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 16, 2024SaaS Pricing for Exits: Sell Your Business for 4-8x
Juan Ignacio Garcia tried to acquire three SaaS businesses and failed every time because nobody would finance the deal. So he built Boopos, a marketplace with built-in acquisition financing. Most SaaS businesses sell for 4-8x profit multiples - but SaaS pricing for your exit depends on retention, financials, and deal strategy.
Learn the complete playbook for SaaS pricing when selling a SaaS business, from preparing financials and getting 4-8x SaaS valuation to choosing marketplaces and negotiating with multiple buyers.
🔑 Key Lessons
💰 SaaS pricing for exits starts with 24 months of monthly P&L: Buyers want revenue trends, seasonality, and profitability. Without clean financials, you cannot get credible SaaS pricing on a marketplace.
🤝 Secure an early offer to create competitive tension around SaaS pricing: Even a lowball letter of intent gives you leverage. It signals demand and creates urgency that drives up the SaaS valuation.
🏢 Choose your marketplace based on deal size for better SaaS pricing: Self-serve platforms work for smaller deals. Curated platforms pair sellers with pre-vetted buyers for better selling a SaaS business outcomes.
📉 The biggest red flag is a seller who hides information during SaaS pricing negotiations: If a seller does not cooperate during due diligence, the post-sale SaaS exit transition will be harder.
🔄 Start with fast financing, refinance later for better rates: Many buyers close quickly with alternative lenders then switch to SBA loans once the business stabilizes.
Chapters
Introduction
What Boopos does and how it differs from other marketplaces
What type of SaaS businesses sell well on marketplaces
Overview of the selling and buying process
Essential steps to prepare your SaaS business for sale
How marketplaces and brokers affect SaaS pricing and valuation
Typical SaaS pricing multiples for businesses on marketplaces
Factors that drive higher multiples from 4x to 8x
Choosing the right marketplace for your business
How to get your listing noticed by the right buyers
Self-serve marketplaces vs. curated advisory models
Negotiating and closing when selling a SaaS business
Why you should keep a lowball offer instead of dismissing it
The due diligence and asset transfer process
How long closing typically takes
Switching gears to the buyer's perspective
Why Juan tried to buy three businesses before building Boopos
Common mistakes buyers make when evaluating a business
Red flags to watch for during buyer due diligence
Financing options for SaaS exit acquisitions
SBA loans vs. acquisition financing vs. cash buyers
How Boopos buyer approval works
Listing criteria vs. underwriting criteria on Boopos
How financing speed affects deal negotiations
Getting started on the Boopos marketplace
Where to find Juan and Boopos
Resources
Full show notes: https://saasclub.io/397
Join 5,000+ SaaS founders: https://saasclub.io/email
50 min
May 09, 2024SaaS Partnerships: Two Exits to 19,000 Companies
Bob Moore quit his VC job the day before Lehman Brothers collapsed. He bootstrapped RJ Metrics, sold it to Magento, then spun out the same technology as Stitch and sold it for $60M in 18 months. Now his SaaS partnerships platform Crossbeam serves 19,000 companies at 8-figure ARR.
Learn how to sell the same company twice, why SaaS partnerships require solving the cold start problem with joint onboarding, and how partner-led growth and network effects tipped after 100 companies on the platform.
🔑 Key Lessons
🔄 Spin-out exits unlock hidden value in SaaS partnerships: Bob kept RJ Metrics' ETL technology after selling to Magento, relaunched it as Stitch, and sold it to Talend for $60M in 18 months.
🤝 Solve the cold start problem by onboarding SaaS partnerships in pairs: Crossbeam created joint jam sessions that onboarded two partner companies simultaneously, because no single company could derive value alone.
📉 Monolithic products lose when buyers purchase ecosystem-led growth stacks: RJ Metrics went from rapid growth to flat revenue after Amazon Redshift let buyers assemble a modern data stack.
🎯 SaaS partnerships network effects take years before they tip: Crossbeam spent two years reaching 100 companies before the partner-led growth loop kicked in and users invited their own partners.
