Category Visionaries

Shelley Copsey, CEO & Co-Founder of FYLD: $48 Million Raised to Transform Field Work Execution Category

FYLD has raised $48M to transform how infrastructure field workers execute their daily tasks safely and efficiently. In a recent episode of Category Visionaries, I spoke with Shelley Copsey, CEO and Co-Founder of FYLD, about creating a new category in field work execution and building during a pandemic. The company has achieved 3x ARR growth last year and is on track to double bookings revenue this year, with near-zero churn rates.
Topics Discussed:
The daily challenges of infrastructure field workers in utilities, roads, and railways
Creating and capturing demand in a new software category
Enterprise sales strategy in the infrastructure sector
Scaling during COVID with remote customer discovery
The reality of labor shortages in field operations
Building customer trust in critical infrastructure
GTM Lessons For B2B Founders:
Rethink conventional wisdom on market problems: While many discuss a labor shortage in field operations, FYLD's data shows 30-35% standing time across companies. Shelley explains, "I'm not convinced that there is a labor crisis... when you begin to look at that level of standing time, I think you've got to question if we've got a labor shortage or we've just got a problem of understanding what the people in the field are doing." Sometimes the most discussed market problem isn't actually the root cause.
Design pricing models that encourage full adoption: FYLD shifted from per-seat licensing to enterprise-wide deals after realizing usage limitations undermined platform value. Shelley notes, "If what your premise is by collecting large volumes of data, you can help people do their jobs better and more efficiently, your go-to-market model can actually undermine delivering the benefit from the platform." Pricing should align with your product's value creation mechanism.
Leverage industry-specific collaboration dynamics: In infrastructure, safety improvements aren't viewed as competitive advantages but as shared responsibilities. As one CEO told Shelley, "If you can help me keep workers safer, more mums and dads are going to think that this is a good career for their kid... if we can all keep people safer, we're all going to be able to grow as an industry." Understanding these dynamics can accelerate market penetration through referrals.
Navigate complex stakeholder alignment: Enterprise sales in infrastructure require buy-in from COOs, heads of safety, CIOs, and CFOs. Shelley shares, "Enterprise sales cycles are well known to take 9, 12, 15 months. In the infrastructure industry, we're moving a bit quicker than that." Success requires systematically addressing each stakeholder's priorities while maintaining momentum.
Build for end-users first: FYLD maintains an 8/10 customer satisfaction score among field workers, unprecedented in their industry. Shelley emphasizes, "There's no point going out and selling a product related to fieldwork if the field workers hate using the platform and won't adopt it." In B2B, while buyers sign the checks, end-user adoption drives long-term success.
 
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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
 
 

Funding the Future: Susan Liu, Partner at Uncork Capital

Welcome to another episode of Category Visionaries — Funding the Future. In today's episode, we're speaking with Susan Liu, Partner at Uncork Capital, a seed-stage venture capital firm investing out of a $200 Million fund.
Here are the most interesting points from our conversation:
Shift to Seed-Stage Investing: Susan transitioned from later-stage investing at Scale Venture Partners to focusing on seed-stage at Uncork Capital, driven by her passion for working with founders at the earliest stages of their journey.
State of Enterprise Software: The current enterprise software market is challenging, with traditional SaaS seeing budget constraints. However, AI-driven solutions are gaining traction, often backed by separate AI budgets within enterprises.
AI Investment Strategy: While there’s a surge in AI startups, Susan emphasizes the importance of founder-market fit and differentiation, as many companies are tackling similar problems in the AI space.
Evaluating Early-Stage Startups: Susan looks for a strong founding team with market experience, a large addressable market, and a compelling product wedge when evaluating seed-stage opportunities.
Traits of Successful Founders: Founders with deep industry experience, grit, and the ability to learn quickly tend to have a higher success rate, particularly in B2B markets.
Advice for Series A: For seed-stage founders preparing for Series A, Susan advises demonstrating strong revenue growth and capital efficiency, as these are key factors that attract investors in the current market.
 
