Coffee Meets Cloud

PTO, Patriotism and Leveling Up

This week, Rachel and Cassandra are holding down the fort while Caramie is away, and the conversation covers everything from work-life balance to fireworks, Salesforce community, and a little Nintendo nostalgia.
The episode starts with a discussion about the importance of real PTO - actually disconnecting, setting boundaries, and creating healthy team cultures where people can truly recharge. From there, they celebrate America’s 250th birthday, sharing stories about fireworks, family traditions, and what patriotism means to them.
The hosts also congratulate the newest Salesforce MVP class and talk about the heart of the Salesforce community: helping others, giving back, and building connections without worrying about titles or recognition.
Of course, no Coffee Meets Cloud episode would be complete without a few fun detours. Rachel and Cassandra debate whether birthdays should be replaced with “leveling up” like a video game, reminisce about Nintendo classics and Wii Bowling, and start planning future Coffee Meets Cloud road trips—including visits to Super Nintendo World and Dolly Parton’s new truck stop near Nashville.
Plus, they give a shout-out to listeners who have requested their Keep Your Coffee Strong stickers.
☕ Want one? Email us at coffeemeetscloud@gmail.com and we’ll get one in the mail!

The Little Podcast That Could: One Year of Coffee Meets Cloud

One year ago, three friends hit record and hoped for the best.
In this special anniversary episode, we're celebrating one full year of Coffee Meets Cloud with a look back at the moments, lessons, laughs, and hard pivots that got us here. From the episode that never made it out of the vault to the inside jokes that somehow became part of our brand, we're reflecting on how the show has evolved—and why friendship has always been at the center of it.
Along the way, we hand out the first-ever Coffee Meets Cloud Awards, play a revealing round of Never Have I Ever: Podcast Edition, make predictions for where the podcast (and each of us) will be one year from now, and share some exciting plans for year two—including merch, sponsorship goals, and a fresh look for the show.
This episode is equal parts celebration, gratitude, and chaos—the perfect representation of who we are. Whether you've been with us since episode one or you're just finding the podcast, thank you for spending part of your journey with us.
And because anniversaries call for gifts, we're giving away a free Coffee Meets Cloud anniversary sticker! Just send us a message on social media or email CoffeeMeetsCloud@gmail.com with your mailing address. The sticker is on us—we just ask that you tell someone about the podcast.
Here's to one year of coffee, cloud, squirrels, Salesforce tangents, and the incredible community that's grown alongside us. We're just getting started.

The Women We Lose in Tech (And How We Change the Story)

This week, we’re joined by Lillie Beiting—Salesforce architect, author, speaker, and co-founder of 50x35, a storytelling initiative sparked by a startling reality: nearly half of women leave the tech industry by age 35.
We discuss the stories behind that statistic—the pressure to put on “armor” at work, the women who paved the way before us, and the responsibility today’s leaders have to reach back and make the path a little easier for those coming next.
Then, in true Coffee Meets Cloud fashion, the conversation takes a hard left into a passionate debate about kids, screens, handwriting, and whether technology is replacing the very struggle that helps us learn. From cursive and critical thinking to attention spans and the value of doing hard things, we ask: What are we losing in our rush to make everything easier?
Plus, we talk Dreamin’ events, the power of the Salesforce community, and why some of the best innovation happens when practitioners share what they’ve learned.
Want to learn more about 50x35 or share your own story? Visit: https://www.50x35.org/
Catch Lillie speaking on June 25th about Salesforce Experience Cloud Security Architecture by registering at: https://ezprotect.io/event/salesforce-experience-cloud-security-architecture/

From Cursive to ChatGPT

Technology has become a permanent fixture in our classrooms—but what are students gaining, and what might they be losing?
In this episode, we dive into the growing role of technology in education and explore an increasingly important question: Which skills should children still practice deliberately because technology doesn't build them automatically?
From handwriting and spelling to critical thinking, problem-solving, and navigating disagreement, we discuss how school-issued devices, AI tools, and digital-first learning environments are changing the way children learn. While technology creates incredible opportunities, it can also make it easy to outsource skills that were once considered foundational.
We also explore:• Whether convenience is replacing capability in education• The impact of AI and automated tools on critical thinking• How personalized algorithms can limit exposure to different viewpoints• The connection between technology, dopamine-driven behavior, and rising anxiety among young people• What parents can do to help children develop skills that screens can't teach
As parents and technology professionals, we're not advocating for less innovation—we're asking how we can be more intentional about preparing kids for a world where technology is everywhere.
Resources Mentioned:
Olympic Minds Podcast: Leadership Beyond Limits (Episode 34 featuring Sherry Winn)https://www.youtube.com/playlist?list=PLCQ7Pa1beyOKTIc9hByCe62XS7ouJWzZy
The Anxious Generation by Jonathan Haidthttps://www.anxiousgeneration.com

