UNPACK3D Podcast

Can an AI-native ERP get great before AI makes SAP good enough? Wiley Jones, co-founder and CEO of DOSS, explains why he built an ERP that behaves like a codebase. He covers how agents shrink months of implementation into a software pipeline and why agents should be priced like labor. He also shares a contrarian take on why the big consultancies will thrive.This episode is brought to you by Stifel Bank, trusted banking and venture debt partner for Sierra Ventures’ portfolio. Learn more at stifel.com.Chapters:(0:00) Introduction(1:54) From hardware engineer to ERP founder(5:01) Finding the wedge(9:01) Why ERP should behave like code(15:28) System of schema vs. system of record(20:29) Agent-run implementation(26:22) Giving the intelligence away(30:49) The race against SAP(34:28) Pricing agents like labor(39:11) Building a company second brain(51:36) Hot take: consultancies will thriveWhere to find Wiley Jones:LinkedIn: https://www.linkedin.com/in/wileycwjonesDOSS: https://doss.com

Vercel COO Jeanne DeWitt Grosser thinks this is the best time in history to be in sales — even as her own team automates away half of RevOps. Fresh off building go-to-market at Stripe through hypergrowth, she breaks down how to move up-market without blowing up your roadmap, why "maybes will kill you," and what AI actually changes about the job.This episode is brought to you by Stifel Bank — trusted banking and venture debt partner for Sierra Ventures' portfolio. Learn more at stifel.com.Chapters:(0:00) "Maybes will kill you"(1:24) Meet Jeanne DeWitt Grosser, COO of Vercel(2:36) Google → Dialpad → Stripe → Vercel(5:30) Building Stripe's sales machine from scratch(9:53) Why moving up-market is a company decision(16:08) AI-native companies & the forward-deployed engineer debate(27:12) Whales, buffaloes, and fins(32:25) Treating GTM as a product(44:00) Why it's the best time ever to be in sales(50:47) Building GTM tools with "half a human"(59:10) The AI-era salesperson: what changes, what doesn'tWhere to find Jeanne:LinkedIn: https://www.linkedin.com/in/jeannedewitt/Company: https://vercel.com

Fraud is about to go fully autonomous. AI agents that buy stolen identities, open accounts, and drain them with no human involved. Soups Ranjan, founder and CEO of Sardine, has spent 20+ years fighting financial crime at Coinbase, Revolut, and now across ~400 institutions worldwide. He walks us through the AI-vs-AI arms race, a 250,000-account attack cracked in five minutes, and why you should always let a little fraud through.This episode is brought to you by Stifel Bank — trusted banking and venture debt partner for Sierra Ventures and Geodesic. Learn more at stifel.com.Chapters:(0:00) The "scamdemic": $1 trillion lost to fraud(1:47) 20 years fighting fraud: PhD, Coinbase, Revolut, then Sardine(5:38) Why crypto was the hardest fraud problem to crack(9:38) Deepfakes, phishing, and fully agent-run fraud(16:50) Risk-based onboarding and the 5-billion-device network(19:25) The 250,000 fake-account attack cracked in 5 minutes(22:40) Catching one fraudster across 30 banks(25:54) A machine-learning founder learns to sell to banks(41:05) Sanctions screening at 95% automation(46:57) Shipping fast without AI slopWhere to find Soups Ranjan:LinkedIn: https://www.linkedin.com/in/soupsranjan/Company: https://www.sardine.ai

The two moats that made enterprise martech defensible — owning the data and charging per seat — are cracking at the same time. Scott Brinker, creator of the martech landscape and VP of Platform Ecosystem at HubSpot, explains why the CRM/CDP data moat just got weak, what "systems of context" are, and where the next big companies get built.This episode is brought to you by Stifel Bank — trusted banking and venture debt partner for Sierra Ventures' portfolio. Learn more at stifel.com.Chapters:(0:00) Cold open: "Prompt engineering? That's so 2024"(1:07) From 150 tools to 14,000: why Scott mapped martech(3:28) Systems of context — and why the CDP never delivered(8:02) The three-layer martech stack, explained(12:10) What "context" actually means for AI agents(16:10) AI SDRs and the rise of "context graphs"(23:13) Why the CRM and CDP data moat just got weak(32:46) Incumbents vs. startups: who wins the context layer(36:46) AEO, agentic commerce, and the new buyer journey(53:52) Will AI agents kill seat-based pricing?Where to find Scott Brinker:LinkedIn: https://www.linkedin.com/in/sjbrinkerWebsite: chiefmartec.com

Marcel Santilli helped scale HashiCorp from $6M to $100M ARR, was CMO at Scale AI, and now runs GrowthX.ai- an AI-native growth company serving Ramp, Reddit, and Webflow that just raised $12M from Madrona. His contrarian take: AI is making marketing harder, not easier, because most companies can't clearly define who they're for or what they're building. We unpack his vision for turning marketing into engineering: codified workflows, human-in-the-loop judgment, and why knowledge work desperately needs its own "GitHub moment."Chapters:(0:00) Cold open — "AI is amplifying crap"(1:00) Welcome and Marcel's background(1:59) Building media properties at IBM and HP(4:04) Scaling HashiCorp from $6M to $100M ARR(6:27) Finding white space in a 14,000-tool market(10:43) Content as the atomic unit of organic growth(15:52) Why AI makes marketing harder, not easier(20:46) Process architects, input calibrators, and bar raisers(26:11) The GitHub moment marketing never had(36:00) AEO: hype vs. reality(42:08) The future marketing org: smaller and sharper(45:55) Is AI a bubble? Revenue as fuel, not a drugThis episode is brought to you by Stifel Bank — our trusted partner for fund banking and wealth management. Learn more at stifel.com.Where to find Marcel Santilli:LinkedIn: https://www.linkedin.com/in/marcelsantilli/GrowthX.ai: https://growthx.ai