MarTalks- The #1 Ecommerce and MarTech application podcast

Darrell Rosenstein

The Martalks Podcast is the leading source of the information and news from the Composable Commerce, MarTech and supply chain applications industries. Hosted by Darrell Rosenstein, the founder and managing partner of The Rosenstein Group. www.rosensteingroup.com https://www.linkedin.com/company/the-rosenstein-group 

  1. 15h ago

    Justin Michael on Why the Series A "Go Enterprise" Decision Blows Up 18 Months Later

    The board wants enterprise logos. Eighteen months and five expensive hires later, the pipeline is full and nothing has closed. Justin Michael has watched this movie enough times to tell you exactly where it goes wrong — and what the board should have been looking at instead of the pipeline number. Justin Michael is the author of 12 books on enterprise software sales, including Tech-Powered Sales and Combo Prospecting, and spent 13 years selling in ad tech, MarTech, and mobile before moving into executive coaching. He has trained over 1,000 enterprise sellers across 200+ teams at companies including Salesforce, HubSpot, Matterport, and Proofpoint, working markets from DACH to Australia to Singapore. WHAT YOU WILL LEARN Why the mid-market to enterprise jump fails, and what to keep running while you make itHow to spot the "Rolodex myth" before you sign a $600K VP of Sales packageWhen to hire a VP of Sales instead of a CRO, and how much equity the role actually needsWhy AI has not yet reduced enterprise headcount, and what that means for a Series A modelHow to tell when your team's AI-generated outbound is quietly killing your C-level accessWhich two signals actually predict a private company is ready to buyKEY TOPICS 06:06 The board says "go enterprise" and why it blows up  07:58 What the board sees in pipeline vs. what is actually there  11:19 The three biggest GTM hiring mistakes at Series A and B  17:20 The founder as bottleneck: VP of Sales vs. CRO  20:14 Pilots, tranches, and the dying art of the seven-figure deal  26:01 How to evaluate a go-to-market team in 30 minutes  27:15 The silent sales floor  28:32 Where AI budget actually pays off  31:59 Headcount as the real buying signal  34:07 Does AI mean you hire fewer reps?  35:59 The slop failure mode founders do not catch  46:36 Two tools and two changes to deploy Monday morning GUEST LINKS Justin Michael on LinkedIn: https://www.linkedin.com/in/michaeljustin/ Books and coaching: https://www.amazon.com/gp/product/B0DRPP4Q1T LISTEN AND FOLLOW MARTALKS Apple Podcasts: https://apple.co/4wNap4X Spotify: https://bit.ly/4fF2ukm Darrell Rosenstein on LinkedIn: https://www.linkedin.com/in/darrellrosenstein/ The Rosenstein Group: https://rosensteingroup.com/ Keywords: enterprise sales hiring, Series A go-to-market, VP of Sales vs CRO, AI SDR, outbound prospecting strategy, MarTech sales leadership, sales pipeline qualification Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

  2. Aug 3

    Delivery Success with Agentic AI: Lessons from the Zuora IPO and LeanData — with Agam Vasani

    CFOs are no longer giving you 18 months to prove a software investment. The tolerance is now one quarter — or less. In this episode, Darrell sits down with one of the most operationally precise post-sale executives in enterprise SaaS to talk about what it actually takes to deliver on an AI promise, not just sell one. Agam Vasani scaled Zuora's professional services organization through their IPO and rebuilt LeanData's post-sale motion from scratch — cutting implementation cycles from nine months to thirty days. He brings a clear-eyed, operator's view on why execution is the real product, why renewal should be a non-event, and what retention thresholds investors are actually using to fund the next round. What You'll Learn: → How to use the SIGNAL Framework to evaluate any AI solution before you commit budget or resources → Why post-sale delivery is the primary revenue lever in SaaS — and why most boards still treat it as overhead → The exact retention thresholds VCs use at Seed through pre-IPO, and where the AI-native bar is today → How Agam reduced LeanData's implementation cycle from nine months to thirty days without a bigger team → What "stickiness score" means in practice, and how to measure adoption before it shows up as churn → The professional services revenue ratio that determines IPO readiness — and the CEO mistake that distorts it Key Topics & Timestamps: 03:07 — Post-sale kinetic energy: the real NRR driver  05:00 — The SIGNAL Framework for AI evaluation  09:05 — Execution failure vs. product gaps: the career risk distinction  10:53 — Why CFO ROI timelines have collapsed in the AI era  15:11 — The LeanData turnaround: six months to thirty days  26:49 — The stickiness score and what it actually measures  29:44 — Professional services revenue ratio and IPO readiness  35:34 — Retention thresholds VCs use at each funding stage Connect with Agam Vasani: LinkedIn: https://www.linkedin.com/in/avasani/ Hosted by Darrell Rosenstein | The Rosenstein Group  12,000+ listeners | 750+ C-level guests Keywords: agentic AI, customer success, post-sale delivery, SaaS NRR, enterprise AI implementation, professional services, LeanData, Zuora IPO, retention thresholds, AI adoption Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

