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In this episode of Monetizing SaaS, I sit down with Niklas Halusa, co-founder & CEO of Nautical Commerce.Niklas started his career in investment banking and VC before realizing he wanted to found and build. That journey led him to build Nautical Commerce, a platform that allows founders to launch and scale multi-vendor marketplaces without rebuilding commerce infrastructure from scratch.What We Cover in This Episode:- The hidden challenges of building and scaling marketplaces- Why Amazon, Shopify, and Etsy don’t just take a GMV percentage—they monetize additional services- Why early-stage pricing isn’t about financial efficiency—it’s about learning- How pricing should evolve as a company scales- The hardest trade-offs in launching a marketplace startup- What Nautical Commerce is building to “arm the marketplace rebels”Niklas has been through every pricing model—flat fees, value shares, onboarding costs, and feature-based pricing. His learnings?- Early-stage companies should optimize for learning, not revenue extraction- Pricing should reduce friction to buy- Founders should talk to customers constantly about willingness to payWe also discuss:- The critical trade-offs of launching a marketplace startup- How pricing should evolve as a company scales- What Nautical Commerce is building to enable marketplace entrepreneursIf you’re building a SaaS product, a marketplace, or thinking about pricing & packaging, this has been one of my favorite conversations on Monetizing SaaS.⏱️ Chapters:00:00 – Intro & Welcome02:00 – Niklas' journey: From finance to tech to founding Nautical06:30 – The key differences between investing and operating10:45 – Why marketplaces are just infrastructure for commerce14:15 – Incentivizing supply vs. demand in a marketplace18:40 – The insight that led to founding Nautical Commerce22:05 – The trade-offs of building for startups vs. enterprise25:10 – The hidden challenges of pricing a marketplace30:30 – Why pricing is stage-dependent for venture-backed startups34:20 – Pricing & packaging at Nautical: Lessons from iteration38:50 – The future of marketplace pricing: From GMV to service monetization42:45 – How Amazon captures more value without increasing take rates46:00 – Reducing friction in pricing & the importance of willingness to pay50:20 – Niklas' vision for arming the marketplace rebels53:00 – Final thoughts & where to learn more#SaaS #PricingStrategy #Marketplaces #Startup #Ecommerce #MonetizingSaaS #NauticalCommerce
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Zach Hawtof is the CEO and co-founder of Tightknit, a platform that helps businesses run communities on Slack. Before founding Tightknit, Zach spent nearly six years at Salesforce, where he became deeply immersed in the power of community at enterprise scale. He later joined Airkit, where he learned the zero-to-one startup journey before taking the leap to build Tightknit in 2023.In this episode:- The power of community: why businesses should invest in it- What Salesforce taught Zach about product, marketing, and go-to-market- How AI and the changing workplace are reshaping how professionals engage with communities- The future of community-led growth in B2B SaaS- The journey of Tightknit's pricing strategy, from early experiments to its evolving monetization model𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀:1️⃣ Know Your Buyer First, Then Price Accordingly – “Different teams think about pricing differently. Engineers expect usage-based models, marketers want predictability. Your pricing model should align with how your buyers think.”2️⃣ Make Pricing Transparent but Scalable – “Early on, we show customers everything about our pricing, but we also think about how we grow with them. The key is balancing simplicity with expansion levers.”3️⃣ Optimize for Adoption Before Optimization – “Right now, we’re focused on getting the right customers at the right entry points. Optimization comes later. The goal is to fit where our customers are today and scale as they grow.”⏳ Chapters:00:00 Introduction and Zach’s Background05:12 Lessons from Salesforce and Airkit13:47 The Role of Community in B2B SaaS20:33 Building and Scaling Tightknit30:12 The Future of Community-Led Growth40:58 Tightknit’s Pricing Journey and Lessons Learned48:06 The Importance of Aligning Pricing with Buyer Mindset#pricingtips #b2bsaas #communitybuilding #monetization
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Saknas det avsnitt?
