SaaS Backwards - Reverse Engineering SaaS Success

Send us a textConsolidating sales and marketing into the office of the CRO might be a controversial topic, but it can be healthy for demand and sales functions to become enmeshed.In this episode of the SaaS Backwards podcast, our guest Cliff Simon, CRO of Carabiner Group, explains how aligning demand and sales functions can create a more cohesive and effective go-to-market strategy.Cliff shares his belief that companies need to have a unified leader at the very top of everything go-to-market. He breaks down how sales and marketing are two sides of the same coin, and why looking at everything through a revenue lens is critical for success.We also discuss Cliff’s collaboration with Nick Toman, author of The Challenger Customer and Carabiner Group’s Chief Product and Strategy Officer. Cliff highlights Nick’s expertise in market research, referencing his latest report, "Commercial Success in 2025 Hinges on GTM Strategy."Topics covered in this episode include the evolution of enterprise sales as SaaS companies scale, achieving capital efficiency in go-to-market strategies, and measuring progress in enterprise sales.Looking for ways Carabiner Group can boost your Revenue Operations? Check out the GTM Tech Stack Audit and Analysis Workbook—a valuable resource for mapping the relationship between your GTM strategies and technology stack.Key takeaways from this episode:Advantages of combining sales and marketing under the office of the CROThe state of go-to-market and insights on how to achieve capital efficiencyHow to measure progress in the enterprise saleOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textWith all the current tools and technology available to salespeople, many have naturally slipped into a less personal approach than what used to be the norm. As a result, their calls and emails are ignored, and they struggle to get quality leads.This highlights the need to go “back to the future,” or back to the basics, and adopt a personality-driven, people-forward sales approach to cut through the noise.In this episode, we spoke with Alex Grace, the founder and CEO of Velocity Sales Consulting, about his process when coming into a company as a new sales leader or CRO and how he uncovers why things aren’t going as planned.Alex calls this a welcome change in sales, stating, “You'll hang up on an SDR that's using a line, but you're not going to hang up on a person that sounds like a person.”Alex also discusses a common alignment issue between sales and marketing, noting that one can’t exist without the other and how they should be like an old wrestling tag team, working together to reach a common goal.Overall, Alex shared valuable insights into stepping into a sales leadership role, people’s innate ability to sell, the power of saying no, going back to the basics, and alignment between sales and marketing.Key takeaways from this episode:How to take advantage of top salespeople’s skills to help other salespeople on the team to improveWhat KPIs matter and tracking what makes a meaningful conversationThe consolidation of sales and marketing leadership into the office of the CROOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textAccording to this year’s B2B TrustRadius Buying Disconnect Report, where they surveyed 200 B2B brands and over 2000 tech buyers, 2024 is the “year of the brand crisis.”Across the board, brands are spending 38% on brand marketing and 53% on demand, which is understandable given the shorter time frame to justify ROI. The problem is that buyers make decisions based largely on who they’re familiar with, so those who have established recognition and trust over time will be the winners. In this episode, we brought back TrustRadius CEO Vinay Bhagat, who discusses how to better integrate brand marketing with demand generation to develop that trust. Vinay also stressed the significance of the voice of the customer and the need to activate it across digital channels.Overall, Vinay shared valuable insights into B2B marketing, the critical role of brand and demand generation, and the strategic use of customer voice and intent data.Key takeaways from this episode:The significance of brand recognition in making the shortlist for buyersInsights on generating organic traffic by leveraging high-quality user-generated contentThe varying importance of product demos in the sales processOther resources to check out:Our Previous Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textIn this episode of the SaaS Backwards Podcast, we spoke with Steve Oriola, CEO of Unbounce, a landing page platform empowering marketers by combining their expertise with AI insights to create and optimize high-converting marketing campaigns. Steve discussed Unbounce’s recent acquisition of Insightly, a robust CRM with advanced AI and machine learning capabilities that addresses the needs of mid-sized organizations. He explained how this merger aims to break down silos between marketing and sales, focusing on the entire customer journey rather than departmental divisions.In this episode, Steve shared his extensive experience in the SaaS industry, particularly in marketing and sales applications, and discussed his role in partnering