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

Ludus operates a zero-cost ticketing platform for performing arts organizations, monetizing through patron convenience fees while transferring full ticket face value to venues. What began as a freshman year project for a high school theater director evolved into a company processing millions annually across thousands of customers. After surviving COVID-19’s 95% revenue elimination and competitor market exits, Ludus captured displaced customers and achieved their growth inflection point. In a recent episode of Category Visionaries, CEO and Co-Founder Zachary Collins detailed the execution mechanics behind customer advocacy generation, human-differentiated scaling, and market expansion through systematic word-of-mouth amplification. Topics Discussed: - Monetization alignment between platform and venues through patron-paid fee structures - Crisis survival mechanics: reducing to two employees while maintaining core product functionality - Systematic customer advocacy through documented attribution and public recognition programs - Counter-positioning against AI-first competitors through human-guaranteed support availability - Strategic capital deployment: transitioning from profitable bootstrapping to venture-accelerated expansion - Geographic and vertical expansion from high school theater to community venues and concert halls GTM Lessons For B2B Founders: - Deploy bottom-up penetration to bypass procurement friction and generate authentic adoption signals: Collins chose theater director sales over superintendent-level contracts despite longer individual deal cycles. This approach avoided forced adoption resistance while creating measurable engagement data from actual product usage rather than mandate compliance. The strategic insight: bottom-up sales generate higher-quality expansion opportunities because satisfied end users become internal advocates who influence broader organizational adoption. Implementation requires identifying decision-makers with both budget authority and day-to-day pain points, then optimizing for usage depth over initial contract size. - Transform support incidents into systematic advocacy generation through zero-effort resolution protocols: When database corruption lost customer registration data, Ludus manually contacted every affected parent, reconstructed missing information, and delivered complete solutions in organized spreadsheets. This zero-customer-effort approach generates 97-99% satisfaction scores while creating advocacy moments from potential churn situations. The tactical framework: establish incident response that eliminates customer work entirely, document extraordinary efforts taken, and follow up to ensure complete satisfaction. This converts support costs from pure overhead into measurable advocacy generation with direct attribution to pipeline growth. // 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

Healthcare providers waste $950 billion annually on manual workarounds caused by fragmented EHR systems and integration costs that don’t scale. Shadowbox has developed a patented browser technology that functions as an API, enabling instant EHR data access without traditional integration expenses. In this episode of Category Visionaries, we sat down with Gregory Stein, CEO of Shadowbox, to dissect how the company evolved from serving desperate lab diagnostics customers to building strategic partnerships with established healthcare IT players like HC1 to reach health systems. Topics Discussed: - How the 21st Century Cures Act information blocking provisions remain largely unenforced, allowing EHR vendors to maintain data monopolies through integration fees Shadowbox’s technical architecture: a white-labeled browser that accesses the document object model and API endpoints to extract HIPAA-compliant data without custom integrations - Market entry strategy—targeting financially distressed lab diagnostics providers who couldn’t afford traditional integration costs - The HC1 partnership model: splitting the market by use case rather than geography, with HL7/API integrations going to HC1 and rapid, low-cost deployments going to Shadowbox - Sequential interoperability capabilities that enable multiple vendor touchpoints (prior authorization, eligibility verification, billing) from a single data extraction GTM Lessons For B2B Founders: - Target customers facing existential financial pressure, not optimal market conditions: Shadowbox entered through lab diagnostics—a commoditized, low-margin segment hemorrhaging money where providers faced $5K-$50K integration costs per connection taking 3-6 months. Greg acknowledged labs are ”the redheaded stepchild of healthcare” but their desperation made them willing to pilot unproven technology. The lesson: segments with severe unit economics problems become early adopter pools because status quo costs exceed perceived risk of new vendors. - Build a partnerships function before you have market leverage: Shadowbox hired a partnerships-focused employee early to cultivate relationships with RCM vendors and lab information system providers already selling to target customers. Rather than waiting for customer traction to attract partners, they used partnerships to generate initial traction. Greg emphasized healthcare adoption requires credible references—partnerships provide instant credibility entrepreneurs can’t buy. Map your ecosystem’s existing vendor relationships and pursue co-sell arrangements before achieving meaningful ARR. - Use early customer feedback to migrate upmarket, not pivot laterally: Shadowbox started with labs, expanded to imaging centers, but their true ICP emerged as health systems with 500-1,000 community providers on disparate EHRs where traditional integration economics break down. Greg noted: ”health systems that have major outreach programs where it doesn’t pencil out to have them on their EPIC system.” The migration path moved from small, desperate customers toward larger organizations facing the same core problem at scale. Don’t mistake initial ICP for ultimate ICP—use early segments as beachheads to validate technology before pursuing customers with better economics. // 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