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Alex Sambvani is the CEO and co-founder of Slang.ai, a voice AI platform helping restaurants handle phone-based customer interactions more effectively. Before founding Slang in 2019, Alex worked worked on the data science team at Spotify, which fueled his interest in applying machine learning to solve problems for small businesses. In this episode:- Lessons from Spotify on building scalable AI solutions for real-world problems- Why voice AI is ripe for disruption in the restaurant industry- Slang.ai’s journey in narrowing its use case and defining an ideal customer profile- How founders learn pricing on the fly and why pricing and sales should be taught in school- Balancing market adoption with pricing experimentation- Strategic decisions behind Slang.ai’s current $399/month pricing model- Preparing for the complexities of multi-product pricing, including bundling and unbundling𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀:
Start Small, Iterate Based on Data – "Early-stage pricing is exploratory. Start low to validate demand and refine based on willingness to pay and ROI conversations."Know What You’re Optimizing For – "Pricing is about trade-offs. Be clear whether you’re optimizing for market share, profit, or another metric, and design your pricing accordingly."Prepare for Multi-Product Complexity – "As Slang.ai evolves, Alex recognizes that bundling, unbundling, and addressing legacy plans will be critical challenges as the company scales."Chapters:00:00 Introduction and Background06:02 From Spotify to Entrepreneurship: Why Voice AI?14:18 Customer Conversations and Narrowing the Use Case21:45 Designing Simple and Scalable AI Solutions30:29 Early Pricing Experiments: Finding Willingness to Pay37:12 Why Pricing and Sales Should Be Taught in School39:15 Learning Pricing on the Fly as a Founder42:25 Optimizing for Adoption vs. Revenue in Pricing Decisions44:40 Future Vision: Preparing for Multi-Product Pricing and Complexity#pricingstrategy #b2bsaas #ai #entrepreneurship #b2bgrowth
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Ken Babcock is the CEO and co-founder of Tango, a digital adoption platform transforming how teams document and share processes. Before starting Tango, Ken spent four years at Uber, where he learned the power of operational excellence and decentralized playbooks. His entrepreneurial journey began at Harvard Business School, where he met his co-founders and uncovered the pain points that inspired Tango.In this episode:- Lessons from scaling operations at Uber and applying them to SaaS- How the pandemic shaped Tango’s mission and product vision- Building a product that turns "game-changer" into a common customer review- Why simplifying your pricing model leads to better conversion- The surprising impact of raising prices on retention and customer health𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀:1. Don’t Be Too Generous With Free Plans – “Generosity in free plans can hinder conversions. Identify the key triggers to move users to paid plans.”2. Raising prices positively impacts overall health metrics – “Raising prices, when paired with added value, has improved the overall health metrics of the business every time we've done it."3. Simplify Your Pricing – “Overcomplicated pricing schemes add friction to sales. Simplicity helps customers clearly connect cost to value.”Chapters00:00 Introduction and Background05:14 Scaling Playbooks and Operational Excellence at Uber13:47 Founding Tango and the First Insights20:33 Evolving Product Vision Through Customer Feedback30:12 Pricing Strategies: From Free Plans to Enterprise Sales40:58 Raising Prices and Retention Metrics48:06 The Future of Knowledge Work#pricingstrategy #b2bsaas #entrepreneurship
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Gaurav Vohra was part of the founding team at Superhuman and played critical roles across growth, product, marketing, and analytics. After nearly a decade, he's now advising B2B SaaS and PLG businesses.In this episode:
Building growth engines from zero to scale
Prioritizing retention and bottom-of-funnel work before acquisition
How founders often approach pricing poorly and how to fix itWhy charging early forces higher product quality
Growth’s shift from funnel optimization to strategic product bets𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀:Charge from Day One – "Charging out of the gate forces you to build a better product. You have to meet a higher bar than free competitors."Pricing Is Iterative – "Most founders think pricing is one decision at launch. But it's part of the product. It evolves. You have to revisit it the same way you iterate on features."Avoid the Race to the Bottom – "Undercutting incumbents on price can work if your product is nearly identical. But if you’re selling quality, charge accordingly."Chapters00:00 Introduction and Background06:08 Educational Background and Its Impact11:46 Transition to Superhuman18:00 Belief in Superhuman's Vision25:13 The Role of Growth in Early-Stage Companies33:23 The Evolution of Growth Strategies39:04 Understanding Founder Dynamics49:08 Misconceptions About Pricing#pricingtips #b2b #b2bgrowth
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In this episode, James Wood—monetization expert and head of product at M3ter—returns for a deep dive into pricing lessons from his time at Segment & 12 months leading product at M3ter, as well as insights & thoughts on emerging approaches for AI pricing.🔹 Segment’s Pricing Evolution:James walks us through the transformation of Segment’s pricing—from a $10 flat fee that nearly derailed the business to the shift towards monthly tracked users (MTU) that helped scale to $100M+ ARR. Learn how Segment aligned pricing models with customer value, avoided self-serve cannibalization, and drove expansion revenue through smart packaging.🔹 Complexity in Billing Models at M3ter:James reflects on the complexity of modern billing—how legacy pricing models create friction, but also why pricing intricacies can be necessary. He shares real-world examples of how M3ter handles unusual customer pricing requests and the delicate balance between flexibility and simplicity.🔹 AI Pricing – The Next Frontier:AI is reshaping the pricing landscape. James breaks down how AI products are forcing businesses to rethink cost structures, whether seat-based, usage-based, or outcome-driven models will dominate, and why the AI market may head towards hybrid models that account for both compute cost and delivered value.💡 Key Takeaways:• Align pricing with growth metrics that customers understand.• Don’t disincentivize product usage with restrictive pricing.• For AI, early models may focus on usage, but outcome-based pricing is on the horizon.Chapters00:00 Introduction and Overview of Segment's Pricing Journey09:45 Transition to Meter and Insights on Pricing Models19:50 Exploring AI's Impact on Pricing Strategies📅 This is part two of a special two-episode series with James Wood.#Podcast #SaaS #Monetization #Billing #AI #Pricing
