The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

#265 Non-SaaS Marketing | In this episode, Matt sits down with Sandra Rand, a fractional head of marketing who works with early-stage, non-SaaS B2B companies. She’s led marketing for PE-backed, self-funded, and services-based businesses, where big budgets and SaaS-style playbooks aren’t the norm. She’s also building the Non-SaaS Marketers subgroup inside Exit Five to support others facing the same challenges.Matt and Sandra cover:How non-SaaS teams drive growth without demos, PLG, or huge lead volumeWhy events, word of mouth, and referrals often outperform funnels in these orgsTactical ideas for gifting, partnerships, and pipeline-building on a lean budgetWhether you work in SaaS or not, you’ll walk away with creative, scrappy strategies to build trust and drive results in B2B.Timestamps(00:00) - – Intro (03:04) - – Why Exit Five launched the Non-SaaS group (08:24) - – What makes non-SaaS marketing different (11:44) - – Budgets, sales cycles, and team structure (16:34) - – Why brand and trust matter more (18:44) - – Events > funnels in non-SaaS (28:40) - – How to build brand on a budget (34:10) - – Word-of-mouth and referral tactics (38:50) - – Gifting and relationship-driven growth (44:50) - – Scrappy, creative plays that actually work (50:20) - – What’s next for the Non-SaaS community Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#264 Async Work | In this episode, Dave is joined by Ashley Faus, Director of Lifecycle Marketing at Atlassian, and Dr. Molly Sands, Head of the Teamwork Lab at Atlassian. Ashley brings deep experience in cross-functional B2B marketing leadership, while Molly leads a team of behavioral scientists designing better ways for teams to collaborate. Together, they unpack how Atlassian has rethought marketing org structure, internal comms, and meetings to drive higher output with fewer syncs.Dave, Ashley, and Molly cover:The framework Atlassian uses to reduce meetings and communicate asynchronously (including how to structure updates that actually get read)How to balance transparency with clarity and avoid information overload across Slack, Loom, and ConfluenceTactical ways to structure team rituals, recurring meetings, and brainstorms to focus on output, not performative busyworkYou’ll walk away knowing how to run a leaner, more effective marketing team (without drowning in Slack and Zoom).Timestamps(00:00) - – Intro (03:34) - – Why marketers showed up live: too many meetings, too little output (06:34) - – Meet the guests: Ashley Faus and Dr. Molly Sands from Atlassian (09:04) - – What “Team Anywhere” means at Atlassian (11:04) - – The difference between information sharing and real connection (13:34) - – Why marketing updates often fall flat internally (15:34) - – How to communicate clearly inside the org (and get your message read) (19:04) - – Structuring updates: topic, who it’s for, action, context (22:04) - – When you need a meeting vs. when async works better (26:04) - – “Sparring” meetings: real-time collaboration between equals (28:34) - – What actually builds team connection (hint: not team happy hours) (32:50) - – Async tools Atlassian uses across marketing (35:20) - – Getting quiet team members to contribute in meetings (37:50) - – How Atlassian runs recurring team rituals without wasting time (41:50) - – Cross-functional alignment: structure, scorecards, and shared goals (44:50) - – Best practices for async tools like Loom and Confluence (47:50) - – Do brainstorming meetings even work? Here’s when they do. (50:50) - – What to share with non-marketers (and what to skip) (53:50) - – Why creating focus is the most underrated leadership skill (55:50) - – Final takeaways from Ashley and Molly Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#263 Marketing Strategy | Dave is joined by Jason Lyman, CMO at Customer.io, a customer engagement platform used by over 7,500 companies. Jason has led marketing at Dropbox, BetterCloud, and now heads a 30-person team driving growth across both PLG and sales-led motions.Dave and Jason cover:How to structure a B2B marketing org for scale, alignment, and channel ownershipWhy events are their #1 channel and how creative formats drive real pipelineThe KPI + OKR system they use to prioritize work and measure marketing’s impactYou’ll walk away with a clearer understanding of how to design your team, focus your strategy, and invest in channels that actually drive results.Timestamps(00:00) - – Intro (02:34) - – What Customer.io does and who they serve (03:34) - – Growth story: from bootstrapped to private equity-backed (05:34) - – Team size and breakdown of the 30-person marketing org (07:34) - – Balancing PLG and sales-led within one team (09:34) - – How the org is structured: focus