BUILDERS

How BlueRock identified three distinct buyer personas by asking "How would you describe what we do to your peers?" | Bob Tinker ($25M Raised)

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.
Engineer for the "high urgency, low friction" intersection: Bob's filtering criteria for BlueRock's roadmap requires both dimensions simultaneously. When a prospect revealed they were building their own MCP security tools - a signal of acute, unmet pain - they also asked BlueRock to add prompt security features. Bob's framework forced a "no" despite clear demand because it would violate low friction. The discipline: if a feature request fails either test (not urgent enough OR too much friction), it doesn't make the cut, even when prospects explicitly ask for it.
Accept ICP ambiguity as a feature, not bug, of 1.0 markets: In 2.0/3.0 categories, you can target "VP of Detection & Response" with precision. In 1.0 markets like agentic security, Bob finds buyers across three distinct orgs: agentic development teams building secure-by-default systems, product security teams inside engineering (not under the CISO), and traditional security organizations. His thesis: this lack of crisp ICP definition is actually a reliable signal you're in a genuinely new market. The response: invest in community engagement across all three buyer types rather than forcing premature segmentation.
Shift content strategy from SEO to AEO immediately: Bob identifies the clock speed of marketing change as "breathtaking" - what worked 18 months ago is obsolete. The specific shift: ranking above the fold in Google search is now irrelevant. What matters is appearing in the answer box that ChatGPT or Google Gemini surfaces above traditional results. This isn't incremental SEO optimization - it requires fundamentally restructuring content to feed LLM context windows and answer engines rather than keyword-optimizing for traditional search crawlers.
Treat go-to-market fit as a distinct inflection point: Bob observed a consistent pattern across MobileIron, Box (Aaron Levie), Citrix (Mark Templeton), Palo Alto Networks (Mark McLaughlin), and SendGrid (Sameer Dholakia) - all hit PMF, hired salespeople aggressively, burned cash, and stalled growth while boards grew frustrated. The missing concept: PMF proves you can create value; GTM fit proves you can capture it repeatedly. It's the "repeatable growth recipe to find and win customers over and over again." The tactical implication: after PMF, resist pressure to scale headcount and instead obsess over making your first 3-5 sales cycles systematically repeatable before hiring your second AE.
Build community as primary discovery in fragmented buyer markets: Bob's most different GTM motion versus five years ago: "We're just out talking to prospects and customers - individual reach outs, hitting people up on LinkedIn, posting in discussion boards, engaging with the community." This isn't supplemental to demand gen; it's replaced traditional top-of-funnel. When prospects exist across multiple personas without clear titles, community presence in Reddit, Stack Overflow, and LinkedIn becomes the only scalable discovery mechanism. The benchmark: successful new tech companies have built communities of early users before they've built repeatable sales motions.
Practice systematic unlearning as second-time founder discipline: Bob's most personal insight: "What really got in my way wasn't what I needed to learn. It was what I needed to unlearn." The specific application: he's questioning his entire MobileIron marketing playbook because "blindly applying that eight-year-old playbook to marketing or sales will end in tears." His framework: periodic gut checks asking "What assumptions am I making? How should I think about this differently?" rather than letting inertia drive execution. The meta-lesson: success creates muscle memory that becomes liability without deliberate examination. Second-time founders should actively audit which reflexes to preserve versus discard.
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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
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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. 
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How tiun validated product-market fit with 6-12 months of pilot data before scaling | Sandro Zweig

