Welcome to Category Visionaries — the show dedicated to exploring exciting visions for the future from the founders who are on the front lines building it. In each episode, we’ll speak with a visionary founder who’s building a new category or reimagining an existing one. We’ll learn about the problem they solve, how their technology works, and unpack their vision for the future.
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Justin Leigh, CEO of Workflow Labs: $3.5 Million Raised to Build the Future of E-commerce Management
Episode 700
Wednesday, April 16, 2025 • Duration 26:11
In this episode of Category Visionaries, we spoke with Justin Leigh, CEO of Workflow Labs, an e-commerce management platform that's raised $3.5 million in funding. After running a successful Amazon agency for 14 years, Justin identified a critical opportunity: replacing human-driven processes with automation at scale. Workflow Labs is automating e-commerce management tasks that brands traditionally outsource to agencies or offshore teams, allowing for better economics, faster resolution times, and predictable outcomes in managing product listings across platforms like Amazon.
Topics Discussed:
Transitioning from running a services-based agency to building a software product
The strategy of targeting partners who aggregate brands rather than selling to brands individually
How retail media networks are driving advertising dollars onto retailer platforms
The importance of having clear company objectives that everyone understands
Fundraising approaches for early-stage companies
Making the pivot from automation-focused messaging to comprehensive solution positioning
GTM Lessons For B2B Founders:
Partner with aggregators instead of selling one-by-one: Workflow Labs recognized that selling directly to individual brands would take too long to reach scale. Justin explained, "If we need to close 3,000 brands in two years, you're not going to do that selling them one by one." Instead, they identified partners who already worked with pools of brands—like ad agencies and supply chain providers—allowing them to sign up "tens, twenties, fifties, hundreds at a time."
Align with emerging market trends: Justin identified that retail media networks (Amazon, Walmart, Target) are where advertising dollars are shifting. He positioned Workflow Labs to support this trend: "We said as that shift continues, we support the product. If you're going to advertise a product, you better make sure their title's right, bullets are right, that it's in stock." B2B founders should identify major industry shifts and align their solutions with those trends.
Create market pull through RFP requirements: Workflow Labs uses a "push-pull method" by engaging directly with brands to influence their RFP requirements. Justin noted, "We work very hard to engage with brands directly and say...when you RFP for your advertising services, you better make sure your provider is providing an automated way to keep your products accurate." This creates demand that potential partners must satisfy, making partnership conversations easier.
Pivot based on customer feedback—even when it contradicts your assumptions: Workflow Labs initially thought customers would care about labor cost reduction but discovered their messaging wasn't resonating. Justin admitted, "We thought initially so many wrong things...When you went to the market and said, 'Hey, you have a 50-person team in India and all they're doing is updating titles, we can make 80% of that labor go away,' no one cared." They pivoted to position themselves as a comprehensive solution rather than just automation.
Establish clear, quantifiable objectives: Justin implemented the "rule of three"—focusing on just three key objectives per quarter. He shared a powerful insight about founder transparency: "If you want everybody in your company to row the boat in the same direction...be super clear around what your objectives are." This includes being upfront about exit goals: "Everyone on the team knows what happens when we get to 3,000 [customers], if we can get close to there...that's when liquidity events start to be on the table."
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Sloane Barbour, CEO & Founder of engin: $4 Million Raised to Transform AI-Powered Recruiting
Episode 699
Tuesday, April 15, 2025 • Duration 28:38
engin is pioneering AI-powered recruiting technology that addresses the fundamental inefficiency in the hiring process: 80% of time is wasted on interactions with candidates who will never move forward. With over $4 million in funding, engin is positioned at the intersection of recruitment marketing and automation, focusing on quality over quantity in an increasingly noisy job market. In this episode of Category Visionaries, we spoke with Sloane Barbour, who brings 15+ years of recruiting industry expertise to his role as CEO and founder. He shared insights on how engin is using AI agents to revolutionize the recruiting process for companies, staffing firms, and job seekers alike.
Topics Discussed:
The fundamental inefficiency in recruiting where 80% of time is spent on candidates who never progress
How traditional recruiting technology failed to address unstructured data like resumes and job descriptions
The impact of LLMs on recruiting technology's ability to contextualize unstructured data at scale
engin's strategic positioning shift from ATS to recruitment marketing and automation
The future of work and AI's role in transforming the labor market
GTM Lessons For B2B Founders:
Position where the pain and budget intersect: Sloane repositioned engin "up the funnel" from the commoditized ATS space to recruitment marketing and automation, where companies were spending 3x more and experiencing greater pain points. He explained: "Their problem was they were not talking to good people, they were not talking to relevant people, they were not talking to people quick enough." By addressing the quality issue rather than simply building "a better mousetrap in the ATS category," engin created 3x more value.
Founder-led marketing generates qualified leads: After experiencing diminishing returns from traditional outbound email campaigns, Sloane shifted focus to founder-led content and thought leadership. "Every time I post something that takes me 10 minutes to write up, you know, but maybe almost 20 years to be able to write that thought because of my experience in the space... it very clearly resonates with people." This approach generates higher quality meetings than traditional SDR-driven outreach.
Amar Amte, CEO & Founder of Pegbo: $1.4 Million Raised to Transform Construction Supply Chain Diversity
Episode 690
Friday, April 4, 2025 • Duration 25:42
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.
Pujun Bhatnagar, CEO & Co-Founder of Kintsugi: $8.2 Million Raised to Build the Future of Sales Tax Automation
Episode 600
Tuesday, September 24, 2024 • Duration 25:47
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 Pujun Bhatnagar, CEO & Co-Founder of Kintsugi, a sales tax automation platform that's raised $8.2 Million in funding.
Here are the most interesting points from our conversation:
Sales tax compliance on autopilot: Kintsugi simplifies the complex process of sales tax management, integrating with platforms like Shopify and QuickBooks to automate tax calculations, filings, and compliance with over 48 U.S. jurisdictions.
Post-2018 legal shifts created opportunity: The South Dakota vs. Wayfair ruling radically changed sales tax collection, sparking Pujun's idea for Kintsugi as businesses began grappling with new compliance challenges based on customer location rather than business headquarters.
Avalara's gap in the market: Pujun observed that incumbents like Avalara were slow to adapt to these legal shifts, leaving a gap for Kintsugi to fill with a more nimble, AI-driven solution.
Product-led growth through a seamless onboarding: Kintsugi's GTM strategy focuses on providing immediate value—offering users a self-service platform where they can onboard and see their tax liabilities in minutes, without lengthy sales interactions.
Building trust through transparency: To build trust in a sensitive area like taxes, Kintsugi offers detailed, auditable reports and a guarantee that covers penalties if errors occur. They focus on transparency and reliability.
Scaling fast with the right team: Pujun emphasized the importance of assembling a strong team, scaling from 3 to 47 employees in 10 months, and aiming for exponential growth, with a goal to 10x their revenue in the next 12 months.
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Jake Schuster, CEO & Founder of Gemini Sports Analytics: $7 Million Raised to Build the Future of Sports Analytics
Episode 599
Friday, September 20, 2024 • Duration 20:44
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 Jake Schuster, CEO & Founder of Gemini Sports Analytics, a sports analytics platform that's raised $7 Million in funding.
Here are the most interesting points from our conversation:
Gemini Sports Analytics enables data-driven decisions in sports: Jake identified a gap in the sports industry—where advanced data tools used in other sectors were missing. His platform empowers general managers and decision-makers at professional, collegiate, and Olympic teams to directly interact with data, helping them make informed decisions without needing data science expertise.
Sports management is decades behind in data sophistication: Jake highlighted how many sports organizations, run like overgrown family offices, lag behind Fortune 500 companies in using modern data tools. Private equity groups are starting to bring financial services-level sophistication into the sports industry, creating a market opportunity for Gemini.
Early product missteps helped shape Gemini’s current focus: The company's initial product was built for the wrong user, focusing too much on data scientists. Jake quickly pivoted, shifting focus to non-technical decision-makers who want direct access to insights without relying on analysts.
