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 13, 2022SaaS SEO Strategy: $50/Month to 8-Figure ARR
Tony Summerville started charging $50 a month for fleet management software. One customer thought that meant $75 per vehicle and still said yes. That pricing gap was the first signal his SaaS SEO strategy would drive 4,000 customers.
Learn how Tony built a SaaS SEO strategy that drives 70% of revenue through inbound marketing SaaS methods, ranking #1 for 'fleet software' with SaaS content marketing that compounds.
Tony is the founder of Fleetio. His SaaS SEO strategy bootstrapped for four years before raising $25M. The SaaS content marketing engine now serves 4,000 customers across 75 countries.
🔑 Key Lessons
📝 SaaS SEO strategy compounds when targeting information gaps: Fleetio's first white paper on fuel cards ranked because no competitor covered the SaaS content marketing topic.
🎯 Validate demand by measuring responsiveness: Tony used willingness to meet as an early inbound marketing SaaS signal.
💰 Price for obvious ROI to remove friction: A few dollars per vehicle per month made value obvious without executive approval.
📝 A brandable domain is a SaaS SEO strategy foundation: Renaming from 'Automate' to 'Fleetio' made SaaS SEO possible for fleet management searches.
🚀 SaaS SEO strategy delays the need for outbound: Fleetio didn't invest in outbound until past $10M because SaaS content marketing still had room to grow.
Chapters
Introduction
What Fleetio does
8-figure ARR and 200 people
4,000 customers and the SaaS SEO strategy
How the idea started
Customer development interviews
Early product validation
Per-vehicle pricing
Getting to 100 customers
First hire - Matt the generalist
Building the SaaS content marketing engine
SaaS SEO strategy: ranking #1 for fleet software
Bootstrapping before raising $750K
Why outbound came after $10M ARR
The Fleetio Drive mistake
SaaS SEO strategy reflections from $50 to 8 figures
Lightning round
Resources
Full show notes: https://saasclub.io/317
Join 5,000+ SaaS founders: https://saasclub.io/email
44 min
May 05, 2022SaaS Customer Discovery: 400 Calls to $25K MRR
Gary Vanbutsele spent 18 months building a product nobody paid for. His second attempt at SaaS customer discovery worked - he pre-sold to 5 customers at $5K each. Then SaaS partnerships delivered the real breakthrough.
Learn how Gary ran SaaS customer discovery by contacting 400 consultants for SaaS partnerships, converting 10 into active partners who drove partner-led growth delivering 120 customers.
Gary is the co-founder of Whale. His SaaS customer discovery journey included pre-selling SaaS to 5 businesses, then using SaaS partnerships with consultants for partner-led growth to $25K MRR.
🔑 Key Lessons
🤝 SaaS customer discovery through SaaS partnerships outperformed inbound: 10 consultant partnerships delivered the majority of 120 customers via partner-led growth in 12 months.
🎯 Pre-selling SaaS at $5K validates SaaS customer discovery: After wasting 18 months, Gary pre-sold Whale to 5 businesses to prove willingness to pay.
🤝 SaaS partnerships need a different pitch for partner-led growth: Partners want to hear how the tool helps them differentiate, not just how it helps end users.
🛠️ Push knowledge to users contextually: Whale delivered training inside Salesforce rather than building another static knowledge silo.
📉 Hiring junior people after raising cost six months: Gary hired on personality and budget, then rebuilt with experienced hires.
Chapters
Introduction
What Whale does
SaaS customer discovery metrics: $25K MRR
The first failed product
Pre-selling SaaS to 5 customers
Differentiating in a crowded market
Building the MVP
Growing through SaaS partnerships
Finding 400 partners for SaaS customer discovery
Partner-led growth conversion rates
Why the partner pitch differs from sales
SaaS partnerships deal structure
Hiring mistakes after the seed round
Why inbound marketing hasn't clicked
Lightning round
Resources
Full show notes: https://saasclub.io/316
Join 5,000+ SaaS founders: https://saasclub.io/email
56 min
April 21, 2022Enterprise Sales: 7 Years Bootstrapped to $100M ARR
Alfonso de la Nuez spent six years running usability tests in a Spanish lab before building an enterprise sales engine. His consultancy to SaaS journey reached nearly $100M ARR in enterprise SaaS.
Learn how UserZoom used enterprise sales hustle to land Google and eBay, bootstrapped to $15M before raising $34M for enterprise growth, and how Thoma Bravo valued the business at $800M.
Alfonso is the co-founder of UserZoom. His consultancy to SaaS path and enterprise sales strategy built an enterprise SaaS powerhouse with nearly 400 employees.
🔑 Key Lessons
🏢 Enterprise sales pricing starts with the problem you replace: Alfonso benchmarked against $15-25K per lab study, making $25-35K annual enterprise SaaS licenses obvious.
