UNPACK3D Podcast

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't

Where 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 slop

Where 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/sjbrinker
• Website: 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 drug

This 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

CrewAI just crossed 2 billion agent executions — but founder Joe Moura thinks building agents isn't even the hard part. The real value gap? Getting them to production. Joe joins Vignesh and Arvind to break down why most enterprise AI projects fail at planning, not technology, how Oracle cold-approaching him at the SF Ferry Building validated the business, and what it takes to get Fortune 500 companies actually running agents at scale.

Time Stamps:(0:00) Introduction and Joe's path from Clearbit to CrewAI(4:47) What makes CrewAI different in the agent builder market(10:24) Why code-first, multi-agent, and the no-code platform customers demanded(16:16) Real use cases: KYC automation and fraud detection(18:23) How Joe became the "face" of CrewAI to drive adoption(25:04) Enterprise AI: why planning fails companies more than technology(33:17) The data readiness trap — when security pulls the plug(42:44) Partnership strategy: selling with IBM to the US DoD(46:16) Low-ego CEO: learning sales from his own AEs(52:42) The future: fine-tuning comeback and long-horizon agents

This 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 Joe Moura:

• LinkedIn: https://www.linkedin.com/in/joaomdmoura/
• CrewAI: https://www.crewai.com

For 40 years, the safe bet in enterprise software was Zendesk or Salesforce. Marty Kausas, founder of Pylon, thinks picking either for customer support today might now get you fired.

Before Pylon worked, Marty spent 2 years cycling through 2 co-founder breakups and 5 dead ideas. Today, Pylon has 5x'd revenue two years running, raised a $31M Series B from a16z and Bain Capital, and migrated 150+ customers off legacy support platforms. We cover the "happy grinder" culture, why B2B support is a completely different problem than consumer, the per-seat vs outcome pricing debate, and why Marty thinks buying Zendesk is now the risky move.

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 and intro(2:02) Meet Marty and Pylon(3:06) Co-founder breakups and 5 dead ideas(10:13) Salesforce → Support Force(13:29) LinkedIn as 80% of Pylon's pipeline(22:05) Why B2B support isn't ticket deflection(28:33) Not Sierra, not Decagon(32:34) The context layer(39:34) Shipping 40% faster as a compound startup(55:12) Why you might get fired for buying Zendesk

Where to find Marty Kausas:- LinkedIn: linkedin.com/in/mkausas- Pylon: usepylon.com

Jyoti Bansal was days away from taking AppDynamics public when Cisco made a $3.7 billion offer that changed everything. Now his second company, Harness, is valued at $5.5B — and he's built it on a contrarian thesis: AI is producing more code than ever, but code isn't the finished product. We cover the real story behind the Cisco acquisition, why his best sales reps from AppDynamics failed in the early days of Harness, how he runs 16 product modules as "startups within a startup," and why 70% of engineering time still happens after the code is written.

This episode is brought to you by Stifel Bank.

Timestamps(0:00) Trailer(0:52) Introduction and welcome(2:36) Jyoti's journey from small-town India to Silicon Valley(6:01) Three lessons from AppDynamics that shaped Harness(10:29) Proving value — not just finding the problem(17:23) The sales hiring mistake: matching reps to your stage(27:42) 72 hours from IPO to Cisco's $3.7B acquisition(33:57) Startups within a startup — Harness's M&A playbook(39:06) AI's productivity paradox: more code, less throughput(48:44) The "two AIs" framework and where moats really live(58:50) How Jyoti decompresses

Is "vibe coding" enough for the enterprise? Scott Dietzen explains why professional engineers need an expert AI, not a toy.

In this episode, we sit down with Scott Dietzen, Former CEO of Augment Code and Former CEO of Pure Storage. Scott breaks down why the current "vibe coding" trend—where non-engineers generate simple apps from scratch—fails to address the needs of large-scale enterprise software.

Key Topics Discussed:

• The Context Engine Moat: Why passing 20 million lines of code into a context window doesn't work, and how Augment solves this with a real-time semantic map.
• Agentic AI: Moving beyond simple chat to AI agents that can handle parallel tasks like testing and code reviews.
• Security First: How Augment secured SOC 2 and ISO certifications to win enterprise trust where competitors failed.
• Leadership & Hiring: Scott's framework for building high-trust teams and why he never had to ask for a raise in his career.