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In this episode, James Wood, Head of Product at M3ter, walks us through his career – from Simon-Kucher to Segment and Insight Partners – and how those experiences shaped his approach to pricing strategy. We dive into why usage-based pricing is becoming essential for SaaS, the operational headaches it creates, and how to fix them.🔑 Key Topics Covered:James' career journey: Simon-Kucher, Segment, Insight Partners, and M3terThe rise of usage-based pricing and its impact on SaaS growthWhy manual billing systems leak revenue and how automation solves the problem💡 Three Key Takeaways:Usage-Based Pricing Isn’t for Every SaaS Product – It can unlock growth, but misapplying it can cost more than it earns.Manual Billing Is a Silent Revenue Killer – Many companies lose 5-10% of revenue by not automating usage tracking and billing.Your Pricing Strategy Must Evolve with Your Product – Align pricing with your customer’s journey and willingness to pay, not just internal goals.This episode is packed with insights for SaaS founders and operators looking to refine their pricing models and eliminate revenue leakage. Chapters00:00 Introduction and Career Journey07:38 The Maturing Nature of Usage-Based Pricing15:48 The Growing Awareness of Pricing as a Growth Lever26:15 Balancing Structural Changes with Iterative Changes36:48 Success Stories: Segment and Atlassian
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In this episode, Alexa Gjonca takes us inside the evolving world of monetization—sharing lessons from her time at ProfitWell, Paddle, Seismic, and now Dashlane. Alexa breaks down why great pricing strategies often fail to get implemented, emphasizing the critical role of cross-functional collaboration and deep operational awareness.We dive into the complexities of transitioning from B2C to B2B, the hidden pitfalls of siloed pricing ownership, and why recognizing the true value of a product is foundational to growth. Alexa also reflects on her shift from consulting to operational roles, offering honest insights on navigating failure, aligning teams, and driving meaningful change across an organization.If you’re tackling pricing and packaging challenges or curious about how to build monetization systems that actually scale, this episode is packed with takeaways you can apply today.💡 Alexa shared one of the most profound lessons she learned during her time consulting at ProfitWell:The biggest barrier to successful pricing transformations?A single center of control that's unaware of the operational realities that control how a product is priced and packaged.Companies with pricing siloed in a single function, whether that be product marketing or the executive team, struggled to implement heavily researched and market-vetted recommendations – no matter how data-backed or promising they were. Why?A lack of cross-functional collaboration.Limited awareness of operational realities.Pricing strategies built in isolation from how the product actually works.👉 Alexa’s takeaway: Pricing isn’t a one-person job. It requires shared ownership across teams to bridge strategy and execution.If you’ve ever wondered why pricing shifts stall or fizzle out, this conversation will resonate.🎧 Listen in as Alexa breaks down how to align pricing with reality and build the systems that support growth.Other Takeaways- A single center of control hinders monetization – Successful pricing strategies require cross-functional collaboration, not siloed ownership.
- Understanding the current state is critical – Without a clear grasp of existing technology, processes, and operations, even the best pricing strategies won't succeed.
- Best practices aren't one-size-fits-all – Pricing strategies must align with a company’s growth stage, market position, and product context.
- Transitioning to B2B demands new pricing models – Shifting from B2C to B2B requires rethinking pricing structures and monetization engines.
- Operational excellence drives pricing success – Effective monetization relies on aligning technology, processes, and cross-team communication—not just strategic insights.Chapters00:00 Journey into Monetization02:52 Lessons from ProfitWell05:50 The Importance of Cross-Functional Collaboration09:03 Best Practices in Pricing and Packaging13:02 From Consulting to Operations19:51 Learning from Failures23:00 Lessons from Pricing Failures25:02 Transitioning from B2C to B2B27:48 The Role of Technology in Pricing Strategy33:13 Communicating Across Different Audiences41:00 Formative Moments in Career Development
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In this episode of the Monetizing SaaS podcast, we sit down with Jake Stein, a serial entrepreneur and founder/CEO of Common Paper. Jake shares his journey from building RJ Metrics (acquired by Magento) to Stitch (acquired by Talend), and now tackling inefficiencies in B2B contracts with Common Paper.
Here are some of the highlights:The Journey to Entrepreneurship: Jake's fascination with technology and business started young—from a landscaping business in high school to founding RJ Metrics after realizing he wanted to be on the "founder side" of the calls he took as a VC analyst.Lessons Learned from RJ Metrics: Not anticipating the impact of emerging technologies like Amazon Redshift taught him the importance of staying ahead of ecosystem changes and their downstream effects on business strategy.Insight Behind Common Paper: Contracts should be treated as APIs, not digital pictures of paper, to unlock interoperability and streamline processes for businesses.Other TakeawaysMistakes made at RJ Metrics taught valuable lessons about market evolution and technology.Common Paper aims to revolutionize contract management in the B2B SaaS industry.The significance of having a consistent data model across contracts for better integration.The initial pricing model was overly complex and confusing for customers.Switching to a simpler pricing model reduced customer inquiries significantly.Customer feedback is crucial in shaping product and pricing strategies.Raising prices can lead to better revenue growth despite initial customer acquisition dips.Understanding the psychology behind pricing can enhance customer confidence.A low price can sometimes signal a lack of value to potential customers.Iterative changes in pricing can lead to substantial business impacts.