🎯 Let customers pull you into enterprise sales: UserZoom became real enterprise SaaS only after Google demanded self-serve access.
🤝 Enterprise sales start with hustle, not automation: Alfonso walked across a conference floor to pitch eBay, sparking seven paid follow-on projects.
📉 Bootstrapping flips the enterprise sales fundraising dynamic: Growing to $15M and EBITDA positive attracted a $34M round where investors pitched Alfonso.
🚀 Content marketing builds enterprise sales credibility first: Writing UX methodology articles for years built enterprise growth credibility before generating inbound leads.
Chapters
Introduction
What UserZoom does - enterprise SaaS for UX
Approaching $100M ARR in enterprise growth
Funding: bootstrapped then $136M raised
Consultancy to SaaS origin story
The shift to enterprise SaaS recurring revenue
Why UserZoom targeted enterprise sales from day one
Getting the first 10 enterprise sales customers
Pricing strategy for enterprise SaaS
Content marketing for enterprise sales
Conference hustle and enterprise growth
Investing in product UX
Lightning round
Resources
Full show notes: https://saasclub.io/315
Join 5,000+ SaaS founders: https://saasclub.io/email
47 min
April 08, 2022Bootstrap to Profitability: $60K Lost, Then the Fix
Dave Rodenbaugh lost $60K on a failed SaaS acquisition and $50K building a help desk nobody wanted. Then he acquired Recapture at $3,500 MRR and found the bootstrap to profitability formula.
Learn the 3-criteria checklist for buying SaaS businesses that achieve bootstrap to profitability, why dropping prices from $49 to $29 unlocked Shopify growth, and how a solo founder SaaS can scale through partnerships.
Dave is a solo founder SaaS operator behind Recapture. His bootstrap to profitability journey from $3,500 MRR to mid-6-figures includes two failed SaaS acquisition attempts worth $60K.
🔑 Key Lessons
🎯 Evaluate with a 'close to the money' test for bootstrap to profitability: Recapture succeeded because merchants could see exactly how much revenue it recovered.
📉 Building 18 months without validation is costly: Dave spent $50K on a help desk - a failed SaaS acquisition of his own time that taught hard lessons.
💰 Price at or below the platform base cost for bootstrap to profitability: Dropping from $49 to $29 matched Shopify's fee, unlocking conversions this solo founder SaaS needed.
🤝 Build partnerships by solving partner customer pain: Embedding Recapture into partner onboarding drove the most reliable bootstrap to profitability channel.
📉 Ads without attribution drain your bootstrap to profitability budget: Shopify ads showed 53 cents return per dollar - growth didn't drop when spending stopped.
Chapters
Introduction
What Recapture does
Revenue as a solo founder SaaS
From WordPress plugins to SaaS
Failed SaaS acquisition #1 - UW Robot
Failed attempt #2 - help desk without customers
Lessons from buying SaaS businesses
The 3-criteria bootstrap to profitability checklist
Why Recapture checked every box
Buying Recapture at $3.5K MRR
The pricing discovery for bootstrap to profitability
Paid acquisition on Shopify - the 53% ROAS disaster
Growing through strategic partnerships
Lightning Round
Resources
Full show notes: https://saasclub.io/314
Join 5,000+ SaaS founders: https://saasclub.io/email
53 min
March 25, 2022Net Revenue Retention: CAC, LTV, and Churn Explained
Most SaaS founders get their SaaS metrics wrong. Paul Orlando says if you have one number for CAC and one for LTV, you haven't started measuring net revenue retention properly.
Learn how to calculate customer acquisition cost by channel, model LTV as a river, track net revenue retention by cohort, and why negative SaaS churn is the gold standard.
Paul is a USC professor and author of Growth Units. His breakdown of SaaS metrics including net revenue retention, customer acquisition cost, and churn models helps founders measure what matters.
🔑 Key Lessons
📉 Break SaaS metrics down by acquisition channel: A blended customer acquisition cost hides which channels scale for net revenue retention.
💰 Model LTV as a river, not a single SaaS metric: Map monthly cash flows with retention rates to reveal actual payback periods.
🔄 Track cohort-based net revenue retention: Comparing monthly cohorts shows whether product changes actually reduce SaaS churn.
🚀 Target negative net revenue retention as the ultimate goal: When remaining customers expand faster than churned ones leave, you achieve negative churn.
🧠 The CAC-to-LTV ratio is a starting point for SaaS metrics: Bootstrapped founders may need 1:5 while growth companies accept 1:1.