StrongestLayer is building AI-native email security architecture designed for threats that defeat pattern-matching systems. The company pivoted from security awareness training after early customers discovered its phishing detection plugin caught advanced threats that legacy gateway solutions missed. In a recent episode of Category Visionaries, we sat down with Alan LeFort, CEO of StrongestLayer, to discuss why architectural generation matters more than vendor reputation in email security, and how they’re using transparent proof-of-concept methodology to displace 20-year incumbents. Topics Discussed: - Why AI-generated attacks with n=1 datasets break signature-based detection architectures - The convergence of legitimate marketing automation and phishing techniques (lookalike domains, intent signals, AI-personalized messaging) - How 2% of attack types represent 90% of breach value, forecast to reach 17% of volume by 2027 - Transparent POC strategy achieving 85% meeting-to-POC and 100% qualified-POC-to-technical-win conversion - Stage-based ICP selection: targeting 1,000-10,000 seats for sub-6-month sales cycles with enterprise compliance requirements - Harvard Kennedy School research: AI enables 88% employee profiling from public data, 95% cost reduction for targeted campaigns, and 60% click rates versus 12% baseline GTM Lessons For B2B Founders: - Deploy transparent POCs as category displacement weapons: When attacking entrenched incumbents, StrongestLayer runs one-week POCs behind existing email security gateways with zero commercial pressure—just visibility into what’s being missed. At a sub-1,000-seat company running behind a top-three market leader, they surfaced 80 advanced threats in one week. This approach converts 85% of first meetings to POC and 100% of qualified POCs to technical wins. The insight: In technical categories where buyers are sophisticated, removing evaluation friction and letting comparative performance speak eliminates trust barriers faster than enterprise reference selling. - Stage-match your ICP to burn rate tolerance, not TAM: Alan deliberately excludes Fortune 500 despite universal email security need: ”When their procurement team is bigger than your whole company, not a good scene.” Instead, they target 1,000-10,000 seats—enterprises with SOC2/compliance obligations but without Fortune 500 security budgets or staffing. These accounts close in under 6 months. The framework: Define ICP by sales cycle length your runway can sustain, then expand segments as capital position improves. Your ICP should evolve with company stage, not remain static based on ideal long-term positioning. // 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

Lincode Labs is transforming quality control in automotive manufacturing through AI-powered visual inspection systems that replace traditional machine vision cameras with advanced computer vision technology. After nine years and $10 million in funding, the company has established itself as an early mover in bringing modern AI to one of manufacturing’s most conservative sectors. In this episode of Category Visionaries, I spoke with Rajesh Iyengar, a fourth-time founder with multiple exits, about his methodical approach to market validation, the operational realities of selling into automotive manufacturing, and the counterintuitive GTM strategies that enabled market penetration in a notoriously risk-averse industry. Topics Discussed: - Pre-incorporation market validation methodology: surveying 300-400 manufacturers over one year - Positioning within existing ”vision systems” budget categories versus creating new AI category - Manufacturing engineer versus quality engineer buyer persona discovery and implications - Trade show strategy for demonstrating complex AI technology to skeptical prospects - Geographic arbitrage: leveraging Silicon Valley for fundraising, Michigan for customer proximity - Structured investor feedback collection across 400-500 pitches for business model refinement GTM Lessons For B2B Founders: - Execute systematic pre-incorporation market validation at scale: Before incorporating Lincode, Rajesh spent an entire year surveying 300-400 manufacturers through a structured questionnaire approach. Starting with 8-10 manufacturing contacts, he expanded through LinkedIn outreach to validate core assumptions about AI adoption, deployment complexity, and willingness to pay. This wasn’t casual customer discovery—it was quantitative market research that de-risked his fourth venture before committing capital. B2B founders should design systematic validation processes that generate statistically meaningful data rather than relying on anecdotal feedback from a handful of prospects. - Position within existing budget categories to accelerate procurement cycles: Despite building AI technology, Rajesh deliberately positioned Lincode within the established ”vision systems” category rather than creating a new AI category. As he explained, ”as far as customer is concerned, whether it’s AI or not AI, they’ll put us into a category of vision systems... so they can assign the budgets.” Creating new categories extends sales cycles as procurement teams struggle with budget allocation and vendor evaluation frameworks. B2B founders should analyze how their innovation maps to existing enterprise budget line items and position accordingly, reserving category creation for later market education phases. // 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

