Tom Drummond, founder and managing director at Heavybit Industries, dissects the seismic shift from graphical interfaces to conversational AI—and why most SaaS companies are thinking about it wrong. This isn't about adding chatbots to legacy products. It's about fundamentally rethinking what software means when voice becomes the primary interaction mode and agents become your customers. Drummond reveals why rapid execution trumps defensibility, how API-first companies will dominate the agent economy, and why trust—not technology—remains the ultimate bottleneck.

Key Takeaways:

1. Large Language Models Are Creating the Biggest Interface Shift Since the GUI

• The fundamental breakthrough isn't AI intelligence—it's natural language interpretation that frees computing from screens
• This democratizes access beyond anything the mobile revolution achieved, making software ubiquitous without requiring visual interfaces
• The transition will be generational: today's builders remain skeptical while the next generation will trust AI as naturally as we trust Wikipedia

2. Visual Interfaces Won't Disappear—They'll Become Trust Mechanisms

• GUIs will shift from primary interaction mode to verification and confidence layer for voice-driven commands
• Humans need visual confirmation not because they're old-fashioned, but because they require ownership and accountability
• The winning pattern: conversational interfaces for input, visual interfaces for trust and evidence

3. Software Must Do More When Friction Disappears

• If you previously delivered value by creating forms to fill out, you've been selling toil—not solutions
• When a 22-second phone call replaces a 10-minute form, your platform value collapses unless you deliver actual outcomes
• The new bar: integrate across systems, automate end-to-end workflows, and eliminate entire categories of work

4. Momentum Is the Only Moat That Matters at Early Stage

• Defensibility discussions are premature when the entire market is being redefined and expectations reset
• Investors have shifted to momentum-based evaluation even at seed stage—growth velocity trumps articulated competitive advantages
• Execute aggressively with AI internally before worrying about competitive positioning: ship faster, operate leaner, reimagine everything

Lightning Round Insights:

• Learning accelerator: Experiential over theoretical—don't read about programming, program; don't study sales, sell
• Career wisdom: Agency and aggressive opportunity capture matter more than perfect strategy in high-change environments
• Daily AI tool: Continue (Heavybit portfolio company)—enables rapid internal tool development with model-agnostic approach and custom data sources

Chapters:

00:00 - Introduction and Heavybit's Investment Thesis
04:33 - The Language Model Revolution: From Screens to Voice
12:13 - Rethinking Product Design: Phone Numbers Over Websites
21:36 - Key Challenges: Trust, Pricing, and Agent Distribution
30:04 - Differentiation Strategy: Momentum Over Moats
36:56 - Why Switching Costs Still Matter for Sustainable Growth
40:04 - Lightning Round and Closing Thoughts

Visit our website - https://saassessions.com/
Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

Bhaskar Roy, Chief of AI Products and Solutions at Workato, breaks down the fundamental shift from app-centric thinking to agent-first architecture. This conversation cuts through the AI hype to reveal how enterprises are moving beyond simple content generation to deploy agents at the core of business processes—from quote-to-cash workflows to IT helpdesk operations. Roy reveals the critical gap between low-agency experimentation and high-value automation, outlines the governance frameworks required for autonomous agents, and explains why getting hands-on is the only way to separate signal from noise in the agentic era.

Key Takeaways

1. The Agency Gap: Most Companies Are Stuck in Low-Value Territory

• Gartner research shows most companies remain in low-agency activities like content creation and email writing, while maximum ROI comes from agents executing core processes like order-to-cash and supply chain management
• SaaS is deterministic and requires months for customization, while agents adapt and execute in real-time
• The transformation eliminates bottlenecks where process experts depend on developers for integrations

2. Purpose-Specific Agents with Enterprise Skills Beat General-Purpose Approaches

• Agents must be narrowly focused with defined skills—finance agents restricted to finance users, each agent limited to relevant capabilities only
• Governance controls agent-to-agent collaboration, with supervisor agents coordinating and ensuring compliance
• Agent authentication ensures agents respect user permissions—only updating data the individual user can access

3. App Events and Enterprise Acumen Enable Proactive Intelligence

• Agents listen to events across systems—new hires, leads, tickets—then reason, contextualize, and take autonomous action
• Enterprise acumen monitors KPIs continuously and proactively recommends actions as metrics fluctuate
• The shift from reactive to proactive requires human-in-the-loop now, but full autonomy approaches rapidly

4. The Mindset Shift: From App-Centric to Agent-First Thinking

• Stop thinking about which app to use—start asking which agent can handle core business processes better
• When agents become core to business, reliability matters—platforms must provide innovation with enterprise-grade trust
• Reading about AI isn't learning—build agents, test them, discover what's real versus hype

Chapters:

