SaaS Backwards - Reverse Engineering SaaS Success

Guests: Ken Lempit, James Ollerenshaw, and Rob Curtis

Voice is the new frontier in SaaS — but are we ready for the implications?

In the third episode of our AI Series, Ken Lempit is joined again by James Ollerenshaw and Rob Curtis to explore how voice and AI are colliding to transform the way B2B SaaS companies operate — from the way products are built and sold to how customers are supported.

We dive into:

• The shift to voice-first ...

Guests: Ken Lempit, James Ollerenshaw, and Rob Curtis

AI isn’t just a bolt-on anymore—it’s rewriting the rules of SaaS from the ground up.

In this episode, Standup Hiro co-founder Rob Curtis and tech strategist James Ollerenshaw join host and GTM expert Ken Lempit to unpack how Agentic AI is forcing SaaS leaders to rethink everything: product design, go-to-market, customer trust, and even internal culture.

From natural language interf...

Guest: Sjoerd Handgraaf, Chief Marketing Officer at Sharetribe

The most overlooked growth lever in SaaS? Positioning.

In this episode, Sharetribe CMO Sjoerd Handgraaf reveals how redefining product positioning transformed their trajectory—and why many SaaS companies are still getting it wrong.

Handgraaf takes us inside Sharetribe’s journey from chasing big logos to doubling down on their true customer: non-technical marketpl...

Guest: James D. Wilton, Founder & Managing Partner of Monevate

The advent of AI is forcing a complete rethink of traditional SaaS pricing—particularly the long-standing dominance of user-based pricing. 

In this episode, pricing strategist James Wilton explains why AI-native products are undermining the foundations of per-seat pricing models. 

Unlike traditional SaaS, where users are the proxy for value, AI tools often perform task...

Guests: Ken Lempit, James Ollerenshaw, & Rob Curtis

AI is transforming SaaS—but not in the way most leaders think.

Forget the headlines claiming "SaaS is dead." The real shift isn't just in tools—it's in how fast software is built, marketed, and bought.

In this episode, Rob Curtis (VC-backed founder), Ken Lempit (SaaS GTM strategist), and James Ollerenshaw (AI advisor) break down what AI means for the future of...

Guest: Guy Rubin, Founder & CEO at Ebsta

Most B2B SaaS leaders know their top performers carry the team, but few understand why the performance gap keeps widening.

The reality is that just 14% of reps are now responsible for 80% of revenue, and the gap between A-players and everyone else has grown to 11x. Fixing this isn’t about more training or new tools—it’s about creating consistent, data-driven sales execution across the enti...

Guest: Srikrishnan Ganesan, Co-Founder & CEO of Rocketlane

Most B2B SaaS leaders know that onboarding is important but underestimate its impact.

The reality is that 97% of churn at first opportunity is decided in the first 90 days, making onboarding the most critical stage in the customer journey and the defining factor in revenue growth and long-term customer success.

In this episode, Sri Ganesan, Co-Founder and CEO of Rocketlane...

Guest: Christina Richards, Fractional CMO & Author of Rise of the AI-Powered CMO

Most B2B marketers think they’re using AI effectively. The reality? Many are barely scratching the surface—and failing to leverage AI as a true revenue driver.

Christina Richards, fractional CMO and author of Rise of the AI-Powered CMO, breaks down how AI is transforming go-to-market strategies, reshaping demand generation, and redefining the role of...

Guest: Zach Wright, Co-Founder & CRO of Syft AI

Most sales teams are still stuck in outdated prospecting tactics—mass email sequencing, generic outreach, and hoping something sticks. The reality? These methods are failing fast, and sellers who rely on them are drowning in low response rates and missed pipeline goals.

Zach Wright, co-founder and CRO of Syft AI, breaks down why traditional sales prospecting is broken and what today...

Guest: Peter Cohan, Author of Doing Discovery

Most sales teams think they’re great at discovery. The reality? About 80% are getting it wrong—and it’s the single biggest reason why deals stall, go to a competitor, or die with “no decision.”