Chapters
Introduction
How Growth Units came about
Overview: CAC, LTV, and net revenue retention
What is customer acquisition cost
Breaking CAC down by channel
Growing versus scaling
Fixed vs. variable CAC
How much should CAC be
What is LTV as a SaaS metric
LTV as a river
Cohort analysis for net revenue retention
CAC-to-LTV ratio benchmarks
Three SaaS churn models
Negative net revenue retention explained
Lightning round
Resources
Full show notes: https://saasclub.io/313
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
March 17, 2022Failed Software Startup: 10 Products Before PMF
Jeb Banner built almost a dozen products that went nowhere over 12 years. His failed software startup streak broke only when he separated product from his agency and found product-market fit targeting nonprofits.
Learn why a failed software startup inside an agency never survives, how Boardable achieved product-market fit by targeting nonprofit boards, and what hidden conversion signals a data scientist uncovered.
Jeb is the CEO of Boardable, a board management platform. After 10 failed software startup attempts as part of his agency to SaaS journey, Boardable reached 7-figure ARR with 2,000 customers in 40 countries.
🔑 Key Lessons
📉 A failed software startup inside an agency can't compete for attention: Jeb built 10 products over 12 years - the pattern broke when Boardable became a separate entity.
🎯 Target acute pain to prevent another failed software startup: Nonprofits with 50 board members and one admin felt pain far more than for-profits, enabling product-market fit.
🛠️ Build for complexity, then sell simplicity: Solving nonprofit complexity first created an advantage when expanding - a finding product-market fit lesson.
🤝 Recognize when product-led growth breaks down: Boardable's PLG stalled in the agency to SaaS transition because the user was not the buyer.
🧠 Data science finds hidden conversion signals no failed software startup expects: Deleting an agenda item in a trial predicted conversion better than any firmographic data.
Chapters
Introduction
What Boardable does
Business size, revenue, and funding
How a client request sparked the idea
Why nonprofits for finding product-market fit
Building the MVP
Using Capterra for growth
Product-led growth to sales transition
Lead scoring with a data scientist
The agenda deletion conversion signal
The failed software startup pattern over 12 years
Separating product from agency to SaaS
Why Boardable finally achieved product-market fit
Competitive landscape
Lightning round
Resources
Full show notes: https://saasclub.io/312
Join 5,000+ SaaS founders: https://saasclub.io/email
44 min
March 10, 2022Niche SaaS: Handwritten Letters to $9M ARR
Tom Staff bought a PHP textbook and taught himself to code. That side project became Street Group, a niche SaaS for UK estate agents now doing over $800K MRR - all built on vertical SaaS principles.
Learn how Heather and Tom used handwritten letters, exclusivity pricing, and deep industry-specific SaaS knowledge to build a niche SaaS to $9M+ ARR with zero outside funding.
Heather is the co-founder of Street Group, a niche SaaS company for real estate. Their vertical SaaS approach with three products across the niche market created a moat outsiders can't replicate.
🔑 Key Lessons
🎯 Niche SaaS wins when you know the industry cold: Heather and Tom grew up around estate agents, giving them vertical SaaS insight outsiders could never match.
📉 Exclusivity pricing creates a niche SaaS ceiling you must break: One-agent-per-area drove urgency but capped the niche market until they dropped prices 35%.
🚀 Pick an unsaturated channel for niche SaaS growth: Handwritten letters got 5% response because nobody else was doing direct mail in their industry-specific SaaS market.
💰 Charge a premium from day one and collect upfront: GoCardless direct debits with monthly advance billing eliminated cash flow problems for the niche SaaS entirely.
🛠️ Build the niche SaaS product nobody else can afford: Three years and millions invested in a modern CRM created a vertical SaaS moat competitors couldn't replicate.
Chapters
Introduction
Three niche SaaS products for estate agents
Revenue and team size
Origin story - Tom teaching himself PHP
Handwritten letters for niche SaaS first customers
Why direct mail for industry-specific SaaS
Exclusivity pricing for vertical SaaS
Getting first 10 niche SaaS customers
Scaling beyond 10 - trade shows and campaigns
Dealing with copycat competitors
Breaking the exclusivity ceiling
Why no outside funding
Building the niche SaaS CRM
Lightning round
Resources
Full show notes: https://saasclub.io/311
Join 5,000+ SaaS founders: https://saasclub.io/email
45 min
March 03, 2022B2B Product-Market Fit: 3 Years Lost, Then Breakout
Khadim Batti spent three years building a product nobody needed. Then he deleted it and started finding product-market fit from zero. The SaaS pivot turned a support tool into a $600M company.
Learn how Khadim achieved B2B product-market fit by sending 500 cold emails, closing before writing code, and narrowing from SMB to enterprise CRM for product validation.
Khadim is the co-founder of Whatfix, valued at $600M+ with $140M raised. His B2B product-market fit journey included a complete SaaS pivot after 3 years of finding product-market fit the wrong way.
🔑 Key Lessons
🎯 B2B product-market fit requires killing your darlings: Khadim shut down Search Enabler after 3 years, proving that a SaaS pivot can unlock real growth.