🚀 PLG and freemium accelerate SaaS partnerships adoption: Crossbeam's free tier attracted 19,000 companies and built network effects density, while paid tiers captured revenue from power users.
Chapters
Introduction
Bob's favorite quote and Crossbeam overview
Business size, revenue, and team
The RJ Metrics origin story (2008)
Quitting the day Lehman Brothers collapsed
Challenges acquiring the first customers
Surviving the emotional rollercoaster of early days
How Bob learned to code
Raising $20M in venture capital for RJ Metrics
How Amazon Redshift disrupted RJ Metrics
The modern data stack and losing to Looker
The $2.6 billion mistake
Spinning out Stitch from RJ Metrics
Selling Stitch to Talend for $60M in 18 months
The founding of Crossbeam and SaaS partnerships in 2018
Solving the cold start problem and data trust
Joint jam sessions and onboarding SaaS partnerships in pairs
How network effects tipped after 100 companies
How long Bob sees himself working on Crossbeam
Lightning round
Resources
Full show notes: https://saasclub.io/396
Join 5,000+ SaaS founders: https://saasclub.io/email
1 hr 4 min
May 02, 2024SaaS Sales Process: From Failed Outbound to 7-Figures
Lars Gronnegaard left Trustpilot with a clear SaaS sales process plan. Then reality hit. His first 10 customers looked nothing like the ICP. Cold outreach needed 180 days to show results. It took a LinkedIn content strategy hitting 300,000 views to finally reach 7-figure ARR.
Learn how a documented SaaS sales process replaced tribal knowledge, why 28-day outbound cycles beat 180-day sequences for SaaS go-to-market validation, and how personal LinkedIn profiles drove the majority of inbound leads.
🔑 Key Lessons
🎯 Narrow your ICP before scaling your SaaS sales process: Dreamdata confused a large TAM with a broad ICP. Growth only returned when they narrowed the SaaS go-to-market to mid-sized B2B SaaS companies.
📉 Cut outbound cycles to 28 days for fast SaaS sales process validation: Dreamdata's cold outreach needed 180 days. Lars shortened cycles to four weeks to get data fast enough to iterate on the sales playbook.
🚀 LinkedIn content strategy beats company pages for inbound: Co-founder Stefan hit 300,000 views in three months by posting from personal profiles instead of pitching from the company account.
🤝 Document your SaaS sales process before hiring salespeople: Dreamdata's scaling attempt failed because tribal knowledge could not transfer to new hires without a formal sales playbook.
🛠️ Validate with duct tape before building real product: Lars landed 10 customers and $100K ARR using BigQuery dashboards, proving the SaaS go-to-market worked before investing in engineering.
Chapters
Introduction
Lars' favorite quote
What Dreamdata does and who it serves
Revenue, team size, and company stage
The origin story at Trustpilot
Finding the third co-founder Stefan
Transitioning from Trustpilot to full-time
First customers with duct-taped prototypes
Building per-customer solutions before real product
Defining the initial ICP
Why the first 10 customers diverged from the ICP
Going narrow with ICP as advice for founders
Cold outreach and the 180-day SaaS sales process problem
LinkedIn content strategy as growth engine
Personal profiles vs company accounts on LinkedIn
Paid search and micro-category keywords
Scaling sales and realizing the sales playbook was missing
Training salespeople without a formal SaaS sales process
Building and documenting the sales playbook
Fundraising during the pandemic and Ukraine war
Lightning round
Resources
Full show notes: https://saasclub.io/395
Join 5,000+ SaaS founders: https://saasclub.io/email
49 min
April 25, 2024B2B SaaS Sales: 5 Years to Build What Oracle Said Was Impossible
Thomas Cottereau spent five years building what Oracle's engineers said was technically impossible. When he demoed the B2B SaaS sales platform at Salesforce, a lead engineer tested every feature by midnight and emailed: 'It works as you said. Come to my office tomorrow.'
Learn how weekly office visits earned a strategic partnership for B2B SaaS sales, why HP saved millions using SightCall for remote visual support, and how persistence and a working product beat pitch decks in enterprise sales.
