Insight Health is automating the clinical work that surrounds the patient visit — from history capture and intake to referrals and chronic disease follow-ups — so that specialty providers can deliver more care with the capacity they already have. The company completed its first fully autonomous patient interaction for an oncology practice on the West Coast and has since surpassed four million AI-powered encounters. In a recent episode of BUILDERS, we sat down with Jaimal Soni, Co-Founder & CEO of Insight Health, to hear how a founding team of engineers and practicing physicians built the credibility, infrastructure, and go-to-market motion to move fast in one of the hardest industries to sell into.

Topics Discussed:

• Why up to half of a first specialty visit is history capture — and why that insight shaped the entire product roadmap

• How Insight Health chose mid-market healthcare (seven to sixty providers) to close its first paid customer in under four months — while Kaiser-scale enterprises take twelve to eighteen months

• Why they built an AI scribe, offered it for free, and how that decision turned EHR companies from competitors into a distribution channel How the team built Safe AI — their proprietary real-time and near-real-time evaluation framework — when no off-the-shelf evals solution existed for live patient interactions 

• The three-stakeholder map required to win any healthcare deal: clinical champion, administrative champion, and economic buyer 

GTM Lessons For B2B Founders:

• Pick your initial segment based on sales cycle math, not just market size. Insight Health chose mid-market healthcare because those organizations close in three to four months. Kaiser-scale enterprises take twelve to eighteen months and require infrastructure Insight Health simply didn't have at the time. Jaimal's framing: "You never want to go out fishing for a whale in a dinghy." The lesson is tactical — run the procurement cycle math for each segment before you pick your entry point, and match it honestly to what your team can actually support and deploy.

• Post-close is where discovery actually matters most. Jaimal's biggest carry-out from seven years at Segment was that discovery is not a pre-sales activity. Economic buyers change. Deployment scope shifts. Champions lose their internal standing. The teams that treated discovery as a closed chapter after signing were the ones caught flat-footed when accounts churned or contracted. Build a standing cadence for re-qualifying the key stakeholders inside your accounts after the contract is signed.

• Healthcare deals require three distinct stakeholders — and only one of them needs to be a champion. Insight Health mapped this buying committee directly from their physician co-founders' experience on the procurement side: a clinical champion (often the CMO or a lead clinician carrying the torch internally), an administrative champion responsible for day-to-day operations, and an economic buyer who signs off on spend. Critically, the economic buyer does not need to be a champion — they just need to not block the deal. Conflating these roles wastes sales cycles. Enter every enterprise deal knowing which of the three you have and which you still need to develop.

//

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

Schematic is building the infrastructure layer between the application and the billing system — solving the entitlements problem that quietly kills commercial agility at scaling software companies. In a recent episode of BUILDERS, we sat down with Fynn Glover, Co-Founder & CEO of Schematic, to learn how a lived operator problem and 100 discovery conversations led to a conviction that entitlements management is to monetization what Auth0 was to authentication.

Topics Discussed:

• The entitlements problem: why hard-coding feature access to billing plan IDs creates commercial and technical debt

• How 100 discovery conversations surfaced product engineering as the true ICP — and why finance and sales couldn't see it

• The two-sided market thesis: legacy companies forced to re-architect and startups who can avoid the mess

• Why content was Schematic's primary GTM mechanism before the product existed

• How Fynn mines transcripts for language shifts and re-runs WTP validation every six months

GTM Lessons For B2B Founders:

• Use your own experience as the discovery opener: Fynn didn't lead with structured questions. He shared his story — six months to change pricing at a high-growth cybersecurity company — then listened for prospects to name the root cause before he did. When they stopped blaming the billing system and started describing the app-to-billing intersection as the problem, he had signal. Finance and sales couldn't see it. Product and engineering could, because they were building the glue.

• Separate "is this a problem" from "would you buy a solution": Once Fynn had consistency on the problem, he ran a distinct step — asking whether the infrastructure felt core to the company's product or non-core, careful not to bias the answer. The more he heard "none of this is related to our actual product," the more conviction he built that companies would buy it off the shelf. Two questions, sequenced: the first surfaces pain, the second surfaces build/buy intent.

• Publish before you have a product when creating a category: Fynn knew Schematic would take years to build something enterprises would trust. Content became the mechanism to attract people who believed in the problem before a product existed. His framing: content doesn't need direct ROI — it needs to bring the company energy, reputation, and market utility.