Cerebrium is a serverless AI infrastructure platform orchestrating CPU and GPU compute for companies building voice agents, healthcare AI systems, manufacturing defect detection, and LLM hosting. The company operates across global markets handling data residency constraints from GDPR to Saudi Arabia’s data sovereignty requirements. In a recent episode of Category Visionaries, I sat down with Michael Louis, Co-Founder & CEO of Cerebrium, to explore how they built a high-performance infrastructure business serving enterprise customers with high five-figure to six-figure ACVs while maintaining 99.9%+ SLA requirements. Topics Discussed: - Building AI infrastructure before the GPT moment and strategic patience during the hype cycle - Scaling a distributed engineering team between Cape Town and NYC with 95% South African talent - Partnership-driven revenue generation producing millions in ARR without traditional sales teams - AI-powered market engineering achieving 35% LinkedIn reply rates through competitor analysis - Technical differentiation through cold start optimization and network latency improvements - Revenue expansion through global deployment and regulatory compliance automation GTM Lessons For B2B Founders: - Treat go-to-market as a systems engineering problem: Michael reframed traditional sales challenges through an engineering lens, focusing on constraints, scalability, and data-driven optimization. ”I try to reframe my go to market problem as an engineering one and try to pick up, okay, like what are my constraints? Like how can I do this, how can it scale?” - This systematic approach led to testing 8-10 different strategies, measuring conversion rates, and building automated pipelines rather than relying on manual processes that don’t scale. - Structure partnerships for partner success before revenue sharing: Cerebrium generates millions in ARR through partners whose sales teams actively upsell their product. Their approach eliminates typical partnership friction: ”We typically approach our partners saying like, look, you keep the money you make, we’ll keep the money we make. If it goes well, we can talk about like rev share or some other agreement down the line.” This removes commission complexity that kills B2B partnerships and allows partners to focus on customer value rather than internal revenue allocation conflicts. - Build AI-powered competitive intelligence for outbound at scale: Cerebrium’s 35% LinkedIn reply rate comes from scraping competitor followers and LinkedIn engagement, running prospects through qualification agents that check funding status, ICP fit, and technical roles, then generating personalized outreach referencing specific interactions. ”We saw you commented on Michael’s post about latency in voice. Like, we think that’s interesting. Like, here’s a case study we did in the voice space.” The system processes thousands of prospects while maintaining personalization depth that manual processes can’t match. // 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