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.
Strategic revenue trade-offs accelerate ecosystem development: tiun deliberately adjusted pricing to "pay out more to our businesses to grow a bit faster"—prioritizing transaction volume and ecosystem density over near-term take rate. This economics decision reflected that their value proposition strengthens with ecosystem scale: users need to encounter tiun across multiple properties for the solution to deliver its full promise. When building network effects or marketplace dynamics, model whether lower monetization drives the velocity needed to reach critical mass faster than optimizing for immediate margins.
Integration speed directly determines category creation velocity: Sandro identified that "if the sales cycle is too long and integration is too complicated, people won't do it. Especially since it's a product that doesn't exist and there is no market for it yet." They focused on reducing implementation to 2-3 weeks, recognizing that asking companies to replace existing auth and payment infrastructure requires minimal switching costs. For emerging categories where customers must displace incumbent solutions, integration complexity often determines adoption more than feature superiority.
Build investor relationships 12+ months before raises: Sandro emphasizes starting fundraising conversations well before needing capital: "If you decide, oh, I need to fundraise right now, then you will automatically get into a cash crunch. Because by the time you have established all the relationships, it just takes such a long time that you run out of money where it really hurts your negotiation power." Treat investor relationship development as continuous rather than transactional—similar to enterprise pipeline development where deals close from relationships built quarters earlier.
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www.GlobalTalent.co
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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. 
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How Toothio built credibility as non-industry founders through strategic SME hires | Ian Prendergast

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: Ian's experience across three labor marketplaces reinforced one principle: excess supply is recoverable, excess demand is catastrophic. With too much demand and insufficient supply, you're "spending a bunch of money to acquire these demand users, but you're not able to fulfill the supply side. So now they're churning out at a high clip, they're going somewhere else. And now it drives up your CAC across the marketplace and reduces your lifetime value." In two-sided marketplaces, founders must resist investor pressure to show demand-side revenue before supply reliability is proven—the temporary revenue bump destroys long-term unit economics.
ICP clarity requires live market data, not pre-launch assumptions: Toothio launched targeting private practices (shorter sales cycles, lower barriers, faster learning) before discovering DSOs were the actual ICP through usage cohorts showing materially higher volume and retention. Ian was explicit: "Once we got into it, we realized...the true ICP is going to be our group practices." The tactical framework: establish presence across plausible segments, instrument everything, collect 1-2 quarters of behavioral data, then redirect resources to wherever retention and expansion metrics are strongest. This data-driven ICP discovery prevents premature optimization around the wrong customer profile.
Hire senior enterprise operators when you have validation plus clear TAM: Toothio broke conventional early-stage wisdom by hiring a Chief Commercial Officer and SVP Sales—roles typically considered "top-heavy"—because Ian had validated product-market fit and identified a concentrated enterprise opportunity (hundreds of DSOs). The result: "Next thing you know, we're in front of five or six of the top eight or ten DSOs in the country." The decision framework: if you have (1) proven unit economics, (2) clear product-market fit signals, and (3) an enterprise TAM with established relationship networks, senior hires with category Rolodexs can compress multi-year enterprise sales cycles into quarters. Without all three conditions, follow conventional wisdom and stay lean.
Outsider economic analysis creates differentiated value propositions: Ian's non-dental background enabled him to "look at the dental office P&L and the core drivers of production with a completely neutral lens and realize that there was a lot of waste." He quantified what insiders hadn't: recruiting costs up 100%+ in five years, dental turnover among the highest of any U.S. industry, and the compounding cost of cancelled patient days (immediate production loss + 20% patient churn × $10-15K lifetime values). This economic framing repositioned Toothio from "staffing vendor" to strategic finance partner. The pattern: outsiders should weaponize their fresh perspective by conducting rigorous economic impact analysis that category incumbents haven't done, then speak to buyers in CFO language rather than operational features.
Industry association involvement is enterprise distribution, not brand marketing: Ian credited local and national dental association sponsorships as "the catalyst to get us on the radar of some of the bigger orgs early" because associations created credibility signals plus network effects at scale. In relationship-driven B2B categories with strong professional associations (dental, legal, accounting, healthcare), sponsorship generates repeated exposure to concentrated decision-maker populations and warm introduction paths that cold outbound can't replicate. Founders should map the association landscape in year one, treat it as a primary distribution channel with measurable pipeline contribution, and staff it with team members who can build genuine relationships—not just write checks.
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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
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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.
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How Implentio turned 20 years of operations expertise into a partnership-driven GTM engine | Jason Bang

