Anthony Lye joined Quid 14 months ago to lead a complete business model transformation. With three decades in Silicon Valley including executive roles at Palantir, NetApp, Oracle, and Siebel Systems, Anthony has operated through every major technology disruption. At Quid, he’s dismantling the traditional SaaS playbook—eliminating seat-based pricing, collapsing the software/services separation, and refocusing the entire company on delivering measurable business outcomes rather than analytics tools. In this conversation, Anthony explains why most SaaS companies will fail in the AI era, how Palantir’s forward-deployed engineering model creates defensible value, and the specific mental models founders need to reimagine their businesses before disruption makes the decision for them. Topics Discussed - How Silicon Valley’s technology oligopolies turn over every five years  - Why AI shifts technology from features to benefits for the first time  - Quid’s transformation from social listening SaaS to outcome-based insights delivery  - The separation of software and services as a structural flaw in SaaS economics  - How forward-deployed engineers at Palantir and Quid collapse the services layer  - Why SaaS failed knowledge workers while email remained dominant Discontinuity theory and how oligopolies resist then capitulate to disruption  - The ”fired tomorrow, compete with yourself” thought experiment for strategy clarity  - How to build executive teams as custodians rather than functional heads GTM Lessons For B2B Founders - Collapse software and services into outcome delivery: Quid eliminated seat-based pricing and module sales, shifting from IT budget to labor budget by selling insights, trends, and actionable information directly. This repositioned the product from a tool requiring sophisticated data scientists to a team augmentation service protecting brand health and driving commerce decisions. The business model change fundamentally altered buyer, buying process, and deal economics. When your product requires customization or professional services to deliver value, you’ve identified a structural opportunity to collapse both layers. - Deploy the ”fired and competing” thought exercise: Anthony’s mentor advised imagining your board fires you tomorrow and you immediately compete against your own company. List the three things you’d do on day one to win. Then ask why you’re not doing those things now. This exercise cuts through organizational inertia and reveals the obvious strategic moves you’re avoiding. The discomfort in your answers indicates where you need to act. - Match decision velocity to execution needs, not comfort: Tom Brett at Menlo Ventures told Anthony to increase from 3-4 decisions weekly to 50. The forcing function prevents overthinking and eliminates ”second guessing paralysis.” Organizations need clarity and direction more than perfect decisions. Write down every decision, communicate it clearly, and publicly reverse course when wrong. This builds a culture where being decisive and correctable beats being slow and theoretically optimal. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Wisdom AI sells to enterprise data teams, empowering them to deploy AI data analysts that automate analytics functions traditionally handled by human analysts. As a former Rubrik co-founder and Google search ranking engineer, Soham identified the analytics problem firsthand while scaling Rubrik from intuition-driven to data-driven operations. In this episode of Category Visionaries, Soham shares how four Rubrik alumni are building a category-defining solution in the data analytics space, the tactical insights from targeting mid-market accounts to optimize deal velocity and onboarding experience, and how AI buying committees shifted from experimental budgets in 2024 to gatekeepers requiring departmental champions in 2025. Topics Discussed: - Leveraging mid-market focus to compress sales cycles while refining onboarding as core product differentiation - The transition from gut-based decisions to data-driven operations and why analytics remains unsolved - Taming LLMs for precision and explainability requirements in enterprise analytics contexts - Strategic navigation of the data ecosystem following the FiveTran-DBT merger and positioning against Snowflake, Databricks, and cloud providers - Overlaying product-led trial motions on enterprise sales to maintain momentum during extended procurement cycles - AI committee evolution from 2024’s experimental phase to 2025’s security-focused consolidation mandate - Pursuing 10x productivity gains versus incremental improvement in established analytics markets GTM Lessons For B2B Founders: - Use mid-market to build onboarding velocity as moat: Rubrik deliberately targeted mid-market accounts despite being an enterprise product that closed eight-figure deals. This served two strategic purposes: compressed sales cycles enabled faster learning loops, and the necessity of quick onboarding forced the team to build exceptional admin experiences that became their primary differentiation. For B2B founders, mid-market isn’t just easier logos—it’s a forcing function for product refinement that creates competitive advantages when moving upmarket. - Find problems through operational scar tissue, not market research: Wisdom AI originated when Soham tried moonlighting as engineering’s data analyst during Rubrik’s scaling phase and discovered he couldn’t do it effectively. This wasn’t a customer interview insight—it was firsthand recognition that even sophisticated technical leaders with dedicated focus couldn’t wrangle data for operational decisions. The problem proved ubiquitous across every business leader optimizing top line, bottom line, and operations. B2B founders building for enterprises should prioritize pain points they’ve personally hit in operational contexts where existing solutions demonstrably failed them. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Runway is building FP&A software that solves what Siqi Chen calls ”the impossible problem”—matching Excel’s speed and flexibility for thinking while functioning as an enterprise finance platform. In this episode of The Front Lines, wew sat down with Siqi to unpack Runway’s mischief marketing playbook, why they enriched hot sauce pre-orders for lead gen, and how they’re implementing AI as a coworker rather than a copilot. Topics Discussed: - The unit economics behind the Burn Rate hot sauce campaign: $40K spend, 5K pre-orders, millions of views  - How Siqi justifies creative marketing spend as CEO and CFO: downside scenarios must break even, upside gets uncapped returns  - Naval’s prescient 2020 advice: don’t call it CFO AI because ”everything’s going to be AI anyway”  - Why finance buyers completely flipped on AI in 24 months—from indifferent to requiring it  - The three emotional triggers that drive FP&A tool adoption: frustration, resentment, anxiety  - Runway’s approach to competing with Excel by changing abstraction layers, not features  - Building AI as a coworker (Ari) that lives in Slack, email, and comments—not a sidebar  - Why proof-of-human marketing compounds in value as AI slop becomes the baseline GTM Lessons For B2B Founders: - Model creative campaigns like venture bets with downside protection: Siqi’s framework: $40K for 200 hot sauces wrapped with $100 bills equals 1.5 deals to break