00:00 - Introduction
00:46 - Journey at Workato: From Integration to Intelligent Agents
03:40 - The Evolution from SaaS to Agentic Workflows
07:51 - Best-of-Breed Apps Creating Data Silos and Integration Challenges
10:54 - Employee Productivity Gains Through Unified Agent Interfaces
13:20 - The Agency Gap: Low-Value vs. Core Business Process Automation
17:32 - Real-World Agent Deployments: Quote-to-Cash and IT Helpdesk
20:12 - Proactive vs. Reactive Agents: Where Does Automation Stop?
24:42 - Trust, Governance, and Control in Autonomous Agent Systems
28:42 - Preparing for the Apps-to-Agents Transition
33:04 - Lightning Round: Getting Hands-On to Shorten Learning Curves

Visit our website - https://saassessions.com/
Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

Every SaaS company is racing to “add AI,” but most are doing it wrong. In this episode, Megh Gautam, Former Chief Product Officer at Crunchbase, reveals the hard truths behind building AI into established SaaS products. From avoiding hype-driven features to building trust through data quality and transparency, Megh shares how Crunchbase rolled out AI-powered capabilities without breaking user trust. He also breaks down the internal alignment, cross-functional execution, and relentless feedback loops required to ship AI features that actually matter.

Key Takeaways -

1. Start with Real User Problems
   1. AI should not be an “add-on story” — it must solve a core customer pain.
   2. Crunchbase began with AI in search, a high-usage, high-friction feature.
   3. Prioritize critical workflows over “nice-to-have” gimmicks.
2. Data Quality Determines Trust
   1. Bad data in = garbage out, especially with AI models.
   2. Crunchbase spent a decade building clean, reliable data pipelines before layering AI.
   3. Trustworthy results require grounding AI outputs in verified “truth sets.”
3. User Trust Demands Transparency
   1. Customers don’t just want answers — they want to know how those answers were derived.
   2. Explainability and confidence thresholds are essential for adoption.
   3. If unsure, don’t hallucinate — caveat results and suggest alternatives.
4. AI is a Company-Wide Effort, Not Just a Product Launch
   1. Designers, engineers, PMs, marketing, and GTM must move in lockstep.
   2. Pricing, packaging, and positioning are as critical as the technical build.
   3. Internal discomfort is normal — priorities will shift faster than in traditional SaaS launches.
5. Continuous Feedback Loops Drive Iteration
   1. Early adopter programs and dense customer feedback cycles are critical.
   2. Patterns of confusion often surface only after repeated customer interactions.
   3. AI workflows blur traditional SaaS team boundaries — ownership must evolve.

Chapters:
 00:10 - Introduction
 00:50 - Megh’s SaaS journey (Twilio, Dropbox, Crunchbase)
 02:45 - AI hype vs. solving real user problems
 06:05 - Why Crunchbase started with AI in search
 10:17 - Data quality as the foundation for trustworthy AI
 15:07 - Overcoming AI skepticism with transparency
 20:01 - Aligning product, engineering, marketing, and GTM on AI launches
 25:46 - Feedback loops and customer education
 30:32 - Lightning Round: Megh’s favorite AI tools
 36:27 - Closing thoughts and key reminders

Visit our website - https://saassessions.com/
Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

In this powerhouse episode, Max Altschuler - founder of Sales Hacker, former VP of Marketing at Outreach, and now General Partner at GTMfund - breaks down what it takes to build and scale B2B SaaS companies with speed and substance. Max shares his journey from being an early-stage operator to becoming a SaaS investor, unpacking the real mechanics behind GTM strategy, community-driven growth, category creation, and what founders often get wrong. This is a masterclass in strategic execution and long-game thinking for SaaS leaders.

Key Takeaways –

1. Betting on Founders: What Drives Early-Stage Investing

• Founder-market fit trumps product perfection - invest in people who are machines.
• Space matters: Great founders + a growing wave = potential breakout.
• Outreach wasn’t a spreadsheet decision - it was a conviction bet on Manny Medina's obsession and clarity.

2. Strategic Distribution Is the New Product

• Distribution is where the new edge is; AI levels the playing field for building.
• GTM is the real differentiator - your ability to generate demand at scale will define outcomes.
• Sales Hacker’s distribution muscle supercharged Outreach’s category dominance.

3. Acquisitions Are Not Just About Revenue, They’re About Velocity

• Sales Hacker wasn’t bought for its revenue but to compound Outreach’s strategic value.
• Community-led growth isn't a tactic; it’s an ecosystem asset.
• Integration didn’t mean conversion - it meant amplification without breaking trust.

4. Lessons in SaaS Scale and GTM Execution

• Don’t underinvest in product expansion; build or buy fast when signals are clear.
• Self-serve isn’t optional anymore; it’s mandatory for market-wide coverage.
• Be obsessed, but don’t burn out your team; clarity in communication scales leadership.