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.
Pre-qualify partnership ROI using your own customer economics: Implentio learned that partner enthusiasm doesn't correlate with lead quality. Jason's example: "That $50 million brand might have $1,000 AOV. And so the number of transactions and shipments they're doing, there's just not enough there for there to be a good ROI on our solution." Implentio now evaluates partner customer lists against specific transaction volume thresholds before investing in relationships. Document minimum viable customer criteria and require partners to verify their portfolio meets those thresholds to prevent pipeline pollution.
Subject matter expertise scales through teaching, not content production: Jason built Implentio's founder brand despite having no Instagram, Facebook, or TikTok, using one principle: "Knowledge is only good if you transfer it and you pass it on." He prioritizes teaching operations concepts over polished content, measuring success by whether someone learns something valuable regardless of conversion. His insight: "If I can teach somebody something, that's a win for me. Even if they don't sign up for my platform." Sophisticated buyers assess expertise through insight depth, not posting frequency.
Wedge entry with acute universal pain, then expand horizontally: Jason's long-term vision is "COO in a box"—comprehensive operational intelligence spanning supply chain, fulfillment, and customer service. But Implentio launched with 3PL invoice reconciliation because every scaled e-commerce brand outsources fulfillment and struggles with billing validation. The wedge criteria: universal problem (every target customer has it), acute pain (directly impacts margin), and immediate ROI (quantifiable savings exceed platform cost). Once embedded in the finance workflow, Implentio can expand into adjacent operational data problems without re-selling the value of centralized ops intelligence.
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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
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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.
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How Flamingo generated 1,000 waitlist signups before launching a product using a free community tool | Michael Assraf

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
GTM Lessons For B2B Founders:
Build lead-gen infrastructure before you have a product to sell: Four months before launching Open Frame, Michael shipped OpenMSP—a free tool that analyzes MSP tech stacks and suggests open source replacements. It wasn't a waitlist landing page; it delivered standalone value while capturing intent data. This generated 1,000 qualified signups and 200 Slack community members while simultaneously validating paid acquisition channels. By launch, he knew Facebook cost $6-8 per lead while outbound failed completely. Most founders build product first, then scramble for distribution. Michael inverted the sequence.
Fire fast on sales hires in early stage, or don't hire them at all: Michael fired three VP Sales at Vicarious before learning the lesson: "The moment to bring salespeople is not when you are able to sell your product, is when someone else is able to sell your product." The critical test isn't whether the founder can close deals—founders sell vision and relationship. The test is whether a marketing person, SDR, or non-sales hire can generate revenue. Only then do salespeople accelerate an already-working motion. Hiring VP Sales at $50K ARR because the board wants "someone to own revenue" burns 12+ months and $200K+ learning this.
Spend 6-12 months researching before building in unfamiliar markets: Michael conducted 15+ MSP interviews, mapped all 19 tool categories they use with pricing, evaluated open source alternatives by analyzing GitHub commit frequency and pull requests, identified which projects had VC backing for long-term viability, and tested multiple marketing channels before alpha deployment. This allowed him to launch with product-market fit indicators already validated and 70% of his $2.2M still in the bank. The alternative—build fast, iterate with customers—works when you deeply understand the market. When you don't, research is cheaper than pivots.
Target categories where lack of innovation creates adoption momentum: MSPs represent 30-40K companies in the US alone, part of a $380B global market growing 12% annually. Yet VCs historically avoided the space assuming low ACV and high churn. The dominant platforms—ConnectWise, Datto, Asea—have existed 20+ years with minimal AI adoption or architectural modernization. Michael specifically chose MSPs because "in cyber security you would never get traction that we're getting right now unless you're spending millions of dollars." In crowded categories, distribution cost kills you. In starved categories, any credible innovation gets attention.
Architect your product so adoption mechanically improves customer unit economics: Open Frame attacks both sides of MSP margin compression simultaneously. The open source tool suite eliminates the 30% of revenue paid to commercial vendors. The dual AI agent system (end-user self-service + technician orchestration) reduces the 25-30% spent on labor. Michael didn't find a problem and then figure out monetization—he reverse-engineered a solution where product adoption directly expands customer margins. When your product makes customers structurally more profitable, adoption isn't a marketing problem.
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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
 