• Re-run willingness-to-pay every six months: Fynn ran 10-15 WTP conversations before founding Schematic and has continued every six months with new prospects and existing customers. Pricing assumptions drift — recalibration keeps positioning grounded in what buyers actually value now.

• Treat call transcripts as a language intelligence feed: One of the biggest workflow changes for Fynn has been mining call transcripts to track how buyers describe their bottlenecks over time. As the market shifts from seat-based to hybrid pricing, buyer language shifts too. Transcripts let him track that at scale rather than relying on intuition.

//

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

KP Reddy hasz chased the same mission for 30 years: eliminate the change orders and unanswered questions that derail construction projects. Web-based construction management in 1994. A Building Information Modeling textbook in the early 2000s. Now with Zero RFI — backed by General Catalyst — he's running an AI roll-up of construction services businesses to answer every question before a shovel hits the dirt. In this episode: acquisition criteria, investor filtering, why owning the asset beats selling software, and the S-curve trap that kills most construction tech companies.

Topics Discussed:

• Why founder-to-founder credibility wins acquisition conversations

• The house-of-brands model and the customer logic behind it

• How KP screens investors: roll-up experience, fund structure, and portfolio construction activity

• The two-part SaaS survival test and when owning the asset is the better GTM move

• The $5 billion, three-year deployment roadmap

• The $5M ARR head fake and the S-curve plateau in construction tech

GTM Lessons For B2B Founders:

• Founder-to-founder credibility closes acquisitions: The target founder has one question — how does my life get better after this? PE experience doesn't answer it. "You actually have to have been in the shoes of the founder that you're buying." Add a world-class tech stack, because these companies have already tried AI. Both matter.

• You're acquiring customers, not a company: Zero RFI keeps acquired company names intact. Customers chose that boutique deliberately. "None of us want to really be reminded that our Porsche is actually owned by Volkswagen." A rebrand signals you value your brand over the relationships you just paid for.

• Three gates for investor fit: Gate one — AI roll-up experience. If no, points off. Gate two — fund structure. Last check out of a 10-year fund means DPI math kills the relationship. Gate three — portfolio construction activity. GC's defense and industrial portfolio turned out to be doing massive construction. Re-industrialization made it a real qualifier.

• The two-part SaaS survival test: Two conditions must both be true — enough value captured to survive, and users who can't live without it. KP's diagnostic: "Who loves Salesforce? Management loves Salesforce. The users hate Salesforce." One of two. Where both are uncertain, owning the asset is the more defensible GTM path.

• Build peer advocates before you need them: The first three Zero RFI acquisitions were deliberately under 50 people — to build a cohort that shows up at the next acquisition as living proof. "It's not about me saying it. It's about other people saying it." In a show-me industry, that's the only motion that works.

• The $5M ARR head fake: Construction is so problem-dense that $5M ARR comes easily — and that's the trap. "It doesn't mean you're going to get to 10, 20, 30, 40, 50." Founders who think too narrowly hit the top of the S-curve with no plan to extend the vertical. In construction tech, that plateau arrives faster than any other industry.

// 

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

Endera is one of the fastest-growing specialty bus manufacturers in the United States, supplying electric, CNG, and gas-powered buses to school districts, transit agencies, and airports. In a recent episode of BUILDERS, we sat down with John Walsh, Founder & CEO, to hear how he closed a seven-figure deposit on a bus that didn't exist and what it actually takes to sell to government.

Topics Discussed: 

• How John validated Endera's first product with a seven-figure deposit before building a single bus

• The mechanics of government procurement — state contracts, five-year vendor pools, and how POs get printed 

• Why government is inflation-proof, tariff-proof, Buy America-protected — and the one thing it is not

• How Endera used its legacy gas business to de-risk and fund its EV transition 

• Lessons on lobbyists, C-suite hiring, and matching investor profile to stage

GTM Lessons For B2B Founders:

• Deposit before product: John went to a pilot customer and said, "I'm not going to tell you what you need — you tell me." He flew that operator to Canada, China, and the Midwest, wrote down what they wanted, and closed a seven-figure deposit before Endera had a single bus. A paying customer defines the blueprint so precisely that every problem becomes a good problem. His prior startup failed for the opposite reason — he built something with no validation that anyone would buy it.

