#240: Video Strategy | In this episode, Danielle sits down with Connor Lewis, founder of Studio Lewis, to talk all things B2B video - what works, what doesn’t, and how to actually get started. Connor spent years building in-house video from the ground up before going solo. Now, he works with B2B brands on high-performing video ads and he’s here to break down what he’s learned.

Danielle and Connor cover:

• Why production value doesn’t matter as much as you think
• How to turn existing blog posts and webinars into watchable video
• What’s working on LinkedIn video in 2025
• How to get started with video without hiring an agency or a full-time team
• Simple formats that make video approachable

Timestamps

• (00:00) - – Intro to Connor
• (04:33) - – Learning video by doing: from intern to strategist
• (06:33) - – What’s working in B2B video on LinkedIn in 2025
• (08:00) - – Three types of videos that perform best
• (09:21) - – Why video ads aren’t the best place to start
• (10:14) - – How to turn top blog posts into YouTube videos that rank
• (12:07) - – Using video to refresh blog content and boost SEO
• (12:47) - – How to use video effectively for virtual and in-person events
• (13:41) - – Repurposing Q&A sections from webinars into high-performing short clips
• (15:36) - – Creating shorts from top audience questions
• (16:49) - – The only parts of video that really matter
• (17:36) - – Why “how I” beats “how to” every time
• (19:24) - – The “reverse Rambo” hook format and how to use it
• (21:23) - – How setting and authenticity improve engagement
• (22:52) - – Why stiff, overproduced videos are killing your reach
• (25:30) - – How to get started with video if you don’t have a team or budget
• (27:36) - – Why marketers need to get comfortable on camera
• (27:58) - – Podcasts as a powerful entry point into video
• (28:55) - – How to test video with a simple 4-part limited series
• (30:31) - – Low-budget options that still convert
• (30:59) - – Why product marketers often make the best video collaborators
• (31:43) - – Final advice: don’t wait until it’s perfect, just start!

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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

#238: Brand | In this episode, Dave sits down with Dmitry Shamis, former Head of Brand at HubSpot and now founder of Oh Snap, to talk about what brand really means in B2B and why so many teams are stuck doing busy work instead of meaningful marketing. After leading a team of 150+ creatives and scaling HubSpot’s brand across multiple products, Dmitry shares lessons on building brands that actually stand out.

Dave and Dmitry cover:

• How to stand out in a crowded market
• How to develop and refine your point of view
• Why marketers get lost in busy work and how to stop it
• What to look for when hiring great designers
• The role of AI in B2B marketing today (and what it won’t replace)

Timestamps

• (00:00) - – Intro to Dmitry
• (05:33) - – What brand actually means in B2B
• (07:53) - – Why your POV is the foundation of your brand
• (10:03) - – How to uncover a real, differentiated POV
• (14:02) - – How to stand out in a crowded, same-sounding market
• (16:37) - – Why differentiation requires alignment between product and marketing
• (19:27) - – Building trust with product teams
• (20:16) - – Busy work in marketing: how to spot it and stop it
• (22:58) - – Why marketers burn out and how poor prioritization is killing teams
• (27:02) - – Making the case for brand work when it’s hard to measure
• (28:37) - – The “fishing” analogy: performance vs brand marketing
• (33:08) - – The real opportunity with AI in B2B marketing
• (37:07) - – How AI can eliminate bottlenecks and speed up creative execution
• (38:37) - – Why Dmitry’s starting a creative agency (Oh Snap) and how it’s different
• (41:45) - – How to hire great designers: what to look for beyond the portfolio

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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

#237: Strategy | Udi Ledergor (former CMO, now Chief Evangelist at Gong) helped turn Gong into one of B2B’s most iconic brands—and now he’s sharing how they scaled it to a multi-billion dollar valuation. In this episode, Dave sits down with Udi to unpack lessons from building Gong’s category, brand, and marketing engine (and why B2B marketing needs way more courage).

You’ll learn:

• Lessons from building Gong from 0 to $100M in revenue
• How to make B2B marketing not boring
• How to measure and justify brand investments in marketing
• Why you need to be more courageous with your marketing

Udi also shares stories from his new book Courageous Marketing, featuring specific plays and strategies any B2B marketer can steal.

