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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: Kevin Jacobson, CEO at Foxen 

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Most SaaS companies try to scale by adding headcount and channels. Foxen scaled by tightening fundamentals.

In this episode, Kevin Jacobson, CEO of Foxen, joins host Ken Lempit to explain how an overlooked market — multifamily housing — became a durable SaaS growth opportunity through operational discipline and relationship-driven GTM.

Kevin breaks down why traditional industries lag in SaaS adoption, why consistency matters more than speed, and how Foxen scaled through direct sales, referrals, and systems built to support growth. He also shares lessons from raising growth equity and why systems, not people, ultimately unlock scale.

Key takeaways:

• Underserved markets reward execution over hype
• Consistency precedes scalable SaaS growth
• Direct sales still win in relationship-driven markets
• Systems, not headcount, enable scale

If you’re a SaaS leader selling into traditional industries or rethinking how growth really happens after PMF, this episode delivers a grounded, operator-first perspective.

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Guest: Dave Boyce, Executive Chairman & EVP of Product at Winning by Design 

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Most SaaS companies are still built to sell. Today’s buyers want to activate, experience value, and decide on their own.

In this episode, Dave Boyce, Executive Chairman and EVP of Product at Winning by Design, joins host Ken Lempit to explain why SaaS GTM is shifting from lead handoffs to self-service activation, AI-driven automation, and system-based growth.

Dave shares why PLG isn’t about removing humans, but focusing them on higher-value work — while usage-based pricing and automation blur the line between acquisition, onboarding, and expansion. He also challenges traditional planning models, arguing that people don’t scale, systems do.

Key takeaways:

• Activation is replacing lead handoffs in SaaS growth
• PLG and AI redefine when humans should engage
• Usage-based pricing lowers friction and builds habit
• Systems, not headcount, unlock scale

If you’re a SaaS leader rethinking GTM for an AI-driven, self-service world, this episode delivers a practical, no-hype perspective.

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Guest: David Karandish, Founder & CEO of Capacity  

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Most SaaS companies don’t fail because the technology is bad. They fail because they build point solutions, chase the wrong markets, and struggle to turn AI into real, scalable value.

In this episode, David Karandish, Founder & CEO of Capacity, joins host Ken Lempit to share how his team scaled past 20,000 customers and toward $100M+ in revenue by evolving from an AI point solution into a full SaaS platform for support and contact centers.

David breaks down the pivots behind that growth, why mid-market SaaS often stalls, and how the compound startup model is reshaping modern SaaS — not by doing more, but by integrating smarter.

Key takeaways from this episode:

• Why many AI SaaS products fail before reaching enterprise scale
• The difference between “salad” vs. “brownie” AI projects
• How platform consolidation creates GTM and pricing leverage
• Why GTM motion must align with deal size
• How integration becomes the true SaaS moat

If you’re a B2B SaaS founder, CRO, or CMO navigating AI adoption, platform strategy, or the leap from mid-market to enterprise, this episode offers a grounded playbook for building durable SaaS growth—without the hype.

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Guest: Prasanth Chilukuri, Co-Founder & Managing Partner at Soul Street Ventures 

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The biggest threat to early-stage SaaS growth isn’t competition. It’s founder distraction, unfocused GTM motions, and chasing quick wins instead of building a real business.

In this episode, Prasanth Chilukuri, co-founder and managing partner of Soul Street Ventures, joins host Ken Lempit to reveal why most early-stage SaaS companies struggle long before product issues surface — and how disciplined strategy, a tight ICP, and hands-on founder coaching unlock meaningful, scalable traction.

Drawing on his experience both as a SaaS founder (Tekmetric) and investor, Prasanth explains why “scale with soul” isn’t just a mantra, but a framework for building durable companies that don’t rely on hype, vanity channels, or coast-driven valuation games.

