Category Visionaries

Erik Braund, CEO & Founder of Katmai: $30 Million Raised to Build the Future of Virtual Work

Katmai is reinventing remote work through its innovative virtual office platform that creates spontaneous, natural interaction in a digital environment. With over $30 million in funding, Katmai has developed proprietary 3D audio-video technology that allows teams to work together in a virtual space that mimics the benefits of physical offices while maintaining the flexibility of remote work. In this episode of Category Visionaries, we sat down with Erik Braund, CEO and Founder of Katmai, to learn about his journey from audio-video production to building a deep tech startup that's challenging conventional remote work tools like Zoom and Microsoft Teams.
Topics Discussed:
Katmai's origin as an accidental pandemic pivot from Erik's audio-video production business
The acquisition of early prototype technology and building a specialized team of engineers
The technical challenges of creating a browser-based 3D environment with live audio-video
Katmai's approach to product development through careful beta testing and customer feedback
The transition from deep tech R&D to commercial product and go-to-market strategy
The tension between maintaining stealth mode while gathering essential user feedback
Katmai's expansion from enterprise customers to consumer-facing experiences
The philosophical approach to remote work that focuses on spontaneous interaction
 
GTM Lessons For B2B Founders:
Prioritize real-world functionality over pitch decks: Erik emphasized that for complex, visual products like Katmai, traditional pitch materials didn't work. "We didn't even have a deck for series A because they don't work. The deck doesn't work. You've got to just see it or see a video of it." B2B founders with experiential products should prioritize creating functional demos over traditional marketing materials.
Build around natural behavior patterns: Katmai succeeded by mapping digital interactions to natural in-person behaviors. "We map everything one-to-one of what would it be like to sit next to each other at a table and show each other laptops and have a conversation and then look over the shoulder." Founders should design products that feel intuitive by mimicking familiar real-world interactions rather than creating entirely new behavioral patterns.
Balance technological innovation with methodical rollout: As a deep tech investment, Katmai spent years on R&D before broader release. "Had I known how to frame it on day one, I would have pitched it as a deep tech investment... we're going to be heads down for like two more years, just hashing this out, making it work." B2B founders working on fundamental innovations should set appropriate timelines and expectations for both investors and customers.
Transform scheduled meetings into spontaneous conversations: Katmai's core value proposition addresses meeting fatigue. Erik shared customer feedback: "Katmai turns next week's 30 minute meeting into today's 5 minute conversation." B2B founders should identify where their product can eliminate friction in workflows rather than simply digitizing existing processes.
Implement gradual adoption strategies: Recognizing behavior change is difficult, Katmai recommends an "office hours" approach to adoption. "Take your stand up that you were going to do with your remote team and do it in Katmai. Maybe that's once a week, maybe it's every day... then don't leave when the meeting's over." B2B founders should create clear, incremental adoption pathways that don't require customers to immediately abandon existing tools.
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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

Caleb Avery, Founder & CEO of Tilled: $40 Million Raised to Build (and dominate) the PayFac as a Service Category

Tilled has pioneered "PayFac as a Service," creating a new category in the payments space that allows vertical software companies to embed payments within their platforms without becoming registered payment facilitators themselves. With over $40 million in funding, Tilled offers an alternative to industry giants like Stripe, providing better economics while maintaining high-quality developer tools. In this episode of Category Visionaries, I spoke with Caleb Avery, Founder and CEO of Tilled, about his journey from solo founder to category creator, the challenges of competing with established players like Stripe, and how he's built a successful business by identifying and serving an underserved segment of the market.
Topics Discussed:
Tilled's origin story and Caleb's two-year journey as a solo founder before finding product-market fit
The process of creating and defining the "PayFac as a Service" category
How Tilled positions itself against industry giants like Stripe
Effective content marketing and thought leadership strategies on LinkedIn
The power of speaking at industry conferences to build credibility
Leveraging a mixed strategy of inbound marketing, digital advertising, and channel partnerships
Tilled's vision to expand beyond payments into comprehensive embedded fintech solutions
 
