In this episode of "Women in B2B Marketing," host Jane Serra is joined by Chaenara O’Brien - a sharp strategist who splits her time between leading digital GTM at vFunction and consulting with startups via Thought Bakery.

Chaenara brings a refreshingly grounded, systems-first lens to modern marketing, shaped by a background in energy trading, operations, and engineering services. The conversation unpacks what it really takes to build future-ready go-to-market teams, avoid burnout, and lead with both curiosity and clarity in a time of constant change.

Jane and Chaenara dig into:

• How her career in ops + energy trading led to B2B marketing leadership
• What “scenario planning” actually means - and how to make it actionable
• Why marketers need to stop reacting and start building systems
• How AI is reshaping what it means to “do more with less”
• Creating space for failure and curiosity on high-performing teams
• Why outdated ideas of brand control and executive presence need to go
• What GTM leadership should look like - and where it’s headed
• Outgrowing tech and how to protect your spark

Key Links:

Guest: Chaenara O'Brien: https://www.linkedin.com/in/chaenara/

Host: Jane Serra: https://www.linkedin.com/in/janeserra/

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** Originally published on January 18, 2023 **

This episode is a favorite for anyone who's ever argued about buttons vs hyperlinks, wondered if open rates still matter, or just wants to get better at email without sounding like a spam bot.

Kestrel Lemen is an email powerhouse: part strategist, part storyteller, and hands down one of the most insightful voices in email marketing. Her take on what actually drives conversions, how to balance plain text with visuals, and what marketers still get wrong about newsletters is full of gold.

It’s one I still reference, and if email is even remotely in your job description, you’ll want to give this one a listen.

Want a part two with Kestrel? Leave a review, drop a DM, or just say the word.

— Jane

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In this episode of Women in B2B Marketing, host Jane Serra sits down with Kestrel Lemen, email marketing expert and former Senior Strategist at Seguno Software (now Senior Manager Lifecycle Marketing at Zillow!) From her start in the art world to building Bronto’s London office and becoming an email force in both B2B and B2C, Kestrel’s journey is as fascinating as it is full of lessons.

They get into:

• The difference (and surprising similarities) between B2B and B2C email strategies
• Visual vs. plain text emails - and when each actually performs best
• What’s still true about email above the fold (and what’s totally changed)
• The metrics you should be tracking now - and which ones are just vanity
• Spam triggers, button design, and real talk on segmentation
• How privacy laws like GDPR and Apple MPP are reshaping email as we know it
• Why your “free Yeti cooler” giveaway is probably not the move
• Building emails that convert and don’t annoy
• Plus: how to keep your resume “conversion-optimized” for your future self

If email is part of your job - or just gives you heartburn - this episode is a goldmine.

Key Links:

Guest: Kestrel Lemen: https://www.linkedin.com/in/kestrellemen/

Host: Jane Serra: https://www.linkedin.com/in/janeserra/

Community: Women of Email - https://womenofemail.org/

***Recorded LIVE at WIB2BM LIVE ATLANTA***

In this first-ever LIVE IN PERSON episode of "Women in B2B Marketing," host Jane Serra sits down with Trinity Nguyen (CMO at UserGems) and Kacie Jenkins (SVP of Marketing at Sendoso) for an unfiltered conversation about the mistakes, missteps, and full-on f*ckups that shape great marketing leaders.

They open up about failed campaigns, tool disasters, event regrets, and how they’ve built teams that don’t just tolerate failure - they learn from it. From creating psychological safety to pushing back on prescriptive execs (even the ones with AI patents), this episode is a candid look at what it really takes to lead with empathy, resilience, and a little rebellion.

Packed with tactical advice, personal stories, and plenty of f-bombs, it’s a masterclass in growing your team-and yourself-through the hard stuff.

This live panel unpacks:

• Why failure is a must-have in high-performing marketing teams
• How to build psychological safety without babying your team
• Tactics for turning a f*ck-up into a team-wide learning moment
• The CEO “parking lot” trick for pushing back on prescriptive leadership
• How to evaluate AI tools (and avoid shiny object syndrome)
• What to do when your event investment flops—and how to design ones that actually work
• The power of structured gatherings and thoughtful details at live events
• Career pivots, personal advisory boards, and defining your authentic marketing path
• How to create space for younger team members to build resilience and take ownership

Key Links:

Guests:

Kacie Jenkins: https://www.linkedin.com/in/kaciejenkins/

Trinity Nguyen: https://www.linkedin.com/in/trinitynguyen/

Host: Jane Serra: https://www.linkedin.com/in/janeserra/

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