Category Visionaries

Brian Manning, CEO & Co-Founder of Xona Space: $40 Million Raised to Build the Next Generation of GPS Technology

Xona Space is revolutionizing global positioning technology with a new generation of GPS designed for today's devices and applications. With over $40 million in funding, Xona is developing a constellation of small satellites in low Earth orbit to provide higher precision, stronger signals, and enhanced security compared to traditional GPS systems. In this episode of Category Visionaries, I spoke with Brian Manning, CEO and Co-Founder of Xona Space, to learn how the company is addressing the limitations of current navigation technology and enabling the next wave of autonomous systems to operate safely in challenging environments.
Topics Discussed:
The evolution of navigation technology from celestial navigation to modern GPS
How traditional GPS architecture hasn't fundamentally changed in over 50 years
Xona's approach to building a complementary system with small satellites in low Earth orbit
The three key challenges Xona addresses: precision, power, and protection
Why autonomous vehicles and precision agriculture need more reliable positioning
The company's recent Air Force contract and their focus on both commercial and government applications
Their upcoming launch of the first production-class satellite in June
 
GTM Lessons For B2B Founders:
Validate real-world problems with customer immersion: Brian emphasized getting out from behind your desk to talk directly with customers in their environments. "You can't start a company behind a computer screen... Get out and talk to the customers. It is so enlightening and there's so many things that you will learn that you just never thought of." Understanding how farmers, construction workers, and others actually use positioning technology in the field revealed needs that spreadsheets and assumptions couldn't capture.
Focus on specific markets when demand exceeds capacity: Rather than pursuing all potential use cases, Xona strategically narrowed their focus. "There are just so many use cases and so many potential applications that our pipeline of interest and demand is kind of so huge that we can't actually pursue all of it." By identifying core markets with early adoption potential, they've maintained a laser focus that maximizes their limited resources.
Make new technology compatible with existing infrastructure: Xona deliberately designed their system to work with existing GPS receivers. "We've designed our system to be compatible with most GPS receivers, even without making any hardware changes." This approach significantly reduces adoption barriers, as customers can access improved capabilities through software updates rather than hardware replacements.
Build incrementally toward a massive vision: When tackling something as ambitious as "building a new GPS," Xona broke it down into manageable steps. "We're going to do it one step at a time... You solve one problem and you solve the next. And if you solve enough of them, you're successful." This incremental approach helped them secure ongoing funding by demonstrating clear progress at each stage.
Articulate the broader impact beyond luxury applications: Rather than positioning their technology as enabling premium conveniences, Xona frames their vision around democratizing access to transformative capabilities. "I'm much more interested in how you get the autonomous ambulance to go drive through the snowstorm when a human can't... How do you take the benefits of precision agriculture... and bring those benefits into developing countries?" This approach appeals to both mission-driven investors and practical customers seeking broader global impact.
 
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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
 
 

Nathan Beckord, CEO of Foundersuite: $13 Million Raised to Build the Go-To Platform for Startup Fundraising

Foundersuite has established itself as the leading platform for startups raising capital, with $13 million in funding and a comprehensive suite of tools designed to streamline the fundraising process. In this episode of Category Visionaries, I sat down with Nathan Beckord, CEO of Foundersuite, to explore how his extensive background in investment banking and startup advisory evolved into building a specialized platform that's revolutionizing how founders approach fundraising. Nathan shares his journey from consultant to entrepreneur, and how Foundersuite has grown from a simple CRM into a robust platform serving startups from seed stage through Series B and beyond.
 