  3. Jul 30

    Digitize Before You Automate: Yoav Kutner, Founder & CEO of OroCommerce, on the B2B Commerce Gap (Recorded at the B2B eCommerce Association)

    Everyone in B2B commerce wants to talk about AI. The buyers actually writing the checks are still trying to get off the fax machine. Recorded on the floor of the B2B eCommerce Association's inaugural event, this conversation is about the gap between where B2B technology thinks the market is and where the market actually is — and why the companies that skip the boring digitization step are the ones whose AI projects fail.Yoav Kutner is the Founder and CEO of OroCommerce, the B2B-first digital commerce platform, and a co-founder of Magento. He has spent close to two decades building commerce infrastructure for manufacturers, distributors, and wholesalers — the least glamorous and most operationally complex corner of ecommerce. His customers run multi-ERP, multi-warehouse businesses where the commerce layer, not the ERP, has become the system of record for how orders actually move.WHAT LISTENERS WILL LEARNDiagnose whether your AI initiative is actually blocked by an undigitized business processReframe the commerce platform as the flexible layer above the ERP, not another silo beside itAnswer the sales-team objection to self-service B2B ordering without promising fewer repsUnlock siloed data trapped in AS/400s and other legacy systems without touching the ERPShip in two-week release cycles when your ERP roadmap moves in yearsEvaluate order orchestration across multiple ERPs and warehouses after acquisitionsKEY TOPICS[00:00] Recorded live at the B2B eCommerce Association  [TC] Why B2B commerce runs five to ten years behind the technology narrative  [TC] "All B2B commerce happens inside the platform" — and why that is wrong  [TC] The commerce layer above the ERP: exposing data to customers, sales, and marketing  [TC] Sales-rep resistance to digital B2B, and the user-experience answer  [TC] The self-service checklist buyers actually want: order status, reorder, inventory, project pricing  [TC] Breaking data silos in AS/400-era systems, and feeding new data back to the ERP  [TC] Board pressure for AI before the commerce stack is modern  [TC] Test in weeks, not years: two-week release cadence and targeted customer feedback  [TC] Digitize the process first, then let the AI agents replace it  [TC] Six-plus ERPs, roughly forty warehouses, one order management layer  [TC] The closing read on where B2B digital transformation goes nextLINKSYoav Kutner on LinkedIn: https://www.linkedin.com/in/yoavkutner/  OroCommerce: https://oroinc.com MarTalks, hosted by Darrell Rosenstein  🎙 Apple Podcasts: https://apple.co/4wNap4X 🎧 Spotify: https://bit.ly/4fF2ukm 💼 LinkedIn: https://www.linkedin.com/in/darrellrosenstein/ 🌐 The Rosenstein Group: https://rosensteingroup.com/ Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

  4. Jul 17

    Commerce for Weirdos: ElasticPath CEO Bryan House on B2B, AI-Driven Implementation, and Why Shopify Is a Fintech Company