Learning from past experiences is essential for future decision-making.Chapters00:00 The Journey of a Multi-Time Founder10:27 Lessons from RJ Metrics and Stitch18:52 The Insight Behind Common Paper27:00 Targeting Early Stage Startups34:02 The Journey of Pricing and Packaging47:01 Lessons from a Sales Call#pricingtips #saas #ycombinator
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In this conversation, Ismail shares his journey as a multi-time founder, detailing his experiences from his early interest in math and science to his entrepreneurial ventures across various industries. He discusses the challenges and successes he faced while building companies like Key Crunch, Bitcall, Mersenne, and SuperAgent, emphasizing the importance of iteration, feedback, and finding product-market fit. Ismail also reflects on the lessons learned from Y Combinator and the significance of having a loyal co-founder in the startup journey. In this conversation, Ismail discusses the journey of building AI products, focusing on the importance of understanding customer value, effective pricing strategies, and the evolving role of AI in business. He emphasizes the need for flexibility as a founder and the significance of reasoning in AI, suggesting that future pricing models should reflect the value of reasoning rather than traditional metrics.Takeaways- Ismail's journey began with a passion for math and science.- He transitioned from a nonprofit to entrepreneurship after realizing the potential for impact.- Key Crunch was his first successful venture, followed by the less successful Bitcall.- Mersenne evolved from a consultancy to a profitable software development firm.- The importance of loyalty and trust in co-founders is crucial for success.- Super Agent was born from a desire to leverage AI in advertising.- Y Combinator taught him valuable lessons about survival and scaling.- Iterating quickly and seeking feedback is essential for product development.- The speed of learning and adapting has dramatically increased with modern tools. We built three different products while iterating.- Pricing should reflect the value provided to customers.- Finding internal champions is crucial for enterprise sales.- AI is viewed as a means to optimize costs, not just add software.- The promise of AI is to augment human capabilities.- Charging/Pricing for reasoning is a fundamental question for AI founders.- Current pricing models may not be optimal for AI products.Chapters00:00The Journey of a Multi-Time Founder03:00From Nonprofit to Entrepreneurship05:51The Rise and Fall of Key Crunch and Bitcall09:02Building Mersenne: A Consultancy Success12:09The Birth of Super Agent15:01Lessons from Y Combinator18:13Navigating the AI Landscape21:00The Importance of Iteration and Feedback24:00Finding Product-Market Fit26:52Real Stories from the Field36:15Building and Iterating Products38:10Pricing Strategies for AI Products40:30The Role of AI in Business Optimization44:46Charging for Reasoning in AI50:30Flexibility and Adaptability as a Founder#pricingtips #saas #founder #ycombinator
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In this episode, Claire Vo shares her journey through the tech industry, from founding her own company to leading product at LaunchDarkly. She offers practical insights into product management, highlighting the importance of self-learning, experimentation in B2B SaaS, and engaging directly with customers to shape better products. Claire explains why building strong teams with raw talent and focusing on enterprise value are critical for success.
A key focus of the discussion is pricing and packaging in B2B SaaS. Claire shares strategies for aligning product and pricing roadmaps, managing the complexities of these decisions, and how pricing can become a critical lever for growth. She also reflects on the evolving role of product leaders in the face of rapid technological change and provides actionable advice for those looking to grow in their careers. If you’re interested in product management, pricing strategy, or leadership, this episode is packed with insights.
Takeaways
Claire's journey reflects a fearless approach to learning and growth. Experimentation is crucial but often difficult in B2B contexts. Raw talent in product teams significantly impacts success. CPO roles require a focus on enterprise value, not just product. Customer engagement is essential for effective product management. Self-taught skills can be as valuable as formal education. The importance of understanding customer needs cannot be overstated. You vote with where you spend your time. Running towards problems is essential for growth. How you'll package your offering is one of the hardest parts of product management. You cannot separate product and engineering effectively. Increasingly, an individual can move faster than a small team. No one's going to give you anything you don't ask for. Be fearless in learning and participate broadly.Chapters
00:00 Introduction to Claire Vo's Journey
04:47 The Evolution of a Tech Career
10:04 Founding Experiment Engine and Key Learnings
14:58 The Role of Experimentation in B2B SaaS
19:57 Insights from Being a Chief Product Officer
24:57 LaunchDarkly: The Future of Feature Management
30:03 Customer Engagement and Learning
37:22 Aligning Product and Pricing Roadmaps
44:59 The Changing Role of Product Managers
51:11 Formative Moments in Career Growth
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Mandy Singh is an experienced product leader and SaaS entrepreneur with a diverse background spanning SaaS, AI-powered analytics, & DevSecOps. He's currently a Senior Product Manager at Plotly, working on platform services like Dash Enterprise. Previously, he led the launch of next-gen security tools at Sonatype, developed crypto trading solutions at Botsfolio, and built AI-powered business intelligence tools at EXL. He also founded Psychd Analytics, a social recruitment platform backed by FBStart and IBM, growing it to over 100,000 users and partnering with companies like Reliance Jio. In this conversation, Mandy Sidana shares his journey as a product leader and entrepreneur, discussing his experiences in building products, understanding customer needs, and navigating the complexities of pricing and monetization strategies. He emphasizes the importance of being user-centric, learning from early mistakes as a founder, and the critical role of pricing in product strategy. Mandy also highlights the significance of building relationships with sales and customer success teams, as well as the need for continuous evaluation of product and pricing alignment to drive growth in a competitive market.Takeaways* The importance of being a user champion in product management.* Understanding industry dynamics is crucial for defining strategy.