The Expand Mindset: Scaling Customer Growth in Klaviyo's AI Era

Same Scent, Different Story: Building Dossier for a New Era of Fragrance

In this episode of The Orita Podcast, Aaron Schwartz sits down with Sergio Tache, CEO at Dossier. Sergio shut down a skincare company, nearly deleted an email from Walmart, and built Dossier into the number one perfume brand there anyway. His advice: boring works, basics work, and if you don't make money it's a hobby. • Why Sergio went from banking to hair extensions to a failed skincare brand before landing on fragrance, and what the quick failure taught him about knowing when to stop • How a $45 AOV almost killed Dossier and why a buy-more-save-more test that moved it to $75 saved the company • The Walmart email that almost got deleted and every wholesale mistake a DTC brand can make, including packaging that does nothing on a shelf • Why selling fragrance online is really a question of trust, not smell, and what a 30-day no-questions return policy did for early conversion • The difference between individual AI and enterprise AI, and why your output is still your output no matter what generated it • Why Sergio opens his bank account every single day and thinks cash management is 80% of a CEO's job 👥 Meet the guest Sergio Tache, CEO at Dossier 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] From Banking to Beauty: How Sergio Got Into Entrepreneurship [02:46] The Skincare Failure and How to Know When to Stop [06:34] The Aha Moment: Why Fragrance Made Sense [09:06] Launching Fast vs. Launching Perfect [11:13] How Dossier Kept Speed as It Scaled [13:56] The Basics That Still Work: Unit Economics and AOV [16:59] Price Testing Was the Unlock Nobody Talks About [20:04] Same Bottle, 150 Perfumes: The COGS Logic Behind the Decision [21:33] The Walmart Email That Almost Got Deleted [23:06] Every Wholesale Mistake a DTC Brand Can Make [27:05] DTC vs. Wholesale: Where the Channels Reinforce Each Other [29:56] Selling Scent Online: Trust Over Smell [34:32] How Dossier Handles Complex Customer Questions at Scale [39:17] Individual AI vs. Enterprise AI: A Framework That Actually Holds Up [46:35] Cash Is Not a Finance Team Problem. Its a CEO Problem. 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

Beyond the Belt: Turning DudeRobe From Shark Tank Into a Lasting Brand

In this episode of The Orita Podcast, Aaron Schwartz sits down with Howie Busch, Founder at DudeRobe, that launched on Kickstarter in June 2017. One week later, the head of casting at Shark Tank slid into his DMs. His website went live at 7:30pm the night they aired. • How a career in sports law, NFL representation, and product licensing gave Howie an unfair advantage when athletes started wearing his robe for free • Why the robe turned out to be nearly impossible to knock off, and how that happened completely by accident • The iOS 14 summer that almost broke the business, what a 70% revenue drop taught him about pricing, and why raising prices 50% saved the company • How Howie structured his exit to a billion-dollar apparel company while staying in the seat, and what changed when he finally bought back his time • Why ROAS was the wrong north star and contribution margin was the metric he wishes he had watched from day one • How a customer survey of 600 responses shaped every decision on the She Robe launch, from colors to features 👥 Meet the guest Howie Busch, Founder of DudeRobe 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] From Law School to NFL Agent to Idea Man [03:44] How Kickstarter Led to a Shark Tank DM in One Week [08:26] What Howie's Legal and Licensing Background Actually Gave Him [10:44] Building a Brand With No Website and No Product [16:17] What He Would Do Differently Starting a Brand Today [19:47] Why Nobody Knocked Off DudeRobe and It Wasn't Strategy [22:17] The She Robe and the 600-Response Survey That Shaped It [24:08] How to Decide What Products Belong Under Your Brand [27:12] Website vs Amazon vs TikTok Shop: How Howie Thinks About Channels [32:22] The Metrics Trap: Why ROAS Was the Wrong North Star [35:06] iOS 14, 70% Revenue Drop, and the Summer That Almost Broke Everything [39:41] How Howie Structured the Exit and What Made It a Win-Win [42:23] Buying Back Your Time: What Changed After the Sale [44:48] What It Actually Takes to Build a Brand Worth Acquiring 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