• Government procurement runs on state contracts, not RFPs: Win a spot on a five-year state contract and every school district or transit agency in that state can buy off it directly — no RFP required. That's how POs start printing at scale. For EV, buyers start small: a few units to prove the vehicle can serve their actual routes. Range anxiety is real. Let them touch it, prove the route, then they scale.

• Government is not shutdown proof: The inflation-proof, tariff-proof, Buy America-protected stability of government revenue has one blind spot. John went through two historic shutdowns. Demand defers, it doesn't disappear, and the snapback comes — but the working capital gap is brutal. Stress-test your model against this before you need to.

• Lobby with a scoped objective or don't bother: John's rule — deploy lobbyists only when a specific deal is in motion and you need to open a defined door. Without scope they bill like lawyers and wander. The highest-value play is upstream: shaping bid requirements before an RFP goes live. Government agencies copy old contracts verbatim. Getting the right language in early is far cheaper than fighting requirements after the fact.

• Match investor profile to stage, not just sector: John lost early time chasing a project equity fund with surface-level relevance. His progression: Family Office at formation, Venture as the business scaled, Growth Equity once proven. Climate tech funds passed because the legacy gas business didn't fit the thesis — until EV-only competitors started going under.

• An empty seat beats the wrong C-suite hire: A bad executive is a net negative. John was unambiguous — the wrong person does more damage than leaving the role open, and removal compounds the cost. Raise the bar before you fill the role.

// 

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

Ethic builds customized, tax-smart, and values-aligned investing infrastructure for financial advisors and institutions — a platform that lets advisors personalize across their entire book of business, simultaneously accounting for financial, values-based, and tax considerations at scale. Today, Ethic manages over $9 billion in assets across approximately 300 investment advisory businesses, from boutique wealth managers to large endowments and foundations.

In a recent episode of BUILDERS, we sat down with Doug Scott, CEO and Co-Founder of Ethic, to learn how the company spent eleven years navigating one of the most trust-dependent, risk-averse markets in B2B fintech — and why the GTM decisions that looked wrong on paper turned out to be the right ones.

Topics Discussed:

• Why Ethic chose the advisor and institutional channel over consumer from day one — and what that tradeoff actually cost them early

• How Ethic structured its growth in phases: from zero AUM to the $100M psychological threshold, through Series A product-market fit, to team-of-teams scale at $9B

• Why the translation problem between founder-led sales and a first growth hire is more dangerous than most founders anticipate

• How distribution partnerships with large financial custodians became Ethic's primary growth lever — and the specific execution failure that nearly made the model worthless

• Why VC-recommended GTM playbooks can actively harm companies that operate in trust-based, relationship-driven markets

• How Ethic converted unused office space into a full in-house production studio and launched a podcast that crossed 200,000 YouTube views within weeks of its first episode

GTM Lessons For B2B Founders:

• Choosing the hard channel is sometimes the only viable channel. Most fintech founders default to consumer because the path from zero to one is faster. Doug went the opposite direction — targeting sophisticated financial professionals managing portfolios for families, endowments, and foundations. The tradeoff was brutal: large pools of capital sitting inside an extraordinarily trust-based, risk-averse environment where moving from zero AUM to any AUM is genuinely hard. The first major milestone wasn't revenue — it was crossing $100M in assets under management as a psychological proof point. Founders in regulated, trust-dependent markets should stop benchmarking their early traction against software companies. The milestones are different, the timeline is longer, and the motion has to reflect that reality from the start.

• The founder-to-first-hire translation problem will quietly kill your GTM. When you are simultaneously the builder and the distributor, the feedback loop between what clients say and what gets built is frictionless — because it lives inside one person's head. The moment you hand off go-to-market to even one other person, that loop breaks. Doug's first growth hire is still with the company today, but the lesson Doug draws isn't about hiring well — it's about the structural work required after the hire. You need explicit mechanisms to keep client signal flowing back into the product org once the founder steps out of direct selling. Without that, you don't just lose feedback — you lose the ability to course-correct before the misalignment compounds.

//

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

Stratyfy helps community banks and credit unions make better risk decisions — across credit decisioning, fraud detection, and bias detection — in one of the most regulated buying environments in B2B. In this episode of BUILDERS, we sat down with Laura Kornhauser, Co-founder & CEO of Stratyfy, on how she navigated three distinct chapters of the AI era, why gen AI broke her outbound motion, and the bets she's making on the next decade.