Topics Discussed:
The evolution from an investment banking career to founding a startup focused on fundraising tools
How Foundersuite narrowed its focus from a broad suite of founder tools to specialized fundraising solutions
The strategic decision to target the seed through Series B segment as their primary market
Building a sustainable marketing strategy through events, podcasting, and innovative guerrilla tactics
The launch of Funding Stack, a new platform designed for VCs and fundraising consultants
How AI is being integrated throughout the fundraising process to enhance efficiency and outcomes
 
GTM Lessons For B2B Founders:
Start with your unique expertise: Nathan built Foundersuite based on his decade of fundraising experience, turning his specialized knowledge into product features. He explained, "I'm a one trick pony. The only thing I've done ever since college is raise capital for startups." B2B founders should leverage their deep industry expertise when defining their product category and value proposition.
Be willing to kill good products for great focus: Despite positive user feedback on several products in their initial suite, Foundersuite made the difficult decision to eliminate tools that weren't core to their primary value proposition. Nathan recalls, "It was hard to kill something that people did love... but they weren't really paying as much for that." B2B founders should continuously evaluate their product portfolio against market traction and be willing to make tough decisions for greater focus.
Define your "Goldilocks" customer segment: Foundersuite identified their ideal customer segment as seed through Series B companies—not too early (pre-seed) and not too mature (Series C+). Nathan explains, "Too early, you don't have any money, you can't pay us, you're not really fundable. Too late, you have a lot of other resources to help you raise capital." B2B founders should similarly identify where their product delivers maximum value and focus acquisition efforts accordingly.
Use content marketing as a learning opportunity: Foundersuite's "How I Raised It" podcast not only serves as a marketing channel but also provides valuable market intelligence. Nathan shared, "I thought I knew everything about raising capital. And here I am just drinking from a fire hose... I'm learning more than my first six months of doing a podcast than I have in the last five years of actually doing the work." B2B founders should view content marketing as both a growth channel and a customer research tool.
Implement annual marketing experiments: Foundersuite commits to trying one new marketing approach each year. Nathan explains, "One of the things I try and do every year... let's try a new, different marketing experiment." For 2025, they're implementing monthly webinars. B2B founders should similarly build experimentation into their marketing roadmap while maintaining their core channels.
 
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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
 

Jan Willem Rombouts, CEO & Founder of Beebop AI: $5.5 Million Raised to Power Grid Orchestration for the Clean Energy Transition

Beebop AI is pioneering a new middleware layer for power grid orchestration, securing $5.5 million in funding to help utilities and energy retailers optimize energy consumption and costs. In this episode of Category Visionaries, I sat down with Jan Willem Rombouts, CEO and Founder of Beebop AI, to discuss how his background at Goldman Sachs and experience building his first energy tech company shaped his approach to solving one of the energy transition's biggest challenges: balancing power grids in an increasingly renewable-powered world.
Topics Discussed:
Jan Willem's journey from Goldman Sachs' trading floor during the financial crisis to energy tech entrepreneurship
The painful lessons learned building Restore, which pioneered virtual power plants and was later acquired by Centrica
How Beebop AI creates a middleware layer that orchestrates power consumption across customer devices like EVs, solar panels, and heat pumps
Why power grid orchestration is critical to making renewable energy both reliable and affordable
Beebop's strategic flywheel connecting utilities and device manufacturers
The go-to-market strategies that helped Beebop gain traction with major European utilities
 
GTM Lessons For B2B Founders:
Engineer network effects into your go-to-market strategy: Beebop designed a utility-to-OEM flywheel where each new utility customer helps bring device manufacturers onto their platform, creating a powerful network effect. Jan Willem explained: "What we designed was that we would first contract these utilities... our anticipation was that they would be able to engage with these OEMs, with these manufacturers more easily, to essentially invite them to integrate with our platform." This approach turns customers into channel partners who can open doors that would be difficult for a startup to access directly.
Break through complex sales cycles with land-and-expand: When selling to utilities and large corporations with notoriously long sales cycles, Beebop starts with a low-cost, high-value initial offering focused on insights and business case validation. Jan Willem noted: "Our initial proposition is very low cost and very high value... we allow them to see what the business case is... to create somewhat of a solid launching pad on which we can then expand and go to actual operationalization." This approach shortens time-to-value and creates internal champions.
Focus on customer economics, not just your technology: Despite having complex technology, Beebop leads customer conversations with how their solution impacts key metrics like customer lifetime value, margin, churn, and customer acquisition costs. "Before we have explained anything about how new our software is, where it positions in the technology stack, we just show what kind of awesome products they can build... creating tens of percentages of discounts on their energy bills."
Design for global scale from day one: Based on lessons from his first company, Jan Willem deliberately architected Beebop to work with market structures that are universal across regions: "What we did this time... is we chose markets that have a universal footprint and so that look essentially the same whether you're in the UK or you're in Texas or you're in Germany or you're in Sweden." This approach avoids the scaling challenges of having to constantly adapt to different regulatory environments.
Bring process to event marketing: Beebop transformed their trade show approach by adopting a disciplined, metrics-driven strategy learned from Datadog's former CMO. Jan Willem shared: "The big learning for me was to be super intentional. If you go to a trade show, be super clear about exactly how many marketing qualified, how many sales qualified leads you want out of it, and then engineer a team with different roles and responsibilities." This systematic approach yields measurable ROI from events that many startups struggle to achieve.
 
