 2026

Show notes

#393 | Dave interviews Katie Miserany, Chief Communications Officer and Head of Marketing at SurveyMonkey, about why the company rebranded to Momentive to go upmarket and then reversed the decision after going private. Katie explains why sales believed nobody would spend six figures with a company called SurveyMonkey, what changed under the new CEO, and why she now sees the monkey as an advantage. She also covers her path into marketing from communications, why more comms leaders are moving into C-suite marketing roles, and the advice she followed when she took over the function: get close to the growth team and ask your basic questions early so imposter syndrome doesn't cost you the learning.

Timestamps:

(00:00) - Why Katie Feels Like She’s Gotten Twenty Years of Experience in Seven at SurveyMonkey
(05:41) - Why Sales Thought Nobody Would Buy From a Company Called SurveyMonkey
(07:06) - Creating Our Brand Vision and Bringing it to Life
(12:33) - The Campaign That Didn't Move the Needle
(17:04) - Everyone Knows Us - The Version of Us From 2009
(20:08) - The Tactic That Lifted Click-Through by 73%
(25:19) - The Journey From Comms to Head of Marketing
(31:18) - What Comms Actually Does
(37:14) - How to Determine if You Need a Meeting vs an Async Update

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

How I Built that [Agent] - 7 Marketers Show AI Workflows That Save Hours Sep 21, 2026

Show notes

#392 | Everyone’s talking about AI agents right now. It's hard to know what's real and what's just LinkedIn noise. If you haven't built an agent yet, it’s hard to know where to start. If you have built agents, you might be looking for ideas for what to build next.

Wouldn’t it be great if a pro marketer would just share their screen and walk you through their best agents? Here's what I built, this is what it does, and here's how much time it saved me this week.

We agree! That’s why we brought in seven B2B marketers to show the agents they built, and are using at their companies today. Check out this episode of Exit Five Live.

Timestamps

(00:00) - Intro
(03:18) - What an AI agent actually is, and common challenges marketers face with building them
(06:06) - An AI chief of staff, and an agent that hunts for new brands
(10:39) - Claude skills that edit a draft, and an agent for LinkedIn ads creative
(16:11) - Sales call data as an agent's brain, and testing messaging with AI personas
(20:40) - 2,600 personalized landing pages, built and refreshed by an agent
(24:44) - A daily learning digest that turns into a private podcast
(27:30) - Getting a dozen editing skills to work together
(31:43) - Inside the landing page agent: research, edit mode, running at scale
(35:53) - How the cool hunting agent finds and scores new brands

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

How Sprout Social builds revenue marketing around segmentation (with Hailey McDonald, VP of Revenue Marketing) Sep 17, 2026

Show notes

#391 | Dave sits down with Hailey McDonald, VP of Revenue Marketing at Sprout Social, to talk about what revenue marketing looks like inside a 16-year-old social intelligence platform with 30,000 customers. Hailey explains why demand gen has become the hardest role to hire for in B2B. She shares her core framework, how she maps segments against solutions, and how that turns into budget, channel bets, and pipeline tiers by vertical. Dave and Hailey also get into what it takes to go from sales-led company to product-led growth, and what north star metric she uses instead of leads or pipeline. You’ll also hear how reading market signals keeps you from over-investing in a segment that's never going to close. Finally, the difference between a marketer and an executive, whether big companies can vibe-code their way to startup agility, and the truth about incentives.

Timestamps:

(00:00) - Meet Hailey McDonald, VP of revenue marketing at Sprout Social

(00:49) - Why revenue marketing is the hardest role to hire for in B2B

(05:26) - Shifting a sales-led company toward product-led growth

(08:44) - Getting clear on ICP and why segmentation matters

(10:23) - The segmentation framework: mapping segments to solutions

(14:55) - Turning segment priorities into budget and channel bets

(19:42) - What a campaign team does

(31:34) - AI, vibe coding, and keeping a big company current

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

How One Agency Turns One Shoot Day Into 50-Plus Video Ads (With Connor Lewis of Studio Lewis) Sep 14, 2026

Show notes

#390 | Dasha sits down with Connor Lewis, founder of Studio Lewis, who's produced 800+ B2B video ads for ClickUp, Zapier, and Ahrefs. Connor gives away the formula he tells everyone to copy. Plus, the system he uses to turn customer research into a dozen testable scripts. He breaks down three real ads on the record (why Monday.com's Viking ad works, and where the classic motion-graphics launch video actually belongs). He also explains how he got 56 ads out of a single shoot day using hook alternates and the three proof points that get video budget approved, and why he won't put AI-generated video on the feed.

Timestamps

(00:00) - Intro
(07:51) - Good Ad, Bad Ad: Three Examples Broken Down
(18:03) - Why an Ad Doesn't Land
(23:08) - Script Blocks: Turning Customer Language Into Scripts
(29:54) - The Formula to Copy If You're Starting Out
(32:33) - Human Ads vs Motion Graphics
(34:49) - Structuring a 12 Hour Shoot Day
(38:01) - How Six Creatives Became 56 Ads
(40:37) - Where AI Belongs in Video Production
(45:00) - Getting Video Budget Approved and What It Costs

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

What to do when Organic Traffic Drops (with Kristina Frunze, Webview SEO) Sep 10, 2026

Show notes

#389 | Dasha sits down with Kristina Frunze, founder of WebView SEO, who's spent 10 years in SEO and the last 3 running experiments on AI visibility for B2B SaaS. Kristina gives away the framework she uses with every client – SEO is the foundation, AI search is the roof. Plus, the 60/20/20 content split that puts the bottom of funnel pages first. Kristina also talks through the 3-layer attribution model she uses to show leadership what the work is doing when organic clicks are down. She walks through a full client case study on the record (a construction tech company that tripled AI overview citations in six months and lifted bottom of funnel visibility 46%). She also explains the 5-step checklist that makes content worth citing, and why she scores every competitor against real criteria before publishing a comparison page. Also: the Reddit strategy that got her clients' comments wiped out and what replaced it, and why she now believes AI search depends more on off page than on page.

Timestamps

(00:00) - Intro

(03:05) - Decoding SEO, AEO, and GEO

(06:41) - Reframing a Traffic Drop Around Leads

(08:06) - The 60/20/20 Content Split

(14:20) - Three Layers of Visibility Attribution

(21:07) - Tracking AI Traffic Inside GA4

(26:46) - The Checklist for Content LLMs Will Cite

(31:08) - Case Study: Tripling AI Citations in Six Months

(44:26) - The Reddit Strategy That Got Wiped Out

(47:08) - Why Off Page Now Beats On Page

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

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