GTM Lessons for B2B Founders:
Create your own category when existing ones don't fit: When Caleb realized that existing terms like "PayFac in a box" didn't accurately describe Tilled's offering, he invented "PayFac as a Service." This new category clearly communicated their value proposition and differentiated them from competitors. He explains, "The concept behind PayFac as a Service was really resonating with these vertical software companies that were saying, 'I don't want to go be a registered PayFac, I want all of the benefits as though I'm becoming a registered payment facilitator with 5% of the effort.'"
Educate the market on your category through content: Tilled invested heavily in education through LinkedIn posts, blogs, ebooks, and speaking engagements to establish their category. Caleb notes, "Over a period of three or four months, we started introducing this concept of PayFac as a Service...by the time we actually launched the fundraising process, some of the early investors that I talked to were like, 'Oh, yeah, we've heard of that category.'"
Leverage fellow founders for early validation: Even without a product, Caleb reached out to other founders to validate his ideas. "Other founders are very willing to help founders, especially in the early stages where I had nothing to sell them...I was shocked by the response rates that I was getting." This approach helped validate assumptions about pricing, product features, and contractual terms before launch.
Balance personal and professional content for thought leadership: Caleb's LinkedIn strategy combined educational content about payments with personal stories about entrepreneurship and family life. "I think by allowing people to understand who I was as a person, it made me more approachable for some of the companies that were coming to us and saying, 'Hey, we're not ready to make a switch, but we are curious.'"
Apply to speak at industry conferences: Caleb was surprised by how many speaking opportunities were available simply by applying. "It just shocks me how few founders that I know are willing to go apply for those speakerships, but it's really an incredibly easy thing for them to go do." These speaking engagements provided valuable opportunities to reach ideal customers and establish credibility.
Run targeted "conquest" campaigns against market leaders: Tilled runs specific digital advertising campaigns targeting pain points with competitors, using long-tail keywords like "Why is Stripe customer service so bad?" This strategy drives quality leads from customers already experiencing problems with the dominant player in the market.
Embrace channel partnerships in B2B SaaS: Unlike many competitors, Tilled welcomes referrals from ISOs, agents, and payment consultants. "We're one of the few folks in our space, which is still bizarre to me, that embraces a channel strategy...it's been an incredibly lucrative strategy...it's still 30 plus percent of the deal flow for Tilled."
 
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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

Dr. Xiaodi Hou, CEO of Bot Auto: $45 Million Raised to Bring Profitable Autonomous Trucking to Market

Bot Auto is redefining the autonomous driving industry with a pragmatic, economics-first approach. With over $45 million in funding, the company is positioning itself as a trucking company that leverages autonomous technology, rather than a technology vendor selling autonomous systems. In a recent episode of Category Visionaries, I spoke with Dr. Xiaodi Hou, CEO of Bot Auto, who shared his decade of experience in autonomous vehicles and his vision for creating a profitable business that delivers transportation capacity more efficiently than human drivers.
Topics Discussed:
Bot Auto's evolution from deep learning applications to autonomous trucking
The strategic advantages of highway trucking over urban autonomous driving
Why cost per mile (CPM) provides a better North Star metric than miles per intervention
Bot Auto's business model as a trucking company first, technology company second
The industry-wide challenge of rebuilding credibility after years of overpromising
Projected timeline: 30 trucks by 2026, breakeven with 100 trucks by 2027
Lessons learned from previous ventures in autonomous driving
The future impact of autonomous trucking on transportation infrastructure
 