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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
 
 

Harry Croydon, Co-Founder of MIC Global: $13 Million Raised to Build the Future of Embedded Microinsurance

MIC Global, backed by $13 Million in funding, is revolutionizing the insurance industry through embedded microinsurance solutions. In this episode of Category Visionaries, Co-Founder Harry Croydon shares his journey from launching one of the first cyber insurance companies in 1999 to building a global embedded insurance platform that meets the evolving needs of the digital economy.
Topics Discussed:
The evolution of insurance technology from 1999 to present
Surviving the dot-com bubble and post-9/11 market challenges
The emergence of embedded microinsurance as a new category
Building a global insurance infrastructure
Multi-channel distribution strategy through brokers and insurance partners
 
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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
 
 

Amar Kendale, President & Co-Founder of Homeward: $70 Million Raised to Transform Rural Healthcare Through Technology

Homeward, a healthcare technology company that's raised over $70M, is pioneering a new approach to rural healthcare delivery by combining technology with in-person care. In this episode of Category Visionaries, Amar Kendale, President and Co-Founder of Homeward shares how the company is addressing the 23% higher mortality rate in rural America through an innovative care delivery model and technology platform.
Topics Discussed:
Homeward's evolution from initial hypothesis to market-validated solution
The unique challenges of healthcare delivery in rural communities
Building trust in healthcare through local partnerships
Technology's role in scaling healthcare access
Value-based care implementation and criticism
Market entry strategy for healthcare technology companies
 
GTM Lessons For B2B Founders:
Start with Operations, Not Technology: Amar emphasizes the importance of avoiding the "technologist's trap" of building before understanding. As he notes, "There's a trap a lot of technologists fall into... you have a vision for the way that technology can play a role, and you decide to start building first before you really know whether it's exactly the right problem or not." Instead, Homeward built minimal technology initially, embedding their tech team with clinicians to understand workflows before building solutions.
Challenge Initial Assumptions Through Market Testing: Homeward's early hypothesis about rural healthcare needs was incorrect. They assumed people without regular doctor visits needed primary care, but discovered that rural patients had doctors for acute care—they needed supplemental services for preventive care. As Amar explains, "What's different about the way people are consuming healthcare in rural is the thing we have to pay attention to."
Build Trust Through Local Presence: In healthcare, trust is paramount and historically local. Homeward succeeded by hiring local medical assistants and community health workers who understand the communities. "They have a really high degree of cultural competency. They are ambassadors for the Homeward brand... who can help us to spread that message," Amar shares.
Choose Strategic Markets for Scale: When selecting initial markets, Homeward focused on states with large Medicare populations to ensure sufficient scale. "You could easily die by a thousand cuts if you go after too small a market," Amar explains. Their success in Michigan and Minnesota created a template for future market expansion.
Design for Multiple Stakeholders: Healthcare technology requires satisfying multiple stakeholders—patients, providers, and payers. Amar warns, "If you focus on the patient and the payer and you leave out the provider, well, you may never get prescribed and you may never show up in the provider workflow." Successfully navigating this complexity creates defensive moats against competitors.
Partner with Long-Term Vision Aligned Investors: Homeward chose investors who shared their vision for transforming rural healthcare. Their lead investor, General Catalyst, pushed them to think bigger: "We were sheepishly sketching out the path to being a billion dollar business. And Hemant added the zero. He said this is easily a $10 billion business."
Focus on Early Validation and Responsible Growth: Despite rapid expansion (3-4x annual growth), Homeward maintains disciplined growth. Their approach is validated by an 80 NPS score, which Amar notes is "better than we ever did at Livongo or any other place we've been."
 