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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 Amte, CEO & Founder of Pegbo: $1.4 Million Raised to Transform Construction Supply Chain Diversity

Pegbo is revolutionizing the construction technology landscape by helping local, small, and diverse businesses accelerate their participation in the supply chain. With $1.4 million in funding, this construction tech platform is streamlining how emerging businesses win more jobs in an industry that's traditionally been slow to adopt technology. In this episode of Category Visionaries, Amar Amte shares his journey from Google to founding Pegbo, including his initial pivot from an equipment rental marketplace to a supplier diversity procurement platform, and how his outsider perspective has become a competitive advantage.
Topics Discussed:
Pegbo's evolution from an equipment rental marketplace to a supplier diversity procurement platform
How being an industry outsider (coming from Google) provides unique advantages when building in construction tech
The impact of digitization and AI on construction technology adoption and investor interest
Regulatory changes affecting supplier diversity and local business participation in construction
Marketing strategies centered on community-building and promoting people rather than product
The company's approach to rapid growth while maintaining financial discipline
How AI is revolutionizing construction tech by making previously expensive operations highly affordable
 
GTM Lessons For B2B Founders:
Let your product do the selling: Pegbo focuses on demonstrating their product rather than making promises. Amar notes, "The aha moment is product. We are letting our products sell themselves." B2B founders should prioritize building a product that speaks for itself rather than relying heavily on marketing rhetoric.
Make meaningful pivots quickly: When Pegbo discovered customers were asking about minority and small businesses rather than just equipment rentals, they completely pivoted their business model. Within 15 days of pivoting, they had their first paying customer. Founders should be prepared to recognize when the market is pulling them in a different direction and be willing to make decisive changes quickly.
Focus on post-event value: For community events, Pegbo concentrates not just on the event itself but what happens before, during, and after. Amar explains, "If people are not qualified with a general contractor, they just waste a lot of time... What we focus on is what happens after the event." B2B founders should design events with clear pathways to customer value beyond networking.
Strategic resource allocation: Despite raising $1.4 million, Pegbo maintains strict financial discipline. Amar personally paid for his branded Cybertruck rather than using company funds, stating, "I don't want to spend my investors' money on renting toilets and kitchens." Funding should be directed primarily toward product development and customer acquisition.
Embrace regulatory changes as opportunities: Rather than seeing shifting regulations around supplier diversity as threats, Pegbo views them as opportunities. Amar notes that even as some diversity criteria change, "support to local businesses, small businesses are going to stay." B2B founders should look for the consistent underlying needs that persist through regulatory changes.
Start manual, then automate: Pegbo's growth strategy involves first getting orders, performing some services manually to learn, then automating those processes. This approach led to completely automated $23,000 projects without founder involvement. B2B founders should consider a "do things that don't scale" approach initially before building automation systems.
 
