Coffee Meets Cloud

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...

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 w...

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 bac...

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 thin...

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 profe...

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...

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: • Cassan...

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 a...

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.

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...

This episode connects two areas where advocacy matters more than people realize: your health and your career. We share Caramie’s thyroid journey and what it looks like to push for answers when symptoms don’t follow a clear pattern, and why so many issues get dismissed or overlooked early on. Then we shift to what we’ve learned as tech leaders on the hiring side—why strong candidates still don’t ge...

Spring break energy, zero structure—and somehow we covered everything. From HOA governance realities (and why you can’t just change the rules) to the AI tools quietly saving hours of work, this episode is a mix of real-life problem solving and unfiltered banter. We get into: The truth about HOA contracts, voting thresholds, and why enforcement isn’t as simple as people think How custom GPTs, Plaud...

This week on Coffee Meets Cloud, we start with chaos—flu season taking down entire households, a truck getting wedged in a parking garage (yes, really), and an unexpected pickleball injury that escalated quickly. But underneath the laughs, we dig into something bigger: the rise of the “soft life” trend—and why it sounds good but doesn’t always hold up in the real world. What starts as a conversati...

What do neighborhood conflict, AI agents, and teenage drivers have in common? They all test your ability to respond instead of react. In this episode, we unpack a real-world situation involving public conflict and personal boundaries—and what it reveals about leadership outside the workplace. We also pull back the curtain on AI agent development: why what works in testing fails in production, the...

We grew up believing that if we worked hard, followed our passion, and did everything “right”… things would work out. But what happens when you realize the rules you were taught don’t actually work anymore? In this episode, we’re unpacking the biggest beliefs millennials were handed—from “work hard and you’ll be rewarded” to “you can have it all”—and where those ideas start to fall apart in real l...

This week we’re throwing the agenda out the window and catching up. From random life hacks that are saving us money, to the shows we’re currently hooked on, to a debate about what it really means to be a spoiled wife… this episode goes everywhere. Somehow we even end up talking about Jerry Springer and the trash TV that speaks to us. If you like the episodes where it feels like you’re sitting at t...

Everyone says they want the village. But fewer people want to be a villager. In this episode, we start with a catch-up on life with the kids and how wildly different childhood looks today compared to when we were growing up. From constant schedules to digital everything, the landscape of parenting and community has shifted more than we often realize. We also talk about the rising trend of adult ch...

In this lively episode of Coffee Meets Cloud, the three musketeers dive into a whirlwind of fun and insightful discussions! They kick things off with a spirited debate about the last-minute surprise dress-up days at school, sharing tips for navigating the chaos of motherhood. Next, they shift gears to tackle the ever-dreaded performance review season, dissecting the art of understanding feedback....

In this week’s episode of Coffee Meets Cloud, Cassandra and Rachel go “two amigos” style while welcoming their first guest in a couple of months — Brooke Brengartner. From breaking into the Salesforce ecosystem right out of college to navigating the real-world challenges of Marketing Account Engagement, this conversation is packed with honest insights, laughs, and a little builder therapy. In this...

Rachel’s out taking care of family, so it’s just Caramie and Cassandra this week — running on fumes and saying the quiet parts out loud. We unpack a week full of relentless “peopleing,” social batteries drained to 0%, losing our vehicles in Buckhead like exhausted millennials, and operating at energy levels somewhere around 10%. Then we pivot to the bigger question: Is everyone hitting AI fatigue?...

Mom guilt. Aging parents. A “simple” to-do list that breeds overnight. We talk about the moment you realize you’re not just raising kids — you’re slowly becoming the caretaker generation. Plus: Caramie’s new podcast space, spring cleaning reality checks, using ChatGPT as our life assistant, and an accidental deep dive into whether your grocery store bread is low-key toxic. Equal parts therapy sess...

In this episode we cover everything from planning your Disney trip like a Fairy Godmother, to how "the people of Walmart" dress nicer than artists at the Grammys. Pull up your chair, because this one is chaos.

In this cozy yet chaotic episode of Coffee Meets Cloud, we dive into the unpredictable world of winter storms—what to do when the snow starts falling and the winds start howling! 🌨️ But wait, there’s more! Ever wondered what would happen if you slept nude and your house caught fire? We explore that cheeky scenario and what your neighbors might think! 😳 Plus, we share heartfelt updates on our litt...

Somehow we ended up talking about PTO mix-ups, first dance classes, DIY projects, skincare rabbit holes, and why one innocent scroll can convince you that you need a new routine, a new product, and a new personality. This episode is a no-notes, real-life catch-up on being constantly influenced, mildly exhausted, and weirdly impressed by how much the internet seems to know about us. From half-baked...

In this episode of Coffee Meets Cloud, we’re joined by Sarah Margaret O’Brien, a Data Scientist at Southern Company, to discuss building a meaningful career in data, AI, and analytics. Sarah shares her path from Girls Who Code to developing machine learning solutions in the energy industry, along with insights on mentorship, representation, and leadership without a formal title. We also explore ho...