teams vs. centers of excellence (11:34) - – Aligning team goals to sales motions and funnel stages (13:34) - – How Customer.io prioritizes internal marketing requests (15:34) - – Avoiding the “who bangs the table loudest” trap (16:34) - – Cross-functional alignment with sales and product (18:34) - – KPI vs. OKR: how Customer.io uses both (22:50) - – Examples of key KPIs for the business (24:50) - – How OKRs cascade across the org (26:50) - – Why structured goal setting leads to better marketing impact (28:50) - – What channels are working: events are back (29:50) - – Examples of creative event formats that build community (31:50) - – Building pipeline without pitching at events (33:50) - – How Customer.io defines and tracks long-term influence (36:50) - – The decline of SEO and rise of AI-influenced buying (38:50) - – Why positioning is more important than ever (40:50) - – Product and marketing alignment in a modern org (42:50) - – Selling both the product and the roadmap (43:50) - – Jason’s one wish for marketers: better customer data (45:50) - – Personalization, adaptability, and breaking through the noise (46:50) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#262 Content Strategy | Dave sits down with Chelsea Castle, Head of Content and Brand at Close. Chelsea talks about her experience in B2B SaaS and shares how to build impactful content that resonates with your audience.Chelsea and Dave cover:How leveraging internal and cross-functional knowledge can create a content goldmineWhy it is important to repurpose podcast episodes, webinars, and other media into multiple forms of content to maximize their valueStrategies for integrating SEO with authentic, valuable content that resonates with your audience, beyond just ranking for keywordsTimestamps(00:00) - - Intro to Chelsea (01:34) - - Merging Brand and Keyword-Driven Content (01:35) - - Aligning Brand and Content Strategy with Your Goals (01:42) - - New Content Channels for B2B (01:46) - - How to Measure Content Engagement (02:08) - - LinkedIn for B2B (02:12) - - Chelsea’s Experience at Chili Piper (02:17) - - Improving Content for Podcasts (02:22) - - Driving Website Traffic Through Brand Content Strategy (02:22) - - Skyscraper SEO Content Strategy (02:30) - - How to Craft a Brand Strategy (02:31) - - How to Grow Using Gated Content (02:33) - - How to Maximize Search Impact Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#261 AI & Creativity | In this episode, Dave is joined by Mark Schaefer, marketing strategist, keynote speaker, and author of 11 books, including his latest, Audacious: How Humans Win in an AI Marketing World. Mark has spent decades studying the intersection of marketing, tech, and human behavior, and his ideas have helped reshape how B2B brands think about relevance, creativity, and differentiation in a noisy digital world.Dave and Mark cover:Why playing it safe is the biggest threat to B2B marketers in the AI eraHow to create marketing that actually connects by disrupting the story, the channel, or the storytellerReal examples of B2B brands ditching “best practices” and standing out with emotional, human-first marketingYou’ll come away with a fresh perspective on how to stay relevant, creative, and impactful, especially as AI becomes a bigger part of your marketing stack.Timestamps(00:00) - – Intro (03:34) - – Why most marketing is boring (08:04) - – The danger of “best practices” (12:04) - – Why AI is amplifying bad marketing (15:34) - – The rise of raw, lo-fi, human content (18:34) - – What AI can’t replicate: shared experiences (22:04) - – Fear, risk, and the big brand trap (25:34) - – Using AI to enhance, not replace, creativity (31:50) - – The real framework behind Audacious (34:50) - – B2B examples that break the mold (40:20) - – Why now is the time to stand out (44:50) - – Making bold marketing happen inside your org (49:20) - – Liquid Death, Nutter Butter, and brand disruption (53:50) - – B2B doesn’t mean boring (57:50) - – The one question every marketer should ask Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#260 Product Marketing | Dave is joined by Matt De Vincentis, VP of Product Marketing at Atlassian. With a background that spans engineering, product marketing, and leadership at companies like VMware and Palo Alto Networks, Matt shares how Atlassian structures its product marketing team, prioritizes work, and stays tied to business outcomes, even at massive scale.Dave and Matt cover:How Atlassian connects product marketing to revenue and pipeline (and why PMMs need to “own the outcome”)How to build high-trust, high-impact marketing teams, drawing on lessons from firefighting and enterprise leadershipThe async work philosophy Atlassian uses to eliminate unnecessary meetings and increase productivity across