The SaaS Podcast: How B2B SaaS & AI Founders Get Customers

By Omer KhanBusiness Entrepreneurship Technology

The SaaS Podcast: How B2B SaaS & AI Founders Get Customers episodes

May 31, 2023SaaS Product-Market Fit: 5 Founders Share What Worked
What if the fastest way to SaaS product-market fit was to walk into a train station and start asking strangers questions? That is exactly what Jeremy King did before building Attest into an eight-figure ARR business.
Five SaaS founders share hard-won lessons on customer discovery, product quality, monetization, and finding product-market fit - including Rahul Vora's product-market fit engine that helped Superhuman grow after two years of coding with no launch. Learn how to achieve SaaS product-market fit whether you are validating a new idea or measuring traction in an existing product.
Featured founders: Jeremy King (Attest, $1M ARR in 8 months), Melissa Kwan (eWebinar, $750K ARR bootstrapped), Christian Owens (Paddle, nearly $100M ARR), Trevor Kaufman (Piano, $80M ARR), and Rahul Vora (Superhuman, $125M+ raised).
Key Lessons
🎯 Validate by going to customers physically: Jeremy King interviewed 200 consumers at Waterloo Station before building Attest, proving demand existed beyond corporate research departments.
🛠️ Deep product experience beats surface research for SaaS product-market fit: Melissa Kwan did 1,000+ webinars before building eWebinar, knowing exactly what the product needed.
💰 Monetize from day one to compound growth: Christian Owens built every business to make money immediately, using revenue to reinvest rather than chasing distribution first.
📉 Conviction under pressure is not failure: Trevor Kaufman sold his house to keep Piano alive through years of market rejection before reaching $80M ARR.
🔄 Use the 40% benchmark for SaaS product-market fit: Rahul Vora's product-market fit engine asks users "How would you feel if you could no longer use the product?" and targets 40% answering "very disappointed."
Chapters
Introduction and episode overview
Preview of the five founder clips
Jeremy King - Attest: Zero to $1M ARR in 8 months
How Jeremy validated demand through customer discovery
Why Jeremy did the research for free
Overcoming skepticism from store managers
Melissa Kwan - eWebinar: Two years of building in silence
Why Melissa refused to launch before the product was ready
The cost of a bad first impression on early adopters
How 1,000+ webinars gave Melissa deep problem understanding
Managing competition anxiety while bootstrapped
Financial projections as the real urgency driver
Christian Owens - Paddle: Pragmatism and monetizing from day one
How Christian approaches SaaS product-market fit incrementally
Every business must be a real business from day one
Trevor Kaufman - Piano: Selling his house to survive
The belief that kept Trevor going through market rejection
Rahul Vora - Superhuman: The Product Market Fit Engine
How Sean Ellis's research inspired the PMF Engine
The four steps of the Product Market Fit Engine
Closing thoughts
Resources
Full show notes: https://saasclub.io/357
Join 5,000+ SaaS founders: https://saasclub.io/email
45 min
May 18, 2023SaaS Positioning: One Customer for 2 Years to $1M ARR
Thomas Kunjappu spent two years building for just one customer. Then he had to figure out how to sell his SaaS positioning to the rest of the market - without a real website, a sales team, or a category anyone understood.
Learn how Cleary evolved its SaaS positioning three times - from "external internal tools team" to "employee experience platform" to intranet replacement - and why having Square as a big-name logo almost hurt more than it helped in enterprise sales meetings. Thomas shares the services to SaaS transition, category creation lessons, and how referrals outperformed every paid channel.
Cleary crossed $1M ARR, raised $7.5M, and serves companies like DoorDash and Scale. The SaaS positioning breakthrough came when Thomas identified the chief people officer as the primary buyer persona.
Key Lessons
🎯 SaaS positioning evolves through customer conversations: Thomas shifted Cleary's positioning three times, simplifying each iteration based on what resonated with buyers in the enterprise sales process.
🤝 Pre-meetings transform enterprise sales outcomes: After a disastrous 20-person demo, Thomas learned to hold one-on-one meetings with key stakeholders first so they champion the deal.
📉 A big-name logo is not a sales shortcut: Pitching "don't you want to be like Square" backfired because every prospect saw their company as fundamentally different.
🏢 Services-first validates before you build SaaS: Cleary worked as a services provider for Square for two years, retaining the IP while validating with real usage.
💰 Re-segmenting beats category creation for faster revenue: Thomas realized Cleary was replacing existing intranet and onboarding budgets, not creating net-new spend.
Chapters
Introduction
Thomas's favorite quote and the obstacle is the way
What Cleary does and the employee experience platform
SaaS positioning challenges and the intranet comparison
How the idea was born at Twitter
Landing Square as the first customer
Enterprise decision-making with three budgets at Square
Bootstrapping the first two years without fundraising
Challenges of building a custom solution for one customer
Forking the codebase and transitioning to SaaS
Ending the services relationship with Square
Timeline from customer one to customer ten
The pandemic's impact on growth
Enterprise sales lessons and the 20-person room
Why keeping sales meetings small matters
Evolving SaaS positioning from services to employee experience
Category creation vs re-segmenting an existing market
Growth channels beyond referrals
The sales process from discovery to close
Enterprise sales cycle timelines
What growth channels failed and why
Lightning round
Resources
Full show notes: https://saasclub.io/356
Join 5,000+ SaaS founders: https://saasclub.io/email
53 min
May 11, 2023Free Trial Conversion: 70% Close Rate Framework
John Li had 1.5 months of runway when he launched Vimcal. He jumped on SaaS onboarding calls with every user, pitched a $15 subscription at the end, and achieved 70% free trial conversion. One user offered a $5,000 investment check instead.
Learn the 4-step onboarding call framework that drove this free trial conversion rate: tease with keyboard shortcuts, deliver the magic moment (drag-to-schedule), stack top features while excitement peaks, then close. When users matched Vimcal's qualifying profile, the SaaS conversion rate exceeded 90%.
Vimcal grew from near-death to a nine-person team targeting $1.5M ARR. John also shares the waitlist strategy that filtered tens of thousands of signups down to 20%, and why dropping the waitlist and onboarding calls simultaneously caused six months of stalled growth.
Key Lessons
🛠️ Design onboarding around one magic moment for free trial conversion: Vimcal's drag-to-schedule feature cut scheduling from 77 clicks to 8, flipping a mental switch that made users receptive to everything after.
🎯 Qualify users before onboarding to maximize conversion: Vimcal's Typeform filtered signups to 20% by asking about apps used and meeting volume. Matching the ideal profile converted at 90%+.
🤝 Use onboarding calls as a dual conversion and fundraising vehicle: John pitched $15 subscriptions on every call, but investors on those same calls wrote checks that saved Vimcal during COVID.
📉 Never remove your waitlist and free trial conversion calls at the same time: Dropping both gates on launch day stalled growth for six to eight months.
🚀 Capture referrals during the half-life of excitement: Vimcal asks users to share within the first day after their onboarding call, when enthusiasm peaks.
Chapters
Introduction
John's favorite quote and background
What Vimcal does and who it serves
From augmented reality to fitness to calendar
Launching with 1.5 months of runway
Revenue and team size today
Waitlist strategy and qualifying users
Typeform design and qualifying questions
Friction as validation in the waitlist
Competing with free calendar apps
Slots and time travel features
Keyboard shortcuts and speed
Replacing Calendly, Doodle, and other tools
Early buzz and Twitter traction
Growth slowdown after removing waitlist
Contingency planning on his 30th birthday
Lessons from dropping waitlist and calls together
The 4-step onboarding call framework
Summary of teaser, magic moment, milking, close
Built-in virality and referral system
Hiring friends and lessons learned
Vimcal Maestro for executive assistants
Lightning round
Resources
Full show notes: https://saasclub.io/355
Join 5,000+ SaaS founders: https://saasclub.io/email
48 min
May 04, 2023SaaS Growth: How JotForm Scaled to 20M Users
Aytekin Tank was helping millions of people automate their work while doing everything manually himself. When Google launched a competing product, he realized SaaS growth depended on applying his own automation principles to his business.