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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
 
 
 

Dan Rua, CEO of Admiral: $28 Million Raised to Build the Future of Visitor Relationship Management

Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today's episode, we're speaking with Dan Rua, CEO of Admiral, a visitor relationship management platform that has raised $28 Million in funding.
Here are the most interesting points from our conversation:
Creating a New Martech Category with Visitor Relationship Management (VRM): Dan shares Admiral’s mission to help websites build visitor relationships amid the rise of privacy regulations and ad blockers, moving from ad-centric to relationship-centric digital experiences.
Founding Admiral from a Key Industry Shift: After observing the challenges facing publishers due to ad blockers, GDPR, and data privacy regulations, Dan and his team launched Admiral to provide media publishers with a tool for direct, valuable visitor relationships.
Insights from Early Adoption: Securing partnerships with major clients, such as PGA Tour, helped Admiral validate its VRM approach. Dan describes the importance of targeting early adopters who deeply understand the value of long-term audience relationships.
Building Flexibility for Publishers: Recognizing the diverse needs of audiences, Admiral created a flexible, modular approach to VRM, allowing publishers to choose modules—such as adblock recovery or subscription paywalls—to best meet the needs of various user segments.
Prioritizing a Land-and-Expand Sales Model: Inspired by HubSpot’s modular growth strategy, Admiral focuses on starting with one pain point solution and then expanding into other VRM modules once trust is established with customers.
Leveraging Analytics and AI for Automation: Dan explains that future development for Admiral centers on AI-driven automation to optimize visitor engagement, promising an “easy button” solution that intelligently manages visitor journeys to maximize value without complex manual intervention.
 
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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
 
 

Vijay Sikka, CEO & Founder of Sikka: $30 Million Raised to Power the Future of Retail Healthcare Technology

Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today’s episode, we’re speaking with Vijay Sikka, CEO and Founder of Sikka, a retail healthcare technology platform that has raised over $30 Million in funding.
Here are the most interesting points from our conversation:
Sikka’s Origin Story: Vijay’s journey began when he identified operational inefficiencies in his wife’s dental practice, realizing a massive opportunity to optimize revenues for healthcare providers across sectors like dental, veterinary, and optometry.
Tackling Fragmentation in Retail Healthcare: Sikka recognized the severe fragmentation in retail healthcare technology, with 400+ unique practice management systems, and seized the chance to unify them into one cohesive platform.
Strategic Expansion Beyond Dentistry: By 2016, Sikka expanded from a dental focus to retail healthcare at large, leveraging a Twilio-like API model to provide solutions across multiple specialties without forcing practices to retool.
A Channel-Based GTM Strategy: Realizing direct sales weren’t efficient in this fragmented market, Sikka developed a channel strategy, partnering with application builders in healthcare to amplify growth through trusted distribution networks.
Slow and Intentional Funding: Sikka bootstrapped for over a decade, focusing on building a technological moat and waiting until the timing was right before raising venture funding, which catalyzed the company’s rapid growth.
AI as the Core for Future Expansion: With proprietary dental and healthcare-focused AI models outperforming general LLMs, Sikka is set on leveraging AI to enhance insights, benchmarking, and clinical data applications for retail healthcare and beyond.
 
 
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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
 
 

Bill Moore, CEO and Founder of XONA: $30 Million Raised to Build the Future of OT User Access

Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today's episode, we're speaking with Bill Moore, CEO & Founder of XONA, an OT user access platform that has raised over $30 Million in funding.
Here are the most interesting points from our conversation:
The Origin of XONA: Bill shared that XONA began with the goal of simplifying secure remote access for OT environments. Initially focused on making VDI simpler for the DoD, the company expanded into a broader secure access platform used widely in commercial sectors.
From Idea to Market: It took a year from concept to their first paying customer, achieved by working closely with beta customers and testing prototypes in real-world environments before having a fully developed product.
A Market Pivot: Although originally targeting the DoD, Bill discovered a huge opportunity in commercial OT sectors, particularly in natural gas distribution, which led to XONA's focus on industrial controls and OT systems.
The “Guerrilla” Marketing Strategy: Early on, Bill employed a scrappy, grassroots approach to marketing by attending industry events, shaking hands, and networking—long before they could afford a booth or formal marketing campaigns.
Category Creation in OT: XONA is redefining identity and access management for OT, where users interact with machines and operational processes rather than data. This approach requires distinct solutions from traditional IT systems, creating a new market category.
Global Expansion: XONA is now operating in over 35 countries through its partnership with GE, focusing on OT cybersecurity in sectors like power generation, manufacturing, and other critical infrastructure.
 