GTM Lessons For B2B Founders:
Position as a service provider, not a technology vendor: Bot Auto deliberately positions itself as a trucking company that happens to use autonomous technology, rather than an autonomous technology vendor. "Transportation itself is a service," Xiaodi explained. "Consider us as a trucking company. We are a trucking company, but in near future we will remove the human driver and then we can operate more efficiently than a traditional trucking company." B2B founders should consider whether selling a service that incorporates their technology might be more viable than selling the technology itself, particularly when customers lack the capabilities to implement complex technologies.
Design for seamless ecosystem integration: Rather than requiring new infrastructure or capabilities from customers, Bot Auto designed their offering to plug directly into the existing transportation ecosystem. "The ecosystem for transportation, for trucking is already there. And if we can be a kind of a painless, transparent replacement like equivalent to a human driven truck and supply the capacity to the ecosystem, then the ecosystem is already there. We don't even need to rebuild the ecosystem," Xiaodi noted. B2B founders should design their offerings to integrate with existing workflows and systems rather than requiring customers to build new capabilities around their technology.
Choose one definitive metric that drives all decisions: Bot Auto uses cost-per-mile (CPM) as their North Star metric for evaluating all business and technology decisions. "If your cost per mile is too high, no matter how experienced your partner is, or how ambitious you are, or how big your fleet is, if your cost per mile is negative, you will never make money," Xiaodi emphasized. This singular focus creates clarity across the organization. B2B founders should identify a similar "ultimate guideline" that directly ties to profitability and use it to evaluate every investment and initiative.
Focus on industry-wide credibility, not competition: Xiaodi strongly rejected the notion that autonomous trucking is a competitive space. "The autonomous driving industry is facing the biggest problem that is shared by everyone. That is the credibility of the whole industry. We collectively have promised too much and we have delivered too little," he explained. Instead of positioning against other startups, Bot Auto focuses on rebuilding trust in the entire category. B2B founders in emerging categories should consider how collective credibility impacts their success more than individual positioning against similar startups.
Create internal-external alignment: Bot Auto ensures perfect alignment between their internal goals and external messaging. "If your internal goal is to do something and your external presentation promises something very different, that always creates a clash of the company. Like basically you will be ending up with two companies under one stock symbol. That's very bad," Xiaodi warned. This alignment principle shapes how they communicate with investors and the market. B2B founders should ensure their internal metrics and priorities match what they promise externally, avoiding the trap of optimizing for different outcomes internally versus externally.
Use early revenue to discipline innovation: Unlike many deep tech startups with distant revenue horizons, Bot Auto designed their business model to generate revenue relatively quickly. This approach creates what Xiaodi calls a "self-regulation mechanism" that forces practical decisions: "Are you going to increase or decrease the CPM based on your new invention? Sometimes people do develop a flashy technology, but as soon as they realize that they're not going to reduce our cost per mile, then this is bad technology." B2B founders should design business models that generate early revenue to provide market validation and discipline their innovation efforts.
 
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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

Adam Tank, Co-Founder of Transcend: $35 Million Raised to Revolutionize Critical Infrastructure Design

Transcend is fundamentally changing how engineers design our world's essential infrastructure through their generative design platform. With $35 million in funding, including investment from industry giant Autodesk, Transcend is automating and optimizing the planning and conceptual design phases for infrastructure projects that typically cost tens to hundreds of millions of dollars. In this episode of Category Visionaries, we spoke with Adam Tank about how Transcend is creating an entirely new category while helping societies build more sustainable, efficient infrastructure from wastewater treatment plants to power systems.
Topics Discussed:
How Transcend's platform automates preliminary infrastructure design that traditionally requires months of manual work
The shift from a consumption-based pricing model to a flat-rate subscription that accelerated user adoption
Building a brand in a highly technical, conservative engineering market
Leveraging trade partnerships and owned media to educate potential customers
The importance of creating a category around "Generative Design for Critical Infrastructure"
How strategic investment from Autodesk removed concerns about startup viability
The challenge of selling to technical stakeholders who are resistant to change
 
GTM Lessons For B2B Founders:
Validate before building: Adam emphasizes trying to sell your solution before building it. "A lot of entrepreneurs fall into this mindset of 'if you build it, they will come'... Selling it, marketing it, is substantially harder in most cases than building the actual product itself."
Education-first marketing for technical buyers: When selling to engineers, plan for 10x more educational content than you might expect. "If I thought we needed to spend four hours a week doing it, we're spending 40 hours a week doing it across both sales and marketing teams." Create webinars, case studies, and detailed content that helps your technical audience understand and trust your solution.
Invest in owned media channels: Don't rely solely on platforms you don't control. Transcend created a newsletter reaching 16,000 engineers worldwide that isn't directly branded as Transcend but provides immense value and establishes authority. "If you rely on SEO only, or LinkedIn only... anything can change overnight."
Leverage trade partners for amplified reach: Instead of building everything yourself, tap into established networks in your industry. "We'll spend upwards of $5,000 to tap into someone else's network... and we'll get a thousand or more registrants and we've had half or more show up to the webinar, which is almost unheard of."
Challenge assumptions with data: Events are often assumed to be critical for relationship-based B2B sales, but Transcend found that "online events, webinars, our newsletters, our social media even, are far more consistent generator of high quality leads than events are for the spend."
Rethink pricing to encourage adoption: For complex products requiring significant user education, consumption-based pricing can unintentionally discourage exploration. "We made a big change about a year and a half or so into the company to move away from that consumption based pricing into just a flat rate model... We just want them in the tool, we just want them playing around with it."
Balance founder personal brand with company visibility: Adam maintains what he calls a "70-20-10" approach—70% water industry focus, 20% Transcend, and 10% personal. "People like to buy from people. They don't buy from companies. So the extent that a company can have a face that's out front that they can get to know and trust... is super important."
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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

