SaaS Backwards - Reverse Engineering SaaS Success – Details, episodes & analysis

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Why SaaS companies stall at $10M, how execution breaks down, and what founders must change to scale  

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Guest: Mark Abbott, Founder & CEO at Ninety  

Most SaaS companies don’t hit a wall because demand dries up — they hit it because execution doesn’t keep pace with growth.

In this episode of SaaS Backwards, Mark Abbott, Founder and CEO of ninety.io, explains why SaaS companies predictably stall as they grow and how founders underestimate the leadership and operational shifts required at each stage. Drawing on decades as an operator, investor, and board member, Mark walks through the five unavoidable stages of company growth and why stage three is where most companies get stuck.

The conversation explores why speed becomes a liability, why leadership requirements change as teams scale, and how operating discipline and culture quietly determine whether a SaaS company breaks through its ceiling or plateaus indefinitely.

Mark also unpacks the Entrepreneurial Operating System (EOS), the mindset shift from lifestyle entrepreneur to long-game founder, and why operational systems are not overhead — they’re a competitive advantage. This conversation is essential listening for SaaS founders navigating product-market fit, team scaling, and leadership complexity.

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Guest: Lara Shackelford, SVP of Growth Marketing at iCapital 

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Most SaaS companies are investing heavily in AI, yet many struggle to see meaningful ROI. In this episode of SaaS Backwards, Lara Shackelford—SVP of Growth Marketing, MarTech, and CRM at iCapital—breaks down why AI initiatives fail without the right systems, governance, and change management.

Lara explains how AI-powered revenue systems should be designed across the full customer lifecycle, from demand generation through customer success. She introduces the concept of “agent sprawl,” outlines why AI readiness assessments are critical before scaling automation, and shares practical examples of signal-based marketing and sales automation that actually work.

This conversation is essential listening for SaaS CROs, CMOs, and RevOps leaders looking to align AI strategy, revenue operations, and go-to-market execution.

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Guest: Braydan Young, Co-Founder and CEO at SlashExperts

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Buyers don’t want another “book a demo” button—they want proof from people like them.

In this episode, Braydan Young, Co-Founder and CEO of SlashExperts (and previously co-founder of Sendoso), joins host Ken Lempit to share how buyer-led growth is reshaping SaaS sales and why the old way of running references at the end of the deal cycle is broken.

Key insights from this episode:

• Why moving customer references earlier can shorten sales cycles by 4–6 weeks
• How authentic peer conversations double conversion rates compared to demos
• What CROs can learn from Sendoso’s hypergrowth—and its “we grew too fast” moment
• Why handwritten notes and simple gifts outperform flashy, expensive ones
• How to turn the “dark funnel” into a competitive advantage

If you’re a B2B SaaS CMO or CRO looking to accelerate pipeline, increase deal size, and close faster with fewer wasted demos, this episode is a must-listen.

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The B2B world is different today, and (unfortunately) there’s no one formula that works across the board. It’s not outbound versus inbound. It’s not advertising versus content.

Every organization has a unique formula that will consistently drive meaningful conversations with targeted prospects.

Therefore, you'll never see a productive organization where there's a lot of animosity between marketing and sales leadership.

In this episode, Ben Page-Fort, who works with early and growth stage FinTechs to develop and execute go-to-market strategy, talks about how sales and marketing alignment is no longer a goal—it’s a must have.

And it’s all hands on deck to find the right formula because we’re all in the same boat.

Key Takeaways:

• Hiring for today (their skillsets match the current needs of the organization) and not by trying to anticipate future needs.
• The importance of setting qualitative goals and key performance indicators with all revenue growth stakeholders committing to driving results.
• When joining a new organization as a marketing or sales leader, it's important to understand and respect what is already working and avoid making drastic changes without fully understanding the existing strategies and successes. 

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup 

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There’s nothing like an economic slow-down to thin the herd. Companies take longer to buy, consolidate resources, and rethink their go-to-market strategy.

So why are companies doubling down on yesterday’s strategies?

Normally the host of SaaS Backwards, Ken Lempit, President of Austin Lawrence, sits in the guest seat this week to answer questions about how SaaS leaders need to approach marketing to engage today’s buyer.  

Key Takeaways from this episode:

• Demand generation involves both demand capture (or lead generation), which is a short-term focus, and demand creation, where you’re creating relationships over the long term with potential customers not yet in a buying motion.
• Creativity is back. With the proliferation of content and generative AI, it’s the creatives that are going to figure out how to stand out from the crowd. 
• Why all B2B SaaS marketers should read "The Challenger Customer" if they’re using thought leadership content. 