🔑 Key Lessons
🏢 B2B SaaS sales platforms take years, not months: SightCall's prototype took 4 months, but building a globally scalable enterprise SaaS platform required 5 years of bridging telecom and software.
🤝 Strategic partnerships unlock B2B SaaS sales you can't reach alone: Thomas showed up at Salesforce every week until he earned a demo, and that partnership delivered HP as the first enterprise sales customer.
🧠 Build technology others believe is impossible for a B2B SaaS sales moat: Oracle said SightCall's cloud-based visual support was not feasible. Proving them wrong created an unreplicable advantage.
📉 Post-fundraising is harder than the B2B SaaS sales fundraise itself: Each round brought scaling pressure that introduced silos and political tension, temporarily slowing growth.
🎯 Validate with a working product, not slides: Salesforce had been faking cloud video at Dreamforce with hidden hardware. Thomas showed a real demo and they requested API access the same day.
Chapters
Introduction
Thomas's favorite quote and why it inspired SightCall
What SightCall does and how visual support works
How augmented reality guides customers through repairs
SightCall's 200 enterprise customers including GE Healthcare
Business size - 8-figure ARR, 100 people, global offices
Going back to 2008 - bootstrapping and the origin story
Working at UUNet and the MCI WorldCom cultural shock
Designing the platform in a basement every night
Technology-first approach versus lean startup methodology
Four months for a prototype, five years for enterprise SaaS
Raising a 1 million euro seed round
How persistence and a blunt email secured the first investor
Landing HP through B2B SaaS sales via Salesforce
How Thomas became a Salesforce partner by showing up every week
The Wemo trademark dispute and forced rebrand to SightCall
Series A - raising $8.4 million and the pressure that followed
Enterprise sales and marketing go to war after the fundraise
Series B - raising $42 million and scaling challenges
Lightning round
Resources
Full show notes: https://saasclub.io/394
Join 5,000+ SaaS founders: https://saasclub.io/email
57 min
April 18, 2024Consultative Selling SaaS: 1,500 Demos to $19M ARR
Andrew Guttormsen did over 1,500 one-on-one demos in 18 months - consultative selling SaaS the hard way. That personal touch turned Circle into a $19M ARR business. A single JV webinar with anchor customers like Pat Flynn drove 300 new customers in one push.
Learn how consultative selling SaaS through founder-led demos built unstoppable word of mouth, why anchor customers accelerated the SaaS sales process, and how expansion pricing doubled ARR.
🔑 Key Lessons
🤝 Consultative selling SaaS builds unbeatable word of mouth: Andrew did 1,500 personal founder-led demos at Circle, creating deep connections that turned customers into vocal advocates across Twitter.
🎯 Anchor customers accelerate consultative selling SaaS pipelines: Circle made Pat Flynn an advisor, built with his input, and used one JV webinar to land 300 customers.
⚡ Gated waitlists create pent-up demand for consultative selling SaaS launch: Circle ran a six-month private beta with manual qualification, building demand that fueled zero to $1M ARR in four months.
🚀 Product-led growth loops compound alongside a consultative selling SaaS process: Every Circle community exposes members to the platform, turning end users into potential customers organically.
💰 Expansion pricing unlocks net revenue retention: Circle added a $30K/year branded app tier targeting the same creators at a later growth stage, helping double ARR from $8M to $16M.
Chapters
Introduction
Andrew's background and what Circle does
Leaving Teachable and starting Circle during COVID
Raising a $700K seed round and $4M seed extension
Validating the idea with creators they already knew
Zero to $1M ARR in four months after public launch
Using Twitter threads to drive waitlist signups
Why 1,500 personal demos created unstoppable word of mouth
Landing anchor customers like Pat Flynn
How one JV webinar drove 300 customers
When influential customers have bad experiences
Dealing with public criticism as a punch in the gut
Growth beyond $1M: weekly revenue meetings and forecasting
Building a SaaS sales process with no sales experience
Doubling ARR from $8M to $19M with pricing and packaging
Moving up-market with a $30K/year branded app tier
Lightning round
Resources
Full show notes: https://saasclub.io/393
Join 5,000+ SaaS founders: https://saasclub.io/email
56 min
April 11, 2024Selling SaaS Without Sales Experience: $2K to $25K
Adam Gavish had never sold anything in his life. As a Google PM, he had to become DoControl's first SDR - selling SaaS without sales experience. He pitched 22 VCs in one week (21 said no), landed a first customer at $2K/year, and scaled deals to $25K+ by treating every call as a founder-led sales feedback session.
