The Front Lines

Anagram is pioneering a new approach to security awareness that treats employees as assets rather than liabilities. With $10 million in funding, the company is reimagining how organizations address their most significant security vulnerability: human error. In this episode of Category Visionaries, we spoke with Harley Sugarman, Founder and CEO of Anagram, about his journey from venture capitalist to founder and how he's challenging decades of ineffective security awareness training with a human-driven security platform that drives real behavior change. Topics Discussed: The fundamental problems with traditional security awareness training How AI is amplifying attackers' capabilities and the need for better human defenses Anagram's approach to personalized, puzzle-based, and in-the-moment security training The shift from treating humans as "risks to be mitigated" to valuable security assets Founder-led marketing strategies in the security industry Pivoting from security professional training to broader security awareness GTM Lessons For B2B Founders: Identify opportunities where market perception doesn't match reality: Harley noticed a massive gap between what CISOs considered their biggest vulnerability (human error) and how they addressed it (outdated, ineffective training). "If you ask 100 CISOs where an attack will come from, 90-95 will say one of their people will click on a phishing link," yet solutions remained antiquated. This disconnect signaled an opportunity to create a truly differentiated product. B2B founders should look for areas where customer actions don't align with their stated priorities, as these represent prime opportunities for innovation. Frame your solution to break industry paradigms: Rather than accepting the industry framing of "human risk management," Harley positioned Anagram around "human-driven security" — shifting from seeing employees as liabilities to valuable assets. "I hate that framing so much because it puts the onus on the human," he explained. "What I have been trying to frame our company around is this idea of human-driven security, which is taking humans and making them a line of defense." This reframing helps differentiate Anagram from competitors and resonates more positively with both security leaders and end users. Use data to overcome status quo inertia: In industries with deeply entrenched practices, the biggest challenge is often skepticism about whether a new approach can actually work. Harley's solution? Let the data make the case. "For us, we are very insistent on looking at the data showing customers, 'Hey, before you introduced us, this is the number of incidents you were seeing. After you introduced us, this is the number of incidents you're seeing.' And I think that's ultimately the thing that changes minds." Data-driven results help overcome the "it's always been this way" mindset that can derail innovative B2B solutions. Employ a land-and-expand strategy for complex purchases: Anagram uses a methodical approach to win over skeptical buyers: "We very much take a land and expand strategy where we'll go in, augment a specific part of the program, show them that this is actually making a meaningful difference in the data, and then that becomes a very easy business case." For B2B founders selling complex or paradigm-shifting solutions, demonstrating tangible value in a limited implementation can pave the way for broader adoption throughout the organization. Don't dismiss "old school" outreach tactics: Despite the emphasis on modern marketing techniques, Harley found success with traditional outbound methods: "So far, it has been pretty much exclusively outbound. So emails, LinkedIn, cold calling...which still works, by the way. I was shocked." B2B founders, particularly those targeting enterprise customers outside the tech bubble, should remember that traditional outreach methods can still be highly effective even when they seem outdated in startup circles. Embrace personal branding with authenticity: After initially feeling uncomfortable with founder-led marketing, Harley found success by finding an authentic voice while taking inspiration from founders like PostHog's James Hawkins. "It does feel cringy. I hate most social media things... It was very much an intentional decision to step out of my comfort zone." By focusing on engagement metrics rather than personal comfort, Harley discovered that his personal content consistently outperformed company posts. B2B founders should measure the results of their personal branding efforts rather than judging them solely on comfort level. Know when to pivot quickly: Perhaps Harley's most critical decision was recognizing when their initial product wasn't gaining traction and pivoting decisively: "The biggest decision that we made was pivoting... I'm really proud of the fact that we very quickly made the decision to basically throw away all this work that we had done and move into this more general purpose awareness tool." B2B founders should be willing to abandon their original vision when market signals indicate a better opportunity, even if it means discarding substantial work.   //   Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   //   Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM     

Craig Letton has transformed the beverage industry's approach to marketing with hyble, a martech platform that has grown from under $1 million to nearly $20 million in annual revenue in just seven years. With only $8 million raised across three funding rounds, hyble has achieved remarkable capital efficiency while expanding from Scotland to become a global player serving major beverage companies worldwide. In this episode, Craig shares how his experience in the family print business led to identifying a critical need in the beverage industry: a solution that helps salespeople create high-quality marketing materials in minutes instead of days or weeks. Topics Discussed: hyble's evolution from a family print business to a global martech platform for the beverage industry How Craig identified a market need from personal experience in field sales The challenges and strategies of winning a contract with the largest wine and spirits distributor in the U.S. Why Craig relocated his life from Scotland to Boston after winning a game-changing contract The impact of changing consumption trends in the alcohol industry hyble's approach to growth through international expansion and adjacent verticals     //   Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   //   Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM     

Realtime Robotics is transforming manufacturing through AI-powered robotics automation, having raised $70 million to build a SaaS platform that enables system integrators to deploy robotic solutions in half the time with half the labor. In this episode of Category Visionaries, we sat down with Peter Howard, CEO of Realtime Robotics, to explore his journey from multiple successful IPOs to tackling one of manufacturing's most persistent challenges: making robotics deployment economically viable and operationally reliable. Topics Discussed: The evolution from hardware-based robotics solutions to cloud-based SaaS platforms Realtime Robotics' position within the product lifecycle management software category The gap between robotics hype and production reality in manufacturing environments Strategic pivots and market repositioning based on customer feedback and industry resistance The challenge of selling transformational technology to risk-averse manufacturing organizations Deterministic AI for robotics versus probabilistic AI for language models

  Persana AI is transforming how B2B teams handle go-to-market operations by unifying fragmented data sources and deploying intelligent agents to automate complex workflows. With $2.3 million in funding and a growing community of 6,000 sales professionals, Persana has evolved from a simple email personalization tool to a comprehensive agentic platform that helps companies identify, reach, and convert their ideal prospects. In this episode of Category Visionaries, we sat down with Rush Shahani, Co-Founder and CTO of Persana AI, an agentic platform that helps B2B teams move faster and close more deals by automating the most complex parts of go-to-market execution. Persana connects and reasons over hundreds of fragmented data sources — like CRMs, enrichment tools, hiring signals, and intent data — and uses LLM-powered agents to automate workflows such as prospecting, lead scoring, and sales outreach. What used to take sales and marketing teams weeks of manual work now happens in seconds, helping teams turn insights into action and convert pipeline faster. Rush is also the author of the upcoming book “LLM Reliability” with Manning Publications, where he shares practical strategies for making large language models dependable in real-world use cases — from reducing hallucinations to improving execution accuracy.   Topics Discussed: Persana's evolution from LinkedIn search platform insights to comprehensive B2B orchestration The shift from email personalization to predictive prospect identification and data unification How reinforcement learning creates customized AI models for each company's unique sales motion Building strategic partnerships with data providers to create a unified orchestration layer The company's approach to combating negative perceptions around AI SDR tools Persana's vision to become the operating system for all B2B go-to-market processes   GTM Lessons For B2B Founders: Focus on data quality over feature quantity: Rush emphasized that their breakthrough came when they realized "the moat wasn't in the personalization. The moat was actually being able to predict who is the right account to reach to, who are the right people to reach out to." Rather than competing on email generation features, Persana built their competitive advantage around superior data aggregation and intelligent prospect identification. B2B founders should prioritize building defensible moats around data quality and prediction accuracy rather than adding more surface-level features. Scale existing sales motions rather than replacing them: Persana takes a fundamentally different approach from typical AI SDR tools by focusing on amplifying what already works. As Rush explained, "We take your existing team's motion and then scale that to what you would have a team of 20 do." This approach preserves the human expertise and proven processes while automating the execution at scale. B2B founders should design AI tools that enhance and scale proven human workflows rather than attempting to replace them entirely. Build win-win partnership ecosystems: Persana's growth has been largely driven by strategic partnerships with data providers, where both sides benefit from the relationship. Rush noted, "You gotta think about how do you actually help your revenue, but you want to make sure they are getting the benefit of also being on Persana. We're giving them that visibility." Rather than viewing data providers as vendors, they created a partner ecosystem where each provider gains distribution and visibility through the Persana platform. B2B founders should structure partnerships as mutual value creation rather than transactional relationships. Leverage reinforcement learning for company-specific AI models: Unlike generic AI tools, Persana builds customized models for each client through reinforcement learning. Rush explained, "Through reinforcement learning we're actually able to take that data in. And as you continue using Persana, the more emails you send, the more outreach data we have... we're able to capture that data, make sense of it just for your company." This creates increasing value over time and stronger customer lock-in. B2B founders should consider how their AI tools can learn and adapt specifically to each customer's unique context and data patterns. Use community and social proof for organic growth: Persana has built a 6,000-person Slack community and leverages customer-generated content for growth. Rush noted, "There's some people that have made courses on how to use Persana that drives tons of traffic. So just building that organic ecosystem." They also created a certification program for GTM advisors who can sell Persana to their clients. B2B founders should invest in community building and enable customers to become advocates and educators for their platform.  

Ethos is revolutionizing training and education with their adaptive readiness platform, which transforms passive learning materials into interactive, engaging lessons. With over $34 million in funding, Ethos has expanded from elite athletics to serving 40+ Department of Defense customers across Air Force, Space Force, Navy, and Marine Corps, while also developing a substantial commercial presence. In this episode of Category Visionaries, I spoke with Sasha Seymore, Co-Founder of Ethos, about the company's journey from a basketball playbook solution to becoming a critical technology partner for military readiness and corporate training. Topics Discussed:   Ethos' evolution from a sports team training tool to a defense technology company The AI-powered platform that converts passive materials into interactive "Rosetta Stone-like" training experiences How Ethos reduced failure rates by 50% at military training facilities, saving millions The changing perception of defense tech in Silicon Valley Navigating the complex Department of Defense procurement system The critical need for modernizing military training technology Expanding from DoD contracts to commercial applications in life sciences and manufacturing Ethos' vision for creating comprehensive knowledge and competency mapping systems   GTM Lessons For B2B Founders: Cross-sector application thinking is powerful: Sasha and his co-founder identified how learning methodologies that worked in athletics could apply to military training and beyond. B2B founders should regularly explore how their core technology could create value in adjacent or seemingly unrelated sectors, as the principles that make a solution effective in one domain often translate to others when properly adapted. Leverage educational institutions' innovation programs: Ethos used Stanford's "Hacking for Defense" program to validate their solution with real military stakeholders, accelerating their entry into the defense sector. B2B founders should identify and participate in specialized innovation programs that connect startups with enterprise customers for rapid problem validation and relationship building. Traditional marketing doesn't work in non-traditional markets: For DoD sales, Ethos discovered that LinkedIn ads and conventional outreach failed; instead, credibility came from demonstrating excellence and leveraging senior advisors who understood the ecosystem. B2B founders entering specialized markets should identify the unique information channels and trusted sources that decision-makers rely on rather than applying standard marketing playbooks. Revenue split strategy between government and commercial: Ethos maintains a 70% DoD and 30% commercial revenue split, with plans to move toward 50/50. Their approach of proving technology in one sector before expanding provides multiple growth paths and resilience against market fluctuations. B2B founders should consider how maintaining presence in multiple sectors can provide both stability and expansion opportunities. Balance innovation with insider knowledge: When entering complex markets like defense, Ethos found success by pairing their innovative technology with advisors who understood the internal workings and procurement processes. B2B founders need both breakthrough products and industry-specific expertise to navigate specialized markets effectively.   // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM     

Atlas Invest is revolutionizing real estate financing as a marketplace connecting borrowers with institutional investors. With $13 million in funding, the platform provides an alternative to inefficient traditional lending models by offering borrowers quick, simple financing while enabling investors to access what Tal calls "the holy grail of asset classes" - real estate-backed bridge loans. In this episode of Category Visionaries, we sat down with Tal Shahar, CEO and Co-Founder of Atlas Invest, to discuss his journey from military special forces officer to venture capitalist to founder, and how Atlas is building a platform that delivers superior returns to investors while providing crucial financing for real estate developers. Topics Discussed: Tal's experience as an officer in Israeli special forces and how it shaped his approach to entrepreneurship The transition from venture capital at Deep Insight to founding Atlas Invest How Atlas addresses inefficiencies in real estate bridge loan financing through technology The platform's dual-sided marketplace connecting borrowers and institutional investors Atlas's ability to generate 12% net IRR for investors compared to traditional funds' 8% Strategies for building both sides of a marketplace business simultaneously The challenges of securing the first deals that validated the business model Atlas's approach to brand building and marketing experiments in the real estate space The evolving vision to become the go-to platform for all real estate financing needs   GTM Lessons For B2B Founders: Exercise disciplined due diligence in your own ventures: Before leaving his VC position, Tal created a comprehensive due diligence list and spent six months validating Atlas's potential during nights and weekends. B2B founders should apply the same rigorous validation processes to their own ideas that VCs would use, testing assumptions methodically before fully committing resources. Leverage market disruptions as entry points: Atlas launched during a period of rising interest rates when banks were pulling back from lending, creating an opportunity for new entrants. As Tal explained, "When we started Atlas, it was a crazy market environment... that actually enabled us to step into the market when each side was okay with us not having a lot of the other side." B2B founders should identify and exploit market dislocations that weaken incumbent advantages. Build marketplaces by continuously balancing both sides: Rather than solving the chicken-and-egg problem once, Atlas constantly rebalances supply and demand. Tal noted, "We're continuously balancing... Sometimes the challenging part is the deal flow, sometimes it's the investors. If it was always only one, maybe it's not the best product-market fit." The shifting nature of the challenge is actually a positive signal for marketplace businesses. Use white-glove service to win initial customers: For Atlas's first deals, personal relationships and exceptional service were critical. "It was a lot of white glove service... we're selling basically enterprise in a way," Tal shared. The team did "whatever it takes to win it, to make it successful." B2B founders should be prepared to deliver extraordinary service to early customers, especially in high-value transactions where trust is paramount. Test marketing channels empirically, not based on assumptions: Atlas discovered that LinkedIn performed poorly for their paid campaigns while Meta worked well, contrary to expectations for a B2B financial service. "I'm a big believer of not relying on our assumptions... always using data to make the decision," Tal emphasized. B2B founders should start with small tests across multiple channels, measure results objectively, and periodically retest channels that previously underperformed.     //   Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM       

SuperAnnotate is revolutionizing how companies manage their AI training data with a comprehensive infrastructure platform. Having raised over $53 million in funding, SuperAnnotate has evolved from a specialized algorithm for autonomous vehicles to a centralized data hub that enables enterprises to collaborate with multiple service providers and internal teams. In this episode of Category Visionaries, we spoke with Vahan Petrosyan, CEO and Co-Founder of SuperAnnotate, who shared his journey from PhD student to tech founder and unpacked his vision for creating what he describes as "a database for training data" - similar to Databricks but specialized for AI training data. Topics Discussed: SuperAnnotate's evolution from algorithm to comprehensive data labeling infrastructure The journey from academic research to founding a tech startup How an early contract with an autonomous driving company validated their solution The strategic pivot from competing with service providers to creating a collaborative ecosystem The transformation of their go-to-market strategy to create stickier enterprise relationships SuperAnnotate's focus on building a centralized training data platform for enterprise AI The importance of automation and "SuperAnnotate agents" for AI data operations How customizability has enabled SuperAnnotate to support diverse generative AI use cases   //   Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM   

Regal AI is revolutionizing the contact center landscape with its voice AI agent platform that's transforming how businesses communicate with customers. With $82 million in funding, Regal has positioned itself at the forefront of the AI revolution in customer service. In this episode of Category Visionaries, I spoke with Alex Levin, CEO and Co-Founder of Regal AI, about the company's journey from building tools to optimize human agent performance to pioneering voice AI agents that can handle customer interactions with unprecedented effectiveness. Topics Discussed: Regal AI's pivot from optimizing human agent calls to developing AI agents The economics of AI agents compared to human agents (10-20¢ per minute vs. $1 per minute) How AI agents achieve 97% containment rates versus the 20-40% traditional benchmark The challenges of enterprise sales in the contact center space The evolution of Regal's go-to-market strategy as AI capabilities have rapidly advanced The future of voice as the primary channel for brand engagement   GTM Lessons For B2B Founders: Timing your product evolution is critical: Alex emphasizes the importance of not moving too early or too late when pivoting to new technology. "If you invested too early, it was a waste, but if you wait too late then all the first trials