a global teamWhether you lead a team or want a seat at the table, this episode breaks down how to structure, scale, and lead product marketing the Atlassian way.Timestamps(00:00) - – Intro (03:04) - – Matt’s path from engineer to Atlassian VP (06:19) - – Why technical backgrounds can be both a strength and a curse in PMM (10:04) - – What product marketing looks like at a $5B company (11:04) - – “Own the outcome, not the task”: tying PMM to revenue (13:24) - – Why product marketers should care about pipeline (even if they don’t own it) (14:49) - – How brand and creative marketers can still align to business outcomes (17:19) - – Measuring inputs vs. outcomes (and how to stay focused on the right one) (18:04) - – How Matt applies firefighting lessons to leading marketing teams (19:44) - – Triaging “fire drills” and protecting your team’s focus (21:34) - – How to prioritize ruthlessly (and what real prioritization means) (24:04) - – From IC to VP: how your mindset and responsibilities shift (28:35) - – Why leaders should double down on strengths—not fix weaknesses (30:50) - – How self-assurance became Matt’s superpower as a leader (33:50) - – The StrengthsFinder approach Matt uses with his team (35:50) - – The value of executive coaching for marketing leaders (37:20) - – The goal: build the best marketing team anyone’s worked on (38:50) - – Why trust and 10x thinking unlock great marketing work (41:20) - – Where product marketing sits inside Atlassian’s org (42:50) - – How Atlassian uses Loom and async work to eliminate unnecessary meetings (45:20) - – What qualifies as a real meeting at Atlassian (46:50) - – Why async work helps global teams move faster (49:50) - – How Atlassian balances async with intentional in-person gatherings (51:50) - – Why trust changes how Slack and email are interpreted (52:35) - – How Atlassian thinks about AI’s role in marketing (54:50) - – Why it’s hard to stand out in an “AI-washed” market (56:05) - – Matt’s mission: help make work suck less (57:20) - – Final thoughts and wrap-up Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#259 Paid Ads | In this episode, Dave is joined by Pranav Piyush, founder and CEO of Paramark, a platform helping B2B marketers run real experiments to measure ad performance. Pranav brings a sharp point of view on attribution, channel performance, and how to actually prove what’s working across your paid media mix.Dave and Pranav cover:Real-world results from 7 B2B ad campaigns, including branded search, YouTube, billboards, and Performance MaxWhy most marketers are misusing the word “test” and how to run true experiments with lift, control, and causalityHow even small teams can apply experiment design (on a $10K budget or less) to make smarter spend decisionsWhether you're managing a big budget or just getting started with paid campaigns, this episode will help you think more critically, and confidently, about where and how to invest in B2B marketing.Timestamps(00:00) - – Intro (03:34) - – Why Paramark pulled real data from 7 B2B ad campaigns (06:04) - – Attribution vs. experimentation: what most marketers get wrong (09:34) - – Correlation vs. causation explained (with a LinkedIn example) (12:19) - – How to run a real test (hint: you need a control) (13:34) - – Branded search test results: $1M+ saved, no performance loss (18:34) - – Why strong SEO makes or breaks branded search tests (19:34) - – Billboard test: how one brand proved real lift with out-of-home (23:04) - – What “digital out-of-home” looks like in B2B (24:34) - – YouTube ad tests: one big win, one big flop (29:50) - – How to run tests with small budgets ($500–$10K) (34:20) - – Connected TV (CTV) test results from a Series F SaaS brand (36:20) - – What happens when a multichannel test works—but isn’t efficient (38:20) - – Paramark’s Exit Five sponsorship test (real numbers shared) (41:50) - – Why content needs to drive short-term lift, not just long-term “brand” (44:50) - – How Pranav used LinkedIn to drive inbound from day one (46:50) - – Your attribution model is lying, give your audience more credit (48:20) - – When 7 ad tests fail in a row…and the 8th one works (49:50) - – Performance Max test: why it worked for one brand (51:50) - – How long to run a test? Use data, not gut (53:50) - – Bonus: Pranav’s hiring playbook for his first marketing leader (57:50) - – Wrap up and final takeaways Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