Summer Woes and Southern Manners

This week on Coffee Meets Cloud, we’re diving into the chaos, comedy, and contradictions of modern life — from surviving summer break with overstimulated kids to navigating workplace burnout, AI adoption, Southern etiquette, and personal loss.
We unpack the idea that today’s kids may be losing the ability to simply be bored, how AI is quietly reshaping the way we think and work, and why tech professionals are living years ahead of the general public when it comes to AI adoption. Along the way, we share our own experiences using tools like ChatGPT and Claude for everything from meal planning to productivity — and where we think the line between convenience and cognitive atrophy starts to blur.
The conversation also takes a more personal turn as we talk about grief, health journeys, family genetics, and the emotional whiplash of adulthood. From endocrinology appointments and anti-inflammatory diets to losing beloved pets and grandparents in the same week, this episode balances humor and heartbreak in the way only real friendship can.
And of course, we couldn’t resist ending with a conversation about Southern manners, raising respectful kids, workplace meeting culture, and whether being underestimated might actually be a superpower.
It’s thoughtful, funny, honest, and a little all over the place — exactly like summer.

Out of Office, Out of Tune, Out of Patience

This week, the Coffee Meets Cloud crew goes everywhere — from Botox injections and gray hair to remote-work ethics, family guilt, performance culture, and the pressure to constantly “have it together.”
What starts as Friday chaos (kids home from school, dog drama, tech issues) quickly turns into one of the most honest conversations yet. The hosts unpack aging without apology, the money and mental load behind “maintenance,” shifting workplace expectations for women, and why visible spending doesn’t automatically mean someone is wealthy.
They also dive into remote work boundaries, green-dot culture, “mouse jigglers,” time fraud, and the dangerous obsession with measuring presence instead of outcomes. Along the way: stories about over-employed contractors, high performers who finish 8 hours of work in 4, and the uncomfortable truth about how many organizations reward optics over actual value.
Layered underneath the humor is a bigger conversation about identity, performance, guilt, and learning how to prioritize the life happening right in front of you.
Until then, keep your coffee strong.

Retuning Life, One String at a Time

What do you do when people disappoint you?
This episode started with a commencement speech about guitars going out of tune… and somehow turned into one of our most honest conversations yet.
We talk about friendship heartbreak, parenting through disappointment, learning who your real people are, and why life isn’t about having a huge circle — it’s about knowing who actually shows up.
Also:• Cassandra reviews an energy drink that tastes like sunscreen• Rachel buys patriotic metal roosters• Caramie accidentally starts a conversation about emotional survival
Basically: laughter, life lessons, and chaos. Our favorite kind of episode.

The Risk You Don’t Know You’re Taking: Why Employer Benefits Aren’t Enough

In this episode of Coffee Meets Cloud, we sit down with insurance agency owner Mark Irwin for a conversation that hits closer to home than most people realize.
From life insurance and disability coverage to the hidden gaps in employer-provided benefits, we unpack the risks many families don’t discover until it’s too late. Mark breaks down the common misconceptions around workplace coverage, what actually happens when you change jobs or retire, and why “having benefits” doesn’t always mean you’re truly protected.
We also keep it real and practical — covering the difference between term and whole life insurance, the overlooked importance of disability coverage, and the simple questions everyone should ask about their current policies.
Whether you’re early in your career, raising a family, or just trying to make smarter financial decisions, this episode is packed with insight that could change the way you think about protection and long-term stability.
And of course, we start with coffee, comfort food, and Mark’s journey into the insurance world before diving into the bigger conversation.

Innovation, Leadership, and the People We’re Losing

This episode explores what it really takes to drive innovation—and why it’s not about doing everything yourself.
We unpack the rising number of women leaving tech, the deeper causes behind it, and what leaders can do differently.
Plus, a candid conversation about remote work habits and how your day-to-day presence impacts your team more than you think.

Coffee, Kids, and Conferences

This week, we’re bringing you the real mix of life behind the scenes—coffee in hand, kids in chaos, and conference season in full swing.
We kick things off at home, sharing the very unfiltered realities of parenting—from sick-day surprises and school challenges to navigating speech support, ADHD wins, and the long wait times that come with today’s healthcare system. Along the way, we get into the moments no one prepares you for… and what they’re quietly teaching us about patience, consistency, and emotional regulation.
Then we shift gears into conference mode—breaking down what it’s really like attending events like Dreamforce, TrailheadX, and Google Next. From packed sessions and badge logistics to flight struggles and navigating Hartsfield-Jackson Atlanta International Airport, we’re unpacking the parts no highlight reel shows.
We close by connecting it all—how the same skills we’re building as parents (self-regulation, awareness, consistency) are the exact ones that show up in how we lead teams, make decisions, and show up professionally.
Because whether you’re managing a toddler meltdown or a high-stakes project… the playbook isn’t all that different.