 
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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership.
www.FrontLines.io
The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. 
www.GlobalTalent.co

Brian Giamo, CEO & Co-Founder of Activate OS: Raising $4M+ to Build an Equipment Management Operating System for Construction

Activate OS is transforming equipment management in the construction industry with a networked approach that connects fleet owners with their equipment providers. Starting as a consulting project to solve equipment management challenges for Caterpillar, Activate OS has evolved into a comprehensive platform that facilitates real-time collaboration between construction companies and their equipment dealers and rental partners. In this episode of Category Visionaries, we spoke with Brian Giamo, CEO and Co-Founder of Activate OS, about the company's journey from a consulting business offshoot to a SaaS platform that's creating network effects and delivering measurable value to some of the largest construction projects in the country.
Topics Discussed:
Activate's origin story as a consulting project for Caterpillar
The evolution from broad market approach to a focused go-to-market strategy
How Activate connects fleet owners with equipment dealers and rental companies
The three-stage go-to-market model that creates network effects
The shift in VC interest toward construction tech verticals
Future vision for expanding into transaction facilitation and AI-enabled services
GTM Lessons For B2B Founders:
Get laser-focused on your entry point: Brian's team initially tried selling to equipment dealers and rental companies first, expecting them to distribute to fleet owners. After struggling, they flipped their approach to target fleet owners first, which created natural pull from the dealers. As Brian explained, "The natural way that this works is acquire the fleet owner, get them connected to provider, they mutually see value and benefit in keeping their equipment up and running."
Sell outcomes, not software: Activate OS doesn't position itself as merely selling software. Brian emphasized, "We're really selling a result. We're really selling production of those assets on a job site and more effective communications to enable that." This outcome-focused approach resonates with customers who care about equipment uptime, not technology.
Create strategic network effects: Activate's three-stage go-to-market model (1. acquire fleet owner, 2. connect them to providers, 3. convert providers to distribution partners) creates powerful network effects. Each new customer expands their reach to 5-10 equipment providers who then become potential distribution channels themselves.
Be patient with product-market fit: It took Activate nearly six years to truly crystallize their go-to-market approach and product-market fit. Brian acknowledged, "I would say we really have sort of just arrived there in 2022 or 2023. It took a lot of years."
Leverage strategic investors from your industry: Activate raised over $4M without traditional fundraising, instead bringing on strategic investors including a major Caterpillar dealer. These industry insiders provided both capital and valuable market insights, creating mutual benefits beyond just 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

Ty Wilson, CEO & Co-Founder of Tab Commerce: $4 Million Raised to Build the Commerce Layer for Restaurant Supply Chains

Tab Commerce is pioneering the first corporate card built specifically for restaurants, tackling the complex back-office operations of a traditionally low-margin industry. With $4 million in funding, Tab is creating a comprehensive spend management platform that addresses the unique challenges restaurant operators face. In this episode of Category Visionaries, I spoke with Ty Wilson, CEO and Co-Founder of Tab Commerce, to learn how his family restaurant background and pandemic-era insights led to building a fintech company that's transforming restaurant profitability through better spend management.
Topics Discussed:
Tab Commerce's evolution from supply chain solution to specialized corporate card for restaurants
The complex, fragmented nature of restaurant back-office operations and purchasing
How Tab is growing through strategic industry association partnerships
The challenges of distribution and relationship-building in the restaurant technology space
Tab's vision to become the standard commerce layer for the $1.5 trillion restaurant supply chain
 