even at mid-five-figure ACVs. But the real play was generating 5,000 pre-orders, enriching the top 200, and converting ICP matches at ”well above 1%” into pipeline. The math ensures you don’t lose money in downside scenarios while creative execution delivers uncapped upside. For B2B founders: calculate your break-even deal count, then structure campaigns where lead gen mechanics provide a safety net under the brand play. - Hire for proof of work, not creative credentials: When Cal (Taika co-founder) cold-emailed Siqi with designed mockups of Burn Rate hot sauce and Runway jerseys, that was the interview. Siqi was already a Taika customer who remembered the 415 phone number branding on the can. His advice: ”There’s no better resume than someone saying ’hey, I submitted a pull request’ or ’here’s some designs.’” For creative roles especially, evaluate the artifacts directly rather than filtering through credentials or pitches about what they could do. - Sell to emotion-driven active searchers, not satisfied users: Runway identified three specific emotions that trigger FP&A software searches: frustration (manually pulling from 20+ data sources monthly, copy-pasting QuickBooks exports), resentment (department heads treating finance requests as ”the stupid form” and ignoring deadlines), and anxiety (one error in 10 million Google Sheets cells breaks the entire model). These aren’t rational pain points—they’re emotional breaking points that drive active solution-seeking. Don’t build go-to-market around convincing satisfied Excel users. Instead, optimize for discovery when these specific emotions converge. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

MishiPay has scaled from processing $10 million to over $250 million in annual transactions by abandoning product purity for market pragmatism. What started as a mobile-first scan-and-go solution evolved into a comprehensive checkout platform spanning self-checkout kiosks, RFID systems, mobile POS, and traditional cash registers—now deployed across 2,000+ stores in North America, Europe, the Middle East, and Australia. In this episode of Category Visionaries, we sat down with Mustafa Khanwala, CEO and Founder of MishiPay, to dissect why the ”inferior” product often wins in retail tech, how trust-building mechanics differ fundamentally across geographies, and what it actually takes to maintain startup agility at enterprise scale. Topics Discussed: - The seven-year journey from consumer mobile app to B2B checkout infrastructure - Why MishiPay nearly failed by over-indexing on superior UX instead of adoption curves - The 2022 pivot that unlocked triple-digit revenue growth with flat headcount - How checkout solution requirements vary by customer visit frequency (weekly grocery vs. annual travel retail) - Trust-building in enterprise sales: face-to-face requirements in Middle Eastern markets vs. video-first Western sales cycles - Delivering two-week go-live timelines and 10-minute UI changes while maintaining 99.9999% uptime - AI integration strategy: internal efficiency first, then customer-facing analytics and autonomous POS management GTM Lessons For B2B Founders: - Adoption friction kills better products: Mustafa spent years refusing to build self-checkout because scan-and-go was objectively superior UX. The company nearly died defending this position. ”Should we have started on some of our other products in 2019 instead of 2022? Probably.” The lesson isn’t about building inferior products—it’s about understanding that customers evaluate ”better” through implementation risk, training overhead, and behavior change required. B2B founders must map the gap between current state and ideal state, then build the bridge products that de-risk each transition step, even if those bridges feel like compromises. - Customer frequency determines viable solution complexity: Scan-and-go requires significant user education investment that only generates ROI with weekly-plus usage. In travel retail where 70-80% of customers visit 1-2x annually, that education cost never pays back. MishiPay now matches solution types to visit patterns: scan-and-go for high-frequency grocery, staff-assisted mobile POS for low-frequency travel retail, RFID self-checkout for mid-frequency fashion. B2B founders should calculate the learning curve payback period against actual usage frequency—if users won’t encounter your product enough times to justify the learning investment, you need a different entry point regardless of how good the end-state experience is. - Enterprise stability with startup agility is a wedge, not a platitude: Every vendor claims this. MishiPay operationalizes it through specific SLAs: two-week store go-lives, 10-minute button changes, two-day promotion additions, two-week payment method integration—all while maintaining 99.9999% uptime that enterprise POS demands. This isn’t about ”moving fast,” it’s about architecture decisions that enable rapid customization without stability trade-offs (mobile-first, cloud-native, API-driven). B2B founders should define their agility claims in measurable timelines and uptime guarantees, not adjectives. If you can’t operationalize ”flexibility” into specific hours or days for changes, it’s not a differentiator. // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Assembled is the AI customer support platform powering hundreds of modern enterprises including Stripe, Robinhood, Salesforce, and Ashley Furniture. The company’s largest customer operates a 20,000-person contact center. With products spanning AI chat and voice agents that resolve 70-80% of tickets to sophisticated workforce management and forecasting systems, Assembled’s core thesis challenges the industry narrative: the best support teams orchestrate humans and AI in perfect balance rather than replacing one with the other. In a recent episode of Category Visionaries, we sat down with Ryan Wang, CEO and Co-Founder of Assembled, to explore the company’s journey from eight months to first customer to becoming the infrastructure behind customer experiences at scale. Topics Discussed: - The reality gap between AI support demos and production deployment - Why sophisticated buyers now demand quality benchmarks and latency metrics over feature lists - The hidden complexity in contact center work: KYC compliance, fraud review, and multi-system workflows - How the Klarna ”fire everyone” approach failed and what it reveals about the market - Patrick and John Collison’s all-company support rotations at Stripe - The product-market fit question that ended six months of wrong direction - Enterprise destiny baked into early product decisions - Converting LinkedIn discomfort into a systematic storytelling engine - Path dependence from workforce management to AI automation products - Why customer support problems rhyme with operations challenges across industries GTM Lessons For B2B Founders: - Quality-first positioning wins when buyers move past demo amazement: Ryan observed a critical market shift. Sophisticated buyers now run rigorous bake-offs with training data variability and ask for latency metrics, quality benchmarks, and production performance data. The last three AI deals Assembled closed required detailed competitive evaluations. When messaging emphasizes cost reduction over quality improvement, you lose credibility with buyers who understand that turning off support entirely would be free—they’re investing in lifetime value and loyalty creation. Position around the buyer’s actual objective hierarchy: quality first, efficiency as validation. - The product-market fit question that encodes your entire GTM strategy: Ryan’s co-founder asked prospects ”What is software that you must have or you hate your options?” This single question revealed multiple strategic insights simultaneously: you’re targeting painkillers in established categories, pursuing replacement sales against weak incumbents, and entering markets with demonstrated willingness to pay. For Assembled, this naturally surfaced workforce management—a must-have category with Windows 95-era tools serving 20,000-person teams. The question’s elegance is how it filters for product-market fit and GTM approach in one conversation. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Keye helps private equity investors accelerate deal evaluation through AI-powered quantitative analysis. In a recent episode of Category Visionaries, I sat down with Rohan Parikh, Co-Founder and CEO of Keye, to explore how his team bridges the gap between AI capabilities and the 100% accuracy requirements of financial due diligence—enabling PE firms to say no to deals earlier and focus resources on the right opportunities. Topics Discussed: - Why ChatGPT-style search and summarization tools fail in PE workflows—summaries don’t drive investment decisions - The technical challenge of achieving 100% deterministic accuracy while maintaining AI contextualization capabilities - How market timing created unexpected GTM momentum: PE operating partners watching portfolio companies transform with AI became receptive to internal tooling - Persona-specific cold email strategies that demonstrate workflow understanding rather than biographical personalization - Design partner economics in conservative industries: accepting ＜1% hit rates to find firms willing to bet $10-20K on early-stage solutions - Building multichannel GTM in a relationship-driven industry where brand recognition signals data security capability GTM Lessons For B2B Founders: - Identify where AI creates workflow compression, not just automation: Most tools attempted to replicate ChatGPT for finance—search, summarization, document Q&A. Rohan rejected this approach because ”summaries don’t lead to decision making” in PE. Instead, Keye focused on the quantitative analysis workflow: data scrubbing, creating multiple views, combining datasets, and extracting insights about customer cohort performance and business health. The North Star wasn’t faster summaries—it was enabling investors to evaluate more deals with the same selectivity. B2B founders should map where their technology collapses decision timelines rather than simply automating existing tasks. - Engineer for domain-specific accuracy thresholds: Financial analysis operates under ”unless it’s 100%, it is 100% wrong” constraints. When AI models delivered 99% accuracy on mathematical operations, Rohan’s team built a hybrid architecture—completely deterministic calculations with AI layered on for contextualization. This wasn’t a product compromise; it was recognizing that PE professionals ”have gone through the same process over 50 years” and won’t trust systems that occasionally miscalculate. B2B founders in regulated or high-stakes domains must architect for their industry’s reliability requirements, not force general-purpose AI into unsuitable applications. - Exploit second-order market timing effects: Keye launched when PE firms were experiencing technology shifts through their portfolio companies—operating partners were ”very wary of what AI has brought into the picture” because they witnessed it firsthand in their investments. This created a unique moment where ”both technology has been brought in, but at the same time the willingness to look at technology has also drastically improved.” Five years earlier, this GTM motion would have failed. B2B founders should identify when their buyers are experiencing transformation in adjacent contexts that make them receptive to internal change. // Sponsors:  Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Voltiris has developed spectroscopy-based solar panels that filter light for greenhouse crops while generating renewable energy. Unlike traditional opaque panels that cause 60-80% yield reduction in high-tech greenhouses, Voltiris’s technology harvests only the light wavelengths unused by photosynthesis. In this episode, we sat down with Nicolas Weber, Co-Founder and CEO of Voltiris, to explore how a former BCG consultant and a PhD spectroscopist are navigating multi-season validation cycles with family-owned greenhouse operations across Northern Europe. Topics Discussed: - Why spectroscopy expertise unlocked a solution to greenhouse energy challenges - The technical reality: traditional solar creates 60-80% yield loss in high-tech greenhouses - Earning credibility with second and third-generation greenhouse operators - Time as constrained resource: multi-season validation in agriculture markets - System-level thinking required to manage complex greenhouse operations - Offline GTM in conservative B2B agriculture: fairs, referrals, and crop advisors - Platform strategy: expanding from solar to complete greenhouse energy management GTM Lessons For B2B Founders: - Time constraints differ fundamentally in hardware: Voltiris faces season-dependent validation cycles where ”you can throw as much cash as you want on a tomato, it’s going to take one year to demonstrate that it works.” Most growers demand 2-3 full growing seasons before adoption. Hardware founders must structure runway, investor expectations, and partnership terms around immovable biological or physical timelines—not software-style iteration speeds. - Product-market fit exists before product in infrastructure plays: Voltiris confirmed demand preemptively. Nicolas explains: ”If the technological promise holds, there is demand...the growers, they already told us from the beginning we’re waiting for solution like this to come.” When selling infrastructure that solves existential problems (energy transition, electrification mandates), validate market pull before achieving technical proof. This inverts typical startup sequencing but derisks decades of R&D investment. - Treat early customers as co-creation partners, not transactions: Voltiris positions initial deployments as ”joint creation” rather than sales. Nicolas’s pitch: ”This is the future vision. Are you ready to build it with us and do you want to jump into that shit with us?” In markets with 25-30 year product lifecycles and 3-year company track records, transactional selling fails. Structure partnerships with shared risk, transparent data access, and collaborative problem-solving. - Master domain expertise at operator level, not executive level: Voltiris’s technical co-founders became greenhouse operations experts, not just energy technology experts. Nicolas credits this: ”My two co founders are now among the best experts you have in terms of how to run a greenhouse.” In complex B2B environments (agriculture, manufacturing, logistics), founders must understand day-to-day operations—not just C-suite pain points—to build credible solutions. // Sponsors:  Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Nightfall AI is pioneering AI-native data