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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
 
 

Alon Talmor, CEO & Founder of Ask-AI: $20 Million Raised to Power the Future of Enterprise AI

Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today's episode, we're speaking with Alon Talmor, CEO & Founder of Ask-AI, an AI technology company that's raised $20 Million in funding.
Here are the most interesting points from our conversation:
AI's Impact on SaaS: Alon believes AI will eventually disrupt and consolidate the SaaS industry, transforming enterprise software and making many existing solutions obsolete.
Post-Exit Reflections: After selling his first company to Salesforce, Alon shared the psychological challenges of finding new goals post-exit, noting the sense of emptiness that can follow achieving major career milestones.
Founding Ask-AI: Inspired by cutting-edge AI research, Alon started Ask-AI in 2020, recognizing early the massive potential of generative AI before the technology gained widespread adoption.
Rise of Generative AI: While not surprised by the capabilities of ChatGPT, Alon was taken aback by the massive public hype and acceptance, which accelerated demand for AI solutions like Ask-AI's enterprise support tools.
Navigating a Crowded Market: With increasing competition in the AI space, Alon emphasizes the importance of early, face-to-face sales efforts and strategic partnerships to secure initial customers and stand out.
Investor Strategies: Alon advocates for raising capital from numerous smaller investors during early funding rounds to maximize networking opportunities and avoid relying solely on large VCs.
 
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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
 
 

Ofer Ronen, CEO & Co-Founder of Tomato.ai: $12 Million Raised to Build the Accent Softening Category

Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today's episode, we're speaking with Ofer Ronen, CEO & Co-Founder of Tomato.ai, an accent softening platform that's raised $12 Million in funding.
Here are the most interesting points from our conversation:
AI in contact centers: Ofer has built three startups focusing on contact center AI, seeing the potential for AI to solve language processing problems and improve customer service experiences.
Large-scale deals take patience: Closing large contracts, like the $300 million call center deals Ofer managed, typically involves 18 months of navigating gatekeepers, pilots, and bake-offs.
Human empowerment, not replacement: Unlike many AI initiatives aimed at automation, Tomato.ai focuses on enhancing human agents with AI, particularly through accent softening to improve customer interactions.
Accent softening for global agents: Tomato.ai uses AI to modify agents’ speech in real-time, reducing accents to help agents communicate more clearly, reduce repeat explanations, and improve the customer experience.
Focusing on a niche for success: Ofer stresses the importance of focusing on a narrow problem—starting with Filipino and Indian accents—and perfecting it before expanding.
Creating a new market: Accent softening AI is a nascent category, and Ofer is positioning Tomato.ai to be a leader in a potentially multi-billion-dollar industry as demand for AI-enhanced communication grows globally.
 
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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
 
 
 

Martha Dreiling, Co-Founder & COO of Reserv: $28 Million Raised to Build the Future of AI-Powered Insurance Claims

Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech's most innovative B2B founders. In today's episode, we're speaking with Martha Dreiling, Co-Founder & COO of Reserv, an AI-powered insurtech company that has raised $28 Million in funding.
Here are the most interesting points from our conversation:
AI-Driven Claims Processing: Reserv is the first AI-powered third-party administrator (TPA) focused on insurance claims, providing both claims handling and deep data insights for underwriters.
Venture Incubation Start: Reserv was born from dissatisfaction with legacy claims processing systems, launching through a partnership between Bain Capital Ventures and Altai Ventures.
Fast Growth and Impact: Founded in May 2022, Reserv processed its first claim just five months later, showcasing their ability to scale quickly while leveraging modern SaaS platforms and AI.
Climate Change’s Impact on Insurance: The rising importance of claims handling due to climate change and a tightening insurance market has increased the demand for more seamless, data-driven processes.
Empowering, Not Replacing, Adjusters: Reserv’s technology focuses on empowering claims adjusters with AI, automating mundane tasks while maintaining the essential human element of empathy in high-stakes claim situations.
Go-To-Market Complexity: The go-to-market strategy includes handling a complex network of stakeholders—MGA’s, insurance carriers, and policyholders—ensuring that every part of the value chain is well-serviced.
 
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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