Topics Discussed:

• How Stratyfy evolved through three AI chapters: explainability, bias mitigation, and the gen AI era

• Why ChatGPT created confusion — not tailwinds — for ML companies in regulated industries

• How AI-generated spam killed cold outreach and what replaced it

• Why the "build vs. buy" trap is especially dangerous for smaller financial institutions

• Stratyfy's bets on transparency, deterministic AI, and the agent-native future

• Why "we need to use AI" is a dangerous mandate — and what the right frame is

• How data preparation became a dedicated product and a pipeline on-ramp

GTM Lessons For B2B Founders:

• Reposition within a category redefinition — don't run from it: When gen AI went mainstream, all AI became synonymous with gen AI in buyers' minds. Rather than distance from the label, Stratyfy mapped their ML-based, explainable approach onto the transparency and bias concerns gen AI had surfaced. The market's fear became their proof point. When a macro trend rebrands your category against you, map your differentiation onto buyer anxieties — don't explain why you're different from the trend.

• Cold outreach is dead in trust-gated markets — inbound trust compounds instead: AI spam has saturated inboxes so thoroughly that even high-quality cold outreach no longer lands. What replaced it: warm intros, in-person presence, and relationships built over years. The payoff: Stratyfy now has bank CEOs and boards coming to them — not to evaluate a product, but to rethink their third-party AI risk management practices entirely.

• Education-first content earns access that product content cannot: Stratyfy published a third-party risk management guide for the AI era — no product tie, no pitch. It helps institutions evaluate any AI vendor, Stratyfy included. In a market flooded with vendor noise, content that helps buyers do their job earns trust faster than anything product-focused.

• Problem-first beats mandate-first: Organizations struggling have "use AI" as the objective. The ones succeeding do three things: find partners who understand their regulatory environment, get their data in shape, and let technology choices follow from the problem. A technology mandate keeps you in a features conversation; reframing around operational problems puts you in a partnership conversation.

• Data preparation is both a revenue line and a pipeline on-ramp: Stratyfy built a dedicated data prep, cleaning, and ingestion product after recognizing that data readiness was blocking customers from unlocking AI value — from Stratyfy or anyone else. For founders whose product requires data maturity, building that upstream capability isn't a distraction. It's a faster path to production and a natural expansion motion.

//

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

Lightyear is the AI-native platform automating how enterprises manage their telecom — internet connectivity, dark fiber, data center space, phone systems, and everything in between. With over $65 million raised, 400+ enterprise customers including Fortune 50 and Fortune 10 companies, and top channel partner status with four of the top ten US ISPs, Lightyear has become the system of record for enterprise network operations. In this episode, Dennis Thankachan breaks down the GTM journey: from COVID-era pivot and 30 investor rejections to a repeatable enterprise sales machine.

Topics Discussed:

• How a COVID-forced pivot moved Lightyear from SMB connectivity to enterprise telecom

• Using a pre-product consultative motion to land early enterprise logos and validate the TAM

• Why 30 investor rejections came down to pitching to satisfy rather than convey truth

• The discovery framework Dennis built to systematize enterprise sales before hiring reps

• Demand gen channels that scaled (and outsourced shortcuts that burned money)

• Hiring early reps for domain expertise and ambiguity tolerance over polish

• How proprietary, hand-built telecom data positions Lightyear to win with agentic AI

GTM Lessons For B2B Founders:

• Stop adjusting your pitch based on investor feedback: Dennis's 30 rejections came from a specific failure mode — answering questions to satisfy rather than be honest, and adjusting the pitch based on investor feedback rather than what was best for the business. "The less and less I cared what investors thought, the more success I had with investors." Conviction is detectable. The moment founders perform it rather than have it, investors feel it.

• Use pre-product consulting to write your product spec: Lightyear's first enterprise wins were fully manual — mapping workflows, rationalizing telecom rates, identifying cost savings enterprises couldn't see because there's no public gauge of market pricing. That work, Dennis said, let them "map out all of the different workflows on what we needed to build from a software product." Early customer work shouldn't just validate demand — it should define exactly what to build.