📉 Building 15 months without customers wastes B2B product-market fit time: Khadim coded for over a year, then threw away 40% of features after product validation failed.
🤝 Sell before building to validate B2B product-market fit: Whatfix signed its first customer before writing production code.
💰 Test pricing in person for B2B product-market fit signals: Khadim validated from $10 to $1,000/month by watching prospects' face-to-face reactions.
🎯 Narrow your market to accelerate B2B product-market fit: Focusing on enterprise CRM at 1,000+ employee companies made everything converge.
Chapters
Introduction
What Whatfix does
Revenue, employees, and $140M raised
The Search Enabler story and failed product validation
How the Fix It button became the SaaS pivot
Starting over with zero customers
500 cold emails and finding B2B product-market fit
Testing pricing from $10 to $1,000
Getting the first 10 customers
Going too horizontal
Narrowing to enterprise CRM for B2B product-market fit
Using Dreamforce to accelerate sales
Hiring salespeople as technical founders
From $1M to $10M ARR in 9 quarters
Lightning round
Resources
Full show notes: https://saasclub.io/310
Join 5,000+ SaaS founders: https://saasclub.io/email
45 min
February 24, 2022SaaS Retention: From 2% Survey Response to Full Fix
Tony Sternberg launched ProsperStack with a post-cancellation survey. Only 2% responded. That's when he realized his entire approach to SaaS retention and SaaS churn was wrong.
Discover how Tony rebuilt ProsperStack as an embedded cancellation flow for real-time SaaS retention, achieving churn reduction by intercepting 100% of cancel actions at the moment they happen.
Tony is the co-founder of ProsperStack, which fights SaaS churn through smarter cancellation flows. His SaaS retention tool intercepts active churn at scale.
🔑 Key Lessons
📉 Post-cancellation surveys miss most SaaS retention data: ProsperStack's email survey captured only 2% - reaching customers after SaaS churn happens is too late.
🛠️ Embed your SaaS retention tool inside the churn moment: By becoming the cancel flow, ProsperStack intercepted 100% of actions for real churn reduction.
💰 Price based on SaaS retention value, not self-doubt: Tony raised pricing from $29 to $200 after realizing customers got 3-10x returns on spend.
🤝 Video outreach outperforms cold email for SaaS retention sales: Personalized 30-second demos drove 90% of new business for ProsperStack.
🎯 Set up vesting from day one to protect against departures: Four-year vesting with a one-year cliff made a co-founder's exit clean and amicable.
Chapters
Introduction
What ProsperStack does for SaaS retention
Revenue, customers, and team size
How the SaaS churn reduction idea was born
The first MVP - a post-cancellation survey
Realizing 2% engagement killed SaaS retention
Rebuilding as an embedded cancellation flow
How the SaaS retention flow works
Why self-serve didn't work
Switching to demo-based sales
Personalized video for SaaS churn outreach
Active churn vs passive churn
Raising pricing from $29 to $200
Handling a co-founder departure
Lightning round
Resources
Full show notes: https://saasclub.io/309
Join 5,000+ SaaS founders: https://saasclub.io/email
35 min
February 17, 2022SaaS Product Validation: 5 Interview Tactics That Work
Most founders think they know what problem their product solves. Michele Hansen's SaaS product validation framework proves them wrong through customer interviews and customer discovery.
Learn Michele's approach to SaaS product validation - from finding product-market fit signals to the 'reaching for the door' question, and why 5 customer interviews reveal enough to act.
Michele is the co-founder of Geocodio and author of Deploy Empathy. Her SaaS product validation methods helped dozens of founders with customer discovery at Calm Fund.
🔑 Key Lessons
🎯 SaaS product validation starts with listening, not pitching: Customer interviews should never include selling - prospects with real pain voluntarily ask about your product.
🔄 Use the 'reaching for the door' question in customer discovery: Thank the person, ask 'Anything else?' and wait - the most honest answers come in that silence.
🧠 Mirror and rephrase wrong for deeper SaaS product validation: Restating wrong triggers over-correction, revealing details that finding product-market fit requires.
📉 Low response rates signal weak SaaS product validation: If prospects won't talk about the problem, it likely isn't painful enough to build a business around.
🎯 Five customer interviews reveal SaaS product validation patterns: Five conversations surface themes - if you hear five different things, your scope needs narrowing.
Chapters
Introduction
What Geocodio does
Why the book is called Deploy Empathy
How Deploy Empathy complements The Mom Test
Setting up a SaaS product validation scenario
Customer discovery vs. sales
The pain-frequency chart for finding product-market fit
How to recruit customer interview subjects
Using a discovery script
Building rapport for SaaS product validation
The reaching for the door question
Interactive interviews and the undemo technique
Where to find Deploy Empathy
Resources
Full show notes: https://saasclub.io/308
Join 5,000+ SaaS founders: https://saasclub.io/email
42 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.