In this episode, the JotForm founder walks through the six-step Automation Flywheel that powered scaling SaaS operations from a solo project to 20 million users and 500 employees - all while maintaining 50% annual SaaS growth. Learn how 3,000 Gmail filters replaced Inbox Zero, CI/CD lets new developers ship code on day one, and automated HR onboarding eliminated missed documents.
JotForm has maintained bootstrapped SaaS growth for 17 years across seven cities, proving that SaaS automation compounds faster than headcount.
Key Lessons
🚀 SaaS growth starts with automating what you hate: Aytekin was doing everything manually while selling automation tools to customers. Applying his own principles freed time for product work.
🧠 Adopt an automation-first mindset for faster SaaS growth: Refusing to repeat manual tasks builds compounding systems that accelerate scaling SaaS over time.
📉 Audit your workday before buying any tool: Hourly time tracking for one week reveals which tasks consume time unnecessarily, creating a prioritized automation roadmap.
⚡ CI/CD eliminates the scaling bottleneck in product development: JotForm moved from six-month releases to continuous deployment, letting new developers ship on day one.
🔄 Treat automation as a flywheel, not a one-time project: Six steps (Divide, Conquer, Design, Implement, Refine, Iterate) compound productivity gains with each cycle.
Chapters
Introduction
Aytekin Tank returns after five years
JotForm SaaS growth update: 20M users, 500 employees, 50% revenue growth
Why Aytekin wrote Automate Your Busywork
The origin story: hating manual form creation
Competing with Google and the automation wake-up call
No-code tools making SaaS automation accessible
Main themes in the book: automation-first mindset
The Automation Flywheel overview: six steps in three pairs
Divide and Conquer: auditing your workday and mapping workflows
Design and Implement vs. Refine and Iterate
Managing thousands of automations without losing control
Gmail email automation with 3,000 filters
Automating product development with CI/CD
Building your own tools vs. buying best-of-breed
Automating HR onboarding with JotForm
How the onboarding automation workflow works
Advice for founders getting started with automation
Book details and closing
Resources
Full show notes: https://saasclub.io/354
Join 5,000+ SaaS founders: https://saasclub.io/email
49 min
April 27, 2023SaaS Product Validation: 100 Interviews Before Code
Brandon Foo spent four years building his first startup only to realize nobody needed it. The second time, he flipped the playbook - running SaaS product validation through 100+ customer interviews and charging $30 via Stripe before writing a single line of code.
Learn how Paragon used iterative SaaS product validation to pivot from a Firebase-like backend to an embedded integration platform, then scaled to millions in ARR with $16M in funding. Brandon shares the sell-before-you-build strategy, finding product-market fit through customer discovery, and why LinkedIn ads became his best B2B growth channel.
Paragon now serves 100+ customers with 90+ pre-built integrations, helping software companies connect with Salesforce, Slack, and HubSpot without building from scratch.
Key Lessons
🎯 Sell before you build for faster SaaS product validation: Brandon got customers to pay $30 via Stripe before writing code, proving demand without months of wasted development.
📉 A nice-to-have product kills growth even with great UX: Polymail had tens of thousands of users but was a $5-$10/month app with no urgent pain point.
🔄 SaaS product validation means finding what people don't want first: Paragon's initial idea was invalidated through customer discovery, but those same conversations surfaced the real opportunity.
💰 Raise prices iteratively to test willingness to pay: Starting at $30, then $50, then $100 measured how serious the pain point was at each level.
🚀 LinkedIn outperforms other paid channels for B2B acquisition: After iOS 14 killed Facebook/Instagram targeting, LinkedIn became Paragon's most consistent growth channel.