Dave here. Interrupting the regular podcast feed for a 3 minute story and rant about why I love the job of marketing and what it might mean in a world where AI is advancing so rapidly and changing the role of marketing. Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#257 AI Strategy | Dave is joined by Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier. Kieran is a rare blend of technical operator, creative strategist, and team builder. He’s spent his career pushing the edges of B2B marketing, most recently through his work leading AI transformation initiatives at scale.Dave and Kieran cover:How AI is reshaping B2B marketing workflows, content creation, and team structureWhy the best marketers will specialize at the “outer edges” of creativity or technical execution (and what happens if you stay stuck in the middle)Kieran’s leadership philosophy: how he manages 300+ people while staying deeply involved in creative executionWhether you’re leading a marketing team or sharpening your own skills, this episode offers a clear look at how AI is changing the game and how B2B marketers can stay creative, strategic, and indispensable in the process.Timestamps(00:00) - – Intro (02:34) - – Kieran’s marketing journey (04:34) - – His 2-year mission framework (06:34) - – Advice for early-career marketers (08:04) - – Why the grind still matters (09:34) - – Ireland’s SaaS and startup scene (10:34) - – Balancing operator vs. manager (12:34) - – AI-generated “How to work with me” (15:04) - – Kieran’s push-and-pull leadership style (16:34) - – Giving direct creative feedback (18:34) - – Why “collaborative brainstorms” fail (19:34) - – The value of strong opinions (20:34) - – Learning through tough feedback (21:34) - – ChatGPT as a creative partner (23:34) - – Claude vs. ChatGPT vs. Gemini (25:34) - – Prompting differences in GPT-3.5 vs. 4.0 (29:50) - – Decision fatigue and AI loyalty (30:50) - – Where AI is taking B2B marketing (31:50) - – From answers to actions (33:50) - – Micro-audiences and personalization (35:50) - – The return of branded traffic (36:50) - – Why AI reignited Kieran’s spark (38:50) - – Avoiding AI-induced multitasking burnout (40:20) - – Deep work vs. whack-a-mole (41:20) - – Don Draper meets ChatGPT (42:20) - – Picking a lane: tech vs. creative (43:50) - – The value of podcasting practice (44:50) - – Building a prompt muscle (46:50) - – How Kieran trains GPTs (48:50) - – Prompting tips for marketers (49:50) - – The future CMO: part IC, part leader (50:50) - – How agencies will evolve with AI (51:50) - – In-person is back (52:50) - – Overrated AI use cases (53:50) - – Favorite tool: GenSpark (55:50) - – Mistakes marketers make with AI (56:50) - – Does anyone care if it’s AI? (57:50) - – Lessons from fatherhood (58:50) - – Final thoughts and wrap-up Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#256 Email Deliverability | In this episode, Dan is joined by Sarah McNamara, Revenue Operations & GTM Strategy Lead at Vector, and Alex Fine, co-founder of Understory, an agency helping B2B SaaS companies scale with outbound, paid, and email. Both Sarah and Alex are experts in email strategy, specifically the behind-the-scenes mechanics that make or break your deliverability.They break down what B2B marketers often overlook when it comes to getting emails opened, read, and replied to, and share practical tactics to improve performance across newsletters, outbound, and lifecycle campaigns.Dan, Sarah, and Alex cover:Why email deliverability issues are more common than you think and how to spot them earlyThe metrics that actually matter (hint: opens and clicks aren’t on the list)How to protect your domain reputation and warm up inboxes the right wayIf email is part of your GTM motion, this episode will help you reach more inboxes and stop your messages from disappearing into the void.Timestamps(00:00) - – Intro (03:44) - – Meet Sarah and Alex (05:49) - – Why email deliverability matters more than subject lines (08:04) - – How to tell if you have a deliverability problem (10:19) - – The most useful (and overlooked) deliverability metrics (12:39) - – Why replies matter more than opens or clicks (15:04) - – Tools Alex and Sarah use to monitor deliverability (17:19) - – Should you buy a dedicated IP? (19:14) - – How to evaluate platforms for deliverability (21:34) - – Getting sales to care about data hygiene (24:04) - – Deliverability tips for small senders and solopreneurs (29:05) - – Subdomains vs. secondary domains (31:55) - – How many inboxes per domain is too many? (34:00) - – Best practices for cold outreach (36:50) - – How security bots skew your open and click data (39:50) - – What counts as “spam” (and how filters decide) (43:05) - – How to re-engage cold or inactive lists (45:50) - – What to A/B test in subject lines (and when it’s pointless) (49:00) - – How to build a healthy, opt-in list from scratch (51:50) - – When to stop emailing cold leads (54:05) - – Welcome sequence tips for engaged subscribers (57:00) - – How to warm up a new domain (01:00:20) - – Final takeaways and advice Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#255 Leadership | In this episode, Dave is joined by Kelly Hopping, CMO of Demandbase, a B2B company known for pioneering account-based marketing. Kelly leads a 70+ person marketing org that spans brand, demand gen, product marketing, events, and SDRs, and she shares exactly how she structures and operates that team to drive results.Dave and Kelly cover:How to design and run a full-funnel marketing team that includes SDRs, content, field, and brand, and keep them aligned on pipelineThe annual planning strategy Kelly uses to balance short-term targets with long-term positioning (including what changes quarter to quarter)How her team is using AI right now and what she’s doing personally to stay sharp as the pace of change acceleratesWhether you're a first-time CMO or just trying to scale your B2B marketing engine, this one is packed with insights from someone who’s operating at a high level.Timestamps(00:00) - – Intro (03:34) - – What Demandbase actually does (05:34) - – How the Demandbase marketing team is structured (08:04) - – Who owns what: brand, content, demand, SDRs (10:34) - – Account-based marketing + broad demand gen (13:04) - – What a CMO actually does at this stage (15:34) - – Kelly’s early CMO learning curve (18:34) - – Planning your first 90 days as a CMO (20:34) - – Balancing pipeline today vs. positioning for tomorrow (23:04) - – What changed between a bad Q4 and strong Q1 (28:50) - – How Kelly thinks about yearly pipeline pacing (31:50) - – Staying relevant in a fast-moving MarTech world (34:20) - – Why marketers need to work like product teams (37:50) - – “I am the ICP”: Why product marketing works better (39:20) - – Kelly’s #1 job as CMO: Make sales love marketing (41:50) - – Becoming a peer to product and revenue leaders (44:20) - – Best-performing channel right now: in-person events (45:50) - – Brand, attribution, and pipeline are all connected (47:20) - – How Kelly’s team is using AI today (48:50) - – The future of marketing roles in an AI-powered world (51:20) - – Why she’s still learning new AI tools herself (53:50) - – Why AI is fun again for marketers (54:50) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#254 Brand | In this episode, Dave sits down with Kira Federer, VP of SMB Marketing at Paramount Advertising, and formerly at companies like Reddit and Glassdoor. Kira shares her journey from sales to product marketing and the lessons she’s learned along the way.Dave and Kira discuss:How to align marketing and sales through co-creation to ensure your sales team uses the content you createThe value of a strong messaging framework and how it drives consistency in B2B marketingWhy you need to time your product launches and ensure that marketing resonates with both your team and the market at the right momentTimestamps(00:00) - - Intro to Kira (06:28) - - Kira’s Career Journey From Sales Enablement to Product Marketing (09:42) - - Challenges of Building Community / Getting Connected with Exit Five (15:58) - - How To Get Sales To Use Content from Marketing (18:33) - - How to Align Marketing and Sales Teams (26:55) - - Effective Messaging and Having a Core Company Narrative (32:03) - - Why You Should Identify What Differentiates Your Business (35:46) - - How To Create Strong Brand Positioning (38:31) - - Why You Need To Have A Clear Vision And Strong Point of View in Marketing (40:15) - - “The Risk Of Insult Is The Price Of Clarity” Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#253 Lifecycle Marketing | In this episode, we’re joined by two expert lifecycle marketers: Charlotte Hardin, Lifecycle Marketing Manager at Rebuy Engine, and Naomi West, Senior Product Manager at Customer.io. Charlotte and Naomi bring years of hands-on experience running email, onboarding, and retention programs inside B2B SaaS companies.They break down how B2B teams can use lifecycle marketing to drive more revenue, boost product engagement, and strengthen customer relationships, without needing a massive team.Charlotte and Naomi cover:How top B2B teams build high-performing welcome sequences, and why they’re constantly worth revisitingThe role of experimentation and how to prioritize AB tests that deliver learnings (even with small audiences)Strategic ways to keep users engaged post-onboarding, including behavior-based triggers and surprise-and-delight momentsTimestamps(00:00) - – Intro (03:04) - – Meet Charlotte and Naomi (04:49) - – How they define lifecycle marketing (06:34) - – What they’ve changed their minds about recently (09:44) - – Plain text vs. designed emails (11:34) - – Their frameworks for experimentation (14:04) - – How to test in low-volume environments (16:24) - – Common mistakes in A/B testing (17:34) - – What a day in lifecycle marketing looks like (19:44) - – How they (actually) use AI in their