Key takeaways from this episode:

• Why misaligned ICPs and GTM distractions quietly stall early-stage SaaS
• How to test, retest, and refine GTM motions using real customer behavior
• Why AI discoverability is reshaping marketing efficiency (and what to do about it)
• How venture style differs across regions — and why it matters for founders
• Why founder coachability, discipline, and mindset are the strongest predictors of growth
• How unique SaaS data assets create new value (and why most companies underuse them)

If you’re a B2B SaaS founder, CRO, or CMO navigating early-stage go-to-market, evaluating AI’s impact on your product, or preparing for institutional capital, this episode offers a practical, grounded playbook for building a company that truly lasts.

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Guest: Mark Walker, CEO at Nue.io 

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SaaS pricing isn’t breaking because of AI — it’s breaking because most revenue systems were never built for the speed and complexity of today’s models.

In this episode, Mark Walker, CEO of Nue.io, joins host Ken Lempit to unpack why modern SaaS and AI companies are abandoning legacy CPQ and billing stacks for a flexible, unified revenue infrastructure built for rapid change.

Key highlights:

• Why legacy CPQ + billing can’t support modern SaaS pricing
• How committed consumption + bank-billed models are reshaping monetization
• Why speed of configuration is now a GTM advantage
• What RevOps must rethink as pricing experiments explode
• How elite teams thrive on hard problems and high-velocity execution

If you’re a B2B SaaS founder, CRO, CMO, or RevOps leader navigating complex pricing models, upgrading your revenue stack, or preparing for next-gen AI monetization, this conversation will change how you think about scaling.

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Guest: Brent Adamson, Co-Author of The Framemaking Sale & Co-Founder of A to B Insight

SaaS sales teams obsess over beating competitors—but the real battle isn’t across the table. It’s in the buyer’s mind.

In this episode, Brent Adamson—co-author of The Challenger Sale and The Challenger Customer and Co-Founder of A to B Insight—joins host Ken Lempit to reveal why most SaaS deals are lost to no decision at all, and how his new book, The Framemaking Sale, helps buyers build the confidence to act. 

Brent explains how the sales playbook has evolved from “teach them what to think” to “help them trust themselves”—and why the future of B2B growth depends on changing how we sell, not what we sell.

Key insights from this episode:

• Why no decision—not competitors—is killing SaaS deals
• How to turn buyer anxiety into deal confidence
• Why “trusted advisor” means helping customers trust themselves
• How marketing and sales can guide smarter, faster SaaS buying
• The mindset shift every B2B sales leader needs now

If you’re a B2B SaaS CRO, CMO, or founder looking to increase close rates, reenergize your go-to-market, and win against the status quo, this conversation will change how you think about selling.

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Guest: Melanie Nabar, Vice President at Volition Capital 

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SaaS founders often see only two funding paths—venture or private equity—but there’s a smarter middle lane that keeps control where it belongs: with the founder.

In this episode, Melanie Nabar, Vice President on the Software Team at Volition Capital, joins host Ken Lempit to unpack how growth equity works, when it’s the right fit, and the scale-up mistakes that stall promising SaaS companies.

Key insights from this episode:

• Why growth equity can fuel SaaS scale without losing control
• The biggest post-funding hiring mistake founders make
• How AI is reshaping go-to-market efficiency in SaaS

If you’re a B2B SaaS CMO, CRO, or founder navigating scale-up challenges, funding strategy, or go-to-market transformation, this episode will help you see where real growth capital fits—and how to make it work for you.

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Guest: Rob Belcher, Managing Director at SaaS Capital

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SaaS founders often think equity is the only path to growth—but giving up ownership isn’t the only option.

In this episode, Rob Belcher, Managing Director at SaaS Capital, joins host Ken Lempit to break down how growth debt works, what investors really look for in valuations, and how B2B SaaS leaders can finance smart without losing control.

Key insights from this episode:

• Why growth debt can fund SaaS expansion without heavy dilution
• The financing ladder every founder should understand—from angels to private equity
• How valuation multiples are shifting and what drives them higher
• The role of clean contracts, retention, and growth rate in exit outcomes
• Why AI is creating a “priced for perfection” split in SaaS valuations

If you’re a B2B SaaS CMO or CRO navigating fundraising, growth efficiency, or exit strategy, this episode will help you sharpen your playbook.

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