GTM Lessons For B2B Founders:
Study success relentlessly: Ty shared he constantly goes deep on companies he admires, calling it "one of the best uses of my time." He studies everything from their podcasts to press materials, which directly inspired Tab's corporate card product after researching Ramp. B2B founders should identify "company crushes" and systematically analyze their business models, marketing strategies, and product innovations for applicable insights.
Vertically-focused products win over horizontal solutions: Tab recognized that generic spend management tools don't work for restaurants' unique workflows. "Every vertical will have their own spend management platform because every vertical has their own workflows and needs and go-to-market strategies," Ty explained. B2B founders should embrace deep vertical specialization rather than building generic solutions, as vertical focus builds immediate trust with customers who want industry-specific solutions.
Strategic industry associations can solve distribution challenges: Unlike conventional digital marketing tactics which failed ("LinkedIn ads... doesn't work at all"), Tab found success by partnering with restaurant industry associations. Ty relocated his office to be five minutes from the Texas Restaurant Association and co-branded a card with them. For B2B founders targeting fragmented industries, leveraging established industry groups can provide credibility, access to engaged audiences, and cost-effective distribution channels.
Relationship-based sales beats transactional approaches: In an era of increasingly transactional software sales, Tab deliberately built a relationship-focused sales organization. "Software sales has become super transactional. And I think that's hurt industries like restaurants and other brick and mortar businesses because they're very relationship based," Ty noted. B2B founders should consider whether their target market responds better to high-touch, relationship-driven sales approaches rather than modern, low-touch methods.
Discover "landmines" through persistent market testing: Ty revealed it took over two and a half years to gain meaningful traction, during which they encountered numerous "landmines" – seemingly intuitive product ideas that actually failed in practice. For example, they initially tried to digitize chef-supplier ordering before realizing the existing phone/text workflow was actually more efficient. B2B founders should rigorously test assumptions and be prepared to pivot from apparently obvious solutions that the market rejects.
 
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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

Mahesh Veerina, CEO of ParkourSC: $90 Million Raised to Pioneer Dynamic Decision Intelligence for Supply Chain Networks

ParkourSC is transforming supply chain management with its dynamic decision intelligence platform, raising $90 million to tackle the industry's most pressing challenges. In this episode of Category Visionaries, we sat down with Mahesh Veerina, a four-time entrepreneur with multiple successful exits, to explore how ParkourSC is creating a new category focused on unlocking trapped value in fragmented supply chain systems. From his early success taking Ramp Networks public in 1999 to his current mission revolutionizing pharmaceutical supply chains, Mahesh shares invaluable insights on building category-defining companies.
Topics Discussed:
Mahesh's entrepreneurial journey through three successful exits including an IPO
How ParkourSC pivoted from IoT sensors to supply chain intelligence
The pandemic's role in accelerating supply chain visibility as a critical business need
Why life sciences and pharma presented the perfect initial market
Creating the "dynamic decision intelligence" category in supply chain technology
Building a platform that integrates fragmented enterprise systems with real-time data
The strategy for partnering with innovative "change agents" within large companies
How ParkourSC's technology reduces supply chain planner "noise" by 50-60%
GTM Lessons For B2B Founders:
Market conditions can validate your vision: Supply chains were "back office" until COVID put them in the spotlight. Mahesh explains, "Any channel you switch on, it's supply chain—running out of milk and bread and essentials." This external validation can accelerate market acceptance of your solution.
Find the value unlock through adjacent innovation: Rather than replacing existing systems, identify where trapped value exists. Mahesh notes, "Companies spend billions of dollars building their ERP systems... We are a category coming either as adjacency or sitting on top of some of these systems to unlock value." This approach reduces friction to adoption.
Target industries with regulatory pressure and high-value problems: ParkourSC chose pharma/life sciences because it's "heavily regulated" with "$35 billion worth of product lost yearly to expirations and cold chain issues." Regulatory compliance and high-dollar waste create urgent problems worth solving.
Co-create with innovative customers: Mahesh advises finding "innovators" within large companies who want to be change agents. "These are the early adopters that take bets... They bring a problem, give you a sandbox to play in." One such customer partner even became ParkourSC's Chief Strategy Officer.
Expand from a narrow solution to platform vision: Start with solving one specific problem exceptionally well. Mahesh shares, "We got into the logistics, cold chain logistics... but very quickly found within these organizations it's great value but very narrow problem." They expanded systematically from logistics to operations, planning, and inventory—"the mother of all there, that's where all the money is stuck."
 
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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

Amr Awadallah, CEO & Founder of Vectara: $53 Million Raised to Build the RAG-as-a-Service Category

Vectara is pioneering the field of Retrieval Augmented Generation (RAG), addressing the critical challenge of hallucinations in AI systems. With over $53 million in funding, Vectara has positioned itself as the go-to platform for enterprises seeking to combat "RAG sprawl" while building AI assistants and agents that are accurate, secure, and explainable. In this episode of Category Visionaries, I sat down with Amr Awadallah, CEO and Founder of Vectara, to explore his journey from Egyptian immigrant to serial entrepreneur and his vision for creating AI systems that enterprises can truly trust.
Topics Discussed:
Amr's journey from Egypt to Stanford in 1995 and how it transformed his career aspirations
The entrepreneurial "infection" at Stanford that led Amr away from academia
Founding and selling his first startup, Activia, to Yahoo in just one year
The comparison of creating successful companies to the joy of having children
How Vectara addresses the critical problem of hallucinations in large language models
The concept of "RAG sprawl" and why enterprises need centralized governance
Amr's framework for evaluating startup opportunities: technological inflection points, real problems, and great teams
Why this AI revolution is a bigger technological inflection point than the internet or big data
 
GTM Lessons For B2B Founders:
Focus on your unique value proposition: Amr emphasized the importance of standing out in a crowded market by focusing on what makes you unique. Vectara doubled down on accuracy and hallucination detection, becoming known as the company to combat AI hallucinations. B2B founders should identify what they can be known for that differentiates them from competitors.
Choose your go-to-market strategy deliberately: When deciding between product-led growth or enterprise sales, commit fully to the approach that fits your business. For enterprise sales, implement account-based marketing focused on your ideal customer profile, host targeted field events, and use strategic dinners with compelling speakers to attract key prospects.
Don't try to boil the ocean: The number one reason companies fail after team issues is lack of focus. Early-stage founders should maintain agility to test different approaches but quickly narrow focus based on where they're getting traction. Treat use cases as "two-way doors" - try them, keep what works, and move on from what doesn't.
Build for the coming AI agent revolution: Amr predicts we'll move from the current "AI assistant phase" (requiring human oversight) to the "AI agent phase" (fully autonomous AI) within one year. B2B founders should position their products for this transition, particularly focusing on accuracy and trust as critical requirements for enterprise adoption.
Leverage technological inflection points: Major technological shifts create gaps that allow startups to disrupt established players. Amr has built companies around three major inflection points: the internet (Activia), big data (Cloudera), and now large language models (Vectara). B2B founders should identify inflection points relevant to their industry and build solutions that capitalize on the new opportunities they create.
 
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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

Cassandra Gholston, CEO & Founder of PartnerTap: $9 Million Raised to Revolutionize Partner Orchestration

PartnerTap is transforming how enterprise companies collaborate with their partners through account mapping and co-selling technology. With $9 million in funding, PartnerTap helps technology giants like Salesforce and SAP unlock revenue opportunities by enabling secure data sharing between partner ecosystems. In this episode of Category Visionaries, I sat down with Cassandra Gholston, CEO and Founder of PartnerTap, to explore how her experience in software sales led her to build a solution that's changing how large enterprises drive revenue through partnerships.
Topics Discussed:
PartnerTap's core technology for account mapping and co-selling between enterprise partners
The data-sharing challenges that prevent effective partner collaboration in enterprise sales
How PartnerTap securely connects partner CRM data to identify mutual customer alignment
The Fempire community that Cassandra built to connect women leaders in tech
Why customer retention is more crucial than fundraising for startup success
Pivoting from a bottom-up sales motion to an enterprise-focused approach
Maintaining founder energy and excitement throughout the startup journey
 