loss prevention (DLP) for enterprises navigating cloud, SaaS, and AI application proliferation. Founded in 2017 by former Uber engineers who witnessed data breaches firsthand, Nightfall addresses the architectural limitations and false positive problems plaguing legacy DLP solutions. By leveraging machine learning and large language models across three distinct layers—content classification, risk assessment, and forensic investigation—Nightfall delivers 10x accuracy improvements while enabling secure AI adoption. In this episode of Category Visionaries, I sat down with Rohan Sathe, Co-Founder & CEO of Nightfall AI, to explore their strategy for displacing entrenched incumbents and positioning as the security enabler for organizational AI deployment. Topics Discussed: - Nightfall’s founding thesis addressing DLP coverage gaps created by cloud and SaaS migration - Three-layer AI architecture: content classification, behavioral risk analysis, and agent-assisted forensics - Positioning against legacy DLP’s rules-based approaches and exact data match workarounds - Market education shift post-ChatGPT: from ”don’t use AI” to ”enable AI securely” - Purple brand differentiation strategy in security’s dark-themed visual landscape - Conference ROI reallocation: executive suite meetings versus booth presence at RSA and Black Hat - Mid-market to enterprise expansion pattern through peer-to-peer word-of-mouth - Founder-led LinkedIn strategy balancing market education with competitive displacement narratives - Sales team composition: domain practitioners versus traditional sales profiles GTM Lessons For B2B Founders: - Structure POVs to prove quantifiable superiority on one dimension: Rohan revealed Nightfall benchmarks against Google and Microsoft DLP APIs, demonstrating 10x accuracy improvements during proof-of-value cycles. When challenging mature categories, identify the single metric where you demonstrably outperform and architect evaluations to surface that gap. The key isn’t claiming superiority—it’s creating controlled comparisons where buyers verify it themselves. - Deploy AI across three workflow layers, not as a monolithic feature: Nightfall applies AI distinctly at content classification (identifying sensitive data with high precision), behavioral analysis (distinguishing risky data movement from standard workflows), and investigation assistance (helping analysts focus forensic efforts). This creates compounding value and defensibility. Map where AI can reduce friction at multiple decision points in your customer’s workflow rather than treating it as a single capability. - Replace field marketing spend with curated CISO access: Nightfall redirected budget from RSA and Black Hat booths to private suites hosting scheduled executive meetings. Rohan emphasized engaging ”chief information security officers who sign the checks” in intimate settings rather than booth traffic. For enterprise sales, calculate cost-per-meeting with economic buyers and reallocate spend accordingly. //  Sponsors:  Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

BlueRock is building an agentic security fabric to protect organizations deploying AI agents and MCP workflows. With a $25 Million Series A, founder Bob Tinker is tackling what he sees as a 10x larger opportunity than mobile’s enterprise disruption. Bob previously scaled MobileIron from zero to $150 million in five years and took it public in 2014. In this episode of Category Visionaries, Bob shares the strategic mistakes that cost MobileIron its category positioning, why go-to-market fit is the missing framework between PMF and scale, and how B2B marketing has fundamentally transformed in just 18 months. Topics Discussed: - Taking a company public: the killer marketing event versus the unexpected team psychology challenges of daily stock volatility - Why agentic AI workflows create unprecedented security challenges at the action and data layer, not just prompts - The strategic timing of category definition: MobileIron’s cautionary tale of letting Gartner define you as ”MDM” when customers bought for security - Where enterprise buyers actually get advice now that Gartner’s influence has diminished - AEO (Answer Engine Optimization) replacing SEO as the primary discovery mechanism for B2B solutions - Why 1.0 categories have fundamentally unclear ICPs versus 2.0/3.0 products with crisp buyer personas - The ”high urgency, low friction” framework for prioritizing what to build in nascent markets - Go-to-market fit: the repeatable growth recipe that unlocks scaling post-PMF - Unlearning as competitive advantage for second-time founders GTM Lessons For B2B Founders: - Time your category noun definition strategically: MobileIron focused exclusively on solving the problem (the verb) but waited too long to influence category nomenclature. Gartner labeled it ”Mobile Device Management” when customer purchase drivers were security-focused, not management. This misalignment constrained positioning for years with no way to correct it. The framework: lead with verb, but proactively shape the noun before external analysts do it for you. Bob’s doing this differently at BlueRock by distinguishing ”agentic action security” from ”prompt security” early, even while the broader market sorts out AI security taxonomy. - Use customer language as category discovery, not invention: Bob’s breakthrough on BlueRock positioning came from asking prospects: ”How would you describe what we do to your peers?” One prospect distinguished their focus on ”the action side - taking AI and taking action on data and tools” versus prompt inspection and AI firewalls. This customer-generated framing revealed the natural fault lines in how practitioners think about the problem space. The tactical application: run this exact question with your first 10-15 qualified prospects and pattern-match their language, rather than workshopping category names internally. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

tiun is building auth and payment infrastructure that consolidates two traditional categories into one streamlined solution. By combining social login with instant payment functionality, tiun eliminates the standard account creation and credit card entry flow, reducing user onboarding to a two-click process. Operating as merchant of record, tiun serves online entertainment businesses, content creators, news publishers, and SaaS platforms. The company currently reaches 10 million users monthly through customer website placements and is growing transactions 15-20% month-over-month. In this episode of Category Visionaries, Sandro Zweig shares how tiun evolved from targeting news publishers to building a broader entertainment ecosystem, the challenges of creating a market for a combined category, and the data-driven approach to proving ROI before scaling. Topics Discussed: - Evolution from news publisher focus to entertainment and SaaS ecosystem strategy - Consolidating auth and payment infrastructure into a single category - Case study metrics: 20% uplift in paying users with under 1% subscription cannibalization - The 2.5x lead generation improvement versus traditional subscription models - Building market-specific ecosystems as a B2B2C go-to-market strategy - DACH penetration strategy before US expansion - Achieving organic exposure through customer website placement - Reducing integration