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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.
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Why First Resonance killed their PLG motion and rebuilt for enterprise manufacturing sales | Karan Talati

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
GTM Lessons For B2B Founders:
Kill upmarket plans when your core segment outpaces them: First Resonance planned to move from scale-ups to traditional defense and aviation giants. They didn't execute. Karan found that staying with scaling startups delivered faster growth and higher ROI than "long sales cycles" with customers "averse to modern technology." The lesson isn't about patience with enterprise—it's about recognizing when your initial segment is expanding faster than you can capture it. If your TAM is growing 40%+ annually from customer expansion alone, moving upmarket is a distraction.
Test PLG fast, kill it faster in multi-stakeholder environments: First Resonance ran a PLG experiment and "quickly learned it does not" work in manufacturing. The buying process involves "centralized, coordinated, orchestrated, many decision makers, many influencers." But they kept the instrumentation. They use "product utilization and usage and engagement" data to "package subsequent value" for renewals and expansion. The tactical move: instrument your product like PLG, sell like enterprise, and use analytics to drive net dollar retention during annual renewals.
Treat cloud service provider status as a wedge, not overhead: As a cloud service provider to defense contractors, First Resonance maintains compliance with CMMC, FedRamp, and NIST 800-171. Rather than viewing this as cost center, Karan noted "regulations are getting easier, not harder" and that this is "a benefit to innovators." For B2B founders selling to regulated industries: invest in compliance infrastructure early, monitor regulatory roadmaps (like FedRamp 20x), and position compliance as competitive moat when competitors can't move as quickly.
Pattern match your wedge vertical to adjacent disruption: First Resonance saw their aerospace playbook repeat in nuclear energy "literally in the last three, four years." The pattern: legacy incumbents "too big to fail" but "so large and inertial, so hard to move, that startups are going to have to come in and close that gap." When one vertical shows this pattern, adjacent industries with similar incumbent dynamics are expansion candidates. The key signal: former SpaceX/Tesla talent founding companies in that vertical.
Design brand for the incoming generation, not the incumbent buyer: With the old guard "rapidly retiring" and manufacturing becoming "cool," First Resonance built a brand with "bold colors and straight lines" that "combines cybernetic systems with inspiration from the Matrix." Karan explicitly rejected softer design trends: "throw all that out." For technical products in industries with demographic shifts, design for the 30-year-old engineer who will champion your tool, not the 55-year-old executive who signs the contract.
Deepen rather than proliferate when customers expand physically: First Resonance doesn't worry about logo count because their customers are "scaling in terms of factory square footage and the number of teams." Their expansion motion: "observe product analytics and customer signals and package subsequent value" for upselling during renewals. The tactic works because aerospace and energy have "a tailwind of decades." For infrastructure software with usage tied to physical operations: if customers are adding factories or production lines, you don't need new logos—you need seat expansion and module attach.
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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
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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
 
 

How ZayZoon built 300+ payroll partnerships to reach 15,000 businesses without direct sales | Tate Hackert

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.
High-touch relationship GTM beats automation until you hit scale: Tate's core partnership advice: "Pick up the phone...be gritty as hell. Those first hundred customers that you do, be gritty." He emphasized personal outreach builds "pattern recognition and learnings that you receive from being ultra curious." For partnerships specifically, bring "humility, transparency and the expectation that you're building a ten year plus relationship, not being transactional." Automation scales what works—but relationship GTM discovers what works.
 