About the GTMfund:
GTMfund is an early-stage venture fund backed by 300+ of the most respected go-to-market leaders from companies like Salesforce, Zoom, and Snowflake. It focuses exclusively on backing SaaS startups with strong GTM execution and strategic potential.

Connect with Max Altschuler | Check out GTMfund

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In this episode of the SaaS Sessions podcast, Jacob Bank, founder of Relay.app, shares his journey from academia to startup founder, discussing the challenges of building a product in the AI space. He emphasizes the importance of validating ideas, finding early customers, and experimenting with various marketing channels. Jacob also highlights the significance of cohort retention as a measure of product-market fit and the need to balance innovation with competition in a rapidly evolving market.

Key Takeaways –

1. You’re not failing - your distribution is
Building is easy; getting customers is the battlefield.
Early channels (Reddit, network, cold email) only take you so far.
Most startup advice is outdated or irrelevant to your context - test everything yourself.

2. Validate with precision, not ego
The Mom Test changed how Jacob gathered honest feedback.
10 well-run interviews can kill or greenlight an idea.
Getting “likes” is not validation - retention and willingness to pay are.

3. Every growth stage needs a new motion
0 → 10: Scrappy hustle (Reddit, LinkedIn DMs, direct outreach).
10 → 100: Partner marketing, SEO, and high-intent blog content.
100 → 1000: Viral LinkedIn content + YouTube for education + community-led growth.

4. PMF isn’t hype - it’s cohort retention
Retention is the only true sign of product-market fit.
Competitive pressure is a forcing function to build better products.
Don’t be afraid to pick a fight in a crowded space - just know your edge.

Connect with Jacob Bank:
🔗 Jacob Bank - https://www.linkedin.com/in/jacobbank/
📅 Join his Build an AI Agent with Me sessions - https://events.relay.app
🌐 Try Relay.app for free: https://relay.app

Relay.app is an AI agent builder that connects your tools into smart workflows. Designed to bring humans into the loop where automation fails, Relay combines intuitive UX with AI-native capabilities, enabling teams to move faster without drowning in manual ops.

Chapters:
00:10 – Introduction
00:50 – Jacob’s journey from academia to Google to Relay
02:14 – The pain of early go-to-market and what didn’t work
06:09 – Using The Mom Test to validate early MVPs
07:59 – Breaking through with traction experiments
10:52 – Reddit, Product Hunt, and the weak links in early GTM
13:49 – From 10 to 100: What channels actually scaled
15:18 – Facing the 100 → 1000 wall
16:37 – Cracking virality with LinkedIn
21:29 – Mid-funnel levers: YouTube and email
27:13 – Competing in a mature category and why it’s a good thing
33:15 – Defining and validating PMF the hard way
38:27 – Retention is king—no tricks, just product
40:28 – Lightning round
42:41 – Final thoughts + how to join Jacob’s live AI agent sessions

Visit our website - https://saassessions.com/
Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

In this episode, we dive into the evolving landscape of B2B SaaS attribution with Deepinder Dhingra, Founder and CEO of RevSure.ai. DD shares insights from his 20+ years in enterprise software, analytics, and AI, unpacking how SaaS companies can harness AI-driven attribution to improve GTM strategies. He explores the challenges of attribution complexity, the role of AI in unifying data, and actionable frameworks for building an effective attribution model. DD also shares his thoughts on the future of AI in SaaS and key misconceptions about being a founder in this space.

Key Takeaways:

1. The Evolution of Attribution in SaaS
- Past GTM motions: Outbound, focused on sales-driven efforts.
- Present complexity: Consumerization of GTM with multiple teams (marketing, SDR, BDR, sales).
- Challenge: Fragmented data across tools requires a robust attribution strategy.

2. AI’s Role in Attribution
- Data Harmonization: AI connects data from CRMs, marketing automation, ABM tools, and offline channels.
- Revenue Graphs: Building linkages across touchpoints like leads, campaigns, and opportunities.
- Predictive Insights: Real-time data analysis to optimize spend and strategy.

3. Common GTM Team Pitfalls
- Misaligned Goals: Teams focus on “who gets the credit” rather than actionable insights.
- Lack of Full-Funnel Thinking: Insights should span marketing, SDR, and sales efforts.
- Overreliance on Rules-Based Models: Shift to data-driven, machine learning approaches like marketing mix models and incrementality testing.

4. Building an AI-Powered Attribution Framework
- Collaborative Effort: Align marketing, sales, and ops under a shared vision.
- Tech Stack Audit: Ensure compatibility with your GTM motion.
- Real-Time Monitoring: Use leading and predictive indicators to measure success.