with founders to help them realize their visions. Steve provided insights into potential partnerships with investors as a CEO candidate. He explained that the right investor should have at least one of three things: operating experience, strong pattern recognition, or deference to the operator.The conversation also touched on capital efficiency in go-to-market strategies. Steve emphasized the need for early investments in marketing and sales to get the flywheel effect, leading to long-term efficiency and growth. CEOs and CMOs of SaaS companies and founders considering partnering with investors or bringing in a CEO to help scale their business will find this episode relevant and insightful.Key takeaways from this episode:The significance of brand equity in driving business success, especially in competitive marketsThe role of AI in marketing and sales software and the value of machine learning applications in optimizing tasks and decision-makingThe importance of founders partnering with experienced CEOs to scale their businesses effectivelyOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textPaid advertising is often one of the largest budget items for SaaS companies, making it a critical channel for facilitating sales and driving growth.In this episode of the SaaS Backwards Podcast, we flipped the script and had our very own Ken Lempit, President and Chief Business Builder at Austin Lawrence Group, as the guest. Ken shared his insights on the challenges SaaS companies face in achieving capital efficiency in their go-to-market strategies, particularly focusing on advertising.Our conversation explores the prospect experience as a foundational element of successful advertising campaigns. Ken discusses key areas where companies have the most control and can significantly impact the prospect experience, including optimizing landing pages and providing sales reps with proper training and resources.This episode highlights the significance of taking a holistic approach to advertising strategy, continuous optimization, and being hands-on with internal teams and external agencies to ensure advertising budgets are spent effectively.Ken's insights into diagnosing issues within existing campaigns and media spend and his actionable tips for optimizing advertising performance make this episode an invaluable resource for SaaS marketing leaders and CEOs.Key takeaways from this episode:A holistic model for understanding where advertising touches across the business and how to view all elements that contribute to successful advertisingInsights into how to diagnose problems in current campaignsThe importance of looking at the entire prospect experience and optimizing landing pages and follow-up processesOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textTo drive sales and growth, SaaS companies need to have clear messaging, target the right prospects, and leverage industry expertise.In this episode of the SaaS Backwards Podcast, we spoke with Will Robinson, CEO of Encapture, a platform specializing in intelligent document processing for industries like banking, lending, and insurance. Will discussed the challenges associated with selling to highly regulated banking institutions and his strategies for overcoming them, emphasizing the importance of building a strong business case and navigating complex decision-making processes.Our conversation also touched on Encapture’s journey of shifting from a professional services model to a SaaS model, including the changes in culture, sales strategies, marketing approaches, and the integration of AI technology into their product. In this episode, Will provides valuable insights for SaaS CEOs on marketing tactics, targeting prospects, and the value of clear and simple messaging.Key takeaways from this episode:Strategies for navigating the complex sales cycle in financial institutionsEffective marketing strategies for generating leads and building credibilityHow SaaS leaders can build trust with potential buyers through simple and relatable messagingOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textListen, assess, plan, execute, iterate. This week’s podcast guest Janet Jaiswal outlines these as the essential steps in developing and implementing successful marketing strategies in the SaaS industry.Janet Jaiswal is Blueshift's Global VP of Marketing and has 20 years of experience in B2B SaaS marketing, working with companies like IBM, eBay, and PayPal. In this episode of SaaS Backwards, she discusses her expertise in scaling companies through effective go-to-market strategies and the importance of process, technology, and skill sets at different stages of a company's growth. In our conversation, Janet provides insights into the relationship between SEO and content marketing, the importance of identifying and refining the Ideal Customer Profile, and the critical role of product marketing in driving alignment between marketing and product management. Overall, this episode provides a comprehensive look at the strategies and tactics that SaaS marketing leaders can use to drive growth and enhance profitability for their organizations.Key takeaways from this episode:The changing landscape of search engine algorithms and the importance of