Justin Leigh, CEO of Workflow Labs: $3.5 Million Raised to Build the Future of E-commerce Management

In this episode of Category Visionaries, we spoke with Justin Leigh, CEO of Workflow Labs, an e-commerce management platform that's raised $3.5 million in funding. After running a successful Amazon agency for 14 years, Justin identified a critical opportunity: replacing human-driven processes with automation at scale. Workflow Labs is automating e-commerce management tasks that brands traditionally outsource to agencies or offshore teams, allowing for better economics, faster resolution times, and predictable outcomes in managing product listings across platforms like Amazon.
Topics Discussed:
Transitioning from running a services-based agency to building a software product
The strategy of targeting partners who aggregate brands rather than selling to brands individually
How retail media networks are driving advertising dollars onto retailer platforms
The importance of having clear company objectives that everyone understands
Fundraising approaches for early-stage companies
Making the pivot from automation-focused messaging to comprehensive solution positioning
GTM Lessons For B2B Founders:
Partner with aggregators instead of selling one-by-one: Workflow Labs recognized that selling directly to individual brands would take too long to reach scale. Justin explained, "If we need to close 3,000 brands in two years, you're not going to do that selling them one by one." Instead, they identified partners who already worked with pools of brands—like ad agencies and supply chain providers—allowing them to sign up "tens, twenties, fifties, hundreds at a time."
Align with emerging market trends: Justin identified that retail media networks (Amazon, Walmart, Target) are where advertising dollars are shifting. He positioned Workflow Labs to support this trend: "We said as that shift continues, we support the product. If you're going to advertise a product, you better make sure their title's right, bullets are right, that it's in stock." B2B founders should identify major industry shifts and align their solutions with those trends.
Create market pull through RFP requirements: Workflow Labs uses a "push-pull method" by engaging directly with brands to influence their RFP requirements. Justin noted, "We work very hard to engage with brands directly and say...when you RFP for your advertising services, you better make sure your provider is providing an automated way to keep your products accurate." This creates demand that potential partners must satisfy, making partnership conversations easier.
Pivot based on customer feedback—even when it contradicts your assumptions: Workflow Labs initially thought customers would care about labor cost reduction but discovered their messaging wasn't resonating. Justin admitted, "We thought initially so many wrong things...When you went to the market and said, 'Hey, you have a 50-person team in India and all they're doing is updating titles, we can make 80% of that labor go away,' no one cared." They pivoted to position themselves as a comprehensive solution rather than just automation.
Establish clear, quantifiable objectives: Justin implemented the "rule of three"—focusing on just three key objectives per quarter. He shared a powerful insight about founder transparency: "If you want everybody in your company to row the boat in the same direction...be super clear around what your objectives are." This includes being upfront about exit goals: "Everyone on the team knows what happens when we get to 3,000 [customers], if we can get close to there...that's when liquidity events start to be on the table."
 
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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

Sloane Barbour, CEO & Founder of engin: $4 Million Raised to Transform AI-Powered Recruiting

engin is pioneering AI-powered recruiting technology that addresses the fundamental inefficiency in the hiring process: 80% of time is wasted on interactions with candidates who will never move forward. With over $4 million in funding, engin is positioned at the intersection of recruitment marketing and automation, focusing on quality over quantity in an increasingly noisy job market. In this episode of Category Visionaries, we spoke with Sloane Barbour, who brings 15+ years of recruiting industry expertise to his role as CEO and founder. He shared insights on how engin is using AI agents to revolutionize the recruiting process for companies, staffing firms, and job seekers alike.
Topics Discussed:
The fundamental inefficiency in recruiting where 80% of time is spent on candidates who never progress
How traditional recruiting technology failed to address unstructured data like resumes and job descriptions
The impact of LLMs on recruiting technology's ability to contextualize unstructured data at scale
engin's strategic positioning shift from ATS to recruitment marketing and automation
The future of work and AI's role in transforming the labor market
 