workflows (23:34) - – Building a reporting foundation for lifecycle (28:50) - – Naomi’s example of measuring aha moments (30:50) - – Quick definitions of lifecycle marketing (32:20) - – Tips for writing lifecycle campaigns that actually matter (32:50) - – Favorite lifecycle campaigns they’ve run (34:50) - – Why revamping welcome flows is always worth it (36:50) - - Frameworks they use for building new flows (39:50) - – What to do *after* onboarding ends (41:20) - – Using behavior-based triggers and milestones (43:20) - – Surprise and delight moments in B2B (44:50) - – Creating assets with a lean team (47:50) - – Systems and templates that save time (49:50) - – Navigating multi-year sales cycles with lifecycle content (52:50) - – Why benchmarks are often misleading (54:50) - – Final advice: audit often, talk to your team, and keep learning (56:50) - – Wrap-up and where to find Naomi and Charlotte Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#252 Category Creation | Dave is joined by Josh Lowman, Founder and Creative Director of Gold Front, a category design studio that’s worked with brands like Uber, Notion, and Qualtrics. Josh is a leading voice in strategic brand positioning and category creation. He’s spent over a decade helping high-growth B2B companies define what makes them irreplaceable in crowded markets.Dave and Josh cover:Why most category creation efforts fail (and what to do instead)The four real paths to category leadership: create, transform, niche, or go soloHow B2B marketers can align product, brand, and messaging around a single strategy to stand out and scaleWhether you're launching a new product or repositioning an existing one, this episode is a masterclass in strategic clarity.Timestamps(00:00) - – Intro (03:04) - – Josh’s backstory and founding Gold Front (06:19) - – How Gold Front became a category design studio (08:34) - – What “category creation” really means (11:49) - – Why being irreplaceable is the real goal (14:54) - – The four paths to category leadership (18:39) - – Why Drift didn’t succeed in creating a true category (22:34) - – Clay and Notion as category-of-one examples (25:24) - – Marketing vs. actual customer perception (31:05) - – Can Exit Five be more than the “Dave Gerhardt community”? (34:00) - – How to scale brand DNA beyond the founder (36:50) - – Defining Exit Five’s ethos as a company (39:10) - – Strategy as a company-wide unifier (42:00) - – Advice for CMOs on driving strategy with CEOs (44:35) - – Why strategy is always the root cause (46:05) - – Vibe marketing and the rise of right-brain thinking (48:50) - – Josh’s mental health journey and long-term therapy (52:20) - – LinkedIn, self-worth, and staying grounded (54:50) - – Weightlifting, discipline, and mental clarity (57:50) - – Daily habits that improve mindset (01:01:05) - – What 30 days of silent meditation does to your brain (01:05:50) - – Final thoughts on presence, self-work, and leadership Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#251 Website Optimization | In this episode, Danielle is joined by Guy Yalif, Chief Evangelist at Webflow; Talia Wolf, Founder and CEO of Getuplift; and Scott Cappuzzo, Web Strategist at Webflow. Together, they dig into what actually makes a B2B website convert and why most homepages are missing the mark.This panel brings deep experience in conversion rate optimization, UX strategy, and messaging clarity, sharing practical tips and live feedback from real B2B websites submitted by Exit Five members.Danielle, Guy, Talia, and Scott cover:The #1 mistake B2B marketers make on their homepage and how to fix it with customer-driven messagingSmart ways to test and optimize (even if you don’t have high traffic)How to write CTAs that meet buyers where they are in the journey (and get more clicks)Whether you’re planning a homepage redesign or just want to tighten your headline and CTA copy, this session will help you make smarter website decisions grounded in expert feedback and real examples.Timestamps(00:00) - – Intro (02:34) - – Meet the expert panel (05:14) - – The biggest homepage mistake (07:54) - – What customers *really* want (08:34) - – The CTA copy test (09:44) - – Why A/B testing isn’t always right (12:24) - – Personalization you can actually use (14:34) - – What’s a “good” conversion rate? (17:54) - – CTA clarity vs. creativity (21:34) - – Why messaging must come first (23:34) - – How to do helpful personalization (32:00) - – Emotional drivers in B2B (34:00) - – Live teardown #1: ContactMonkey (40:40) - – Visuals, CTAs, and clarity (46:00) - – Live teardown #2: StreamTech (51:20) - – Outdated visuals and lost messaging (54:55) - – Chatbots: thoughtful vs. disruptive (56:10) - – Live teardown #3: CallTrackingMetrics (58:50) - – Final ratings + wrap-up Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#250 Customer Insights | Matt sits down with Shoshana Kordova, a 3x founding product marketer and former journalist who now helps B2B tech startups craft customer-infused messaging through her consultancy, Peel Product Marketing. Shoshana recently launched a customer insights playbook for the PMM Jetpack, equipping marketers with tools and templates to run more effective customer interviews.Matt and Shoshana cover:Why a customer insights program is more than “just talking to customers” and how to turn interviews into a repeatable system that drives messaging, positioning, and case studiesHow to collaborate across teams (especially with CS and product) to get buy-in and avoid stepping on toesThe most common mistakes B2B marketers make with interviews and how to get the kind of insights you can actually useWhether you're a product marketer, content strategist, or leading a GTM team, this episode is packed with actionable takeaways to build messaging that resonates.Timestamps(00:00) - – Intro (02:39) - – Meet Shoshana: From Journalism to Product Marketing (03:49) - – What Is “Customer-Infused Messaging”? (05:34) - – Why Customer Insights Beat Surface-Level Deliverables (07:34) - – How to Work with CS and Sales Without Stepping on Toes (10:34) - – Navigating Competing Priorities Across Teams (12:54) - – Selling the Value of Customer Interviews Internally (16:54) - – The 6 Steps to Building a Customer Insights Program (18:49) - – Step 1: Aligning Goals with Stakeholders (20:29) - – Step 2: Building a Customer Interview Pipeline (22:34) - – Step 3: Keeping Stakeholders in the Loop (Hint: Use Slack) (29:05) - – Step 4: How to Run a Great Customer Interview (34:35) - – Focus on Problems, Not Just the Product (37:10) - – Uncovering Real ROI with Better Follow-Ups (38:20) - – Step 5: Documenting What Actually Matters (40:40) - – How to Organize Insights into a Shared Database (43:30) - – Step 6: Putting Insights to Work (Case Studies, Messaging, ICPs) (45:50) - – Should You Hire an External Interviewer? (48:05) - – What’s a Realistic Interview Cadence? (49:35) - – Other Places to Find Customer Insights (When Interviews Aren’t Possible) (51:10) - – Final Tips: Mining G2 Reviews, Webinars, and Internal Teams (52:24) - – Wrap-Up and Where to Find Shoshana Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#249 Cold Email | In this episode, Danielle is joined by four experts in B2B outbound: Zoe Hartsfield (Apollo), Will Allred, (Lavender), Maximus Greenwald (Warmly), and Alex Fine (Understory). Together, they dive into the good, bad, and “please don’t ever send this” of cold email strategy. Each guest brings firsthand insight from scaling outbound at fast-growing B2B companies and helping clients do the same.Danielle and the crew cover:The biggest reasons cold emails flop and what great ones do differentlyHow to use personalization, targeting, and timing to get replies (not unsubscribes)The right way to blend automation and human touch in your outbound strategyIt’s an inside look at how marketers and founders approach outbound messaging, across strategy, execution, and scale.Timestamps(00:00) - — Intro and guest lineup (04:04) - — Why most cold emails fall flat (06:04) - — Common copy mistakes: too much “I,” not enough “you” (07:34) - — The automation vs. personalization debate (09:49) - — When *not* to send a cold email (12:04) - — What targeting gets wrong (and how to fix it) (14:04) - — Teardown #1: Robotics email with 0% replies (16:19) - — Subject line issues, tone, and CTA feedback (18:34) - — Teardown #2: CRM campaign with profanity (20:19) - — Why this email screams “marketing,” not “outbound” (24:50) - — Teardown #3: Direct debit email repurposed from a nurture (27:20) - — Why HTML-heavy emails kill deliverability (29:05) - — Teardown #4: Founder-led cold email from Breakout (31:20) - — What worked: relevance, format, and intent (33:50) - — Teardown #5: Cybersecurity email to bank execs (35:50) - — Final takeaways on relevance, timing, and strategy Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#248 Marketing Strategy | Dave sits down with Jaleh Rezaei, founder and CEO of Mutiny, the personalization platform for B2B websites. Jaleh brings a unique blend of founder perspective and deep marketing expertise from her time building go-to-market teams at VMware, Gusto, and now Mutiny. She’s on a mission to help marketers ditch the spammy, scaled playbooks of the past and refocus on what really drives pipeline today: buyer experience. Dave and Jaleh cover:Why the current use of AI is making marketing worse and how to use it to build better buying experiences insteadWhat marketers get wrong about speed (hint: it’s not about doing more, it’s about doing what matters)The