SaaS Interviews with CEOs, Startups, Founders

Siddharth Sinha, co-founder and CEO of Dresma, builds an AI platform for studio-quality, localized e-commerce imagery. He discusses usage-based pricing tied to content volume. He explains studio partnerships driving over half of revenue. He covers AI model costs, programmatic SEO with free tools, and scaling enterprise accounts to ~$500K annually.

Raf Howery, the founder and CEO of Kukun, shares his journey scaling a property data platform for banks and fintechs while staying bootstrapped. He reveals how Kukun grew to nearly $5M ARR with just two sales reps and a unique dual monetization strategy. Raf discusses leveraging product-led growth to drive enterprise adoption and the importance of bundling products to increase average contract value. He also touches on navigating funding with minimal dilution and how a consumer-facing experience effectively attracts enterprise clients.

Gabriel Ciordas, founder and CEO of Flipsnack, shares his journey of scaling a digital publishing platform to $15M ARR with 28,000 customers, all without VC funding. He details how mastering SEO and self-serve onboarding has driven organic growth. Gabriel discusses the unique dual pricing strategy—ranging from $16/month for self-serve to $200,000/year for enterprise clients. He also reveals insights on managing a small team for SEO, balancing high-ACV enterprise deals with low-touch sales, and plans to reintroduce a freemium model.

Scott Davis, President and co-founder of Volley, has taken his communication platform for automotive BDCs from just four customers to over $14M a year without external funding. He discusses the intricacies of selling to car dealerships, emphasizing this niche's untapped potential. Scott breaks down creative pricing strategies and shares insights on maintaining profitability and an efficient sales structure. He also delves into future growth plans, including the impact of AI, and his thoughts on a tempting $70M acquisition offer.

Sabari Nair, co-founder and CEO of Skillveri, shares his journey scaling a VR vocational training platform to $1.5M ARR, now serving over 100 schools. He discusses how a shift from hardware to SaaS and immersive training is revolutionizing skilled labor education. Sabari reveals the secret behind their $350K contracts and how reseller partnerships outperform direct sales. With a roadmap for $10M ARR and a unique hybrid revenue model, he highlights the importance of demos and objective skill grading in a competitive market.

Join Andrew Fennell, founder of Standout CV, as he shares how he built a successful resume builder that pulls in millions of visits—without any employees! He discusses his SEO-driven strategies, revealing how content can outperform ads in competitive markets. Andrew dives into the shift from one-time payments to subscription models that skyrocketed his revenue. He also shares clever tactics for reducing churn and maximizing lifetime value, alongside effective digital PR campaigns that landed him major media coverage. A must-listen for aspiring SaaS entrepreneurs!

Vlad Malanin, a surgeon-turned-AI scientist and co-founder of SpeedSize, shares his journey scaling an AI media optimization SaaS from $400K to $6M ARR with only 25 employees. He discusses how SpeedSize helps brands maintain image quality while boosting performance and the importance of a partnership-led go-to-market strategy. Vlad reveals the challenges he faced during wartime, including dwindling cash reserves and tough founder decisions. Discover his insights on capital efficiency, enterprise pricing, and the path to retaining founder control while navigating growth.

Romain Torres, founder of ArcAds.ai, rapidly scaled his AI-driven video ad platform from $5K to $10M ARR in just 20 months without outside funding. He shares how he validated demand pre-product and the viral tweet that skyrocketed signups. Key growth engines discussed include paid ads, influencer marketing, and sales hiring, alongside challenges like product failures that led to refunds. Romain delves into usage-based pricing and the importance of retaining customers despite initial churn, emphasizing a product-first approach in a noisy market.

Jason Pearsall, Founder and CEO of Club Caddie, scaled his vertical SaaS ERP for golf courses from $450K to $9M ARR in just five years. He shares his journey of building a tailored product to solve real operational issues and highlights the power of data-driven strategies like SEO and AEO for market penetration. The discussion dives into the intricacies of structuring his acquisition by Constellation Software, emphasizing the value of long-term earnouts. Plus, he reveals insights on effective targeting and nurturing relationships in a niche market.

Callum Mckeefery, a bootstrapped SaaS founder, scaled Reviews.io from his kitchen table to an impressive $82M exit. He discusses the power of viral loops and how he achieved $12M ARR without giving equity to staff, rewarding them in other ways instead. Callum candidly shares how his son's rare genetic condition influenced the timing of the sale and his new venture, Partner.io, aimed at enhancing partner tech. He also reflects on post-sale challenges and the emotional journey behind his success.