Timestamps

• (00:00) Intro
• (02:52) Augment: The Anti-Vibe Coding
• (05:39) From Chat to AI Agents
• (11:04) The Problem with Fine-Tuning
• (13:05) Building a Context Engine
• (23:23) Security as a Moat
• (29:40) Hiring for Trust
• (43:30) PLG vs. Enterprise Sales
• (54:37) The Myth of the Solo Founder
• (57:19) Leadership & Burnout

In the final episode of the year, we sit down with legendary operator and "company helper" Gokul Rajaram. Gokul shares his unfiltered thesis on the current AI landscape, explaining why he is bearish on infrastructure and middleware companies while betting big on the application layer.

We dive deep into his "Compound or Die" philosophy, why startups need to launch their second product immediately after finding product-market fit, and the return of the "996" work culture in Silicon Valley.

Key Topics Discussed:

• The Big Three in AI: Why Document Processing, Browser Automation, and Voice Agents are the most exciting unlock right now.
• The Infrastructure Trap: Why the model layer and "middleware" companies are being squeezed, and why application layer companies have the real leverage.
• Compound or Die: Why the old rule of waiting for $10M ARR to launch a second product is dead, and why you must build a compound startup now.
• Metrics that Matter: Why you should ignore top-line growth in favor of Gross Revenue Retention (GRR) and Net Revenue Retention (NRR).
• The New Work Ethic: The reality of "996" (9 am to 9 pm, 6 days a week) and "007" (12 am to 12 am, 7 days a week) culture in AI-native companies.
• Future Roles: The rise of the "AI Ops" engineer and the return of the "Forward Deployed Engineer"

Timestamps

• (01:10) - Introduction and Gokul’s journey from Google to Angel Investing.
• (04:05) - AI themes to watch and avoid
• (11:03) - How to build defensibility at the Application Layer.
• (19:50) - "Compound or Die": Launching your second product early.
• (22:27) - Why GRR and NRR matter more than top-line revenue.
• (30:03) - Advice for non-AI native SaaS companies: Pivot or Perish.
• (35:50) - The future of Voice AI and why middleware might be dead.
• (43:58) - Founder Archetypes and the return of intense work culture (996/007).
• (53:07) - Emerging Roles: The AI Ops Engineer and Forward Deployed Engineers.
• (1:00:00) - Gokul’s mental model for decompressing: The "Second Brain".

In this episode, we sit down with Jason Wenk, Founder and CEO of Altruist. Jason shares the "lightbulb moment" he had watching Robinhood take off, realizing that Registered Investment Advisors (RIAs) were stuck using archaic, disjointed technology while consumers were getting sleek, digital experiences.

We unpack how Altruist is taking on the industry giants (the "Duopoly") through vertical integration and why Jason believes legacy custodians have zero incentive to innovate. We also dive deep into the controversial side of company building: the return of "hardcore" work culture, hiring for intensity, and why Jason believes the era of soft startups is over.

• (00:00) Intro & The Origin Story: From starting at Morgan Stanley at 19 to the serial entrepreneur journey that led to founding Altruist.

  
  

• (18:18) Disruption Thesis: The "Robinhood Moment" & Vertical Integration: How seeing the mobile trading revolution inspired Jason to rebuild the custodial stack, and why the "Duopoly" incumbents (Schwab/Fidelity) struggle to innovate due to high margins and inertia.

  
  

• (39:22) The Playbook: Scaling to Billions: Altruist’s Go-to-Market strategy: How they gained initial traction by targeting the "hungry and underserved" small advisors that the giants ignored, and eventually moved upmarket.

  
  

• (42:20) The AI Future: "Hazel" and The Bionic Advisor: Why Altruist is pivoting hard into AI agents, how "Hazel" renders traditional CRMs obsolete, and Jason's prediction on when AI will replace human financial advice (featuring the $15k fence story).

  
  

• (57:03) Founder Mode: Culture, Intensity & Performance: A deep dive into building a "hardcore" culture, the return of the "996" mindset, and Jason's personal routine (including the gene mutation that lets him thrive on 4.5 hours of sleep).