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Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io
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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.
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How AODocs generates better cost-per-lead from 2,000-person regional events than 30,000-person conferences | Stéphan Donzé

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:
Transparent post-mortem communication converts crises into trust: When AODocs hit unexpected Google Cloud platform limitations in 2014-15—breaking deployments for customers running mission-critical workflows—they published detailed explanations of root causes outside their control and remediation plans. Stéphan explained: "We've always been extremely transparent...Yes, we screwed up here. Here is the thing we put in place so that it doesn't happen again." This approach consistently strengthened customer relationships during their worst incidents. For founders in business-critical infrastructure: your crisis response protocols matter more than preventing every outage.
Bootstrap via complementary services revenue until product-market fit: AODocs funded development by merging with a Google Cloud consulting firm that deployed early Gmail enterprise implementations. Services profits subsidized product R&D while providing direct customer access. Stéphan described the deal structure: "I have a software company that has no revenue, but I can suck the profit of the service company until I make revenue." The model worked until 2022 when AODocs became independently profitable. For technical founders: identify services businesses with your target customer base as bootstrap partners, not just revenue sources.
Partner technical capability trumps partner pipeline size: AODocs initially partnered with Google Cloud resellers (SATA, Onix) who had enterprise access but couldn't scope or deploy document management implementations. The inflection point came shifting to system integrators with actual DMS practices. Stéphan noted: "These guys don't really understand document management...they could not really help us deploy our product because they don't understand what we're doing." For complex B2B products: vet partners on technical delivery capacity, not just lead generation promises.
Platform products require 12-month marketing onboarding: AODocs learned marketing hires need equivalent ramp time as engineering roles—not two one-pagers and go-to-market. Stéphan's realization: "It takes a year before someone is able to write the right things and to sense the essence of the product." This applies specifically to platforms with multiple use cases, not point solutions. For founders with horizontal platforms: budget full-year onboarding before expecting marketing productivity, or hire people who've sold similar complexity before.
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.
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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
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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.
 
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How Calico educates buyers on agentic AI systems when no budget line exists | Kathleen Chan

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.
Create category clarity by defining what you're not: In a market where "AI could mean things to many different people," Calico differentiated by explicitly stating what their system cannot do. Kathleen prioritized "dispelling the notions of what we are and what we aren't" over overselling capabilities. This matters because sophisticated buyers—especially in industries with low tech adoption—need to understand boundaries before they'll trust promises. The tactic builds credibility in noisy markets where everyone claims AI magic.
Hire evangelists who outlast founder doubt: Calico's most impactful GTM decision was bringing on early team members who could evangelize value through the inevitable "zigzaggy" early stage—when "it's exciting one day and the worst day ever the next." These people interface directly with customers regardless of whether the founder is having doubts or frustrations. Kathleen's insight: in B2B relationship-driven sales, your early GTM hires' conviction directly determines whether customers stick through product evolution. Hire for authentic belief, not just skills.
Deprioritize content in high-noise environments: Calico deliberately delays LinkedIn content until later stages because "folks are a little bit more muted to all the LinkedIn content coming at them." With AI making content easier than ever to create, Kathleen sees audiences questioning whether to take it seriously and whether AI-generated content has less value than human-generated. Her approach: authenticity trumps quantity. For B2B founders, this means investing in formats that can't be easily faked (video, in-person) before scaling written content.
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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
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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

How Freeplay built thought leadership by triangulating insights across hundreds of AI implementations | Ian Cairns

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.
Build authority through cross-portfolio insights: Rather than positioning as AI experts, Ian built trust by triangulating learnings across "hundreds of different companies" and sharing pattern recognition. Their messaging became "don't just take Freeplay's word for it—here's what we've seen work across environments." This approach resonated because no single company had enough AI production experience to claim definitive expertise. Aggregated insights became more valuable than individual case studies.
Time market entry for the infrastructure adoption curve: Ian deliberately positioned Freeplay for companies "3, 6, 12 months after being in production" rather than competing for initial AI experiments. They recognized organizations don't invest in formal evaluation infrastructure until they've proven AI matters to their business. This patient approach let them capture demand at the moment companies realized they needed serious operational discipline around AI systems.
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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
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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