GTM Lessons For B2B Founders:
Position where the pain and budget intersect: Sloane repositioned engin "up the funnel" from the commoditized ATS space to recruitment marketing and automation, where companies were spending 3x more and experiencing greater pain points. He explained: "Their problem was they were not talking to good people, they were not talking to relevant people, they were not talking to people quick enough." By addressing the quality issue rather than simply building "a better mousetrap in the ATS category," engin created 3x more value.
Founder-led marketing generates qualified leads: After experiencing diminishing returns from traditional outbound email campaigns, Sloane shifted focus to founder-led content and thought leadership. "Every time I post something that takes me 10 minutes to write up, you know, but maybe almost 20 years to be able to write that thought because of my experience in the space... it very clearly resonates with people." This approach generates higher quality meetings than traditional SDR-driven outreach.
Create transparent sales processes with clear metrics: From his experience managing 60+ salespeople, Sloane emphasizes establishing transparency and accountability from day one: "The number one most important thing is transparency of expectations... You have to have visibility into their performance on a daily basis." This includes tracking calls made, emails sent, and meetings booked. Without these fundamentals, scaling a sales organization becomes impossible.
Partner networks accelerate adoption during market transitions: A key component of engin's marketing strategy is its "robust partner network" with integrations and APIs that enable co-selling. Sloane noted this has been "super helpful for just kind of navigating this AI transition in recruiting and staffing together," allowing them to leverage existing relationships and platforms.
Strategic fundraising requires thesis alignment: Sloane learned to quickly identify misalignment with potential investors rather than pursuing exceptions: "If you're talking to people more than a call where thesis is off by more than 20%, meaning you're a seed, they're series A... I almost would rather just end the call, 15 minutes, keep them in the phone book for 18 months down the line." This approach prevents wasted cycles with investors unlikely to participate.
 
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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

Daniel Saks, CEO & Co-Founder of Landbase: $12.5 Million Raised to Power the Future of GTM Automation

Landbase is pioneering a new approach to go-to-market automation, using agentic AI to help businesses generate leads that convert. With $12.5 million in seed funding, Landbase is automating the mundane aspects of sales and marketing while leveraging machine intelligence to recommend high-converting campaign strategies. 
In this episode of Category Visionaries, I spoke with Daniel Saks, CEO and Co-Founder of Landbase, about his journey from building the unicorn AppDirect to his latest venture. Daniel shared his vision for creating software that works for you, not the other way around, and how AI-powered tools can help reclaim your day by turning months-long campaign processes into minutes.
Topics Discussed:
Landbase's mission to solve the challenge of generating leads that convert
Using agentic AI to create go-to-market campaigns with high conversion potential
The transition from months to minutes for launching marketing campaigns
Daniel's journey building AppDirect into a unicorn and his decision to start Landbase
The shifting landscape of B2B technology from on-prem to SaaS to AI
Finding motivation beyond material success and focusing on mission-driven work
Landbase's three core OKRs: faster, cheaper, better
How AI can harness data to enhance human performance, not replace humans
Building "GTM1 Omni," Landbase's domain-specific model for go-to-market insights
The concept of "digital trust" and its importance in modern marketing efforts
 
GTM Lessons For B2B Founders:
AI should augment humans, not replace them: Daniel emphasizes that AI's role is to "automate the mundane so humans can do more human things." The most effective AI implementation preserves human agency while enhancing performance through machine intelligence.
Focus on micro-ICPs for higher conversion: Landbase's data shows that targeting micro-ICPs (Ideal Customer Profiles) or niche audiences with specific problems can yield dramatically higher engagement rates—sometimes up to 90% email open rates compared to 1% for broader approaches.
Opportunity in underdigitized industries: Traditional businesses like tool and die manufacturing, landscaping, or mining represent untapped markets for digital solutions. Being the first to create content for these niches can give you a significant advantage.
Digital trust is the new currency: Building trust through your digital presence is critical. This includes having relevant case studies (video performs better than text), third-party ratings and reviews, credible authorities discussing your brand, and strong domain authority through proper backlinks.
The Y Combinator playbook is outdated: Daniel argues that the traditional lean startup methodology of building a point solution around a defined customer market doesn't work in today's AI landscape. Creating a sustainable moat requires thinking differently and taking greater risks.
 