principles of simplifying your go-to-market strategy to cut through noise and align your team around real revenue resultsMarketing is changing fast, but the teams who win will be the ones who prioritize real buyer experiences, move with speed, and stay aligned on what actually drives revenue. Jaleh breaks down how to make that shift before your strategy gets left behind.Timestamps(00:00) - – Intro (02:44) - – Why AI Is Backfiring in B2B (05:19) - – Outbound Is Broken (Here’s the Data) (07:39) - – What Buyers Actually Want (10:04) - – Gimmicks Don’t Scale (11:34) - – How to Build Marketing That Lasts (12:59) - – Why Marketing Is Harder Today (14:34) - – AI Efficiency vs. Buyer Experience (16:04) - – The Right Way to Prioritize Speed (20:05) - – Strategy First, Then Speed (21:55) - – How to Test Big Ideas Fast (24:10) - – Borrowing the YC Mindset (25:50) - – What Good Brand Marketing Looks Like (28:05) - – Best Brand Play: A Children’s Book? (29:50) - – What CEOs Really Want From Marketing (31:30) - – Simplifying Your Marketing Strategy (34:00) - – The Truth About Sales-Marketing Alignment (35:50) - – Common Execution Gaps That Hurt Revenue Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#247 Lead Nurturing | In this episode, Danielle is joined by Samar Owais, founder of Emails Done Right; Sheri Otto, CEO of Growth Lane Strategies; and Sofia Silva, Marketing Manager at Reachdesk.These three email experts came together for a live roast of real B2B lead nurture emails, submitted by marketers from the Exit Five community. You’ll hear the good, the bad, and the fixable, with practical insights on how to improve your own nurture sequences.Danielle, Samar, Sheri, and Sofia cover:The most common lead nurture mistakes B2B marketers make (and how to fix them)Why every email should be treated as a conversation, not just a campaignHow to write nurture emails that create connection, not clicks for clicks’ sakeIf you're building (or rebuilding) your nurture strategy, this one’s packed with real examples and expert feedback to guide your next send.Timestamps(00:00) - – Intro: Welcome to the Lead Nurture Roast (03:02) - – Meet the Experts: Samar, Sheri, and Sofia (06:59) - – What Is **Lead Nurturing, Really? (09:52) - – The Problem with “We” Language in Emails (12:14) - – The Biggest Mistakes B2B Marketers Make (14:39) - – Why AI Isn’t Your Copywriter (16:34) - – Teardown #1: Subject Line Gone Wrong (21:04) - – How to Build a Nurture Sequence Around a Whitepaper (23:44) - – CTA Overload and Why It Kills Clicks (29:54) - – Teardown #2: Great Open Rate, Low Engagement (33:48) - – The One-CTA Rule (And Why It Matters) (36:30) - – Structuring Long Emails for Skimmability (39:02) - – Teardown #3: Cold Lead, Wrong Email (41:35) - – Re-Engagement Emails That Actually Work (44:25) - – Use Social Proof Instead of Product Pitches (46:05) - – Teardown #4: The Overloaded Onboarding Email (49:00) - – What’s a “Micro Conversion” in SaaS Email? (53:35) - – Time-to-Value and the First Action That Matters (55:50) - – This Email Is... a Whole Sequence in One (58:10) - – Teardown #5: Trust Email or Generic Spam? (01:01:05) - – Why Specificity Beats Industry Buzzwords (01:03:20) - – Final Scores and Wrap-Up Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more. 

#246 Sales Alignment | Danielle welcomes Talya Heller, founder of Down to a T, a B2B consultancy helping marketers turn competitive positioning into high-impact sales assets. With experience in engineering, product management, and product marketing, Talya knows how to bridge the gap between what marketing builds and what sales actually uses.Together they unpack:Why most sales decks and battle cards go unused and what to build insteadHow to enable your champion to sell internally with confidenceSimple frameworks for mapping competitive positioning that teams will actually useTalya also breaks down how she researches, builds, and delivers assets that align sales, marketing, and product, all rooted in buyer empathy.Timestamps(00:00) - – Intro & Talya’s background (02:34) - – From engineering to B2B marketing (09:19) - – What is buyer enablement? (11:34) - – Why deals stall after vendor selection (13:49) - – The problem with sales decks (16:19) - – Why battle cards don’t work (18:34) - – Talya’s competitive positioning map (25:50) - – Grouping competitors by approach (28:20) - – Market maps for sales (30:20) - – Where to get the best insights (32:50) - – New formats for enablement (35:05) - – Why context matters (36:50) - – Empathy for your sales team (38:35) - – Closing thoughts on empathy (39:40) - – Where to find Talya online Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Zuddl.We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. Head over to zuddl.com/exitfive to learn more.