complexity to drive adoption in an emerging category GTM Lessons For B2B Founders: - Geographic density creates B2B2C flywheels: tiun’s go-to-market prioritizes ecosystem density within a single market over broad geographic distribution. Users discover tiun on one platform, then encounter it across 3-4 additional properties in their consumption pattern, creating recognition and repeat usage. This required penetrating DACH (100 million people, single language, unified regulations) before considering US expansion. For B2B2C products where end-user familiarity drives business adoption, concentrate on saturating one market until the consumer-side network effect reduces enterprise sales friction. - Validate with 6-12 month pilot data before scaling: tiun ran contained pilots with 3-4 customers for a full year before pursuing their long-tail market. This produced case studies showing 20% paying user uplift and under 1% cannibalization—metrics that directly addressed the primary objection (subscription revenue risk). Sandro notes this extended validation period became essential because ”there is no market for it yet. We’re creating the market.” When creating a new category, resist scaling pressure until you have multi-month data that quantifies business outcomes and neutralizes the biggest adoption barriers. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

The dental industry is chronically supply-constrained: 97% of dentists report staffing as their primary volume limiter, 95% cite extreme recruiting difficulty, yet 75% of hygienists prioritize schedule flexibility above all else. This structural mismatch created the opportunity for Toothio—a labor marketplace connecting dental professionals seeking flexible work with practices facing critical staffing shortages. In this episode, we sat down with Ian Prendergast, Co-Founder and CEO of Toothio, to unpack how he applied labor marketplace principles from hospitality and light industrial verticals to dental, why DSO enterprise customers emerged as the true ICP only after launch, and how being an industry outsider enabled business model innovation that insiders missed. Topics Discussed: - How a single golf course conversation with a dentist exposed the 97% staffing crisis and validated the market opportunity - Translating labor marketplace GTM from Qwick (hospitality staffing) and Steady Install (light industrial) into dental - The supply-demand structural imbalance: dental growing 10.5% CAGR, 40% workforce departure in 2020, insufficient pipeline - Supply-first marketplace development and why quality/reliability required deep supply pools before demand acquisition - The ICP evolution from private practices (faster sales cycles, lower risk validation) to DSO enterprise (higher volume, stickier retention) - Building credibility as outsider founders through strategic SME hires, advisors, and embedding in industry associations - The enterprise motion: hiring CCO and SVP Sales with dental Rolodexs to access top-10 DSO decision-makers - Quantifying previously unmeasured costs: 100%+ recruiting cost increases, industry-leading turnover rates, $1,560+ daily production loss per unstaffed hygienist - Leveraging AI agentic systems to eliminate geographic marketplace constraints for national expansion - The moat-building roadmap: layering SaaS and RCM software over the distribution channel to increase switching costs GTM Lessons For B2B Founders: - Supply depth before demand scale prevents unit economics collapse - ICP clarity requires live market data, not pre-launch assumptions - Hire senior enterprise operators when you have validation plus clear TAM - Outsider economic analysis creates differentiated value propositions - Industry association involvement is enterprise distribution, not brand marketing // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Implentio automates workflows between e-commerce merchants and their third-party logistics providers, starting with invoice reconciliation. The platform tackles a problem every scaled e-commerce brand faces: thousands of rows of billing data in CSVs paired with six-figure invoices that nobody has time to validate. In this episode of Category Visionaries, I sat down with Jason Bang, Chief Product Officer and Co-Founder of Implentio, to explore how two decades running operations—from analyst to COO—led him to build what operations teams have never had: tools as sophisticated as what marketing has been using for years. Topics Discussed: - The margin erosion hidden in 3PL invoicing and why operations teams can’t afford to audit complex billing  - Founder-led growth in tight-knit industry networks where everyone goes to the same trade shows  - Partnership GTM with fractional CFOs, software providers, and 3PLs themselves  - Building a personal brand as an anti-social-media operations leader  - Why operations teams are creative problem solvers trapped in spreadsheets  - The roadmap toward AI-powered operational intelligence that eliminates manual data work GTM Lessons For B2B Founders: - Industry networks unlock faster GTM than traditional outbound: Implentio’s first customers came from Jason’s 20-year operations network—direct texts to brand founders, warm intros to ops teams, relationships from the same trade shows and conferences. His approach eliminated typical B2B sales cycles by going straight to decision makers who already trusted him. For founders with deep industry tenure, exhausting warm networks before building cold outbound infrastructure delivers conversion velocity and cycle time advantages that justify founder time investment despite limited scale. - Partner with companies who own your ICP’s budget allocation: Implentio partnered with fractional CFOs who control purchasing decisions and immediately understand ROI. Jason explained their appeal: ”They see the numbers, they understand the numbers. So I show them an ROI and they’re like, boom, no brainer.” The framework: identify which third parties influence or control budget decisions in your category, then build rev-share referral programs. Mapping your buyer’s external advisors and service providers can shortcut enterprise sales cycles. - Turn industry incumbents into distribution partners by solving their client problems: Despite addressing 3PL billing issues, Implentio positioned 3PLs as partners rather than adversaries. Jason’s philosophy: ”I’m not a 3PL adversary. I actually love 3PLs. I think they serve an important need.” Implentio offers 3PLs a value-add service for their merchant clients while gaining direct customer access. The framework works when you solve what incumbents are contractually responsible for but operationally struggle to deliver, without competing for their core revenue. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Michael Assraf is building Flamingo, an open-source and AI-powered operating system for managed service providers. After exiting Vicarious in May 2024, he spent seven months on market research before writing a single line of code—conducting 15+ MSP interviews, mapping their complete tool stack economics, and testing distribution channels with a free community product. The research revealed a structural margin crisis: MSPs operate on 10-15% margins with 30% of revenue flowing to vendor payouts and 25-30% to technician labor. Meanwhile, private equity consolidation drives customer pricing down while legacy vendors raise prices. Michael closed a $2.2 million pre-seed in February 2025, built OpenMSP as a lead-gen vehicle that generated 1,000+ waitlist signups, and launched Open Frame with 70% of capital still in the bank. In this launch-day conversation, he breaks down why the $380 billion MSP market remains massively underinvested, how Facebook ads outperformed LinkedIn 5:1, and why he’s giving away the core product while charging for hosted deployment. Topics Discussed: - The seven-month research phase: 15+ MSP interviews, mapping 19 tool categories with pricing data, evaluating open source project maturity through commit frequency and VC backing - MSP margin compression mechanics: 30% vendor payouts, 25-30% labor costs, 10-15% net margins being crushed by PE-driven consolidation and vendor price increases - Building OpenMSP as distribution validation: four months before alpha, generated 1,000 waitlist signups and 200 Slack members while testing paid acquisition channels - Why Facebook delivered 40%+ of leads at $6-8 CPL while outbound completely failed with IT-busy MSPs aged 25-50 in central US markets - Launching with 70% of $2.2M pre-seed still in bank by solving for distribution and product-market fit before scaling headcount - Open Frame’s architecture: unified control plane over open source tools (RMM, SSO, zero trust) with dual AI agents—one for end users, one for technicians - Offering both self-hosted (free, GitHub) and commercial SaaS (per-seat pricing starting January 2026) to build trust in an underserved market - The MSP category opportunity: $380B market, 12% annual growth, 30-40K US MSPs, minimal VC-backed innovation against 20-year-old incumbents // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

First Resonance provides factory orchestration and coordination software for scaling hardware companies. Founded by SpaceX veterans in 2019, the company focused on filling the gap between legacy manufacturing systems and the needs of emerging hard tech startups. In a recent episode of Category Visionaries, we sat down with Karan Talati, CEO & Co-Founder of First Resonance, to learn about the company’s journey building Ion—their manufacturing operations platform—and how they’re enabling companies scaling from R&D prototypes to production manufacturing across aerospace, defense, nuclear energy, and advanced manufacturing. Topics Discussed: - Karan’s time at SpaceX during hypergrowth (employee 2,000 to 6,000+) and the transition from single rocket design to production operations - Why First Resonance walked away from pursuing legacy aerospace and defense giants - The failed PLG experiment and pivot to enterprise sales with product analytics for expansion - How the ”new space” pattern is repeating in nuclear energy and other hard tech verticals - Market expansion from aerospace into nuclear energy over the past three to four years - Advanced manufacturing technology convergence enabling electric aviation (battery density, composite manufacturing, 3D printing) - AI’s role in breaking down knowledge silos between mechanical, electrical, and software engineering - Defense contractor security requirements: CMMC, FedRamp, and NIST 800-171 -Brand strategy targeting the new manufacturing workforce versus the retiring old guard // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

ZayZoon pioneered the earned wage access category a decade ago and has become the leading embedded provider through partnerships with over 300 payroll companies. With over $50 million raised and a team of 200, ZayZoon now serves 15,000+ businesses across the US. In a recent episode of Category Visionaries, I sat down with Tate Hackert, Co-Founder and Chief Strategy Officer of ZayZoon, to unpack their B2B2C distribution strategy, the economics of three-sided marketplaces, and how they’re expanding from earned wage access into the connected workplace. Topics Discussed: - Building for two years without revenue while signing payroll distribution partners - Why embedded B2B2C distribution beats direct sales for hourly workforce products - Engineering three-way marketplace economics that align payroll, employer, and employee incentives - The November 2017 trade show that killed their Canadian market strategy - Educating three distinct buyer personas in a category creation motion - Product expansion strategy: when to stay focused vs. when to launch adjacent products - Positioning shift from ”financial wellness” to recruitment/retention/productivity outcomes - The underwriting advantage of payroll-integrated repayment for reducing loss rates - Building 300+ payroll partnerships through relationship-driven GTM GTM Lessons For B2B Founders: - Solve distribution economics before product-market fit: ZayZoon spent 2014-2016 building product and signing payroll partners before generating first revenue in 2016. The insight: ”Why would we go and try to sign up business by business...Let’s sign up the payroll company because they’re this umbrella organization.” For B2B2C models, solve the distribution layer first—even if it delays revenue. Your bottleneck is partner adoption curves, not product readiness. - Structure three-way economics where everyone wins big: ZayZoon discovered payroll companies had ”this gold mine of employees that they hadn’t yet monetized” and built a model where they pay payroll partners ”a really hefty revenue share” while keeping enough margin for ZayZoon and keeping the service low-cost for employees. In platform businesses, the unit economics must be compelling enough that each party actively sells for you, not just tolerates you. - Map your value prop to your buyer’s actual job metrics: ZayZoon’s breakthrough came from reframing earned wage access as solving recruitment, retention, and productivity—the metrics small business owners are measured on. Tate explained the unlock: ”It’s free for me, and it’s deployed seamlessly through the HCM provider that I already use. Yeah, turn it on.” Your features matter less than your impact on the specific KPIs in your buyer’s quarterly review. - Kill underperforming markets immediately, even after years of investment: After building in Canada from 2014-2017, one US trade show in November 2017 generated ”more signed business than we had done in the previous couple of years in Canada.” They put Canada ”on life support” by January 2018. Resource reallocation speed matters more than sunk cost. When signal clarity emerges, move capital and team within weeks, not quarters. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