Built From Skratch: Leading an Athlete-first Brand Through its Next Chapter

In this episode of The Orita Podcast, Aaron Schwartz sits down with Ian MacGregor, CEO at Skratch Labs. Pro cyclists kept complaining about their sponsored drink mix, so Ian and his partner Alan started making something better in secret. Fifteen years later they still haven't raised a dollar of outside money, and Ian thinks that's exactly why the brand still means something. • How a career-ending injury led Ian from the peloton to a company built around a water bottle with a sponsor logo on the outside and a homemade formula on the inside • Why Skratch has said no to major grocery distribution deals and what the cost of that discipline actually looks like in practice • The open book management philosophy Ian uses so every person on the team understands the P&L, not just their own KPIs • Why Ian is pushing his team to use AI as a tool to think better, not a shortcut to skip the thinking, and what he worries gets lost when the learning loops disappear • How Skratch thinks about building capabilities in-house versus partnering, and why the long-term view only works because they never took outside money • What Ian believes is coming for authentic brands as consumers get better at filtering out bullshit product innovation 👥 Meet the guest Ian MacGregor, CEO at Skratch Labs 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Secret Drink Mix: How Skratch Started in the Peloton [05:52] Staying Athlete-First When the Market Pulls You Wider [08:48] The Booster Problem: When Your Best Product Isn't Your Top Seller [10:43] Channel Strategy: Being Where Your Customer Buys [12:29] Going International Too Early and What It Cost [14:12] Food vs. Supplements: Why Transparency Has a Price [17:38] R&D as a Separate Line Item: How Skratch Protects Long-Term Bets [20:25] How Consumer Expectations Have Shifted Over 15 Years [26:27] Open Book Management: Why Every Person Sees the P&L [29:53] Using AI Without Outsourcing Your Thinking [33:38] The Rendering Problem: How Finished Output Narrows Thinking [36:22] Build In-House or Partner: How Skratch Decides [38:25] Why Authentic Brands Win as Consumers Get Smarter [43:40] Aaron and Ian Flip the Mic: Empathy, Compass, and What Enough Looks Like 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

The Expand Mindset: Scaling Customer Growth in Klaviyo's AI Era

In this episode of The Orita Podcast, Aaron Schwartz sits down with Sam Moorhead, Director of Customer Growth at Klaviyo. Sam has spent 15 years learning what separates a seller who closes from one who just checks boxes, and his answer has nothing to do with scripts. • What a PE-backed turnaround taught Sam about radical transparency that HubSpot never could, and how he brought it to Klaviyo • Why showing up to a discovery call without a point of view is just telling your customer you're ready to waste their time • The one question Sam teaches every rep to ask, and why the preamble matters more than the question itself • How Klaviyo is using AI to close the gap between what a CEO sees coming and what their frontline team is actually doing • Why the marketers leaning into AI right now are the ones getting promoted, and what that means for everyone else • How great salespeople bring product insights to engineering in a way that actually gets built 👥 Meet the guest Sam Moorhead, Director of Customer Growth at Klaviyo 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] From Finance Major to HubSpot BDR [04:12] PE Turnaround vs. Founder-Led Growth: What Changed [06:23] Radical Transparency: How Much Is Too Much [09:18] Building Teams That Get to Performing Fast [13:02] Onboarding New Reps: Frequency Over Big Training Days [16:17] Platform Selling: Why Discovery Has to Come First [18:43] How AI Changed Call Prep and Why Point of View Is Everything [21:46] The Why Now Question Done Right [24:14] Give and Get: How Elite Sellers Write the Prescription [28:15] What Customers Get Wrong About Doing It With AI Alone [32:28] Input Metrics, Gong, and Coaching With Real Data [35:10] The Wedge Between CEOs and Frontlines Is AI [39:23] When to Pull in Leadership to Multi-Thread a Deal [42:20] How Sales Should Bring Product Insights That Actually Get Built 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

The Partnership Layer: Building Growth Through Better Relationships

In this episode of The Orita Podcast, Aaron Schwartz sits down with Val Geisler, VP, Partner Programs at Digioh. Val has worked agency side, vendor side, and brand side, and she thinks that makes her exactly the kind of person AI cannot replace. • How Val followed a nonlinear career from theater to Klaviyo to CPG brand to Digioh, and what the through line always was • Why the gap between a personalized email and a generic website is still the biggest missed opportunity in ecommerce • How to run a jobs-to-be-done customer interview that actually surfaces the real goal, not the surface answer • What Digioh learned when they moved identification and ROI dashboards to the homepage instead of hiding them in a reporting tab • Why the most curious person on the team, not the most senior, should be running your customer interviews • Val's case for why soft skills are becoming the hard skills, and why AI optimizes for correct while humans can optimize for true 👥 Meet the guest Val Geisler, VP, Partner Programs at Digioh 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Theater, Retail, and a Nonlinear Career [01:24] From VA to Klaviyo: Following Skills Over Titles [03:26] Why Val Went Brand Side After Klaviyo [05:49] What Digioh Does in One Sentence [06:13] The Email Personalization Gap on the Website [08:46] Buckets vs. Rabbit Holes: How to Start Segmenting [10:13] Quizzes, Buttons, Replies: How to Collect Real Customer Data [13:11] Jobs to Be Done: Hiring a Product to Do a Job [15:59] How to Run a Jobs-to-Be-Done Interview That Actually Works [19:34] The Most Curious Person Wins: Who Should Interview Customers [28:31] Bringing Customer Insights to a Leadership Team That Wants Numbers [30:49] How Journeys and Dashboards Changed Digioh From the Inside [41:28] What Makes a Partnership Actually Mutually Beneficial [45:04] Soft Skills Are the New Hard Skills: What AI Still Can't Do 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel