SaaS Backwards - Reverse Engineering SaaS Success

Send us a textGifting can be a powerful outbound strategy that captures attention far more effectively than an email. In this week’s SaaS Backwards podcast episode, we spoke with Kris Rudeegraap, Co-CEO and Co-Founder at Sendoso, a gifting and direct mail platform that helps revenue teams 6x second call rates, double win rates, and close deals 29% faster.Kris shared how his background in software sales and experience with gifting inspired him to create Sendoso. He provided insights into the company’s initial go-to-market strategy, its evolution from a "growth at all costs" mindset to a more efficient, profit-driven approach, and how this shift has shaped its success.We also discussed common objections and misconceptions about gifting, such as it being “too expensive” or impractical without someone’s address—and how Sendoso addresses these challenges.Kris backed up Sendoso’s impressive results with client success stories: Gong influenced over $30 million in pipeline by mailing pinatas, Guru improved meeting conversion rates by sending cupcakes, and Verkada saw a remarkable increase in ad conversion rates by offering a Yeti mug as a meeting incentive across social media and LinkedIn campaigns.Read more Sendoso success stories here and view customer examples here. Key takeaways from this episode:The power of gifting as an outbound strategyHow Sendoso helps clients select the right gifts for the right people at the right timeInsights into the fundraising process and the current environment for startupsOther 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 textBuilding meaningful connections with individuals using different channels can be more effective than running an ABM program that only provides a shallow understanding of what’s happening within an account. In this week’s SaaS Backwards podcast episode, we spoke with Dmitri Lisitski, Co-Founder and CEO at Influ2, a person-based advertising platform that allows you to reach specific people within target accounts and see who interacts with your ads.Dmitri takes us behind the scenes and discusses how his frustration with imprecise ABM platforms led to the creation of Influ2, which aims to solve this problem by targeting individual decision-makers within an account rather than only providing this broad view.We discuss the orchestration between sales and marketing and the significance of nurturing relationships over time in enterprise sales. Dmitri explains how the best thing marketing can do for salespeople is target the same account they’re trying to chase and influence their decision, build awareness, and track intent. Our conversation also covers the role of thought leadership in generating conversations and supporting the sales process, the impact of AI on content creation, and attribution challenges in B2B marketing.This episode provides valuable insights for SaaS CEOs, CMOs, and B2B marketing and sales professionals.Key takeaways from this episode:The humanization of sales and marketing in the enterprise motionWhy the use of AI in content development falls flat and what to do insteadMeasuring the impact of advertising on revenueOther 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 textWe often emphasize the importance of understanding what’s being talked about in sales conversations to shape content strategy and tell unique, compelling stories.In this week's SaaS Backwards podcast episode, we talk with Parthi Loganathan, Founder and CEO of Letterdrop, a platform designed to help companies do just that.Parthi explains how Letterdrop’s AI assists companies in creating content that resonates with more buyers by leveraging the language their customers actually use, cutting down the time and improving the quality of their thought leadership content. He also shares how Letterdrop supports SDRs in delivering value and helps companies uncover and understand their customers' unmet needs.We also discuss the ongoing shift in SEO, the growing focus on LinkedIn, and the decline of traditional outbound sales tactics such as cold calling and cold emailing.Our conversation with Parthi offers valuable insights for SaaS CEOs, CMOs, and marketing and sales professionals in the B2B space.Key takeaways from this episode:The importance of getting context and relevance right before scaling itWhy cold calling and cold emailing no longer worksInsights on future opportunities for content on LinkedInOther 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 ability to leverage data and prioritize sales and marketing efforts is essential to the success of enterprises with broad addressable markets.Recognizing the struggles enterprises face in managing vast amounts of data, this week’s SaaS Backwards podcast guest Elio Narciso, saw an opportunity to improve how sales reps identify targets and prioritize their efforts.Elio is the Co-founder and CEO of Scalestack, an all-in-one data enrichment, prioritization, and activation platform that allows go-to-market teams to easily map GTM data from many different sources to their ideal customer profile and their sales engine. In this episode, Elio gives us a look into Scalestack’s origins. He recounts his background in advising startups at AWS and how it led him to uncover pockets of inefficiency in their go-to-market motions, such as a productivity gap for sales reps and a general dissatisfaction that companies have with their data.Throughout this episode, Elio reflects on lessons from his past ventures, addresses common sales and marketing challenges, and highlights Scalestack’s mission and capabilities.Key takeaways from this episode:How hiring well is essential for scaling startups and managing that scaleWhy focusing on enterprise clients can be advantageous for a startupStrategy for building partnerships to reach more potential customersOther 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 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.