* Validating monetization strategies early can prevent future struggles.* Plotly's approach focuses on code-based data visualization.* Engaging customers for feedback is essential for product-market fit.* The first 90 days in a new role should focus on learning and absorbing.* Building relationships with sales and customer success is key to success.* Making tough decisions about revenue and customers is part of growth.* Pricing should be viewed as a strategic lever for the business.* Continuous evaluation of product and pricing alignment is necessary for growth.00:00 Introduction to Mandy Sidana's Journey03:00 Lessons from Founding a Startup06:01 Understanding Plotly and Its Market09:11 Customer-Centric Product Management11:53 Navigating the First 90 Days15:03 Building Relationships with Sales and Customer Success17:46 Opportunities for Growth at Plotly21:02 Making Tough Decisions on Revenue and Customers25:08 The Role of Pricing in Product Strategy29:59 Aligning Product Roadmap with Pricing Strategy35:07 Engineering's Role in Pricing Initiatives40:04 Future Trends in B2B Software
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James D. Wilton, founder and managing partner of Monevate, brings over 20 years of experience in pricing strategy and monetization. His career began as a consultant at ZS Associates, followed by leading pricing at RELX and SBI. After three years at McKinsey, James launched Monevate, a consulting firm focused on helping tech startups, scale-ups, and fast-growing companies optimize their pricing strategies.In this conversation, James shares insights from his career and discusses the role of pricing strategy in modern business, the misconceptions surrounding it, and the challenges of implementing usage-based pricing models. He offers practical advice for companies looking to grow their pricing discipline and explores how AI is shaping the future of pricing. The discussion also highlights the importance of building community within the pricing space.TakeawaysPricing is often overlooked in modern MBA programs.Effective communication of pricing strategies is crucial.Discounting can lead to a culture of undervaluing products.Both qualitative and quantitative data are essential in pricing.Pricing strategy should be tailored to specific business situations.Companies often realize the need for pricing strategy at inflection points.Building a community around pricing is challenging but rewarding.Usage-based pricing presents unique operational challenges.Maintaining a logical record of deals is vital for pricing strategy.Integrity in consulting means providing honest advice, even when it's difficult.Chapters00:00Introduction and Background01:43Career Journey and Transition to Pricing10:09Key Learnings from Previous Roles16:13Founding Monovate and Building Community22:34The State of Pricing in B2B SaaS29:29Misconceptions in Pricing Strategy39:40Challenges of Usage-Based Pricing48:44Best Practices for Growing Companies54:11Formative Moments in Consulting
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In this episode, we sit down with Jeff Escalante, now Engineering Director at Clerk. Jeff’s journey began in neuroscience, and over time, he transitioned into engineering leadership roles at incredible companies like HashiCorp, Vercel, and Clerk. He shares valuable lessons from his time at HashiCorp, reflecting on the challenges of managing rapid growth and the dual-focus needed to balance developer and enterprise requirements; discusses the complexities of building authentication systems and the strategic choices behind pricing and packaging at startups; and shares perspective to the infrastructure demands of scaling developer tools and speaks to the principles guiding Clerk’s focus on user experience. For those interested in product strategy, engineering leadership, or developer tools, this is a great conversation.
Takeaways:
Jeff started his career in graphic design before transitioning to tech. He emphasizes the value of agency experience for learning. HashiCorp's growth from 200 to over 1000 employees taught him about scaling. The dual focus on developers and enterprise customers is complex but rewarding. Career paths in tech can be non-linear and should be flexible. Management roles can be fulfilling if approached correctly. Clerk offers a unique solution for user authentication. Components as a service is a game-changer for developer tools. Pricing strategies should align with the value provided to customers. Enterprise sales can distract from product quality and user experience. Focusing on early-stage companies can lead to long-term success. A generous free tier can help startups grow without immediate costs. Complex pricing models can be necessary to reflect usage and features. Building a product for a specific market segment fosters loyalty. Learning from failures is crucial for personal and professional growth. Always be open to new challenges and opportunities.Chapters
00:00 Jeff's Journey: From Neuroscience to Tech
05:57 Lessons from HashiCorp: Growth and Management Challenges
11:53 Navigating Pricing and Packaging at HashiCorp
17:46 The Duality of Developer and Enterprise Focus
22:59 Career Path Insights: The Evolution of Engineering Roles
30:05 Clerk: A New Chapter in Developer Tools
36:23 The Complexity of Authentication Systems
43:02 The Philosophy of selling to startups first and when to move to enterprise
50:38 Building for the Future: Infrastructure and Pricing
01:00:31 Lessons from Failure and Growth Mindset
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Summary
In this episode of "Monetizing SaaS," we dive into the career journey of Kent Keirsey, founder and CEO of Invoke. With a background in economics and years of product leadership at high-profile tech companies like Gather and Greenlight, Kent shares invaluable insights into building and scaling successful products. He reflects on the critical role of culture, strategy, and communication in navigating rapid growth and managing teams effectively. Kent also explores the cutting edge of generative AI, from its technical evolution to its transformative potential in business. He offers practical advice on the importance of change management and champions in driving AI adoption within enterprises, and he discusses the complexities of pricing AI solutions—emphasizing the need for lasting client relationships. His reflections on building Invoke from an open-source project to a thriving business reveal a bold approach to risk and a mindset that values constant learning and an obsession with craft. Whether you're interested in the evolving landscape of AI, strategic growth in SaaS, pricing AI prdocts, or Kent’s entrepreneurial insights, this episode provides a wealth of knowledge and inspiration.
Takeaways
- Generative AI is transforming creative processes.
- Open-source projects can lead to significant business opportunities.
- Human involvement in AI is necessary for quality outcomes.
- Invoke aims to empower users with creative control over AI.
- The product serves a diverse range of users, from enterprises to individuals.
- AI deployment in enterprises is cautious and often starts with small pilots.
- The role of champions is crucial in advocating for AI solutions within organizations.
- Pricing strategies for AI solutions must evolve as the market and technology change.
- The cost of delivering AI solutions is decreasing, impacting pricing models.
Chapters
00:00 Kent's Journey Through Tech and Product Management
04:01 Lessons from Gather and Greenlight
09:56 Navigating Communication in Rapid Growth
13:11 Understanding Universe and Portfolio Management
15:02 The Emergence of Generative AI
19:59 Building Invoke: From Open Source to Business
23:50 Invoke's Product and Its Diverse User Base
29:10 The Evolution of AI Tools in Business
32:02 Navigating Change Management in Enterprises
35:20 The Role of Champions in AI Adoption
38:34 Pricing Strategies for AI Solutions
46:25 Building Long-Term Relationships with Clients
52:58 Embracing Risk and the Entrepreneurial Journey
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Jules Boiteux, founder of Roast My Pricing Page, has a background in product management with roles at Marmelade App, Hull, Livestorm, and Trustpair. In this conversation, he shares his journey from product management to entrepreneurship and the lessons learned along the way. Jules discusses the role of pricing in B2B SaaS, the structure of an effective pricing page, and common mistakes, such as neglecting social proof and FAQs.He explains the differences between value-based and usage-based pricing models and highlights the ongoing development of pricing strategies in the market. Jules also explores future trends in monetization, including the influence of AI and the use of add-ons in pricing models. He emphasizes the importance of building community and sharing experiences to support personal and professional growth.Takeaways- The importance of a well-structured pricing page cannot be overstated.- Common mistakes on pricing pages include neglecting social proof and FAQs.- Value-based pricing often requires a different approach than usage-based pricing.- The market for pricing strategies is currently immature but evolving.- Pricing is a continuous process that requires regular testing and iteration.- Social proof is crucial for converting visitors on pricing pages.- The anatomy of a pricing page includes headlines, plans, and social proof.- Future trends in monetization will likely include more complex pricing models with add-ons.- Building community and sharing experiences is essential for personal and professional growth.Chapters00:00Introduction to Jules Boiteux and His Journey02:31Significant Experiences in Product Management05:53Founding Roast My Pricing Page11:10Understanding the Anatomy of a Pricing Page19:39Common Mistakes on Pricing Pages22:36The Importance of the Pricing Page25:49Value-Based vs. Usage-Based Pricing31:02The Influence of Internal Pricing Practices36:02Market Maturity in Pricing Strategies39:31Systems Governing Pricing and Packaging42:19Future Trends in Startup Monetization45:27Personal Insights and Community Building
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In this episode, Miguel Oller, co-founder and CTO of Makeswift, shares his journey from an aspiring robotics PhD at Georgia Tech to becoming a successful SaaS entrepreneur & CTO. Miguel's career spans founding multiple companies like Shortweb and BLoveIt, before co-founding Makeswift, which was recently acquired by BigCommerce.In this conversation, Miguel dives into key insights from his early startup experiences, including the challenges of co-founder dynamics, navigating commercialization, and developing pricing strategies. He emphasizes the importance of trust and collaboration in building a strong team, the need for constant experimentation in product development & pricing, and the critical role of adaptability throughout the startup journey.Miguel also touches on the transformative impact of AI in shaping future products, and offers advice to aspiring founders—reminding them that strong team dynamics are far more important than just having a great idea. This episode is packed with valuable takeaways for anyone interested in entrepreneurship, technology, and startup success.Takeaways:- It's important to feel comfortable telling stories about your experience.-The startup journey is often a hyperbolic growth chamber.- Co-founder dynamics can make or break a startup.- Embracing unexpected roles can lead to valuable learning experiences.- Product market fit is a continuous journey, not a destination.- Building trust among co-founders is essential for long-term success.- The right technology at the right time can create opportunities.- Startups require a blend of passion and pragmatism.- Iterative processes help in building trust and resolving conflicts.- The journey of entrepreneurship is filled with highs and lows. You must learn how to have productive conflict.- Building trust is essential for effective collaboration.- Commercialization requires constant adaptation and experimentation.- Pricing strategies should align with the value provided to customers.- The journey of a founder is filled with learning opportunities.- Don't over index on the idea; focus on the team.- Learning should be a metric of success in startups.- AI will significantly change product development in the coming years.- Experimentation frameworks are crucial for navigating market changes.- The most formative experiences often come from the journey itself.Chapters00:00Introduction and Purpose of the Podcast02:12Miguel Oller's Journey: From Robotics to Startups06:22Early Startup Experiences: Shortweb and Blobbit12:24Transition to Makeswift: The Founding Story20:08The Evolution of Makeswift and Its Acquisition24:20Co-Founder Dynamics and Lessons Learned28:00Building Trust Through Collaboration31:00Lessons in Commercialization and Market Fit34:03The Importance of Experimentation Frameworks39:03Navigating Pricing Strategies43:56The Future of AI in Product Development48:53The Formative Journey of a Founder
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Spyri Karasavva has had an incredible career in finance, SaaS, and pricing. She's been a financial analyst for a PE fund, worked in product & finance strategy for Stripe, was the first GTM hire at Stytch, is now the founder & CEO of Dealops. In this episode, Spyri shares her career journey and the importance of pricing in B2B sales. She discusses the challenges of deal pricing and the need for effective pricing strategies and guidance. She emphasizes the importance of collaboration between pricing, product, and sales teams and suggests that pricing strategy should be an integral part of the product development process. She also highlights the need for software solutions in pricing enablement, specifically during the quoting process, to enforce finance guidance and optimize deal economics. Takeaways- Pricing is a critical aspect of B2B sales, and non-standard deals often require careful decision-making on product inclusion, pricing, discounts, and payment terms.- Collaboration between pricing, product, and sales teams is essential for effective pricing strategies and guidance.- Pricing strategy should be integrated into the product development process, with the pricing team working closely with customers and users.- Deal pricing teams are best placed under the finance department to ensure alignment with company goals and protect gross margin and cash flow.- Software solutions, particularly during the quoting process, can optimize pricing enablement and provide custom pricing recommendations that align with finance guidance. - DealOps serves companies of all sizes, with a focus on larger companies with complex pricing models and thin margins.- DealOps is a good fit for industries facing price wars or commoditization.- DealOps aims to deliver at least 6 times ROI and capture around 15-18% of the value they create.- DealOps offers both revenue uplift and time efficiencies for sales teams.- Many companies lack good pricing performance data, which can hinder their ability to make informed pricing decisions.- The four-step process for pricing includes determining the right unit metric, setting the list price, deciding on discounts, and enforcing discounts.- Discounts should be aligned with customer segments and behavior incentives.- Monitoring and tracking pricing data is crucial for optimizing pricing strategies.Sound Bites"In the B2B world, it almost doesn't matter what price you have on your website. Most deals that actually get signed have some sort of custom price or are considered non-standard.""I think it's kind of crazy that nobody has really optimized the link between sales incentives, deal economics, and the company's bottom line.""The way to do B2B pricing enablement is through the quoting process. It's the only time that a rep cares a lot about pricing.""We need to deliver at least 6 times return on investment.""We reduce the time that it takes to price a deal from 30 minutes to 3-4 minutes."Chapters00:00Introduction and Background02:49The Importance of Pricing in B2B Sales05:58Collaboration between Pricing, Product, and Sales Teams08:53Integrating Pricing Strategy into Product Development11:50The Role of Deal Pricing Teams15:01Optimizing Pricing Enablement with Software Solutions26:04Serving Companies with Complex Pricing Models and Thin Margins32:08The Challenge of CRM and CPQ Setup37:21The Importance of Pricing Performance Data42:24The Four-Step Process for Pricing47:57Monitoring and Tracking Pricing Datakeywordspricing, B2B sales, deal pricing, pricing strategy, collaboration, software solutions, quoting process, finance guidance, deal economics, pricing, software, companies, complex pricing models, thin margins, revenue uplift, time efficiencies
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Gary Bailey, founder of the Talent Capitalist, is a monetization & pricing expert with a deep background in financial services, accounting, pricing, and AI. In this episode, Fynn and Gary discuss Gary's background in finance and what he learned from the electronification of finance. They go on to discuss the importance of monetization as a discipline. Gary shares his experience in valuing and pricing financial products, as well as the challenges of training young professionals in the industry. Bailey emphasizes the need for pricing education in business schools and the lack of ownership and accountability for monetization within organizations. Gary believes that pricing should live in finance, and that FP&A professionals have a massive opportunity to create value for their organizations should they lean into monetization as a concentrated function. Takeaways- Monetization should be treated as a discipline and taught in business schools to address the lack of pricing education.- Finance departments are well-positioned to own and drive monetization strategies within organizations.- The challenges of valuing and pricing financial products require a deep understanding of math and a focus on creating consistent valuation curves.- The rapid pace of change in the pricing landscape necessitates the development of pricing expertise and the recognition of pricing as a valuable discipline.- The lack of ownership and accountability for monetization within organizations leads to ambiguous pricing strategies and missed. opportunities. FP&A has the analytical skill set for monetization as well as the available time to lean into it.