Timestamps

• (00:00) - – Intro to Udi
• (07:33) - – Early career lessons and building a marketing role from scratch
• (10:33) - – How Gong achieved early product-market fit
• (14:33) - – The importance of picking the right company and founder
• (16:33) - – Why Gong’s focus, clarity, and positioning stood out from day one
• (18:43) - – Why Udi wrote Courageous Marketing and what it’s about
• (19:33) - – What “courageous marketing” actually means
• (22:33) - – Defining brand personality before visual identity
• (26:17) - – Campaign breakdown: Times Square billboards, employee spotlights, and perception hacks
• (29:37) - – The “punching above your weight” formula for early-stage brands
• (33:07) - – How to measure soft ROI and prove brand impact
• (36:37) - – Super Bowl ad, Michael Lewis podcast, and tying brand to pipeline
• (41:22) - – How to budget for experiments and get CFO/CEO buy-in
• (42:37) - – Building a courageous team: culture, process, and psychological safety
• (45:37) - – Gong Labs: Turning product data into content with staying power
• (48:37) - – Product + marketing alignment: the real unlock
• (50:07) - – Where AI fits in the future of courageous marketing
• (52:27) - – Udi’s book Courageous Marketing (and why you should go read it)

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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

#236: Product Marketing | Product marketers are no strangers to change. Whether it’s navigating new responsibilities, proving impact to leadership, or balancing short-term wins with long-term strategy, the role is constantly evolving - and in 2025, that evolution is only accelerating.

This Exit Five Live session is built to help you stay ahead. Dave sits down with Natalie Marcotullio (Head of Growth & Product Marketing at Navattic), Jason Oakley (Founder of Productive PMM), and Eric Holland (Senior PMM at Betterworks and Co-Founder of DemoDash) for a tactical discussion on how to sharpen your skills, adapt to a shifting landscape, and deliver measurable impact.

They cover:

• What a successful product marketing function looks like in B2B
• Tools, frameworks, and metrics that actually matter
• How to align with sales and customer success
• Trends to watch in 2025 and beyond

Timestamps

• (00:00) - – Intro to Natalie, Jason, and Eric
• (03:33) - – Why product marketing is the most important function in B2B marketing
• (05:23) - – Defining the role: What should product marketing actually own?
• (07:33) - – How PMM impacts revenue, growth, and pipeline
• (09:03) - – Differentiation: What it really takes and why most companies get it wrong
• (11:33) - – Real examples of effective positioning in crowded markets
• (16:03) - – What bad product marketing looks like
• (17:33) - – Why PMMs need to market the product more (and not just during launches)
• (20:33) - – Launch marketing, momentum, and creating "marketable moments"
• (22:33) - – Why PMM charters don’t work - and what to do instead
• (24:33) - – How to measure product marketing impact (with or without KPIs)
• (32:07) - – Tying assets and enablement to revenue
• (33:37) - – Tracking usage without a big tech stack
• (36:37) - – Who owns positioning: PMM vs brand?
• (38:37) - – How to shine as a PMM in a sales-led org
• (43:07) - – The death of one-pagers and what to use instead
• (45:37) - – What to look for when hiring a great product marketer

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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

In this episode, Matt sits down with Aditya Vempaty, VP of Marketing at MoEngage, to talk about a topic every marketing leader has wrestled with: reporting on the right metrics. Aditya has led marketing at companies like Nutanix, Amplitude, and Synthego - and he’s learned how to build dashboards and reporting frameworks that actually communicate marketing’s impact across leadership, sales, and finance.

Matt and Aditya cover:

• Why marketing metrics should translate performance into a common language the business understands
• The four buckets of metrics every B2B team should track
• How often you should be reporting on metrics
• The exact 7 metrics Aditya uses to report up, down, and across the org

Timestamps

• (00:00) - – Intro to Aditya
• (03:45) - – Why communicating marketing’s impact is a challenge for many teams
• (06:21) - – The importance of using a common language when reporting to leadership
• (08:59) - – Breaking marketing metrics into four key buckets
• (12:14) - – How pipeline coverage connects marketing to revenue
• (14:43) - – Reporting on efficiency: CAC, cost per opportunity, and more
• (17:58) - – The role of awareness metrics and how to contextualize them
• (21:55) - – How marketing and sales alignment can be measured effectively
• (24:24) - – The 7 core marketing metrics Aditya reports on regularly
• (28:07) - – How often should marketing be reporting metrics?
• (30:51) - – Dashboards, recurring meetings, and what execs actually care about
• (33:43) - – Advice for first-time marketing leaders on building reporting habits
• (35:57) - – Why clarity beats complexity when it comes to data
• (38:39) - – Final thoughts