Learn the playbook for selling SaaS without sales experience, how 50 validation interviews shaped the product before code, and why reframing SaaS sales strategy as feedback eliminated buying fatigue.
🔑 Key Lessons
🤝 Selling SaaS without sales experience starts with feedback: Adam told prospects "I'm not selling, I need your feedback" - a reframe that eliminated buying fatigue and turned cold outreach into startup sales collaboration.
🎯 Validate with 50 conversations before writing code: DoControl's founders spent three months interviewing security professionals using open-ended questions before building anything.
💰 A $2K deal validates more than a $200K pipeline: DoControl's first customer paid $2K/year, but going through procurement proved selling SaaS without sales experience can still generate real enterprise value.
📉 Low pricing signals low quality when selling SaaS without sales experience: When DoControl raised prices from $2K to $25K+, customers perceived the product as solving a harder problem worth more.
🚀 Hit LinkedIn's weekly limit as your founder-led sales channel: Adam grew from 3,000 to 17,000 connections by maxing out LinkedIn messages weekly, converting 5% into calls as a SaaS sales strategy.
Chapters
Introduction
Adam's favorite quote
What DoControl does and who it serves
Revenue, customers, and team size
Origin story - discovering the problem at Google
Decision to leave Google and start a company
Validating with 50 security professionals
How they found people to interview
What questions they asked during validation
The pitch that emerged from customer research
Pitching 22 VCs with no product
Raising a $3M seed round
Working with design partners to build the MVP
Landing the first $2,000 customer
Becoming an SDR - selling SaaS without sales experience
LinkedIn outreach strategy and hitting weekly limits
Balancing customer requests with product vision
Growing deal sizes from $2K to $25K
Learning founder-led sales from scratch
Messaging and differentiation in a crowded market
Different messaging for different sales stages
Competing against established incumbents
DoControl's technical differentiation points
Sales cycle length and enterprise dynamics
Why Adam still does sales every day
Lightning round
Resources
Full show notes: https://saasclub.io/392
Join 5,000+ SaaS founders: https://saasclub.io/email
43 min
April 04, 2024Enterprise SaaS: From Rejection to Raising $72M
An investor told Stephany Lapierre she would never raise capital. She had three kids, no tech background, and no co-founder. But she flipped that rejection into fuel, raised $72M in startup funding for TealBook, and built an enterprise SaaS platform serving over 100 Fortune 1000 customers.
Learn how a non-technical founder overcame enterprise SaaS fundraising rejection, why the 'ZoomInfo for procurement' analogy unlocked SaaS fundraising interest, and how LinkedIn thought leadership replaced a sales team.
🔑 Key Lessons
💰 Enterprise SaaS fundraising requires reducing your risk profile: Stephany couldn't raise capital as a non-technical founder until she recruited a CTO and COO who invested their own money.
🧠 Reframe investor rejection as actionable enterprise SaaS feedback: When an investor listed every reason Stephany would fail, she addressed each gap and returned with a stronger startup funding pitch.
🎯 Use a relatable analogy to unlock enterprise SaaS investor understanding: TealBook struggled until the team positioned it as "ZoomInfo for procurement." When ZoomInfo went public, interest surged.
📉 Outgrowing your tech stack can threaten any enterprise SaaS: TealBook grew 350% in 2021 but its MVP-era platform could not handle enterprise data volumes, forcing a painful full rebuild.
🤝 LinkedIn thought leadership replaces a sales team for enterprise SaaS: Stephany wrote weekly LinkedIn posts and cold-messaged procurement officers to build credibility without a marketing budget.