AODocs manages business-critical documents for enterprises where downtime has real consequences—production lines stopping, construction projects delayed, containers sitting at ports. Founded in 2012 and bootstrapped to profitability by 2022, the company serves Google’s data center builds, aerospace manufacturers’ FAA certifications, and Veolia’s water treatment operations. In this episode of Category Visionaries, we sat down with Stéphan Donzé, Founder of AODocs, to unpack his 14-year journey from Google ecosystem specialist to Microsoft-compatible platform. Stéphan shares unfiltered lessons from the brutal 2014-15 years when cloud platform limitations broke customer deployments, why they’ve reconsidered fundraising every two years but remained independent, and how AI agents finally created the urgency factor their category always lacked. Topics Discussed: - Surviving 2014-15 when Google Cloud platform performance limits broke at scale - Bootstrapping via services company profits until standalone profitability in 2022 - Why long-term document lifecycle management (10-30 year retention) resists VC timelines - Expanding from Google workspace early adopters to Microsoft enterprise accounts - The failed experiment with cloud reseller partners who couldn’t deploy DMS - Why marketing hire ramp time equals technical hire ramp for platform products - Medium-sized industry conferences outperforming 30K-attendee mega-events on cost-per-lead - Positioning as document foundation for reliable AI agent information access GTM Lessons For B2B Founders: - Founder must own category positioning until $10M ARR: Stéphan argues technical founders can’t delegate core messaging early: ”My personal take is that in the tech company the CMO cannot be anybody else than the founder itself at least for the first $10 million.” This comes from watching marketing experts produce ”beautiful words and lots of fluff but still not get the essence of what we’re doing.” For technical founders uncomfortable with marketing: you’re avoiding your most important job in the early years. - Regional 2K-5K conferences deliver better unit economics than flagship 30K events: While AODocs attends Google Next (30,000) and Gartner conferences, smaller regional IT decision-maker events generated superior cost-per-qualified-lead. Stéphan’s finding: ”If you look at the number of dollars you spend per lead that you get, the small events are surprisingly effective.” This contradicts conventional wisdom about flagship event ROI. For enterprise B2B: test regional and vertical conferences before scaling spend on mega-events. - Technology paradigm shifts create replacement urgency: AODocs positioned as ”modern cloud-based document management” for years without forcing function to rip out legacy systems. AI agents changed the calculus entirely. Stéphan’s repositioning: ”If you don’t upgrade your document foundation, you won’t be able to benefit from the AI productivity acceleration.” The urgency comes from AI agents requiring clean, validated document repositories—impossible with SharePoint chaos. For founders in infrastructure categories: look for adjacent technology waves that make your solution prerequisite, not optional upgrade. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Calico is building an agentic AI system for apparel sourcing and production—automating the ”messy middle” of manufacturing that has operated on emails, Excel, and WhatsApp for decades. As a founder who previously built and exited apparel brands, Kathleen Chan experienced the pain firsthand: opening a Shopify store takes minutes, but actually producing inventory requires staying up until 2am managing factory communications. In this episode, she shares how Calico is creating a new category during the 2025 tariff crisis, when sourcing directors are rewriting playbooks that haven’t changed in 50 years. Topics Discussed: - How Calico functions as an AI co-pilot for sourcing directors and production managers - Creating a category when no budget line exists for agentic AI systems - Leveraging the 2025 tariff environment as an adoption catalyst - Why six months of paid acquisition produced high signups but zero quality customers - Sequencing GTM tactics from unscalable one-to-ones to conferences to content - Building authenticity in a market saturated with AI slop and generic LinkedIn content - Hiring early evangelists who maintain conviction through the startup zigzag GTM Lessons For B2B Founders: - Match GTM motion to how your market transacts, not what scales: Calico tested paid acquisition for six months before realizing relationship-building converted better despite being unscalable. In apparel manufacturing, decades-long supplier relationships can’t turn on and off overnight—the buying motion reflects this reality. Kathleen’s approach: early-stage requires one-to-one dinners and networking to answer nuanced questions; mid-stage shifts to conferences for broader reach; late-stage deploys LinkedIn content once the market understands your category. The sequencing matters because each stage builds on the previous one’s trust foundation. - Brutally audit customer quality, not conversion metrics: Calico’s paid acquisition drove signups and ”conversions by marketing sense,” creating a false signal of product-market fit. After six months, the math revealed these customers cost more to acquire than those from relationship channels and had lower quality. Kathleen’s lesson: vanity metrics provide a ”weird little dopamine hit” that masks broken unit economics. For B2B founders in complex sales cycles, track cost-per-quality-customer, not cost-per-signup. - Use macro disruption to collapse sales cycles: The 2025 tariff crisis created an ”impossible challenge” for Calico’s ICP—sourcing directors forced to rewrite playbooks built over decades while tariffs changed via tweet. Rather than fighting the chaos, Calico positioned itself as the solution to this specific moment, anchoring customer conversations on tariff-driven urgency. This transformed education from abstract (”here’s what agentic AI can do”) to concrete (”here’s how we solve your tariff problem today”). B2B founders should identify trigger events that make the status quo untenable. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Freeplay AI emerged from a precise timing insight: former Twitter API platform veterans Ian Cairns and Eric Schade recognized that generative AI created the same platform opportunity they’d previously captured with half a million monthly active developers. Their company now provides the observability, evaluation, and experimentation infrastructure that lets cross-functional teams—including non-technical domain experts—collaborate on AI systems that need to perform consistently in production. Topics Discussed: - Systematic customer discovery: 75 interviews in 90 days using jobs-to-be-done methodology to surface latent AI development pain points - Cross-functional AI development: How domain experts (lawyers, veterinarians, doctors) became essential collaborators when ”English became the hottest programming language” - Production AI reliability challenges: Moving beyond 60% prototype success rates to consistent production performance - Enterprise selling to technical buyers: Why ABM and content worked where ads and outbound failed for VPs of engineering - Category creation without precedent: Building thought leadership through triangulated insights across hundreds of implementations - Offline community building: Growing 3,000-person Colorado AI meetup with authentic ”give first” approach GTM Lessons For B2B Founders: - Structure customer discovery with jobs-to-be-done rigor: Ian executed a systematic 75-interview program in 90 days, moving beyond surface-level feature requests to understand fundamental motivations. Using Clay Christensen’s framework, they discovered engineers weren’t just frustrated with 60% AI prototype reliability—they were under career pressure to deliver AI wins while lacking tools to bridge the gap to production consistency. This deeper insight shaped Freeplay’s positioning around professional success metrics rather than just technical capabilities. - Exploit diaspora networks from platform companies: Twitter’s developer ecosystem became Ian’s customer research goldmine. Platform company alumni have uniquely valuable networks because they previously interfaced with hundreds of technical teams. Rather than cold outreach, Ian leveraged existing relationships and warm introductions to reach heads of engineering who were actively experimenting with AI. This approach yielded higher-quality conversations and faster pattern recognition across use cases. - Target sophistication gaps in technical buying committees: Traditional SaaS tactics failed because Freeplay’s buyers—VPs of engineering at companies building production AI—weren’t responsive to ads or generic outbound. Instead, Ian invested in deep technical content (1500-2000 word blog posts), speaking engagements, and their ”Deployed” podcast featuring practitioners from Google Labs and Box. This approach built credibility with sophisticated technical audiences who needed education about emerging best practices, not product demos. //  Sponsors:  Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