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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

#234: Messaging | In this episode, Dave sits down with Emma Stratton, founder of Punchy, to break down what great B2B messaging actually looks like - and how to get it right. Emma has worked with hundreds of B2B tech companies to sharpen their positioning, eliminate vague copy, and train marketing teams to write with clarity and impact. They cover what makes messaging actually resonate and how to spot and fix abstract or weak copy. They also dive into Emma’s process for creating message-market fit, doing customer research, and working with execs and cross-functional teams.

And BONUS: they spend the last 20 minutes talking about personal development, productivity, journaling, and managing your mental energy to be a better marketer (and human).

Dave and Emma also cover:

• How to go from vague to punchy by writing with specificity and buyer empathy
• Why most B2B messaging falls flat and how to avoid the “sea of sameness”
• How to use customer interviews, sales calls, and concrete language to create strong messaging
• Why writing, meditation, and personal rituals are so important for creative energy

Timestamps

• (00:00) - – Intro to Emma
• (04:38) - – What makes B2B messaging actually good
• (08:20) - – Common messaging mistakes (and why "clarity > clever")
• (11:18) - – Positioning vs. messaging: what’s the difference?
• (15:31) - – Why it's hard to name great B2B marketing examples
• (17:55) - – How to sharpen weak messaging and fix vague positioning statements
• (21:03) - – Simplifying complex products without dumbing it down
• (25:17) - – How to write for buyers (not just execs)
• (28:49) - – Using customer interviews and research to build strong messaging
• (33:27) - – Standing out in a crowded, buzzword-filled market
• (36:11) - – How storytelling fits into B2B messaging
• (39:17) - – Messaging advice for early-stage founders and startups
• (42:32) - – How often should you revisit and update messaging?
• (44:42) - – Productivity, managing your energy, and staying focused
• (47:57) - – Journaling, mindfulness, and being intentional with your time
• (51:52) - – Final takeaways

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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

#233: Inside Exit Five | In this episode, Matt Carnevale (Head of Community at Exit Five) joins the team at Circle to break down how we’ve doubled Exit Five community membership and boosted engagement—all by treating Exit Five like a product. He shares our playbook: audience growth, engagement systems, how we use member feedback to shape what we build, and why “curate, don’t create” has been key to scaling. If you’re running (or joining) a B2B community, this is how you make it work.

Matt covers:

• Why we think of community like a product, not just a channel
• How Exit Five grew community membership over 100% in under a year
• The systems we use to drive 40% monthly active user engagement
• The power of “tripwires,” onboarding, and member matchmaking
• How feedback loops shape what we build

Timestamps

• (00:00) - – Intro to Matt
• (04:03) - – Exit Five’s approach to community
• (06:33) - – What it means to treat community like a product
• (10:33) - – Why audience is the foundation of community growth
• (13:33) - – How Exit Five builds and converts audience from LinkedIn
• (16:33) - – Using content tripwires to drive signups
• (18:33) - – Offers that work: Why we use a 7-day free trial
• (21:33) - – How Exit Five got started as a paid community
• (24:33) - – The product mindset: build, test, iterate
• (28:37) - – Using member feedback to drive product decisions
• (30:37) - – Real example: member matchmaking feature
• (32:37) - – Promoting new community features like product launches
• (35:37) - – How we drive 40% monthly active usage
• (37:37) - – The value of member-led events and how we do them
• (40:37) - – Other plays: tagging experts, matchmaking, onboarding
• (43:37) - – Why self-promo was hurting our community and what changed when we cut it
• (45:37) - – Final takeaways + advice for small communities
• (49:37) - – Audience Q&A: re-engagement, matchmaking, content cadence

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Grammarly.

Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?

You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.

That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.

AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:

– Cut down on back-and-forth

– Automate content, research, and reporting

– Eliminate busywork

– Make space for strategy

We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.

Get the report and see how top teams are making AI actually useful.

Visit go.grammarly.com/exitfive to grab it.

***

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