Chapters
Introduction
Brandon's favorite quote (Confucius on living fully)
What Paragon does and who it serves
Company metrics: ARR, team size, $16M raised
Polymail: lessons from Brandon's first startup
How the idea for Paragon originated from integration pain
Why Brandon validated before building this time
Figuring out the ICP through iterative customer discovery
Iterative pricing: from $30 to validating real demand
The pivot from Firebase-like product to integrations
Sell before you build: getting credit cards before code
The Tesla Cybertruck analogy for pre-sales
Initial go-to-market strategy and early traction
LinkedIn ads as the primary B2B growth channel
ABM approach and content-led funnel on LinkedIn
Customer onboarding and integration setup
Scaling from founder-led to team-driven organization
Lightning round
Resources
Full show notes: https://saasclub.io/353
Join 5,000+ SaaS founders: https://saasclub.io/email
53 min
April 20, 2023Enterprise Sales: Services to $1M/Yr Contracts
Neha Sampat bootstrapped a services agency side project for 11 years before spinning it out as a standalone enterprise SaaS company - then raised $169M and grew enterprise sales contracts from $250/month to over $1 million per year.
If you want to understand how to transition from services to enterprise sales and close Fortune 1000 deals, this episode walks you through the entire journey - from building an internal tool to winning enterprise sales with brands like Chase, Asics, and Mattel.
Contentstack started in 2011 as a mobile content form inside Raw Engineering. By 2014, Forrester named it one of three headless CMS pioneers. Neha spun it out in January 2018 with $1M+ ARR, then raised $169M through Series C while growing to 450 employees across 18 countries.
Key Lessons
🏢 Enterprise sales can start from a services tool: Contentstack began as an internal form for agency clients, then evolved into a full enterprise SaaS platform over three years of iteration.
💰 Grow enterprise sales pricing with value delivered: Starting at $250/month and triangulating cost, willingness to pay, and customer value led to $1M/year contracts with Fortune 1000 brands.
🎯 Define a category early for inbound enterprise sales: Being one of the first sites with "headless CMS" in the header meant enterprise buyers found Contentstack organically during the convergence of cloud, mobile, and SaaS.
📉 Bootstrapping too long costs market share: Neha's biggest regret is not raising capital sooner to fund a go-to-market team and capture early enterprise sales before competitors.
🤝 Enterprise sales require multi-threaded selling: Selling to both business and technical buyers at Fortune 1000 companies requires alignment between digital marketing leaders and CIOs.
Chapters
Introduction
Neha's favorite quote and what Contentstack does
What headless CMS means in plain terms
Bootstrapping for the first 11 years
From VMware to building a services agency
Building the first version as an internal tool
Timeline from side project to standalone enterprise SaaS
Pricing from $250/month to $1M/year
Target customer and Fortune 1000 enterprise sales
How inbound worked from day one
Figuring out enterprise pricing strategy
Onboarding enterprise customers and migration
Revenue and customers at the 11-year bootstrap mark
Why Neha didn't raise money sooner
Fundraising challenges as a female founder
Shifting from inbound to demand gen and outbound
Building the partner ecosystem for enterprise sales
Growth struggles and hiring for the next stage
Account-based marketing for enterprise SaaS
Biggest regret and lightning round
Resources
Full show notes: https://saasclub.io/352
Join 5,000+ SaaS founders: https://saasclub.io/email
44 min
April 13, 2023Product-Led Growth: Competing With DocuSign at $30/Month
When Sunil Patro launched SignEasy in 2010, DocuSign already owned the e-signature market. His product-led growth strategy was radical - instead of matching features, he made signing documents so simple that Apple featured the app in all 400+ retail stores worldwide. That competitive differentiation turned a mobile app into a 7-figure SaaS business.
If you are exploring product-led growth to compete against billion-dollar incumbents, this episode shows how simplicity beats feature parity. Sunil reveals how SaaS pricing evolved from $10 lifetime to $30/month without losing users, why expanding from mobile to SaaS was driven by customer pull rather than market assumptions, and what it takes to grow to 50,000 customers as a solo bootstrapped founder.
Sunil Patro is the founder and CEO of Signeasy, an e-signature and contract workflow platform with 50,000 customers, 80 employees, and millions in ARR approaching eight figures.
🔑 Key Lessons
Product-led growth starts with a different perspective for competitive differentiation - SignEasy solved from the signer's side while DocuSign built for the sender.
Platform partnerships scale product-led growth without marketing spend - Apple featured SignEasy in 400+ stores after Sunil committed to day-zero iOS feature adoption.
Raise SaaS pricing as your product value grows, not all at once - Sunil evolved pricing from $10 lifetime to $30/month over several years, increasing revenue per user 36x.