GTM Lessons For B2B Founders:
Focus on the enterprise early if that's your market: Despite conventional wisdom to start with smaller clients, Cassandra recognized her solution needed enterprise adoption first. "When you decide you're going to do top-down selling and sell into the largest organizations in the world as a startup, that's a hard road. Most startups are going to go after smaller companies first," she explained. This decision forced PartnerTap to mature faster in areas like security posture and enterprise readiness.
Build a network effect into your GTM strategy: Cassandra targeted companies with large partner ecosystems to create natural expansion opportunities. "Going in and selling to ADP was going to bring a huge partner ecosystem. Their biggest partners became customers. This starts the network effect of PartnerTap," she shared. This approach created a built-in pipeline for future enterprise deals.
Validate your concepts before going all-in: Before leaving her sales career, Cassandra methodically prepared for entrepreneurship: "I banked a lot of commission checks for over a year... We did a lot of nights and weekends where we got a co-working space and built out the wireframes, and we actually had people come in and give us feedback, like people that were our actual eventual users." This preparation reduced risk and validated market need.
Be willing to pivot your GTM approach: PartnerTap initially pursued a bottom-up strategy focused on sellers, but quickly realized they needed partner teams' buy-in first. "We thought we're just going to connect sellers with partner data without the partner team. We realized pretty soon that we had to build a whole other module and pivot the way we were selling," Cassandra explained. Recognizing when your initial GTM hypothesis is wrong and adjusting quickly is crucial.
Make core values actionable, not aspirational: Customer love is PartnerTap's core value, but Cassandra ensures it's lived daily through dedicated Slack channels recognizing team members who exemplify it. Their enterprise-focused success team delivers exceptional service, resulting in zero enterprise customer churn since founding—even through difficult market conditions like COVID-19. As Cassandra notes, "The kiss of death in SaaS is churn."
 
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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
 

James O'Brien, Co-Founder & COO of Ducky: $2.7 Million Raised to Build Internal Data Search for LLMs

Ducky AI operates as a pre-LLM compute layer, enabling businesses to make their proprietary data accessible to large language models without compromising security or privacy. In this episode of Category Visionaries, James O'Brien shares the journey of pivoting from a customer support solution to becoming a machine learning infrastructure tool that helps developers find and transform internal business data for optimal LLM consumption. With $2.7 million in funding, Ducky is positioning itself as the essential bridge between enterprise data and AI systems, making advanced AI capabilities accessible to technical teams without requiring extensive ML expertise.
 
Topics Discussed:
Ducky's evolution from a customer support solution to a developer-focused ML infrastructure tool
The validation process that led to identifying knowledge accessibility as a core market problem
How and why the team executed their pivot in just three months
The challenges of defining an ideal customer profile in the rapidly expanding AI space
Building a go-to-market strategy in Nashville's emerging tech ecosystem
Fundraising lessons learned during the SVB collapse
 
GTM Lessons For B2B Founders:
Listen when developers ask for your infrastructure: James discovered their true product-market fit when developers started requesting access to Ducky's knowledge retrieval infrastructure rather than their customer-facing application. "We had a revelatory moment where we realized that a bunch of developers had asked for access to our infrastructure, our knowledge retrieval infrastructure. And that's kind of what we're good at." This insight led to their pivot toward becoming an API-first tool that matched their technical strengths with the right audience.
Validation is a superpower: The Ducky team excels at gathering unbiased feedback from potential customers. When considering their pivot, they embraced this strength: "I think one of the things that we're best at as a team is validation. I think we're really good at drawing relatively unbiased... input and feedback from people that we're interviewing or talking to." For B2B founders, this emphasis on rigorous customer validation before building can be the difference between success and wasted engineering resources.
Make pivot decisions with data, not emotion: When considering a change in direction, Ducky time-boxed their exploration to three weeks, built multiple prototypes, and showed them to potential customers. "It was pretty clear after three weeks that one was not only a better use of our skills and time, but also a better market fit." B2B founders should approach pivots methodically, setting clear timelines and success criteria for validation.
Design pricing that aligns with value creation: James emphasizes usage-based pricing that fundamentally connects revenue to customer value: "If you use it and it works, you will use it more. And that means that we're doing our job. And that's awesome. That's all I ever want to do, quite frankly, is get paid for actually bringing value to people." This approach creates natural incentives for both the vendor and customer, unlike the multi-year contracts that often create misaligned incentives.
Look beyond AI hype to focus on business problems: James discovered that many companies have been tasked to "do something with AI" without clear objectives. "People are like, 'hey, we got to do something with AI,' but we don't know what that is. And then they think so deeply about, 'hey, how are we going to construct this?'" B2B founders should help customers cut through the hype by focusing on the underlying business value and specific problems to solve, rather than getting lost in technical details.
 
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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