Chapters
Introduction
Stephany's favorite quote on resilience
What TealBook does and the supplier data problem
Size of the business and SaaS fundraising history
Origin story and nine years fighting the idea
Getting started and early validation
The $50,000 check from her husband
Selling $5,000 memberships and the teal coins model
Flipping the model for a $60 billion customer
Why startup funding was harder than expected
Building confidence as a non-technical founder
Shifting the SaaS fundraising narrative
Using LinkedIn thought leadership for enterprise SaaS customers
Rebuilding the platform and technical debt
Lightning round
Wrap up and where to find Stephany
Resources
Full show notes: https://saasclub.io/391
Join 5,000+ SaaS founders: https://saasclub.io/email
46 min
March 28, 2024Scaling SaaS: $52K Investment to $22M ARR With SEO
Jared Brown invested $52,000 with a stranger he met on LinkedIn. Eleven years later, Hubstaff generates $22M in ARR and SEO is still the engine scaling SaaS to 16,000 customers. COVID doubled revenue from $6M to $12M in just 12 months of SaaS growth.
Discover how SEO alone drove scaling SaaS from zero to $22M ARR, why low pricing created viral bootstrapped growth loops, and how continuous onboarding iteration became a self-funded SaaS superpower.
🔑 Key Lessons
🚀 Scaling SaaS starts with meeting existing demand: Jared's earlier projects failed because they required convincing people to care. Hubstaff succeeded because remote managers were already searching for solutions.
🎯 SEO was the only channel needed for scaling SaaS: Dave's search optimization background meant Hubstaff could rely on content marketing and organic rankings for 99% of customer acquisition.
💰 Low pricing fueled viral adoption while scaling SaaS: Hubstaff offered a free plan for three users and charged $5 per additional user, turning every account into a bootstrapped growth distribution channel.
🛠️ Continuous onboarding iteration is a scaling SaaS superpower: Hubstaff treated onboarding like an ongoing project, running monthly iterations rather than optimizing once and leaving it.
📉 Shortening trial from 30 to 14 days boosted conversions: The shorter window pushed users to engage immediately, and daily usage in the first 5-10 days predicted long-term SaaS growth.
Chapters
Introduction
Jared's favorite quote and making a dent in the universe
What Hubstaff does and who it serves
Business size - $22M ARR, 16,000 customers, 100+ team
How a LinkedIn cold message started Hubstaff
Why Jared said yes to a stranger's pitch after 3 months
The $52,000 total investment to launch the product
Rebuilding the product from scratch with a 10x developer
How they spent the $52K and went all-in on product
Building a 2,000-person waitlist before beta launch
Turning on payments and the pricing debate
SEO as the sole growth engine for scaling SaaS to first million
Low competition and why incumbents avoided the space
Getting to $1M ARR by 2016 with slow and steady growth
Why rapid iteration on onboarding was a superpower
Product-led growth before it had a name
Tracking onboarding funnels with KISSmetrics and Mixpanel
Daily active users and the 5-10 day habit formation window
Lessons from failed side projects before Hubstaff
Meeting existing demand vs creating a new market
From $6M to $12M ARR during COVID in 12 months
Post-COVID normalization at 3x pre-pandemic remote levels
Realistic goals - dreaming of $40K MRR in the early days
What separated Hubstaff from competitors who failed
Lightning round
Resources
Full show notes: https://saasclub.io/390
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
March 07, 2024SaaS Retention: How Narrowing Your Niche Reignites Growth
Brennan Dunn raised $500K, grew RightMessage to $35K MRR in a year, then watched it all slide backward. For two years, SaaS retention flatlined and both co-founders lost motivation. The SaaS churn problem was clear - too broad a market and customers who lacked the data the product needed.
Learn how narrowing niche positioning reignited SaaS retention, why hands-on onboarding turned a customer retention weakness into a strength, and how Justin Welsh saw 38% higher conversions using RightMessage.
🔑 Key Lessons
🎯 Narrow your niche when SaaS retention stalls: RightMessage targeted everyone from SaaS to plumbing companies. SaaS retention only recovered when Brennan narrowed to pro creators doing $1M+ per year.
🤝 Use personalized onboarding to improve SaaS retention: Instead of waiting for self-serve adoption, Brennan offered paid consulting to implement RightMessage for high-profile creators.