• Build a discovery framework before you hire reps: Before systematizing, Dennis had to answer specific questions through manual selling: What do we discover in the first meeting? How do we demo and convey ROI? Who are the stakeholders? What are the common objections? How do we frame the initial sale for expansion? Only then could they hire a rep and build comp around it. The discovery framework is the prerequisite — not the rep.

• Own long-tail keywords your exact buyer searches — then rebuild for LLMs: Lightyear targets terms like "dedicated internet access pricing" — a few hundred clicks per month, near-perfect buyer intent — ranking organically and running paid against the same terms. Dennis noted they're now rebuilding this approach for LLMs. The logic is identical: own the specific language your buyer searches, and apply it to how AI surfaces answers in your category.

//

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

Exciting Instruments bootstrapped a physical instrument company, closed its first two sales before a working product existed, and delivered its first unit to a customer's bench 13 months after founding. Spun out of the University of Sheffield in September 2021, the company compresses what once required a laser-safe room into a benchtop any scientist can operate. In this episode of BUILDERS, we sat down with Tim Craggs, CEO and Founder of Exciting Instruments, on how he built a commercial engine from scratch, mapped three distinct customer archetypes before he had a sales team, and is now executing a deliberate pivot from academia into biotech and pharma.

Topics Discussed:

• Bootstrapping a hard tech company through personal debt and pre-sales

• Three academic ICPs — and why each required a different purchase rationale

• Why 3,500 hyper-targeted followers outperformed mass reach

• Grant money vs. company money: how budget source changes the sales motion

• How the biopharma pivot forced a product rethink: research tool to targeted assays

• Why a scientific writer is a core GTM hire in technical markets

• Rob's warning: "There are enough ideas to kill a company here"

GTM Lessons For B2B Founders:

• How Exciting Instruments closed sales on physics, not product. Before the finished instrument existed, Tim used a prototype — still on an optics table in a dark room — to prove the underlying science produced usable data. The early customers weren't betting on the engineering; they were betting on the physics.

• How Exciting Instruments mapped three buying triggers before it had a sales team. Three distinct academic ICPs: scientists who previously had to build their own single-molecule rigs; scientists who had to collaborate with single-molecule labs and can now own the capability; and scientists who didn't know this class of experiment was possible. Three buyers, three entirely different conversations.

• How Exciting Instruments built a referral engine through customers, not marketing. Edwin Antony at St. Louis has brought in three to four additional customers through conference talks and word of mouth. That initial sale came partly from a tweet to Tim's 3,500-person following — hyper-targeted, not mass. When Sci Twitter fragmented, Tim tracked where it migrated and shifted his evangelism to LinkedIn.

• How Exciting Instruments changed its GTM motion — not just its pitch — moving into pharma. Academic buyers spend grant money; they need to believe the capability is real. Pharma buyers spend company money and justify the purchase against an existing suite of biophysical tools. For pharma, Exciting Instruments built specific assays for specific use cases: PROTAC ternary complexes, antibody aggregation, membrane protein analysis — each with its own targeted campaign.

• How Exciting Instruments made a scientific writer a core commercial hire. The role: translate expert-level science into language accessible to all biologists. In markets where buyer fluency varies radically across segments, translation is a conversion function.

• How Exciting Instruments avoided being killed by its own ideas. Rob's line: "There are enough ideas to kill a company here." The response: identify the key inflection points, align the team, and drive at those without distraction.

//

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

Robert Kraal has spent nearly three decades at the core of global payments infrastructure — co-founding Bibit (acquired by RBS/Worldpay in 2004), serving as COO and founding Adyen's acquiring proposition from the ground up, and building the technology that let Adyen go direct to Visa and Mastercard by cutting out the acquiring banks entirely. When he evaluated the card network processing vendors back in 2009, he dismissed every one of them as legacy. Fifteen years later, those same vendors still dominate the market. That unchanged landscape became Silverflow. Seven years in, Silverflow processes over 1 billion transactions, is growing 10–15% month over month, and is making a focused push into the US — the world's largest credit card market.