prioritizing content that conveys value quicklyThe challenges and opportunities of ICP expansion and insights into the processWhy product marketing is crucial when scaling a SaaS companyMore Resources from Janet Jaiswal:Masterclass on Product Marketing: A deep-dive into Product Marketing for B2B SaaS scale-upsDefining your ICP: Discover the optimal approach to identifying your true target marketOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textA community can be a "cheat code" for rapid learning and career advancement, and this week’s guest knows that better than most.In this episode, we had the pleasure of speaking with Kathleen Booth, SVP of Marketing and Growth at Pavilion, the world's largest private community for go-to-market leaders. Our conversation explores the concept of community-led growth and how Pavilion encourages this by providing a platform for members to grow their network, sharpen their skills, and develop lifelong connections. Overall, Kathleen provides valuable insights into the intersection of community, social media, and growth strategies for SaaS companies. Key takeaways from this episode:The importance of community-led growth for SaaS companies and strategies for leveraging communities to drive growth and engagementHow CEOs and marketing leaders can use social media to build relationships, drive pipeline, and engage with prospectsThe challenges executives face in prioritizing social media efforts and the need to shift from viewing social media as a "nice to have" to a "must have" for business growthThis episode is ideal for SaaS CEOs, CMOs, and marketing professionals looking to leverage community-led growth strategies, enhance their LinkedIn presence, and drive pipeline through organic and personalized outreach.Other resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textThe transition from product-led growth (PLG) to an enterprise sales motion is a strategic shift that many SaaS companies are making in order to accelerate growth and enhance profitability. This transition is driven by a variety of factors, including the need to scale, reach new markets, and meet the evolving needs of customers. In this episode of the SaaS Backwards Podcast, we had the pleasure of hosting Juan Jaysingh, founder and CEO of Zingtree, an AI-enabled customer experience automation platform.Juan provided insights into why and how his company made the shift from a PLG model to an enterprise sales motion, emphasizing the need to focus on large enterprise customers who benefit the most from Zingtree's complex, no-code workflow solutions. In our conversation, Juan detailed the challenges and organizational changes required to make this transition, including adjustments in personnel, product development, and customer service.Juan's experience and insights provide valuable lessons for CEOs, CMOs, and other professionals in the SaaS industry looking to understand the challenges and strategies involved in transitioning from a product-led growth model to an enterprise sales motion.Key takeaways from this episode:Challenges and considerations for SaaS companies transitioning from PLG to enterprise salesHow to improve customer experience by providing SaaS solutions that can be implemented quickly and show immediate impactHow Zingtree incorporates AI into its platform to enhance customer support workflows and provide relevant information to agentsOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Send us a textTransitioning from a Product-Led Growth (PLG) motion to an enterprise sales motion requires strategic alignment and effective change management within a SaaS Marketing team.In this week’s episode, we discussed the challenges and considerations in this transition with Karen Budell, the CMO of Totango + Catalyst, two SaaS software companies collaborating to drive sustainable revenue through customer relationships. Budell highlights the significance of grasping the nuances of the buyer's journey and understanding the shift in market dynamics when transitioning from a PLG approach to targeting enterprise customers.She also focuses on the importance of change management during this transition and tackling challenges head-on to ensure a successful integration and go-to-market strategy. She likened it to moving in with a partner and combining belongings, emphasizing the necessity of open and honest conversations within the team.This episode also touches on the importance of thought leadership and the role of written content, industry events, and proprietary events in marketing. Executives involved in mergers and acquisitions within the SaaS industry and marketing professionals interested in transitioning marketing strategies from PLG to enterprise sales will find value in Karen’s insights.Key takeaways from this episode:Why early learnings, customer feedback, and market insights are essential for crafting a successful merger strategyThe crucial role thought leadership plays in influencing the buying committeeThe need for alignment, transparency, and clear communication in agency relationshipsOther resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes 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---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.