Expand your ICP based on customer pull, not assumptions - SignEasy's mobile to SaaS pivot happened because existing users asked for team-level features.
Measure invisible UX improvements through time-to-complete metrics - SignEasy tracked document completion times across cohorts to verify that product-led growth features drove retention.
Chapters
Introduction
Sunil's favorite quote and employee-first philosophy
What SignEasy does and business metrics
The Mexico trip that sparked the idea for SignEasy
Market research and the signer's perspective gap
Building the first version with a remote developer
Getting featured by Apple and organic product-led growth
SaaS pricing evolution from $10 lifetime to $30/month
Transitioning from mobile app to B2B SaaS
Why customer demand drove the mobile to SaaS expansion
Expanding the ICP from signers to business teams
Acquiring B2B customers through referrals and SEO
Competing against DocuSign with competitive differentiation
How simplicity became SignEasy's product-led growth advantage
Challenges of being a solo founder
Lessons from hiring senior executives too early
Lightning round
Resources
Full show notes: https://saasclub.io/351
Join 5,000+ SaaS founders: https://saasclub.io/email
54 min
April 06, 2023Sales Pipeline: Outbound Drove 90% of $13M ARR Bootstrapped
Daniel Wikberg built his first CRM in 120 hours from his apartment. His server was a computer under his desk that crashed weekly. That scrappy start turned into a B2B SaaS sales platform generating $13M in ARR with 1,800 customers - all bootstrapped. The sales pipeline he built through outbound SaaS sales drives 80-90% of revenue.
If you need to build a sales pipeline that competes with Salesforce and HubSpot, this episode shows how. Daniel shares why targeting 1,500 named accounts beats inbound for revenue, how onboarding trials with real customer data shortens the sales cycle, and why land and expand pricing turned $5K starter accounts into $50K+ annual contracts.
Daniel Wikberg is the founder and CEO of Upsales, a CRM and marketing automation platform with 1,800 customers, a 70-person team, and $13M ARR. He took Upsales public in Sweden while keeping 74% ownership.
🔑 Key Lessons
Outbound B2B SaaS sales outperforms inbound for sales pipeline revenue - one enterprise deal from the 1,500-account target list equals 20 inbound customers.
Land and expand pricing beats bundled tiers for growth - switching to seat-plus-add-ons gave Upsales 15-20 upsell paths per account, turning $5K deals into $50K+ contracts.
Skip demos and onboard with real data to shorten the sales pipeline cycle - importing prospect data during trials builds trust faster and qualifies serious buyers.
A 5% close rate is survivable if you keep iterating on outbound SaaS sales - Daniel closed 5 of 120 prospects in his first five months, then doubled effectiveness with honest feedback.
Focus on the mid-market gap to compete with giants - Upsales found a gap between simple CRMs and Salesforce that neither end served well.
Chapters
Introduction
Favorite quote and background
What Upsales does and who it serves
Origin story - from sales rep to SaaS founder at age 20
Building the first product in 120 hours
First customers through word of mouth
Current metrics - 70 people, 1800 customers, $13M ARR
Competing against Salesforce and HubSpot
Getting to the first 10 customers
How brutal feedback improved the close rate
Outbound as the primary sales pipeline driver
The 1500 named account target list
Outbound sales process and skipping demos
Onboarding trials with real customer data
Switching to land and expand pricing
Hiring challenges and balancing junior vs senior
IPO story - going public at $6M revenue
Lightning round
Resources
Full show notes: https://saasclub.io/350
Join 5,000+ SaaS founders: https://saasclub.io/email
43 min
March 30, 2023SaaS Metrics That Drove $10M to $40M ARR in Two Years
Two years ago, LinkSquares was doing $10M in ARR with 70 people. Today it is at $40M ARR, 430 employees, $161M raised, and an $800M valuation. The SaaS metrics that drove that growth were not vanity numbers - they were unit economics tracked with relentless discipline.
If you are scaling SaaS past $10M and need a framework for go-to-market predictability, this episode delivers the playbook. Vishal Sunak explains how scrubbing customer data by industry and company size revealed which segments to double down on, why tracking SaaS unit economics like CAC payback and burn multiple impressed investors more than raw growth, and how the CEO role shifts from doing everything to making the hardest decisions.
