Unlearn with Asher Mathew & Kelly Sarabyn breaks down the news, trends, and CEO priorities shaping the technology ecosystem. From AI and platforms to partners, capital, talent, and regulation, we connect headlines to what leaders need to rethink — and execute — now.
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July 26, 202654 min
Ep 50: Workday’s Partner Playbook | Marketplace Maturity | Own the Number | AI With Humans
In Episode 50, we celebrate a major Unlearn milestone: 50 conversations about what business leaders need to rethink. Saqib Sheikh joins the show to break down how Workday is building its partner ecosystem across strategic partnerships, ISVs, benefits, payroll, and Workday Marketplace. This is a practical conversation about what happens when partnerships move from “nice to have” to a real growth motion with revenue, operations, product, and customer experience behind it. We cover: • Why Workday works with more than 1,500 partners, but focuses deeply on a smaller set of strategic relationships • How benefits and payroll partners extend Workday’s platform for employees • Why marketplaces cannot stop at search and listings • How Workday Marketplace moved from discovery to transactions • Why customer context matters: industry, geography, company size, and maturity stage • What it takes to run a marketplace across product, partner ops, finance, sales ops, and marketing • Why partner teams should own real metrics like sourced revenue, co-sell, and revenue share • How Workday thinks about co-sell attribution and partner revenue • Why AI can help customers browse and decide, but payroll, benefits, and finance still need deterministic systems • Why the best AI strategy is not replacing people, but helping them work differently 50 episodes in, one lesson keeps showing up: partnerships matter most when they are tied to customer outcomes and business outcomes. If you want to understand how a company like Workday thinks about marketplace strategy, partner revenue, and AI, this episode is worth listening to all the way through.
July 11, 202656 min
Ep 49: Building AI-Native Companies | Services vs. Software | The Future of Work
In Episode 49, we sit down with Connor Jeffers, Founder of Aptitude 8 and CEO of Hapily, to explore what it takes to build an AI-native company. After scaling one of HubSpot’s leading services partners and launching a venture-backed SaaS business, Connor shares how AI is changing software development, marketing, partnerships, and the way startups compete. We cover: * Why AI is making small teams dramatically more productive * Lessons from building both a services company and a SaaS company * How HubSpot’s ecosystem created opportunities for founders * Why product design is becoming more valuable than engineering capacity * Building software for in-person events and customer engagement * The future of partnerships in an AI-first world * Where AI is creating the biggest productivity gains—and where it isn’t If AI allows companies to operate at two or three times their previous scale, what does that mean for the future of teams, products, and competition? Whether you’re a founder, operator, partnership leader, or executive navigating AI, this episode offers practical insights into how the next generation of companies will be built.
April 6, 2026Episode 4855 min
Ep 48: AI Stack Playbook | AWS x Cerebras | Build the Channel First | Inference Race
In Episode 48, we break down a hard truth about AI: the companies that win will not be the ones with the best models. They will be the ones with the best partner strategy. Alan Chhabra joins the show to unpack the AI stack and why distribution, not product, is becoming the real advantage. We cover: • Why AI is a stack game and no company can win alone • The AWS x Cerebras partnership and what it signals about the future of infrastructure • Why hiring sales before building a partner ecosystem is a mistake • The shift from hundreds of partners to a few high leverage relationships • How AI deals are now sold top down to executives, not bottom up • Why inference speed is critical to unlocking real AI adoption • The emergence of neo clouds and the global race for compute capacity • How partner leaders are becoming more important than ever in this market Is AI a technology revolution or a distribution war? The answer is both. But most companies are still operating like it is just a product problem. If you want to understand how the AI market is actually being won, this episode is for you.
March 29, 2026Episode 471 hr 5 min
Ep 47: Anthropic’s Ecosystem Play | AI Services Boom | Events Are Back | CEO Reset
In Episode 47, we break down a major shift happening in AI right now: it is not just changing products, it is reshaping services companies and forcing entirely new operating models. Brendan Tolleson, CEO of RevPartners, joins the show. We cover: • Anthropic launching a marketplace and $100M partner fund and what it signals for AI GTM • Why frontier AI companies are going partner first instead of product first • The rise of smaller, AI native services firms driving innovation in the market • New data showing most AI adoption is still internal, not customer facing • How services firms are evolving from delivery to product and IP creation • Why events are becoming one of the highest ROI channels for pipeline generation • The blurring line between services companies and software companies • Why CEO turnover is rising as companies navigate this transition Is AI actually transforming how services companies operate? Or are most still experimenting without clear ROI? The reality is we are still early. Most companies are applying AI internally, but the real shift will come when it becomes embedded in how they deliver value to customers. If you care about AI, services, go to market, or how companies are evolving their operating models, this episode breaks down what is actually changing.