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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

Matt Einig, CEO & Founder of Rencore: $15 Million Raised to Build a Comprehensive Cloud Governance Platform

Rencore is a leader in Microsoft 365 governance, helping organizations manage the security, costs, and lifecycle of their cloud resources. With $15 million in funding, Rencore has evolved from a bootstrapped consulting business to a venture-backed software company serving nearly 500 enterprise customers worldwide. In this episode of Category Visionaries, I spoke with Matt Einig, CEO and Founder of Rencore, about his 12-year journey from building a niche code analysis tool to creating a comprehensive cloud governance platform that addresses the growing challenges of cloud sprawl, security, and cost management in the Microsoft ecosystem and beyond.
Topics Discussed:
Rencore's unconventional path from consulting tool to enterprise SaaS product
The transition from bootstrapped business to venture-backed startup after 7+ years
How customer interviews shaped Rencore's pivot to cloud governance
The pandemic's role as a massive accelerator for cloud adoption and Rencore's growth
Building a technology-agnostic platform that can quickly adapt to market changes
The balance between bootstrap mentality and venture growth mindset
Establishing thought leadership in the Microsoft ecosystem through content creation and community engagement
GTM Lessons For B2B Founders:
Leverage existing customer relationships when pivoting: Matt's team interviewed over 300 existing customers to identify their next opportunity, using their established base to discover new market needs. Matt explained, "We used this connection that we have, this customer base, and figured out a new problem." B2B founders should view their current customer base as a valuable research pool when considering new directions.
Build credibility before you need it: Matt spent years building visibility in the Microsoft ecosystem, speaking at 30-40 events annually and earning Microsoft MVP status for 10 consecutive years. This established credibility made marketing their new product much easier. B2B founders should invest in ecosystem credibility early, as it becomes a powerful asset when launching new products.
Content consistency trumps perfection: Matt's approach to thought leadership wasn't about occasional brilliant pieces but consistent, valuable content creation over years. "If you really want to do it, you have to put a lot of effort in... and it's eventually only all about consistency," he shared. B2B founders should commit to regular, thoughtful content rather than sporadic attempts at viral marketing.
Design for future expansion: Rather than building a solution specific to Microsoft 365 governance, Rencore created a technology-agnostic platform that could easily integrate new data sources. "That choice to build something generic instead of something very specific proved to be an extremely good decision," Matt reflected. B2B founders should design core architecture with future expansion in mind, even when starting with a focused use case.
Maintain operational discipline through funding transitions: Despite raising venture capital, Matt maintained the operational discipline developed during bootstrapping. "We didn't change our attitude that much... we tried to stay realistic," he explained. This approach helped them weather economic downturns. B2B founders should preserve the operational rigor of bootstrapping even after securing venture funding.
 
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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

Derek Szeto, Co-Founder of Walnut Insurance: $7 Million Raised to Lead the Embedded Insurance Revolution

Walnut Insurance is pioneering embedded insurance solutions, making it easier for platforms and businesses to offer relevant insurance products at the right moment in the customer journey. With over $7 million in funding, Walnut has partnered with major brands like Neo Financial, Tim Hortons, and Atco to create seamless insurance experiences. In this episode of Category Visionaries, I spoke with Derek Szeto, Co-Founder of Walnut Insurance, about the company's journey from its inception within RBC to becoming a leading embedded insurance enabler, working behind the scenes to power insurance solutions that appear naturally within customer experiences.
Topics Discussed:
The three buckets of embedded insurance: fully embedded into products, data-driven implementations, and contextual offerings
How embedded insurance benefits all parties: customers get needed coverage, platforms enhance stickiness and revenue, and insurers receive better risk profiles
Walnut's origin story discovering insurance as an "unrecognized subscription" in consumer spending
Finding the right customer touchpoints for offering insurance products
Establishing Walnut as a technology-first enabler for partners wanting to offer insurance
The challenge of market education in an emerging category
The shift from life insurance to property and casualty products for better conversion rates
Creating one-click insurance journeys that drive strong conversion rates
 