- The best argument for pricing to live in product is to treat pricing as a product itself, with a focus on making it beautiful, easy to onboard, and constantly experimenting and iterating.- The Talent Capitalist helps small businesses recruit for the job of a 'motivation architect' and trains existing employees in this discipline.- Monetization as a discipline involves creating value, measuring value, negotiating value capture, implementing systems to capture value, and determining the price point.- The future of monetization in the world of AI involves AI assisting individuals in configuring their own pricing based on their unique needs and value perception.- Understanding what people want is crucial in implementing big ideas and achieving incentive alignment.Sound Bites"I'm an accountant at heart, and accountants like certainty.""We had to develop a system which had hundreds of these features, like insurance, and each of those features had a value.""FP&A has the analytical skill set to be really skilled and strong around monetization, but they are the function in the business that has the most latency in their job to go pursue that discipline with the right amount of focus, the right amount of attention.""If you see pricing and billing and monetization as a product in itself, then the number one thing that says to do is to one, make it look beautiful, two, to onboard people onto it kind of easily. And, and then to constantly be experimenting and iterating."Chapters00:00Introduction and Background02:03The Thread that Unites Interests06:29Bringing Controls to the Banking World10:30Teaching Monetization as a Discipline18:04The Role of Finance in Monetization23:31The Lack of Pricing Education and Ownership30:10The Latency of FP&A in Pursuing Monetization33:03Recruiting for the Job of a 'Motivation Architect'36:28The Five Steps of Monetization as a Discipline40:55The Future of Monetization in the World of AI58:57Understanding What People Want: A Crucial Lessonkeywordsmonetization, pricing, finance, valuation, financial products, training, ownership, accountability, FP&A, monetization, pricing, product, services, mental model, value-based pricing, performance-based pricing, AI, future, understanding, formative moment
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Scott Mitchell, former CTO of SalesLoft, takes us through his career journey and shares hard-earned insights into the intricacies of pricing, packaging, and monetization in B2B SaaS. From the importance of culture and trust in scaling a company to the technical and strategic components of pricing, Scott offers a wealth of knowledge for any technical leader. He emphasizes the crucial role that a foundation of core values and a willingness to be vulnerable play in building trust within an executive team, especially when navigating complex changes.Scott dives into the architectural components of monetization, detailing how tools like Salesforce CPQ, billing systems, and custom provisioning come together to support a company's evolving pricing and packaging models. At SalesLoft, he spearheaded a major overhaul of their pricing and packaging strategy, transitioning from a rigid system to one where pricing changes became a metadata exercise—seamlessly decoupling pricing and packaging from the application code. For product & engineering leaders facing the challenge of aligning product and monetization roadmaps, Scott's experience offers invaluable guidance. He also shares his thoughts on the future, discussing how generative AI could impact software development. If you're a CTO looking to better understand the intersection of technology and monetization, and how to build an adaptable infrastructure that keeps pace with the market, this episode is a must-listen.
Takeaways
Culture and trust are crucial in scaling a company, and they can be intentionally built through vulnerability and shared experiences. Pricing and packaging in B2B SaaS can be complex and require careful consideration of the customer funnel, from purchase to feature consumption. Architectural components of monetization include Salesforce CPQ, billing systems, and provisioning. A strong foundation of core values provides a lens to ensure that culture evolves in the desired direction. Building a provisioning system is necessary to adapt to changing pricing and packaging models. Turning pricing changes into a metadata exercise can streamline the process and reduce the need for extensive engineering projects. Aligning the product roadmap with the monetization roadmap is crucial for capturing the value of new features and capabilities. Decoupling pricing and packaging from application code can improve application design and flexibility. "All of this comes down to trust." "Culture kills strategy." "Poorly managed pricing and packaging can be a very significant, a very expensive challenge for companies." "That event was like a major rework to pricing and packaging. The goal was to turn pricing changes into a metadata exercise."Sound Bites
"All of this comes down to trust." "Culture kills strategy." "Poorly managed pricing and packaging can be a very significant, a very expensive challenge for companies." "That event was like a major rework to pricing and packaging. The goal was to turn pricing changes into a metadata exercise."Chapters
00:00 Introduction and Career Journey
06:23 Building Culture and Trust in Scaling a Company
13:35 The Challenges and Components of Pricing and Packaging in B2B SaaS
21:25 Architectural Components of Monetization in B2B SaaS
25:21 The Role of Core Values in Guiding Culture
27:19 The Need for a Provisioning System in Adapting to Changing Pricing and Packaging Models
27:27 Reworking Pricing and Packaging
30:13 Turning Pricing Changes into a Metadata Exercise
31:37 Repositioning as a Full Platform
34:08 Considering the Debt to Pay Off
37:37 Decoupling Pricing and Packaging from Application Code
43:12 Exploring the Impact of Generative AI
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