March 17, 2026Episode 4647 min
Ep 46: AI Doesn’t Reduce Work | Anthropic at $20B | Salesforce & HubSpot Moves | CEO = Chief AI Officer
In Episode 46, we break down one of the biggest misconceptions about AI right now: it is not reducing work, it is intensifying it. Shailesh Powdwal, VP at Partnerships at Forsys joins the show. We cover: • Research showing AI increases pace, scope, and expectations across teams • Anthropic’s rapid growth and what it signals about the AI market • HubSpot and Salesforce reshaping partner programs for an AI first world • McKinsey’s shift toward agents and the rise of new operating models • How services firms are evolving from time based to outcome based work • Why hardware companies like SanDisk are benefiting from AI demand • CEOs stepping in as Chief AI Officers and what that means for org structure • Why partnerships must shift from influence to owning AI driven revenue Is AI actually making companies more efficient? Or is it forcing a complete reset in how work gets done and measured? The data suggests AI is not a cost reduction story. It is a performance escalation across every function. If you care about AI, partnerships, services, or how companies are restructuring around this shift, this episode breaks down what is really happening.
February 21, 2026Episode 381 hr 2 min
Ep 45: AI vs SaaS? | Anthropic’s Agents | Microsoft Co-opetition | $1T Software Selloff
In Episode 45, Kelly hosts for the first time and friend of the pod Scott Brinker returns to pressure test the SaaS apocalypse thesis. We cover: • Anthropic’s new agent capabilities, including legal automation • The $1T software selloff and Nvidia’s pushback on the collapse narrative • Microsoft positioning against OpenAI and the rise of AI co opetition • Anthropic vs OpenAI’s Super Bowl ad battle and Sam Altman’s response • OpenAI hiring forward deployed engineers and what it signals about product companies moving into services • KPMG and McKinsey data showing most enterprises are still experimenting with agents Are agents replacing applications? Or are software companies embedding AI faster than the market expects? The data suggests we are not seeing the death of SaaS, but a reshuffling of power across models, infrastructure, applications, and services. If you care about AI, SaaS, hyperscalers, or ecosystem strategy, this episode breaks down what’s signal vs noise.
February 14, 2026Episode 441 hr 3 min
Ep 44 | America as a Platform Company: The AI Ecosystem Shift, System Integrators, Anthropic’s SI Role & The Budget Reality
In this episode, Asher and Kelly zoom out to a bigger question: what happens when AI turns nations, platforms, and enterprises into ecosystem companies? Starting with the idea that “America is becoming a platform company,” they explore why the biggest AI winners will be the ones with the largest ecosystems, not just the best models. From Lumen’s transformation from telecom provider to connective AI infrastructure, to the mounting pressure on system integrators to redesign their business models, to Anthropic hiring a revenue owning SI leader at $250K plus OTE, the signals are clear. Adoption beats shipping, and execution beats hype. They also unpack new data from the 2026 State of Partnership Leaders report, including the hard truth about budget authority, and connect it to Salesforce’s latest State of Sales, where partner selling is now nearly universal. If platforms win through ecosystems, someone has to own outcomes. This episode explores who that is and why this moment may redefine the Chief Partner Officer role.
January 24, 2026Episode 431 hr 1 min
Ep 43 | New Format | OpenAi CPO job | Shopify layoffs | Microsoft, Google, ServiceNow Updates | BCG CEO Radar | Kathleen Curry from Workday joins the pod
In this episode, Asher and Kelly kick off a new Unlearn format and talk through what’s really changing across the tech ecosystem. Kathleen Curry from Workday joins the pod. They dig into OpenAI recruiting a CPO-level partnerships role, Shopify’s partnership shakeup, and the latest partner program moves from Google, Microsoft and ServiceNow. The conversation also looks at what the BCG AI Radar tells us about CEOs taking ownership of AI, and why partnerships now have to focus on adoption, expansion, and real customer value.