Whatagraph has evolved from a bootstrap marketing reporting tool to a comprehensive marketing intelligence platform processing data from 12+ sources for marketing teams globally. With over $10 million in funding and a decade of iteration, the Lithuania-based company recently launched ”Whatagraph 3.0”—a fundamental shift from pure sales-led to hybrid PLG motion. In this episode of Category Visionaries, Justas Malinauskas shares the technical and strategic decisions behind their transformation from agency tool to enterprise marketing intelligence platform, including their multi-agentic AI implementation and the SEO strategy that generates 500+ MQLs monthly. Topics Discussed: - Technical architecture evolution from reporting automation to full-stack marketing intelligence - Strategic pivot from sales-led to hybrid PLG/sales-led motion triggered by mission misalignment - Advanced SEO methodology using competitor pain point analysis and search behavior reverse engineering - AI implementation using multi-agentic systems rather than simple LLM integration - Lithuania’s bootstrap-first ecosystem and knowledge-sharing networks among unicorn companies - Go-to-market evolution across three distinct phases over 10 years GTM Lessons For B2B Founders: - Engineer time-to-value as your primary PLG enabler, not feature breadth: Whatagraph achieved 5-minute time-to-value from data connection to dashboard generation—versus the industry standard of hours—by rebuilding their onboarding around AI-powered automation rather than manual drag-and-drop configuration. Justas notes this wasn’t just UI optimization but fundamental product architecture changes: ”It’s basically a lot of knowledge from our last 10 years...we’re able to build it like really multi-agentic platform which helps to build those things in steps, not just like drop something randomly.” For PLG success, optimize your technical stack for immediate value delivery, not comprehensive feature exposure. - Weaponize competitor technical limitations through content strategy: Rather than competing on generic ”best marketing tool” keywords, Whatagraph dominated by creating authoritative content around specific competitor pain points. Their ”Looker Studio being slow” content strategy captured high-volume searches from frustrated users by actually helping solve the problem while positioning their technical advantages. Justas explains: ”The biggest problem was it’s actually very slow...when we have everything in house we can make things like very quick and speedy compared to there.” Target technical pain points your architecture inherently solves rather than fighting brand-to-brand keyword battles. - Align your ICP strategy with your actual technical capabilities, not market perception: Whatagraph’s shift to hybrid PLG wasn’t market-driven but mission-driven. Justas realized their technical product could serve smaller organizations, but their sales-led approach artificially excluded them: ”We were not empowering in the first place people, everyone to make those data driven decisions fast...we were not allowing everyone into the product even if our product was allowing to.” // 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

NumberEight converts mobile sensor data into contextual audience segments without capturing PII, addressing the fundamental breakdown of cookie-based targeting as media consumption fragments across podcasts, gaming, and connected TV. What began as a thesis project for contextual SoundCloud recommendations has evolved into a B2B data platform serving podcast platforms, media sales houses, and agencies. In this episode of Category Visionaries, we sat down with Abhishek Sen to unpack how NumberEight navigates the complex adtech ecosystem and the tactical GTM strategies that drive their expansion across multiple customer segments simultaneously. Topics Discussed: - How NumberEight evolved from a Netherlands thesis project (contextual SoundCloud recommendations) to solving adtech’s identity crisis - Technical architecture: converting mobile sensor data to contextual audience segments without PII collection - Multi-segment GTM approach across podcast platforms (AdSwizz, Triton), media sales houses, and agencies - Why the company targets podcasting and gaming simultaneously despite different data density challenges - Conference strategy: 45+ targeted meetings per event while completely avoiding booths - Building category credibility through IAB Tech Lab standards work and white paper contributions - The breakdown of cookie-based targeting as consumption fragments beyond web browsers GTM Lessons For B2B Founders: - Execute systematic conference preparation to maximize deal flow: Sen books 45+ targeted meetings across 4-day conferences like Cannes Lions through advance relationship mapping and mutual connection identification. The tactical framework: pre-research each prospect’s annual priorities, identify shared connections for warm introductions, and plan specific value propositions for each conversation. Execute daily follow-up during the conference to prevent pipeline degradation. Sen’s insight: ”Prep is incredibly important... we evaluate okay, Brett, head of monetization at ABC Company. Who does Brett know that I know? What is the actual proposition we want to discuss?” - Avoid booth competition when capital-constrained: NumberEight deliberately avoids exhibition booths at major conferences, recognizing the futility of competing against Amazon’s ”entire city mockups” and Google’s massive displays. Instead, they focus on authentic relationship building through targeted meetings and dinner sponsorships. The strategic principle: startups should leverage their authenticity advantage rather than attempting to out-spend established players in awareness channels where they’re fundamentally disadvantaged. - Maintain strict messaging separation between investor and customer tracks: Sen emphasizes the critical disconnect between vision-focused investor pitches and problem-focused customer conversations. His customer insight: ”You tell any customer you’re going to revolutionize... they’re like ’man, you make me money, I’ll be your friend.’” The implementation: develop completely separate messaging frameworks where investor decks emphasize market transformation while customer presentations focus exclusively on measurable business impact and revenue generation. // 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