Vishal Sunak is the co-founder and CEO of LinkSquares, a contract management platform. LinkSquares raised $100M at an $800M valuation by demonstrating SaaS metrics mastery.
🔑 Key Lessons
Scaling SaaS requires SaaS metrics mastery, not just revenue growth - LinkSquares forecasted COGS, CAC payback, burn multiple, and ARR per rep a year in advance.
Double down on winning segments and abandon losing ones fast - Vishal reviewed close rates by industry quarterly, cutting segments with zero wins after 24 attempts.
Build go-to-market predictability by planning a year ahead - LinkSquares mapped out rep count, lead volume, and demo targets 12 months before each growth push.
SaaS metrics discipline protects you when the economy shifts - LinkSquares never adopted growth-at-all-costs, so the 2022 downturn required adjustment, not panic.
A scaling SaaS CEO must shift from doing to deciding - Vishal went from handling security questionnaires to only making the highest-stakes SaaS unit economics decisions.
Chapters
Introduction
Welcome back and favorite quote
What LinkSquares does
Growth from $10M to $40M ARR
Origin story and customer discovery
Cold emailing general counsels
Nine months of customer interviews
Bootstrapping with $34,000
Main growth drivers past $10M ARR
Go-to-market predictability with SaaS metrics
SaaS unit economics focus
Hiring and scaling from 70 to 430 people
How the CEO role has evolved
Managing four companies at once
Navigating the 2022 economic downturn
Lightning round
Resources
Full show notes: https://saasclub.io/349
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
March 23, 2023SaaS Product Validation: Deleting a Year of Code to Find PMF
Mike Adams started Grain with a solution looking for a problem. His first year of SaaS product validation was brutal - the ideal customer profile was literally "anyone who thinks it's cool." After running blind customer research, he threw away the entire codebase and rebuilt around a single feature.
If you are struggling with finding product-market fit or unclear on your ICP, this episode reveals how rigorous SaaS product validation can save years of building the wrong thing. Mike shares how pretending the product was built by someone else unlocked honest feedback, why launching during COVID invited seven copycat competitors, and how qualitative customer research with 15 top accounts completely overturned his assumptions about who uses the product.
Mike Adams is the co-founder and CEO of Grain, serving 1,300 customers including Slack, Zapier, and Webflow. Grain has raised $21 million including a $16M Series A from Tiger Global.
🔑 Key Lessons
SaaS product validation requires brutal honesty from users - Mike pretended Grain was someone else's product so testers gave genuinely honest feedback instead of protecting the founders' feelings.
Starting with a solution instead of a problem delays finding product-market fit - Grain spent a year with no clear ideal customer profile because they built technology first.
Continuous customer research reveals what metrics cannot - qualitative interviews with Grain's top 15 accounts overturned the core assumption about how customers entered the product.
Trusting founder instincts beats following advisor playbooks - Mike followed an independent board member's enterprise strategy that generated zero ROI.
SaaS product validation in horizontal tools needs a T-shaped strategy - build the 80/20 solution for everyone but go deep on one persona to drive adoption.
Chapters
Introduction
Favorite quote and the power of teamwork
What Grain does - shareable highlights from video meetings
Mike's background - Degreed, MissionU, and the path to Grain
Business metrics - $1M ARR, 1,300 customers, $21M raised
How the idea for Grain originated
Starting with a solution instead of a problem
The pivot - throwing away a year of code
Why Grain's first-year ideal customer profile was "anyone who thinks it's cool"
The counterintuitive insight from SaaS product validation
Using userinterviews.com to find first customers
Why launching during COVID was a mistake
Herd mentality and trusting instincts
Why founders should never outsource strategic thinking
Lightning round
Resources
Full show notes: https://saasclub.io/348
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min

About The SaaS Podcast: How B2B SaaS & AI Founders Get Customers

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Building software got easier. Getting customers didn't. Every week, a founder building B2B SaaS or an AI product tells you how they got their first customers, and how they kept them: what worked, what didn't, and what they'd do differently.