December 9, 2025Episode 4255 min
Ep 42 | The Partnership Infrastructure Behind Stripe’s Biggest Innovations
Most people still think about partnerships as a sales channel. Stripe’s Erika Wool doesn’t. She leads product and strategic partnerships and defines her job as helping Stripe build businesses that wouldn’t exist without partners. In this episode, Erika walks through how she moved from consulting and Edelman into Google and Stripe, how product partnerships evolved as Stripe scaled from “easiest way to accept card payments online” to a multi-product platform, and how she explains the value of these bets to executives and the board. Chapters 00:00 – Coming back from break and introducing Erika 00:38 – Erika’s path: think tank, consulting, Edelman, Google, Stripe 09:30 – What product partnerships mean at Stripe today 15:25 – How to articulate the value of product partnerships to executives 21:25 – Keeping integrations alive: SLAs, joint roadmaps, and care after launch 31:30 – How Stripe structures its partnerships org (pillars, partner engineering, strat/ops) 37:05 – Reporting lines, product ownership, and prototyping with partners 43:20 – Building bridges with sales, channel, and customer-facing teams 48:40 – Why Erika chose partnerships and what keeps her in the role 52:00 – Looking beyond tech: Costco, airlines, Walmart, and how AI changes everything Key Takeaways 1. Product partnerships should build businesses, not just integrations : Erika frames her team’s role as helping Stripe build businesses that literally wouldn’t exist without partners, especially in regulated fintech where Stripe is not the bank, card network, or payment method. 2. Value stories need both market insight and user data : To justify a product partnership, you can’t just say “we need this partner.” You have to tie what’s happening in the market, what your users are asking for or missing, and what the commercial model looks like over time – even when the forecast isn’t perfect. 3. Launch is the starting line, not the finish line : Stripe bakes in SLAs, QBRs, and joint business plans with partners, but the real work is ongoing: updating products as both platforms evolve, entering new markets, and deciding which new partner features are worth integrating. 4. Org structure should follow products and partner types : Stripe organizes partnerships by product pillar and partner type (financial partners, payment methods, Terminal, etc.), backed by partner engineering and a dedicated strategy/ops function inside the partnerships org. Regional complexity comes later. 5. Great partnership leaders build bridges to CEOs, CFOs, and GTM teams : Erika’s world requires direct engagement with product and company leadership. At the same time, sales, channel, and CS are key sources of market signal and distribution for what product partnerships create. Key Quotes “You know, there is one motion. It's called B2B, right? Like in your world, you're actually a B2C company first. And then you have all this like B2B stuff on the backside of it. At least that's kind of how I think about it.” - Asher Mathew “I feel like it's something that a lot of partner leaders struggle with because it's not necessarily as straightforward as channel partnerships, where you're very much focused on the transactional layer. It gets much more complex.” - Kelly Sarabyn “You do, you are responsible for how that partner impacts the business that Stripe builds on top of it. And so you've got to know those numbers as well and be able to think about how that will change over time.” - Erika Wool Final Thoughts Product partnerships sit in a messy middle: part product, part strategy, part relationship management, and part internal politics. Erika shows how Stripe built an org where partner engineering, strategy/ops, and product partnerships can prototype, negotiate, and scale with some of the most important companies in the world while still serving Stripe’s users first.
July 2, 2025Episode 4152 min
Ep 41 | Richard Ezekiel on Codifying Partnerships With COELEVATE
In this episode, Asher and Kelly sit down with Richard Ezekiel to unpack his book COELEVATE, a practical framework built from decades in the trenches in Silicon Valley and as part of the venture capital ecosystem. Richard breaks down how to build a “virtual company” between partners, why operational rigor is often overlooked, and how partner professionals can move beyond buzzwords to drive real business value. Chapters 04:28 – From Wired Magazine to Amazon 10:29 – The Partnership T: A Customer-Centric Framework 17:42 – The Real Reason Richard Wrote COELEVATE 24:05 – Why 70% of Partnerships Fail 29:13 – Building a Partnership Like a Virtual Company 34:42 – The Problem with “Alliances” and Industry Nomenclature 42:33 – Scaling with Platform Partnerships 48:12 – AI, Methodology, and What’s Next for COELEVATE Key Takeaways 1. The 70% Problem - Most partnerships fail within two years, not because of execution issues, but because the foundational idea wasn’t strong enough. 2. The Virtual Company Mindset - A great partnership should function like a shared operating entity between two companies. 3. Idea Quality > Execution - You can’t fix a weak idea with flawless execution. Strong partnerships start with high-quality, differentiated ideas that actually matter to the customer. 4. Platform Strategy Isn’t Plug-and-Play - Scaling to one-to-many partnerships doesn’t mean copy-pasting one-to-one motions. 5. It’s Time to Codify the Discipline - We’ve built sales, marketing, and product into academic and operational disciplines. It’s time to do the same for partnerships with a common language, methodology, and structure. Key Quotes "You’re not building a deal. You’re building the architecture for two companies to evolve together. If that framework’s not there, the partnership won’t last." - Richard Ezekiel "Most partner pros don’t realize they can take their skills into entirely new industries. The ceiling moves when you stop thinking of partnerships as just a B2B function." - Asher Mathew "Execution depends on culture. You can’t build a strategic partnership if your company values or brand DNA fundamentally clash, even when the numbers look great." - Kelly Sarabyn Final Thoughts Partnerships are complex, evolving ecosystems that need better tools, better thinking, and stronger foundations. Richard Ezekiel’s book COELEVATE is a serious attempt at codifying what most of us learn the hard way: that sustainable partnerships need structure, creativity, and a real operating model behind the press release. This episode is for anyone trying to bring good ideas to life through collaboration. Tune in to hear what’s next for the discipline and what Richard is building to make the methodology real and usable with AI.
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