    Most B2B manufacturers are still running digital commerce on platforms someone built in-house a decade ago — and the cost to replace them has kept everyone frozen. ElasticPath CEO Bryan House is changing that math, and this conversation is the clearest explanation of why the B2B commerce market is the most underserved greenfield in enterprise software.  Bryan House is the CEO of ElasticPath, the composable commerce platform built for complex B2B use cases in the $50M–$500M GMV range. He scaled professional services through Acquia's IPO, served as Chief of Staff at Acquia, and invested in Molten — the composable commerce startup ElasticPath later acquired — before taking the helm as CEO. What You'll Learn: Why Shopify is fundamentally a fintech company — and why that model collapses in the enterpriseHow ElasticPath handles 10,000 product variations and 1,500-product configurations that break every standard platformBryan's "six weeks, $100K" goal for implementation — and how AI is making it achievableWhy B2B companies with complex catalogs are the biggest untapped opportunity in digital commerceThe hustle mindset framework Bryan uses to hire people who thrive in a dynamic, startup environmentWhy bringing a proven playbook from your last company is one of the most expensive hiring mistakes in the marketKey Topics with Timestamps: 02:23 — Commerce for weirdos: who ElasticPath is built for 04:14 — Shopify as a fintech company, not a commerce platform 07:18 — AI-powered integration with Composer 11:41 — The six weeks, $100K implementation goal 19:33 — Why B2B commerce is the undiscovered country 21:22 — Complex catalogs, contract pricing, and dynamic bundles 37:23 — What thrives in a startup: hustle over pedigree 41:47 — The playbook trap: why senior hires fail 45:19 — The closing question every B2B brand should ask their platform Links: 🔗 Bryan House on LinkedIn: https://www.linkedin.com/in/bhouse/ 🌐 ElasticPath: https://www.elasticpath.com 🎙️ MarTalks on Apple Podcasts: https://apple.co/4wNap4X 🎙️ MarTalks on Spotify: https://bit.ly/3PGs0es Keywords: B2B commerce, composable commerce, ElasticPath, MACH architecture, enterprise SaaS, AI implementation, digital transformation, headless commerce, startup hiring, MarTech Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

  5. Jul 17

    Kelly Goetsch: The Standard That Changes Commerce Forever (And Why 62 Vendors Just Agreed to It)

    The biggest integration problem in commerce — getting a selling channel to talk to a fulfillment system — just got a solution. Kelly Goetsch rallied 62 vendors, including every OMS in the Gartner Magic Quadrant, behind a single open standard. If you've ever paid for a custom integration, this episode is for you. Guest Bio: Kelly Goetsch founded the MACH Alliance and serves as President of Pipe17. He began his career on FootLocker's first ecommerce site and has spent 20 years building at the infrastructure layer of the commerce industry. He's the most connected person in the composable commerce ecosystem and one of the few people willing to call the AI bubble by its name. What Listeners Will Learn: Why composability is a prerequisite to AI — and what the risks are for companies that skip itWhat the Order Network Exchange is and how it could remove $500K–$1M from a commerce replatformThe "Clippy problem": why most enterprise AI is still stuck inside a single application and how MCP changes thatKelly's honest take on the AI valuation bubble and what the Gartner Hype Cycle tells us about what happens nextWhy the churn question is the one hidden inside every consumer AI valuationHow to start a composable journey without a two-year project and a giant SIKey Topics with Timestamps: 01:58 — How to start composable without a massive SI project 05:19 — Composability as a prerequisite to AI 07:07 — The Clippy problem and Model Context Protocol explained 10:12 — Which SaaS companies actually deserve the funding slowdown 12:38 — The churn question inside AI valuations 16:07 — The AI bubble — called directly 18:27 — The Order Network Exchange announcement: 62 vendors, one standard 23:00 — MCP vs. traditional APIs: why it changes everything 30:54 — "Demand the standard" Links: 🔗 Kelly Goetsch on LinkedIn: https://www.linkedin.com/in/kellygoetsch/ 🔗 Commerce Ops Foundation: commerceopsfoundation.org 📺 Full episode on Spotify: https://bit.ly/3PGs0es 🔗 MarTalks on Apple: https://apple.co/4wNap4X Keywords: composable commerce, OMS, order management, MCP, model context protocol, MACH Alliance, B2B ecommerce, AI infrastructure, SaaS bubble, retail technology Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

  6. Jun 25

    How to scale a martech sales function w/ Tod Klubnik

    We speak to Tod Klubnik, about how martech and ecommerce businesses can scale their sales teams at pace. Some of the key questions covered, included:  What are the mistakes to avoid when hiring a large number of sales professionals early in your business’s journey? (2:00)Who should own go to market - sales or marketing? (6:00)And how do martech providers progress from serving SMBs to the enterprise market? (15:00) About our guest Tod Klubnik has 25 years of software and SaaS sales & marketing experience, and has led the sales team in businesses such as BigCommerce and MessageOne.  He now provides board, advisory and part-time consulting services to early and mid-stage companies.  About The Martalks Podcast The Martalks Podcast features insight and comment from thought leaders in Martech and ecommerce sales. It is hosted by Darrell Rosenstein, the founder and managing partner of The Rosenstein Group.  About The Rosenstein Group The Rosenstein Group is your recruiting agency and executive search firm for matching critical revenue talent with innovative technology vendors in the e-commerce, martech and supply chain space. www.rosensteingroup.com  https://www.linkedin.com/company/the-rosenstein-group  Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

    How to scale a martech sales function w/ Tod Klubnik

  7. Jun 6

    Technology Attorney George Brunt on AI IP Ownership, Embedded Legal Counsel, and the Legal Mistakes MarTech Founders Keep Making

    Most founders know they need a lawyer. Almost none of them know they need one before the problem shows up. George Brunt wrote the first shrink-wrap software license in history. Managed 23,000 patents at Alcatel. Raised $83 million. He's been in the rooms most founders will never get near — and the pattern he keeps seeing is the same one. The CEO who waits until there's a contract dispute, a misclassification lawsuit, or a deceptive AI claims inquiry from the FTC is paying three times the price of prevention. And in a funding environment where VCs are doing legal health checks before they write the check, what's in your legal drawer has direct valuation consequences. George and I went deep on the questions most founders aren't being asked: Who actually owns the IP when your developer used AI to write the code? That question is not resolved. Not in case law, not in the patent office, not anywhere. What does a $330,000 annual savings look like when you swap outside counsel for an embedded legal team? He breaks down the math. And what are the five questions a VC should be asking every Series A and B founder in a legal health check that most of them aren't asking? If your legal strategy is "we'll deal with it when we need to" — this one's for you. Full episode link in the first comment. Tag a founder who needs to hear this. Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

  8. Apr 28

    She Cracked the Code on Why You Buy That Military Jacket. Online Retail Has No Idea Why Either.

    Welcome back to MarTalks. This week Darrell sits down with Anabel Maldonado — CEO of PSYKHE AI, ShopTalk startup competition winner, former luxury product copywriter, and the person who has been screaming into the void that e-commerce has been solving the wrong problem for a decade. Here's the stat that should make every retailer put down their coffee: online conversion rates are still hovering around 1.5%. Billions of dollars. Endless A/B tests. Recommendation engines with Stanford pedigrees. And still — the vast majority of products a shopper would actually love never appear in front of them. Not once. Why? Because nobody put product intelligence in the stack. Nobody asked why you bought that military jacket. Not because it has Bellows pockets. Because it makes you feel gritty. It offsets the softness of the rest of your outfit. It aligns with your contrarian streak. You weren't conscious of it. And no algorithm ever tried to figure it out either. Anabel built Psyche to fix exactly that using 700+ psychographic dimensions to match products to people at a level that goes way beyond "you bought blue things, here are more blue things." The results? A 22% lift in conversion for mono brands. A $16 million revenue unlock without a single new SKU, dollar of ad spend, or new customer. Just showing people the right stuff. In this episode: why "personalization" is actually just optimization in a fancy hat, why grocery is the most underrated category for psychographic commerce, why agentic shopping is a discovery problem the entire industry forgot to prepare for, and what a $100M retailer should do in the next 90 days before they become invisible to the agents doing everyone's shopping. Also: the Jay Peterman reference lands perfectly. Obviously. Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.

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The Martalks Podcast is the leading source of the information and news from the Composable Commerce, MarTech and supply chain applications industries. Hosted by Darrell Rosenstein, the founder and managing partner of The Rosenstein Group. www.rosensteingroup.com https://www.linkedin.com/company/the-rosenstein-group 

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