GTM Lessons For B2B Founders:
Start by recognizing untapped market patterns: Derek identified insurance as an "unrecognized subscription" in consumer spending data—a significant expense that didn't get the attention of typical subscriptions like Netflix or Spotify. B2B founders should look for similar overlooked patterns in consumer behavior that indicate market opportunities.
Focus on required rather than optional products: Walnut found significantly higher conversion when focusing on insurance products that are required in customer journeys (like tenant insurance when signing a lease) rather than optional ones. Derek explains, "Life insurance in its very end is a much harder product to embed because life insurance is always optional." B2B founders should prioritize solutions that address mandatory needs over discretionary ones.
Use data signals to drive contextual offerings: The strongest conversion happens when insurance is offered at moments of high relevance. Derek shares, "Thinking about geolocation and travel insurance—an airport is a very good signal, or better yet if you can get them while they're using the Wi-Fi on the plane, that's an even better signal that they might be traveling." B2B founders should identify and leverage precise contextual signals that indicate heightened receptivity to their solution.
Run fundraising like a sophisticated sales process: Derek learned that fundraising requires the same rigor as enterprise sales. "It became much more of a CRM-driven process, more pre-work. So trying to identify the most likely investors... Are they going to be interested in that category? Are they going to be interested in that geography? Are they writing checks of the size that are relevant to their fund?" B2B founders should approach fundraising with the same systematic process and qualification criteria used in sales.
Industry conferences drive disproportionate results: For B2B companies in established industries like finance and insurance, conferences remain highly effective for business development. "We've had a lot of success with conferences like the Money 2020s of the world where folks are all together in one place and we can meet with a lot of different clients, whether that's net new or to meet with existing partners." B2B founders should prioritize high-concentration industry events, especially in traditional sectors.
 
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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

Mark Zurada, Co-Founder of PinPoint Analytics: $4 Million Raised to Transform Public Works Bidding with AI

PinPoint Analytics is revolutionizing the public works construction industry with AI-powered bid intelligence. With over $4 million in funding, PinPoint is building what co-founder Mark Zurada describes as "the Zillow for public works." In this episode of Category Visionaries, I sat down with Mark to learn how PinPoint is bringing data-driven decision making to an industry where the "lowest price bid wins" mentality has traditionally forced contractors into a risky race to the bottom.
Topics Discussed:
The unique challenges of public works construction bidding, where lowest price wins but pricing information is non-standardized
How PinPoint collects and digitizes data from every public works project in the country over the past five years
The company's journey from 2.5 years of intense R&D to launching their first generally available product
PinPoint's ingenious marketing strategy that leverages real-time bid data to target prospects at exactly the right moment
The critical importance of finding specialized investors who understand the niche market
Why few tech founders have ventured into the construction space, and how PinPoint's technical expertise gives them an edge
 
GTM Lessons For B2B Founders:
Target the stakeholders with the highest pain point: PinPoint serves three customer segments (municipalities, engineering firms, and general contractors) but focuses primarily on GCs because they have the most financial risk and greatest need for the solution. As Mark explained, "GCs are our primary target, and they're basically the most at risk. They need this the most."
When creating a new category, seek specialized investors: For companies building in niche markets, corporate venture capital from established industry players can be invaluable. Mark shared, "We really had to find a specialized VC... we ultimately landed a CVC, basically a huge construction conglomerate that felt the pain point. They're like, 'Oh my God, you guys can solve this. We've been trying to solve it forever.'"
Build proprietary data moats: What attracts investors to PinPoint isn't just AI but their unique data assets. "VCs are really gravitating towards us because of the data moat that we have and the IP moat... We are an AI company solving a real-world problem with a great moat around us."
Use your data to drive hyper-targeted sales outreach: PinPoint transforms the bid summaries they collect into actionable sales intelligence. "We know exactly who's bidding almost in real time... We're very focused on hitting our customers at the right time with the right message, with rich analysis on what they did, opening the doors to how our product could have helped them."
Approach complex technical challenges with the right expertise: Sometimes the reason a market remains underserved is that the technical barriers are substantial. "We're really like tech guys building construction software... We know how to do data and analytics and AI extremely well... We just knew how to approach it and surmount some of those early technical problems that would have been super hard if you were coming at it from the other side."
 
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