TwelveLabs is building purpose-built foundation models for video understanding, enabling enterprises to index, search, and analyze petabytes of video content at scale. Founded by three technical co-founders who met in South Korea’s Cyber Command doing multimodal video understanding research, the company recognized early that video requires fundamentally different infrastructure than text or image AI. Now achieving 10x revenue growth and serving customers across media, entertainment, sports, advertising, and federal agencies, TwelveLabs is proving that category creation through extreme focus beats trend chasing. In this episode, Jae Lee shares how the company navigated early product decisions, built specialized GTM motions for established industries, and maintained technical conviction during years of building in relative obscurity. Topics Discussed: - How military research in multimodal video understanding led to founding TwelveLabs in 2020  - The technical thesis: why video deserves purpose-built foundation models and inference infrastructure  - Targeting video-centric industries where ROI justifies early-stage pricing: media, entertainment, sports, advertising, and defense  - Partnership-driven distribution strategy and AWS Bedrock integration results  - Specialized sales approach: generalist leaders, vertical-specific AEs and solutions architects Maintaining extreme focus and avoiding hype cycles during the first three years of building  - Federal GTM lessons: why In-Q-Tel partnership and authentic mission alignment matter more than process optimization  - The discipline of saying no to large opportunities that don’t fit ICP  - Keeping hiring bars high when the entire team is underwater GTM Lessons For B2B Founders: - Hire vertical specialists on the front lines, not just at the top: TwelveLabs structures its GTM team with generalist leaders (head of GTM and VP of Revenue) who can sell any technology, but vertical-specialized AEs, solutions architects, and deployment engineers. These front-line team members come directly from the four target industries and understand customer workflows, buying patterns, and integration points without ramp time. For founders entering mature markets with established tech stacks and complex procurement, this inverted model—generalist strategy, specialist execution—accelerates deal velocity because technical buyers immediately recognize domain fluency. - Infrastructure plays require integration partnerships, not displacement: In established industries with layered technology stacks, positioning as foundational infrastructure demands partnership-first distribution. Jae explained their approach: integration with media-specific GSIs, media asset management platforms, and cloud providers ensures TwelveLabs fits into existing workflows rather than forcing wholesale replacement. This is particularly critical for selling into industries like media and entertainment where technology decisions involve multiple stakeholders across production, post-production, and distribution. The AWS Bedrock integration delivered 30,000+ enterprise agreements in seven weeks—a distribution velocity impossible through direct sales alone. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

With over 30 years in wireless—from helping pioneer intercarrier SMS to running mobile identity operations across Americas and Asia Pacific — Eddie DeCurtis saw what others missed: 967 of 1,000 global mobile network operators lack the infrastructure to monetize CPNI data while protecting customers from fraud. The technical challenge isn’t building APIs. It’s that operators spent billions on 5G infrastructure and now lack capital, internal expertise, and operational frameworks to launch authentication services. In 18 months, Shush went from PowerPoint to 30 employees, supporting 47 network APIs with full GSMA Open Gateway compliance. Eddie shares how understanding regulatory frameworks by jurisdiction, not just deploying technology, became their competitive moat—and why hiring the executive who built T-Mobile USA’s authentication platform gave them credibility no competitor could match. Topics Discussed: - Why operators repeatedly said ”we want to do it, we have no idea how, we have no money, we don’t have a platform” - Validating the thesis with former AT&T Communications CEO John Donovan before launching - Securing a POC with a major operator pre-incorporation—with only a PowerPoint deck - The three-legged stool: technology, network integration, and business operations (where competitors fail) - Why knowing privacy regulations for CPNI data sharing by country became a deal-closer - Reducing network integration from dozens of touchpoints to three specific network elements - Supporting 8 Linux Foundation Camara APIs and TS.43 GBA AKA authentication standard - Going from 3 to 30 employees and launching at Mobile World Congress on a $75/night Airbnb budget GTM Lessons For B2B Founders: - Validate with the person most likely to kill your idea: Eddie deliberately chose John Donovan—former CEO of AT&T Communications, board member at Lockheed and Palo Alto Networks—specifically because ”he’s going to be rough, he’s going to totally ask the really hard questions.” When Donovan’s response was ”go raise $40 million and own this space...you’re not going to be alone for long,” the validation carried weight because it came from someone incentivized to find fatal flaws. Most founders validate with friendly audiences or investors looking for deals. Find the battle-tested executive who has nothing to gain from being kind. - Convert pre-product conviction into design partner commitments: Eddie secured a POC agreement with a major operator before Shush incorporated. ”I had nothing. I didn’t have software. We had an idea, we had a PowerPoint presentation.” This only works when you’ve spent decades building domain expertise and relationships. The lesson isn’t ”sell vaporware”—it’s that deep industry knowledge lets you articulate problem-solution fit so precisely that sophisticated buyers commit before seeing code. Infrastructure founders with 10+ years in-market can accelerate 12-18 months of product-market fit by converting expertise into early design partnerships. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.  Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM