Founder Files

What does it take to build and scale SaaS in one of the toughest industries to break into — healthcare?

Sarah Worthy, CEO & Founder of DoorSpace, shares her journey from enterprise tech into healthcare HR, where she saw a massive opportunity to modernize licensing, credentialing, and continuing education for clinicians.

Topics include:

– Why inspiration alone isn’t enough — market opportunity is everything

– The biggest mistakes founders make trying to scale too early

– How to measure what matters (and what not to obsess over)

– The truth about AI hype and why data ops matter more

– How to sell SaaS into slow-moving, regulated industries like healthcare

💡 New episodes drop every Tuesday at 7 AM EST.

Jess Reagan, Co-Founder & CRO at Paiv, went from leading $200M in solar sales to building a sales enablement platform for the trades.

He opens up about moving from corporate to startup life, why founder-led sales matters, and how fractional CFOs shaped Paiv’s fundraising story.

Hosted by ⁠⁠⁠⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠⁠⁠⁠.

Topics include:

— Founder-led sales vs. hiring early

— Why grit and soft skills beat résumés

— Using fractional CFOs to raise capital

— Building for underserved industries like roofing and pest control

— Balancing family life with the founder journey

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠

Sergey Sundukovskiy, Ph.D., Co-founder, CTO & CPO of Salesmsg, shares how a mid-market texting platform scaled from a handful of employees to 75 across 12 countries — while pioneering AI in customer communication.

From generative AI that drafts messages to voice cloning and sentiment analysis, Salesmsg “textizes” entire businesses.

Lessons on building remote-first teams, balancing product vs. tech as a founder, and defining success in SaaS.

Hosted by ⁠⁠⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠⁠⁠.

Topics include

— Using AI for generative messaging, sentiment, and voice cloning

— Building remote-first teams across time zones and cultures

— Scaling from 2 to 75 employees in five years

— Why mid-market businesses are the sweet spot for SaaS growth

— The future of SMS vs. RCS in business communication

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher

Noel-Edouard Chenu, Founder & CEO of Boundless Digital, joins Founder Files to share how a lean, bootstrapped team is scaling in the enterprise world by simplifying Cisco’s complexity.

From why outbound sales fell flat to how inbound content and Cisco partnerships drive growth, Ned explains the GTM strategy that actually works for enterprise buyers.

He also dives into Boundless’ approach to AI—using it to supercharge sales and development, not replace people—and the financial metrics he tracks to keep the business sustainable.

Hosted by ⁠⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠⁠.

Topics include:

— Why enterprise buyers ignore outbound, and what attracts them instead

— Building on Cisco’s APIs to simplify global network operations

— Using AI for sales call analysis and dev productivity (without layoffs)

— Staying bootstrapped and why it speeds decision-making

— The 3 financial metrics Ned tracks most closely: cash flow, product margins, and deal size growth

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠Talk to Cypher

Ben Nowlan, CEO of Sherpa, joins Founder Files to share what a decade building one of Australia’s largest last-mile delivery networks has taught him about focus, financial discipline, and competing with giants like Uber.

From avoiding the “early adopter trap” to tripling lifetime value in just four months, Ben reveals how Sherpa scaled without losing its core value proposition — and why founders should obsess over the right metrics from day one.

Hosted by ⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠.

Topics include

— How to survive the early adopter plateau and find new growth segments

— Why sticking to your core value prop beats chasing competitors

— The financial metrics that actually matter for sustainability

— Turning a business around through automation and AI

— Competing against global players with a local edge

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠⁠⁠⁠

Jon Ricketts, Founder & CEO of EKOM AI, joins us to explore how AI is reshaping the e-commerce stack.

From SEO shifts to the rise of autonomous software, Jon shares how EKOM AI helps brands optimize discoverability and reduce manual work.

Hosted by ⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠.

Topics include:

– Algorithm updates, AI search, and why product data matters

– Why paid marketing is broken and how to win with organic SEO

– Jon’s founder lessons on growth, churn, and go-to-market

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠Talk to Cypher

Svitlanka Sergiichuk, Co-founder & CEO at Neofin, joins Founder Files to share how they built a global lending platform without venture capital. Instead of raising early, Neofin scaled with revenue, partnerships, and process.

Hear how Neofin uses LLMs to streamline underwriting, localizes in 3 days, and sells to multi-country lending groups, all while staying lean.

Hosted by ⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠Cypher⁠⁠⁠⁠.

Topics include

– Choosing revenue over VC

– Partnering with MasterCard, AWS, and Equifax

– Going global from Eastern Europe

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠Talk to Cypher

Omri Mor, CEO of Routable, joins Founder Files to share how building smarter financial systems can reduce risk, increase speed, and scale your ops without breaking your backend.

Routable helps mid-market and enterprise companies streamline vendor payments, sync cleanly with ERPs like NetSuite, and prevent fraud before it starts — all while keeping auditors happy.

Hosted by ⁠⁠⁠Salma Hatim⁠⁠⁠, Founder & CEO of ⁠⁠⁠Cypher⁠⁠⁠.

Topics include:

– Why 77% of enterprises struggle with real-time ERP data

– How Routable built a 99.8% sync rate with NetSuite

– The role of AI in vendor fraud detection and payment confidence

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠Talk to Cypher

Weston Baker, Founder & CEO of Morphic, joins Founder Files to share how his team turned a creative agency into an AI-powered website platform by doing one thing differently: building systems first.

Hosted by ⁠⁠Salma Hatim⁠⁠, Founder & CEO of ⁠⁠Cypher⁠⁠.

Topics include:

– Turning creative agency roles into modular AI agents

– Bootstrapping without slowing growth

– Why early funding can shrink your outcome

– What founders should automate and when

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠Talk to Cypher

Justin Clements, Co-founder of Pest Share, joins Founder Files to share how his team turned their legacy pest control experience into a subscription-based SaaS platform powering on-demand services for the rental market.

You’ll learn how Pest Share became the “Uber for pest control,” reduced service costs by 70%, and scaled impact with AI — all without technical founders at the helm.

Hosted by ⁠⁠Salma Hatim⁠⁠, Founder & CEO of ⁠⁠Cypher⁠⁠.

Topics include:

– Turning domain experience into software

– Building tech as a non-technical founding team

– How to structure lease-based subscriptions

– When to raise VC and how to vet your investors

– Using AI to boost LTV and reduce headcount

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠Talk to Cypher