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’tIf 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.

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 marketIs 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.

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 transitionIs 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.

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 revenueIs 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.

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 agentsAre 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.

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.

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.

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. Chapters00:00 – Coming back from break and introducing Erika00:38 – Erika’s path: think tank, consulting, Edelman, Google, Stripe09:30 – What product partnerships mean at Stripe today15:25 – How to articulate the value of product partnerships to executives21:25 – Keeping integrations alive: SLAs, joint roadmaps, and care after launch31:30 – How Stripe structures its partnerships org (pillars, partner engineering, strat/ops)37:05 – Reporting lines, product ownership, and prototyping with partners43:20 – Building bridges with sales, channel, and customer-facing teams48:40 – Why Erika chose partnerships and what keeps her in the role52:00 – Looking beyond tech: Costco, airlines, Walmart, and how AI changes everythingKey Takeaways1. 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 WoolFinal ThoughtsProduct 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.

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.Chapters04:28 – From Wired Magazine to Amazon10:29 – The Partnership T: A Customer-Centric Framework17:42 – The Real Reason Richard Wrote COELEVATE24:05 – Why 70% of Partnerships Fail29:13 – Building a Partnership Like a Virtual Company34:42 – The Problem with “Alliances” and Industry Nomenclature42:33 – Scaling with Platform Partnerships48:12 – AI, Methodology, and What’s Next for COELEVATEKey Takeaways1. 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 SarabynFinal ThoughtsPartnerships 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.

Natan Edelsburg, Chief Partnerships Officer at Muck Rack, joins Asher Mathew and Kelly Sarabyn on Unlearn to talk about what happens when a revenue leader outgrows the CRO seat. They unpack how modern PR is evolving, why media training matters more than ever, and how partnerships roles are becoming more dynamic and strategic than ever before. Natan shares his journey from early employee to CPO, the challenges of navigating internal change, and the power of authentic storytelling in a noisy world.Chapters01:03 – Natan’s Journey to Chief Partnerships Officer10:00 – Why He Stepped Down as CRO13:40 – Building a Role Around Partnerships & Evangelism19:50 – Staying Focused on PR in a Distracted Market30:32 – LinkedIn’s Role in Modern Comms37:20 – What Makes a Strategic PR Campaign40:35 – Why Media Training Is Essential43:00 – Using AI for Smarter Media Prep47:50 – Activating Relationships Through LinkedInKey Takeaways1. Modern PR Requires Integration - Great campaigns span paid, earned, shared, and owned channels. PR isn’t just pitching anymore.2. Media Training Isn’t Optional - Executives are expected to show up polished on every channel, not just in interviews.3. Partnerships Can Be Evangelism - Natan’s role blends relationship-building with brand representation, showing CPOs aren’t confined to revenue KPIs.4. AI Should Augment, Not Replace - Smart teams are using AI to speed up busywork—but keeping humans in the loop to protect quality.5. LinkedIn Is an Underrated Power Tool - Relationship capital, activated thoughtfully, still opens more doors than cold outreach ever will.Key Quotes“You still want to do incubation stuff, but the company’s needs are highly specialized. That’s the trade-off every growth-stage exec faces.” - Asher Mathew“While tech stacks change, relationships remain the most durable asset in go-to-market.” - Kelly Sarabyn“Being media trained doesn’t mean being robotic. It means knowing your story and being able to tell it in a way that connects.” - Natan EdelsburgFinal ThoughtsNatan’s story is a reminder that career growth isn’t always up. It’s sometimes sideways, strategic, and self-aware. From building Muck Rack’s comms ecosystem to leading without a team, he’s showing what flexible leadership looks like. And with AI, PR, and social platforms evolving fast, the conversation doubles as a blueprint for staying relevant and trusted in any go-to-market function.