SaaS Interviews with CEOs, Startups, Founders

How do you pivot a banned college ridesharing app into a voice AI company handling 300 million customer service calls?
Brian Schiff is the co-founder and CEO of Flip, a verticalized AI voice assistant that automates customer service calls for transportation, retail, and healthcare brands.
After realizing their Cornell ridesharing app was a dead end, Brian and his co-founder Sam pivoted into voice AI. Today, Flip automates up to 90 percent of routine support calls for over 250 enterprise companies and recently raised a $20M Series A at a $100M valuation.
You'll learn:
How to successfully pivot a failing startup model
Why verticalized AI beats horizontal platforms
How to implement usage-based pricing at $1.50 per call
Why "listen mode" is their best sales tactic
How to maintain 75 percent gross margins with AI
Why they rejected a theoretical $150 million acquisition offer
How to select the right industries for expansion
Why competitive B2C markets are best for AI tools
Brian started his entrepreneurial journey at Cornell's eLab accelerator. He navigated the near-total collapse of transportation revenue during the pandemic to build a highly efficient business growing 3X year over year.


Watch this episode on YouTube: https://youtu.be/gtFt5exyCaI 
Connect with Brian:  https://flipcx.com/
Connect with Nathan:  https://founderpath.com/

How do you completely reboot a dying hardware startup, restructure a heavy cap table, and pivot into a SaaS product doing $15M ARR?
Dan Bladen is the co-founder and CEO of Kadence, a workplace operations system coordinating people and spaces for hybrid work.
After realizing his wireless charging startup was a "vitamin, not a painkiller," Dan pivoted during the pandemic to help companies like Nasdaq, Revolut, and Boeing manage their office space. Today, Kadence serves over 600 enterprise customers.
You'll learn:
How to manage board expectations during a hard pivot 
The exact mechanics of resetting a cap table for new investors
Why shifting from SMB to enterprise accelerated revenue
How they achieved over 130 percent net dollar retention
Why seat-based pricing still works in the enterprise
The math behind saving half a billion dollars in leasing costs
How launching SpaceOps AI drives multi-product expansion
Why high-ticket dinners replaced SEO for customer acquisition
Dan started his career managing technology for a church before founding his first IoT business. He moved his family to the Bay Area just before the pandemic forced him to rethink his entire company operations.
Watch this episode on YouTube: https://youtu.be/2ySF3YMDcnY

Connect with Dan: https://kadence.co/
Connect with Nathan: https://founderpath.com/

How do you build a construction SaaS to $2M in revenue with just $500K raised and get 95% of growth from SEO?


Hmayak Tigranyan is the founder and CEO of Buildern, a construction management software platform serving around 300 customers and generating roughly $2M in revenue today. The company helps residential and commercial builders manage finances and workflows, and it is doing about $160K in monthly revenue with roughly $40K in monthly profit.
What makes this business interesting is that it scaled in a legacy industry without paid acquisition or outbound. Buildern built an inbound engine around high-intent SEO, stayed profitable, and is only now adding a sales team as ACV moves closer to the range that can support quota-carrying reps.


You'll learn:
How Buildern found an underserved construction software niche.
Why Hmayak shut down a $3M dev shop to go all in on SaaS.
How the company raised just $500K and sold only 10%.
What $160K in monthly revenue looks like at a $40K profit level.
Why 95% of revenue came from SEO-driven inbound.
How Buildern chooses long-tail keywords in construction.
Why transparent competitor comparison pages rank well.
How internal SEO execution beat the need for an agency.
What changed once the company started hiring sales reps.
How pricing moved from roughly $6K ACV toward $7.5K to $8K.
What AE quotas and compensation look like at this stage.
How a profitable vertical SaaS company scales with a global team.


Hmayak came into Buildern after years in SaaS development, travel software, and running a dev shop that peaked at about $3M in annual revenue. He launched Buildern in 2021, spent the first two years without paying customers, then used industry-informed angels and product iteration to find the right shape of the product.
This episode is for founders building in old industries, operators trying to scale efficiently, and investors who care about profitable SaaS growth. It is a useful masterclass in vertical SaaS positioning, SEO-led demand generation, and disciplined capital use.