with every company would be with another AI provider, not with us," Alex explains. Their decision to wait until LLMs were capable enough before focusing on AI agents prevented them from wasting resources on soon-to-be-obsolete technology while still allowing them to be early in the market. Enterprise sales requires embracing the process: When moving upmarket, Alex learned that trying to rush enterprise sales leads to poor outcomes. "If you try to rush it in an enterprise environment, which is possible, you're not going to have a good outcome," he shares. B2B founders should understand the sales timeline for their specific industry and be prepared for longer, more complex sales cycles when targeting enterprise customers. Build foundational technology that transcends AI hype: Regal's advantage came from building deep platform infrastructure before AI agents were ready. "Most of the companies that exist today, all they've ever built is this thing that interacts with the customer, the agent itself, the voice and the LLM, which is relatively trivial actually," Alex explains. By building integrations with customer data systems, decision engines, and channel management tools first, they created a more comprehensive solution that could quickly incorporate AI advances when the technology matured. Reconsider conventional marketing channels: Alex notes that traditional B2B marketing approaches are losing effectiveness: "A lot of the traditional channels that used to work just don't work or are not efficient anymore. So paid SEM, traditional sponsorships of online content, writing blog posts in some big paper... a lot of these demand gen channels are just highly ineffective." Founders should prioritize breaking through with authentic founder-led storytelling rather than relying solely on conventional demand generation tactics. The economics of AI can reverse long-standing business practices: Regal AI's solution flips conventional contact center wisdom on its head. As Alex explains, "Instead of calls being the most expensive thing you have, AI calls are the cheapest channel you have. So you lead with those calls and you do as many calls as possible because it's cheaper than any other channel." B2B founders should look for opportunities where AI fundamentally changes the cost structure of traditional business operations.   //   Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM     

Safire is pioneering advanced electrification solutions for defense applications, transforming how military operations are powered in austere environments. With $11 Million in funding and over $7 million in government contracts secured just this year, Safire is developing revolutionary technology to make batteries safer and more efficient for defense applications. In this episode of Category Visionaries, I spoke with John Lee, CEO and Founder of Safire, to learn about the company's journey from a core nanoparticle technology to a full suite of defense electrification products that are changing how soldiers operate in the field. Topics Discussed: Safire's revolutionary silicon nanoparticle technology that transforms lithium-ion batteries into "non-Newtonian fluids" that solidify upon impact The company's evolution from core R&D to developing multiple defense products, including tactical electric dirt bikes, battery-infused body armor, and deployable microgrids The process of securing government contracts and navigating defense appropriations The importance of building relationships with end users in the military and understanding their needs John's background as a Navy contracting officer and former head of government contracts at Palantir Safire's approach to brand development as part of their path to becoming a unicorn   GTM Lessons For B2B Founders: Put mission first to attract talent and customers: John's commitment to protecting lives became his driving force after his experience procuring counter-IED jammers that saved soldiers' lives. He explains, "I couldn't really do anything besides, whatever I do, I want to help protect and save lives." This clear mission has helped him attract talent, customers, and investors who share this vision, demonstrating how a compelling purpose can accelerate GTM efforts. Listen to customer needs before defining your product roadmap: Rather than forcing a single-product strategy, Safire let customer requirements guide their development. As John noted, "We really focused on customer first. And if the customer said, I want you to be just one product company... that may have been okay. But that's not what the customer was asking for." By building solutions to address real military needs, Safire has secured multiple contracts across different applications. Use government R&D contracts as a runway to production: Safire strategically leveraged Small Business Innovation Research (SBIR) contracts to fund their early development while creating a path to larger production contracts. John advises, "It's really important to understand... all the effort it takes to go from the R&D contract into production into program of record and [to] prepare for it." He warns against the "if I build it they'll come" mentality that leads many startups to fail. Invest in lobbying early for long-term ROI: The company prioritized hiring lobbyists immediately after raising their seed round. John revealed, "The $4.5 million contract that we just got awarded last month came from our lobbying efforts... from two and a half years ago. And that was the very first third-party payment I was making as soon as we raised our seed round." This demonstrates how early investment in government relations can deliver substantial returns for defense tech companies. Brand sophistication matters in defense tech: Breaking with industry norms, Safire invested significantly in professional branding before their Series A. John explains this decision: "Every unicorn status company had a great brand before they became a unicorn status company... When we're walking through four-star generals and three-star generals into our offices, into our skiffs... we want to be trusted and we also want to be seen as a sophisticated, responsible contractor." This approach has helped them stand out in an industry where branding is often neglected.   //   Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.  www.GlobalTalent.co   // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM   

Cloverleaf AI is revolutionizing how companies access and leverage public government meeting data, turning hours of meandering discussions into actionable sales intelligence. With $3.5 million in funding, the govtech startup helps enterprises identify early-stage opportunities in state and local government contracts by applying AI to analyze thousands of public meetings. In this episode of Category Visionaries, I sat down with Jeremy Becker, Co-Founder and Chief Revenue Officer of Cloverleaf AI, to explore how his childhood experiences attending local government meetings with his father inspired a solution that's changing how businesses engage with government procurement. Topics Discussed: How Cloverleaf AI uses machine learning to extract valuable insights from public government meeting recordings The challenges of finding and tracking government opportunities without AI assistance Why state, local, and education (SLED) markets represent their strongest differentiator The impact of federal deregulation on state-level government contracting opportunities Cloverleaf's successful pursuit of enterprise clients, including a recent deal with one of the world's five largest companies GTM Lessons for B2B Founders: Focus relentlessly on your beachhead market: Jeremy identified choosing government contracting as their sole focus as their most critical decision. "We tried to boil the ocean...but you just limit yourself so much in what you can learn about your process and how much more repeatable you can get with things if you get smaller." Initially targeting multiple verticals (government affairs, government contracting, political strategy), Cloverleaf found its sales velocity was 5x higher in government contracting than other segments. Translate technical capabilities into customer-centric language: Cloverleaf struggled initially with messaging until they shifted from generic promises like "we'll drive revenue" to more relationship-focused language that resonated with their audience: "Government sales are about building relationships and being proactive. Let us help you get into the room a little bit earlier." This translation of technical capabilities to customer-centric outcomes was crucial for market penetration. Leverage unique data assets in your marketing: Rather than generic content marketing, Cloverleaf uses its proprietary government meeting data to deliver unique insights and analysis that potential customers can't get elsewhere. Their strategy of offering free licenses to journalists and educational institutions creates organic distribution channels while building credibility through third-party validation. Conduct thorough procurement discovery upfront: After a 16-month sales cycle with a major enterprise client, Jeremy emphasized the importance of procurement discovery: "Always better discovery, specifically better procurement discovery from the start would have been a pretty big game changer." Understanding organizational structures, decision-makers, and internal processes early prevents "false summits" where you think the deal is closing only to discover new layers of approval. Validate market selection with sales velocity metrics: When deciding which market to focus on, Cloverleaf analyzed their existing client base using sales velocity (combining cycle time and deal size) rather than looking at individual metrics in isolation. This comprehensive view revealed that government contracting opportunities closed 5x faster than government affairs deals, providing clear direction for their go-to-market strategy.   //   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