#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 Confluence
• Tactical ways to structure team rituals, recurring meetings, and brainstorms to focus on output, not performative busywork

You’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.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 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 ownership
• Why events are their #1 channel and how creative formats drive real pipeline
• The KPI + OKR system they use to prioritize work and measure marketing’s impact

You’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.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 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 goldmine
• Why it is important to repurpose podcast episodes, webinars, and other media into multiple forms of content to maximize their value
• Strategies for integrating SEO with authentic, valuable content that resonates with your audience, beyond just ranking for keywords

Timestamps

• (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.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 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.