Topics Discussed:

• How a 2009 regulatory shift in Europe created the conditions that directly led to Silverflow's founding

• The three-option framework facing any new acquirer: buy legacy, build yourself, or buy modern — and why only one of those options didn't exist until Silverflow

• Silverflow's three customer segments — payment service providers, banks/acquirers, and large retailers — and why each demands an entirely different sales motion

• How Silverflow uses Visa and Mastercard's public license application data as a real-time prospecting signal

• Why selling to banks requires waiting for internal consensus to form before you can enter the conversation

• The "me too" failure pattern Robert sees consistently when investing in payments companies

GTM Lessons For B2B Founders:

• Size the beachhead with math, not instinct. Before building Silverflow, Robert calculated that roughly 200 new acquirers come to market annually — companies reaching the maturity point where they want to go direct to Visa and Mastercard rather than route through acquiring banks. Targeting 10% of that cohort was enough to build a viable business case. That's the kind of TAM-within-the-TAM thinking that turns a broad market thesis into a fundable, focused go-to-market.

• Turn competitor stagnation into your positioning. Silverflow's core bet wasn't that the market was underserved — it was that the vendors serving it had stopped evolving. The same players Robert evaluated in 2009 are still there today, their core technology unchanged, their websites refreshed. Robert's framework for finding investable opportunities applies broadly: look for markets where the dominant players win on switching costs and inertia rather than product quality, then build what the market would choose if it had a modern alternative.

• Map your sales motion to each segment's decision-making architecture. Silverflow runs the same product across three customer types, but the GTM is structurally different for each. PSPs are smaller, move fast, and tolerate risk — they sign and go live relatively quickly. Banks involve legal, compliance, security audits, and multi-layer internal sign-off, making the sales cycle considerably longer. The flip side: once a bank migrates, they're not revisiting that decision for years, making it a fundamentally different unit economics conversation than PSP deals. Robert treats these as distinct motions — not just different speeds, but different trigger conditions and different value narratives.

//

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

Alex Wilson has done this before. He co-founded The Giving Block in 2018, built it into the defining platform for crypto philanthropy, and sold it to Shift4. Four years inside one of the world's largest payment processors — leading crypto and stablecoin product — revealed that nearly all crypto infrastructure is built for trading and on/off ramping, not money movement. Cyclops fills that gap, exclusively for payments companies. In this episode: selling into a 100-200 company market, how Stripe's acquisitions created urgency he pitches against, and what he got wrong about team-building the first time.

Topics Discussed:

• The product gap Alex found building stablecoin solutions at Shift4

• Why Cyclops has a hard ICP boundary and turns away companies outside it

• Navigating multi-stakeholder buying at large payments companies

• GTM playbook for a market of ~100-200 total prospects

• How Stripe's acquisitions of Bridge and Privy created urgency Cyclops pitches against

• Regulatory clarity (Genius Act, MiCA) shifting sales conversations

• Hiring by function — and why AI keeps the marketing headcount small

GTM Lessons For B2B Founders:

•  The ICP boundary is the product strategy. Cyclops works only with processors, PSPs, acquirers, gateways, and orchestrators — and turns away everyone else. "The product wouldn't work very well for them." Competitors list payments alongside nine other verticals and ship the same product to all. A hard ICP isn't a constraint — it's how you build something specific enough to become the obvious choice.

• In a 100-200 company market, pipeline is a relationship graph. "We'd be happy to sign a handful of those customers a year." That math eliminates ad spend — it's direct outreach and flying somewhere for an in-person whiteboarding session. If your addressable universe is this concentrated, relationship infrastructure is your GTM.

• Map the buying coalition before your first call. At large payments companies, "it tends to be a mix of the strategy and sometimes even the corp dev team... but then you've got to get aligned with the product team as well, because they're actually the ones that are going to help you get it on the roadmap." Know the blocker before you walk in.

• Turn the category leader's moves into urgency. Stripe's acquisitions of Bridge and Privy put every major incumbent on notice. Alex pitches into that anxiety: get stablecoin-capable without becoming a crypto company, and without a billion-dollar acquisition. Find who's scaring your ICP and position as the faster, lower-risk path.

• Hire for network in sales, knowledge in engineering, and let AI compress marketing. Payments-networked people into sales and BD. Crypto/fintech backgrounds into engineering. Marketing: "We expect to only have a couple people in the marketing team for a while."

• Design org structure for three to six months out. At The Giving Block, when business boomed, the instinct was to "throw bodies at things... rather than stepping back and thinking, is the team actually set up in the right way to scale?" At Cyclops, every hire gets pressure-tested against what the team needs in three to six months.

//

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