📉 Hiring ahead of revenue kills bootstrapped customer retention: RightMessage burned through $500K in funding by scaling the team before revenue could sustain it, forcing two years of SaaS churn.
🚀 Leverage influential customers to boost SaaS retention credibility: Landing Pat Flynn and Justin Welsh gave RightMessage case studies and "Powered by" visibility that generated inbound leads.
💰 Pair educational content with your product for customer retention: Brennan bundled a segmentation course with software credits, using education as the gateway that brought prospects to the product.
Chapters
Introduction
What RightMessage does
How website personalization works with email data
Predictive intent and the Netflix personalization example
Business metrics: $20K MRR, 250 customers, team of 3.5
Origin story: from JavaScript zip file to SaaS
Raising a $500K seed round through personal network
Launching in 2018 and hitting $10K MRR in month one
Growing to $35K MRR then hitting the wall
The onboarding gap: customers lacked segment data
Burning through funding and SaaS retention decline
Two years of stagnation and losing motivation
The Hail Mary rewrite that failed
Buying out the co-founder with personal savings
Personalized onboarding for flagship creators
From software as a service to software and a service
The ConvertKit playbook: landing Pat Flynn first
How the first deal with Pat Flynn happened
Landing Justin Welsh, Matt Gray, and Dan Go
Using courses as a SaaS retention growth engine
Why creators over SaaS companies as target market
Choosing a market you want to spend 10 years in
Lightning round
Wrap-up
Resources
Full show notes: https://saasclub.io/389
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
February 29, 2024Enterprise Sales: Partner-First Strategy to 4,000 Customers
Simon Taylor showed up at Nutanix headquarters wearing a bright white jacket with a red carnation - and nobody knew who he was. A year later, his enterprise sales through that partner-first strategy had delivered thousands of enterprise customers for HYCU across 78 countries.
Learn how a partner-first strategy for enterprise sales replaced cold calling, why education-first content drew 2,000 webinar attendees for B2B sales, and how an AI integration cut development time from 3 days to 36 minutes.
🔑 Key Lessons
🤝 Enterprise sales starts by solving partner problems first: Simon's first Citrix meeting focused on strengthening their Microsoft relationship, never mentioning his own technology. That partner-first strategy led to 2,000 enterprise customers.
🎯 Position around simplicity for better enterprise sales results: HYCU framed data protection as "one platform like iPhone backup" instead of comparing features, making B2B sales accessible to non-technical buyers.
📉 Cold calling can damage your brand in enterprise sales: HYCU's early cold callers made the company look like telemarketers, undermining the trust needed for enterprise customers.
🏢 Open APIs with revenue sharing scale enterprise sales faster: Instead of building 30,000 integrations internally, HYCU let partners build them via a low-code platform with rev-share deals.
🚀 Education-first content outperforms product pitches in enterprise sales: HYCU invited an FBI agent to a ransomware webinar instead of demoing, attracting 2,000 attendees and building B2B sales trust.
Chapters
Introduction
Favorite quote and Hemingway inspiration
What HYCU does and the data protection problem
Business metrics: 4,000 enterprise customers, $140M raised, 300 employees
The HYCU name and its meaning
Origin story: meeting Goran at a Las Vegas steakhouse
Costa Rica engineering retreat and the 'it can't be done' moment
Two revelations: SaaS disruption and microservices architecture
Enterprise sales - selling a Swiss army knife to skeptical enterprises
Opening the platform as a universal API for partner-first strategy
Why recovery matters more than backup
How to build partnerships the right way for enterprise sales
Partnership example 1: Citrix and the Microsoft relationship
Partnership example 2: Walking into Nutanix in a white jacket
Content marketing lessons and the education-first approach
FBI ransomware webinar and value-driven B2B sales content
Cold calling mistakes and lessons learned in enterprise sales
Anthropic AI partnership and cutting integration time to 36 minutes
How R-Scout works and AI with human certification
Lightning round
Where to find HYCU and Simon
Resources
Full show notes: https://saasclub.io/388
Join 5,000+ SaaS founders: https://saasclub.io/email
59 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.