Peter Cohan, author of Doing Discovery, breaks down why traditional discovery methods are failing and what SaaS sales teams must do differently to uncover real customer value, build compelling busi...

Guest: Ty Tinker, Head of Analytics at AdQuick

What if everything you thought about billboard advertising was wrong?

Ty Tinker, Head of Analytics at AdQuick, breaks down the myth that out-of-home (OOH) advertising is unmeasurable and outdated. In reality, leading SaaS companies—including Dropbox, Salesforce, and Shopify—are embracing billboards, transit ads, and airport placements to drive brand awareness, accelerate sales cycles, an...

Guest: Jon Miller, Co-Founder & CEO of a Stealth AI Startup

Jon Miller, co-founder of Marketo and former CMO of Demandbase, argues that B2B marketing’s traditional playbook—built on predictable demand generation, MQL scoring, and SDR-driven outbound—is broken. 

The “gumball machine” approach, where marketers expect predictable revenue by simply feeding in budget and campaigns, no longer works. Buyers have evolved, becoming more r...

Guest: Kerry Cunningham, Research & Thought Leadership at 6sense 

85% of buyers initiate the first conversation with vendors—on their terms. If your marketing still revolves around capturing leads and pushing outbound sales, you're already behind.

Kerry Cunningham, Head of Research at 6Sense, shares insights from their Buyer Experience Report 2024, revealing how today’s B2B buyers operate—and why most SaaS companie...

Guest: Maxwell Nee, CRO at ScoreApp

Maxwell Nee, Chief Revenue Officer of ScoreApp, shares the strategies behind scaling a low ARR SaaS product to 9,000 paying customers worldwide. By leveraging the principles of quiz marketing, ScoreApp turns engagement into actionable insights, driving top-of-funnel lead generation, accelerating sales cycles, and refining customer experiences. 

The platform’s success stems from a relentle...

Guest: Ken Lempit, President & Chief Business Builder at Austin Lawrence Group

In this episode, Austin Lawrence Group’s Ken Lempit shares a bold approach to overcoming the inefficiency of traditional advertising campaigns. 

He emphasizes a new strategy: combining foundational customer interviews with rapid, real-time testing via high-frequency organic social media posts. 

This iterative approach helps identify messaging ...

Guest: Steve Brothers, CEO of Splashmetrics

With 77% of millennial buyers avoiding sales interactions until they’ve already made a purchase decision, buyers are consistently clear about what they need: fast, personalized, and self-directed answers. 

Yet vendors stubbornly stick to outdated practices, forcing buyers into their processes rather than meeting them where they are.

In this episode of SaaS Backwards, Steve Brothers, CEO of S...

Guest: Beth McHugh, Fractional Product Leader

When deals stall, buying committees often default to doing nothing. Why? Because they didn’t all agree that the problem was worth solving.

In this episode, Beth McHugh explains why pain points alone rarely drive action and how the Jobs to Be Done (JTBD) methodology identifies the “struggling moments” that compel prospects to move forward. These critical moments are when a prospect or team...

Guest: Bob Moesta, Author of “Demand-Side Sales 101”

In this episode, Bob Moesta, author of Demand-Side Sales 101, reveals why uncovering your customers’ “struggling moments” is the single most efficient step for any business. Whether it’s product development, marketing, or sales, understanding the root causes behind why customers make a change transforms every decision you make.

As Bob explains, customers don’t b...

Guest: Peter Cohan, Author of “Great Demo!”

Have you ever walked into a software demo, hoping to learn something new, only to sit through a “Harbor Tour” of irrelevant features? 

You’re not alone – and neither are your prospects.

Peter Cohan, author of Great Demo!, joined us on the SaaS Backwards Podcast to unpack the biggest demo mistakes SaaS teams make:

❌ Starting with the how instead of the why
❌ Overloading prospects with...