SaaS Interviews with CEOs, Startups, Founders

Joey Gilkey, founder and CEO of TitanX and former enterprise seller, bought Phone Ready Leads IP and scaled it into a $9.7M ARR business. He discusses buying IP to move faster than building, the proprietary phone-intent signals and AI moat, high-ACV pricing and expansion-driven growth, and how strategic acquisitions accelerated revenue.

Grant Stanis, CEO of TeamSupport and a seasoned growth leader at private equity-backed software firms, breaks down scaling a B2B support SaaS to 1,000+ customers and $10M–$25M ARR. He discusses pricing per seat, turning support conversations into signals for retention and upsells, relying on referrals and webinars over SEO, expansion-driven revenue, and navigating private equity ownership and big-account dynamics.

Gary Guseinov, serial entrepreneur and CEO who rebuilt CyberDefender into RealDefense, grew it back from ~$7M to ~$70M using acquisition-led, debt-funded scaling. He describes buying back his company cheaply, integrating acquisitions into a shared platform, telemetry-driven just-in-time offers, and a pricing ladder that turns $20 entry products into high-LTV cross-sells.

Tal Kirschenbaum, Co-founder and CEO of Ledge, builds AI-native software that automates month-end close for mid-market and enterprise finance teams. He discusses narrow product focus, pricing tied to complexity (entities, currencies, integrations), growing to $1M+ ARR with ~24 customers paying ~$3K/month, and creating a moat with explainable, auditable AI for finance.

Jared Yaman, serial entrepreneur who scaled Boxed to $187M and spun out Spresso, now runs an enterprise ecommerce SaaS. He discusses converting low-margin retail tech into high-margin software. Topics include the bankruptcy-to-spinout journey, structuring $2M+ enterprise contracts, modular pricing with implementation fees, founder-led sales, debt limits under 10% ARR, and speeding deployments from months to weeks.

Ben Borton, co-founder of PodPlay and former investor/operator behind PingPod, turned venue software into a multi-million ARR vertical SaaS. He talks about validating software inside his own venues, per-court pricing and tiers, spinning the product out into a standalone company, raising an $8M Series A, and scaling to 200 locations and 2,000+ courts.

Ben Currin, CEO of Vantaca — who scaled a vertical HOA SaaS from bootstrap to ~$50M ARR — shares the company’s playbook. He explains finding “sneaky big” unsexy markets. He describes top-down sales into management companies, per-door pricing as the north star, expanding into payments and treasury, and using AI to boost billing, support, and operations.

Matt Spiegel, serial entrepreneur and former criminal defense attorney who founded Lawmatics after MyCase. He discusses scaling a legal CRM to $12M ARR, evolving pricing from low-touch plans to $5k ACV, niche customer acquisition via targeted ads and conferences, handling a cofounder transition and Series A dynamics, and building agentic AI that leverages millions of intakes.

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.