Watch this episode on YouTube: https://youtu.be/An0n18v4j8E 
Connect with Hmayak: https://buildern.com/ 
Connect with Nathan: https://founderpath.com/

How do you grow an AI phone system to 5,000 customers and roughly $3M ARR in under two years while still aiming for $10M in revenue this year?
Jeremy Goillot is the founder and CEO of The Mobile First Company, which launched Allo as its first product. Allo is an AI phone system and dialer for small businesses, now serving around 5,000 customers with average revenue above $160 per month and a goal of reaching $10M in revenue in 2026.
This business is interesting because Jeremy did not stop at a self-serve PLG motion. He started there, saw the churn and activation issues, then layered in demos, lead routing, CRM-based qualification, and expansion to raise ACV and improve retention. The result is a high-volume SMB SaaS business built on strong distribution, fast onboarding, and clear activation metrics.
You'll learn:
Why Jeremy moved from pure PLG to a sales-assisted motion.
How Allo increased average revenue from $18 to over $160 per month.
The exact activation metric that predicts churn.
How the team uses demo routing based on CRM and team size.
Why retargeting was one of the cheapest acquisition channels.
How Allo won SEO with long-form content and original screenshots.
The keyword prioritization system behind their content strategy.
Why 50% of new revenue now comes from expansion.
How the team thinks about CAC quality instead of lowest CAC.
Why Jeremy raised early without waiting for a co-founder.
How he kept about 50% ownership after raising around $20M.
What it takes to sell into SMBs at high volume with only 17 people.
Jeremy previously led growth at Spendesk before starting The Mobile First Company. He launched the company as a solo founder, raised a $5M pre-seed on his own, then built the team around him while keeping significant ownership. His long-term goal is not just one product, but a broader suite of vertical SaaS tools built under separate brands.
If you care about SMB SaaS, PLG versus sales-assisted growth, SEO-led distribution, or building a multi-product software company, this episode is a masterclass for SaaS builders.


Watch this episode on YouTube: https://youtu.be/PUZMvjyS3xw 
Connect with Jeremy: https://www.withallo.com/ 
Connect with Nathan: https://founderpath.com/

How do you turn $200K into a $9.7M ARR SaaS company with a $100M valuation by buying IP instead of building from scratch?


Joey Gilkey is the founder of TitanX, a sales intelligence platform generating $9.7M ARR after launching in 2024. The company serves enterprise sales teams with contracts ranging from $24K to $250K annually, with its largest deals exceeding seven figures.
What makes TitanX interesting is its approach to building a moat. Instead of competing as another data provider, the company sits between data sources and execution layers, using proprietary signals and AI to improve outbound performance. The business scales through high ACV sales, expansion revenue, and strategic acquisitions.


You'll learn:
How Joey turned a $200K IP purchase into a $100M company
Why buying IP can be faster than building SaaS products
How TitanX structures pricing from $24K to $250K ACV
The role of proprietary data in building defensibility
How inbound, outbound, and referrals drive pipeline
Why expansion revenue is core to growth strategy
How acquisitions accelerate ARR growth
The credit-based pricing model and consumption dynamics
How TitanX uses AI to improve outbound performance
The logic behind raising $27M and taking secondary cash
Joey started in enterprise sales before launching multiple businesses and eventually betting his entire net worth on TitanX. After acquiring the IP in 2023, he shut down a profitable services business to focus fully on SaaS, scaling from zero to $9.7M ARR in under two years.
This episode is for SaaS founders thinking about capital allocation, high-ACV sales, and building defensible data products. It's a practical breakdown of how to scale quickly using acquisition, pricing, and distribution strategy.


Watch this episode on YouTube: https://youtu.be/mxiCodnXo6U?si=zebVllHlOY7UlVqO 
Connect with Joey: https://titanx.io/ 
Connect with Nathan: https://founderpath.com/