Pivots came from feedback and honest founder reflection: After six months of product discovery, Jake realized the market for the initial version wasn’t there. He emphasizes the importance of not being too stubborn, even when doggedly trying to make something work, and being open to necessary pivots.
Creating a new budget line item for teams is challenging: Jake shared that Gemini is pioneering a new workflow for sports organizations, which means teams must create new budget categories for the platform. He compares Gemini’s pricing to hiring additional staff to help teams understand the value.
Jake’s solo founder journey as a non-technical leader: As a non-technical founder, Jake turns his naivety into a strength by challenging his team to accomplish things without being limited by perceived technological constraints. He has built a strong engineering team to execute on his ambitious vision.
Jeremy Almond, CEO & Founder of Paystand: $100M Raised to Power the Future of B2B Payments
Episode 598
Friday, September 20, 2024 • Duration 26:32
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 Jeremy Almond, CEO & Founder of Paystand, a B2B payment network that has raised over $100 Million in funding.
Here are the most interesting points from our conversation:
Venmo for Enterprise: Paystand is a next-gen B2B payment network that saves companies millions of dollars by providing radically better economics, processing over $10 billion in payments and supporting around a million businesses.
Building Through Focus: Jeremy emphasized the importance of staying focused. Paystand's growth is attributed to a brick-by-brick approach, first targeting specific markets like Oracle and Microsoft ecosystems before expanding.
Scaling Milestones: Key company milestones were centered around unlocking the next stage of growth—from securing initial customers to making sales repeatable, and then scaling the business through focused enterprise sales strategies.
Blockchain Innovation: Paystand’s payment platform is powered by blockchain, offering instant, automatic payments at zero cost, without reliance on traditional systems like Visa or Mastercard.
Real Business Value, Not Blockchain Hype: While Jeremy is a believer in blockchain, he insists Paystand sells based on real value to customers, such as instant payments and reducing costs, not blockchain hype.
The Next 10 Years: Jeremy envisions a future where businesses use blockchain infrastructure, replacing legacy systems like Visa and Mastercard, ultimately creating more efficient, tax-free financial ecosystems for companies globally.
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Allen Narcisse, Founder & CEO of Gigs: $5.7 Million Raised to Build the Future of Blue Collar Hiring
Episode 597
Friday, September 20, 2024 • Duration 19:12
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 Allen Narcisse, Founder & CEO of Gigs, a blue collar hiring platform that has raised $5.7 Million in funding.
Here are the most interesting points from our conversation:
Combining Rigorous Data and Empathy: Allen shares how his experiences at Uber and Lyft influenced his approach to Gigs. By integrating Uber's data-driven rigor with Lyft's empathy for workers, Gigs aims to provide both high-tech solutions and compassionate user experience.
Empowering Job Seekers: Gigs addresses the issue of low engagement in job applications by empowering users with better job information. The platform focuses on providing detailed job descriptions, pay transparency, and location specifics to enhance job seeker engagement.
Marketplace Dynamics: Allen discusses overcoming the chicken-and-egg problem by initially focusing on job availability before job seekers. This approach ensures that job seekers have a meaningful number of opportunities upon joining the platform.
Creating High-Intent Job Seekers: Gigs aims to improve job matching by offering comprehensive job details that are often missing from traditional job boards. This strategy enhances job seeker readiness and improves the hiring process for employers.
Strategic Job Seeker Acquisition: Allen reveals how Gigs targets job seekers by focusing on specific job listings and their related data. This targeted approach not only optimizes user acquisition but also lowers customer acquisition costs (CAC).
Branding Strategy: The branding of Gigs is designed to stand out from traditional job boards. With a bold red color and minimalist design, Gigs aims to convey simplicity and friendliness, contrasting with the more corporate feel of existing job platforms.
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Hersh Tapadia, CEO of Allstacks: $16 Million Raised to Build the Value Stream Intelligence Category
Episode 595
Thursday, September 19, 2024 • Duration 22:50
In today's episode of Category Visionaries, we speak with Hersh Tapadia, CEO of Allstacks.
Topics Discussed:
An intersectional career between engineering and biomedicine, how Hersh found a career between disciplines
Stakeholder expectations, unexpected challenges and what ‘delivering’ really means
Solving the surprise issue, and why everyone wants to plan for an anticipated outcome
Harmony, building teams, and why individual accomplishment isn’t enough for success
Why value stream intelligence gives employees the tools to create a more satisfying, meaningful workplace experience
Itzik Alvas, CEO & Co-Founder of Entro Security: $24 Million Raised to Build the Future of Non-Human Identity Management
Episode 590
Tuesday, September 17, 2024 • Duration 13:37
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 Itzik Alvas, CEO & Co-Founder of Entro Security, a non-human identity management platform that has raised $24 Million in funding.
Here are the most interesting points from our conversation:
Military Experience Taught Perseverance: Itzik credits his time in the Israeli Defense Force, specifically in the cyber intelligence unit, for shaping his approach to perseverance. This has been crucial in overcoming challenges as an entrepreneur.
Non-Human Identity Management Innovation: After multiple cybersecurity breaches in his previous roles, Itzik identified a massive gap in managing non-human identities and secrets. This personal experience directly led to the creation of Entro Security.
Early Days Post-Seed Raise: The first few months after securing seed funding were highly operational—setting up offices, building the team, and finding early design partners to provide feedback on their solution.
Creating a New Market Category: Entro Security is pioneering the non-human identity management space, addressing the growing issue of programmatic credentials that are often mishandled by DevOps teams, posing significant security risks.
Unique, Memorable Branding: Unlike traditional cybersecurity companies, Entro’s branding is youthful, fun, and memorable, a conscious choice to stand out in an industry that often feels sterile and overly serious.
Go-To-Market Approach: Entro’s sales efforts are focused on direct sales and channel partnerships, with a primary focus on the US market. Itzik emphasizes the importance of aligning go-to-market strategies with event participation based on specific goals like lead generation or brand awareness.
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Ian Kalin, CEO & Co-Founder of TurbineOne: $22 Million Raised to Power the Future of Operational Intelligence
Episode 589
Tuesday, September 17, 2024 • Duration 34:55
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 Ian Kalin, CEO & Co-Founder of TurbineOne, a company revolutionizing operational intelligence that has raised $22 Million in funding.
Here are the most interesting points from our conversation:
Revenue Over Funding: Ian emphasized that while capital raised is important, his primary focus is on revenue growth, highlighting the importance of financial sustainability over just fundraising milestones.
Strategic Seed Extension: TurbineOne strategically executed a seed extension to secure additional capital while fine-tuning their market approach before moving to a Series A, showing the importance of timing and strategy in fundraising.
Importance of Accuracy: Ian stressed the importance of accuracy in financial reporting and fundraising details, reflecting the high stakes of credibility in investor relations.
Focus on Market Opportunity: Ian discussed the massive market potential in operational intelligence, positioning TurbineOne to capitalize on growing needs in sectors such as defense and emergency response.
Operational Challenges: The conversation touched on the operational complexities of managing advanced AI and machine learning tools, from data integration to real-time decision-making.
Customer-Centric Innovation: Ian shared how TurbineOne's product development is deeply customer-centric, driven by direct feedback and the specific needs of operators in high-stakes environments.
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Create transparent sales processes with clear metrics: From his experience managing 60+ salespeople, Sloane emphasizes establishing transparency and accountability from day one: "The number one most important thing is transparency of expectations... You have to have visibility into their performance on a daily basis." This includes tracking calls made, emails sent, and meetings booked. Without these fundamentals, scaling a sales organization becomes impossible.
Partner networks accelerate adoption during market transitions: A key component of engin's marketing strategy is its "robust partner network" with integrations and APIs that enable co-selling. Sloane noted this has been "super helpful for just kind of navigating this AI transition in recruiting and staffing together," allowing them to leverage existing relationships and platforms.
Strategic fundraising requires thesis alignment: Sloane learned to quickly identify misalignment with potential investors rather than pursuing exceptions: "If you're talking to people more than a call where thesis is off by more than 20%, meaning you're a seed, they're series A... I almost would rather just end the call, 15 minutes, keep them in the phone book for 18 months down the line." This approach prevents wasted cycles with investors unlikely to participate.
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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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