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup 

Send us Fan Mail

When a company starts out, verticalization may not be the best thing. In fact, today’s guest Corey Quinn, fractional CMO and GTM strategist prefers to work with companies who went broad first, since there’s value in exploring different verticals and learning the nuances in the different markets.

But at a certain point, verticalization becomes necessary to scale. It reduces complexity, improves marketing, and helps to differentiate from the competition.

In this episode, host Ken Lempit and Quinn discuss how to narrow down and exploit areas of specialization.

Key Takeaways:

• Understanding your best fit customer by conducting qualitative and quantitative analyses of your business.
• The role of thought leadership content and the importance of ensuring subject matter expertise within the chosen vertical.
• Ensuring that your marketing efforts align with your sales process and provide valuable insights to potential customers during sales conversations. 

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup 

Send us Fan Mail

It’s never been harder for marketers generate an audience where you can have impact than it is today.

The media landscape has exploded and the number of choices we have as marketers has never been more varied.

In many ways, we’re now paying for the sins automating a process of building trust and relationships.

In this episode, Anthony Kennada, Co-Founder and CEO of Audience Plus talks with Ken about how the marketing pendulum is swinging back from marketing automation, inbound, and maximizing SEO to its original intent—creating value for an audience in a more authentic way.

Key takeaways:

• How to create the authentic content that B2B buyers care about today. 
• Why first party data will be crucial to personalize content and prove impact in the face of changing data privacy regulations and the decline of third-party cookies.
• How the shift towards owned media will help marketers regain control over their lead-to-revenue process and reduce reliance on third-party platforms and algorithms.

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup 

Send us Fan Mail

As martech SaaS founder, Steve McDonald acknowledges the tendency to believe that their product is so exceptional that customers will naturally flock to it.

But then reality sets in and you realize that maybe Shoeless Joe Jackson wasn’t whispering in your ear after all.

There’s a lot of risk for customers to invest in something new, and content marketing is the obvious way to build trust. But with the volume of noise out there today, your development process must be strategic, methodical, and efficient.

In this episode, Ken and Steve geek out on the role that content plays for today’s SaaS and how thought leadership actually works to spark conversations with prospective customers.

Key takeaways:

• Why podcasting is still an effective way to create thought leadership content efficiently and effectively.  
• Marketers should consider creating themed podcast series that focus on specific topics or industry challenges.
• Why it's important to invest in thought leadership that delivers customer insights early on to establish the company as an expert to spark conversations with prospects. 

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup 

Send us Fan Mail

When joining MadKudu as a Marketing VP, Shannon Curran knew they were so much more than a predictive lead scoring platform.

She wanted to shift the conversation from product-led growth (PLG) to a focus on hybrid funnels and revenue generation. And because it would be a huge challenge to cut through the noise in the MarTech/RevTech space, they engaged an external consultant to conduct research and help with the positioning process.

They explored the competitive landscape, market trends, and the company’s unique value proposition.

Through testing and feedback, they arrived at the positioning as a revenue automation intelligence engine, emphasizing the company's ability to predict and prioritize revenue-generating actions, automate revenue intelligence, and provide data-driven insights for go-to-market teams.

The repositioning efforts showed a 2X increase in demo conversions.

In this episode, Curran talks about: 

1. The importance of positioning before messaging and branding, as it provides a solid foundation for effective communication and differentiation in a crowded market.
2. Vetting new job opportunities: funding, understanding their key metrics (CAC, LTV, churn), board involvement, and the experience of the founders.
3. Using a test and learn approach to their messaging change by conducting bi-weekly tests on their website, paid advertising, and other channels to gather data and feedback. 

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup 

Send us Fan Mail

Outbound selling is here to stay—but to make it work, efficiency is key.

Of course, the task at hand isn’t lost on Salesintel.io CEO Manoj Ramnani, who’s tools are designed to do just that. Salesintel.io is a go-to-market intelligence platform that helps marketing, sales, and revenue operations teams research prospective accounts and find contact information.

Ramnani is most excited about “Predictive AI” where it has the potential to predict future intent based on historical data so that sales teams can target the right prospects and tailor their outreach accordingly. 

For example, if a company has recently purchased Salesforce and is using it for CRM and HubSpot for marketing, and you have six BDRs and AEs, it is highly likely that they would be interested in purchasing a sales cadence software. 

In addition, Ramnani and host Ken Lempit discuss:

• How the sales process is shifting towards a demand generation approach and what it takes to build efficient pipelines and generating meaningful conversations with potential customers. 
• The role of AI and machine learning in enhancing account intelligence and making it more actionable. 
• Outbound sales efforts are still essential, but sales leaders need to embrace the changing sales landscape, leverage AI and account intelligence to drive efficiency, and prioritize personalized and value-driven outbound sales efforts.

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 

🔗 Get your free SaaS GTM Checkup