The Dave Gerhardt Show (from Exit Five)

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

***

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.
***

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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#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/

***

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.
***

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

#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:
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.
***

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

#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:
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.
***

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

#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:
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.
***

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