Lightning Round Insights:

1. Fun Fact About DD: He’s a skilled pickleball player!
2. Challenge to Solve in Indian SaaS: Optimizing cross-border GTM motions.
3. Misconception About Founders: It’s not all fun; founders take the brunt of market brutality and drive teams for competitive speed.

About RevSure.ai:
RevSure.ai is revolutionizing attribution for B2B SaaS companies by leveraging AI to unify data, provide actionable insights, and optimize GTM strategies. Their AI-powered attribution models address the complexities of modern SaaS motions and enable teams to act with precision.

Connect with DD:
LinkedIn - https://www.linkedin.com/in/deepinder-singh-dhingra-66bb54/
RevSure - https://www.revsure.ai/

Chapters:
01:05 - Intro & DD’s Journey in SaaS
02:05 - Evolution of Attribution in SaaS
07:27 - Complexity in GTM Motions and Data Fragmentation
12:10 - AI’s Role in Attribution
15:10 - Common GTM Team Pitfalls
19:02 - Building an AI-Powered Attribution Framework
23:26 - KPIs for Attribution Success
27:42 - Future of AI in Attribution
30:17 - Balancing AI with Human Oversight
32:22 - Lightning Round
36:42 - Closing Thoughts

#b2bsaas #b2b #attribution #marketing #saas

Visit our website - https://saassessions.com/
Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

Episode Summary:
Srikrishnan Ganesan, Founder, and CEO of Rocketlane, joins the SaaS Sessions Podcast to share actionable insights on customer onboarding—a crucial yet often overlooked driver of SaaS success. Sri dives deep into why onboarding sets the foundation for long-term customer satisfaction, retention, and expansion, and offers strategies to optimize this critical phase. This conversation is packed with transformative ideas for SaaS founders and operators, from avoiding common onboarding pitfalls to leveraging AI and standardized processes.

Key Takeaways:
1. Onboarding as a Strategic Driver
- The first 30-90 days are make-or-break: onboarding directly influences churn and Net Revenue Retention (NRR).
- Poor onboarding can result in 25-30% of customers failing to go live, jeopardizing renewals and expansions.
- Early-stage SaaS companies often lack the rigor to drive implementation success, resulting in disengaged customers.

2. Common Onboarding Pitfalls and How to Address Them
- Lack of Rigor: Companies often go at the customer’s pace instead of setting clear timelines.
- Order-Taking Approach: Teams fail to be prescriptive, waiting for customer direction instead of sharing best practices.
- Disorganized Operations: Reliance on spreadsheets and hero-driven processes undermines scalability and consistency.
- Solution: Implement standardized processes, use governance frameworks, and prioritize system-driven operations.

3. The Role of Leadership and Process Design
- Founders often stretch post-sales teams, delaying investments in specialized onboarding leadership.
- Invest in systems that track effort, milestones, and outcomes to scale onboarding.
- Standardize touchpoints like kickoff decks, project plans, and escalation paths to drive a consistent and professional experience.

4. Leveraging Technology and AI for Better Onboarding
- Tools like Rocketlane provide visibility and streamline processes for both customers and internal teams.
- Use AI to automate repetitive tasks, identify early warnings, and enhance follow-up communications.
- Fast and efficient onboarding drives 2x faster expansions and greater advocacy from happy customers.

Lightning Round Insights:
What Sri Wishes He’d Known Starting: How transformative AI would become and its potential to fundamentally reshape product development.

Favorite AI Tools:
- Avoma for sales insights.
- Rocketlane’s own AI-driven features to improve onboarding experiences.

Book Recommendations:
- Made to Stick by Chip and Dan Heath – Learn to package ideas that resonate and stick with your audience.
- Competing Against Luck by Clayton M. Christensen – Understand the "Jobs to Be Done" framework for product development.

About Rocketlane:
Rocketlane is a leading customer onboarding and professional services automation platform, empowering SaaS companies to deliver seamless and efficient onboarding experiences. By streamlining collaboration, improving accountability, and accelerating time-to-value, Rocketlane helps businesses improve retention and expand revenue opportunities.

Chapters:
00:50 - Sri’s Journey: From Freshworks to Rocketlane
01:47 - The Current State of SaaS Onboarding
04:15 - Key Challenges in SaaS Onboarding
07:39 - Building Rigor and Governance in Onboarding
15:23 - Celebrating Go-Lives and Building Advocacy
19:15 - The Impact of Faster Onboarding on Retention and Expansion
27:27 - Ripple Effects of Poor Onboarding
34:04 - Leadership’s Role in Driving Onboarding Excellence
37:04 - Lightning Round

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Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

Lucas Lovell, VP of Product at Paddle, shares his journey from launching a startup in Australia to scaling a SaaS company in Europe. With a focus on global market expansion, Lucas discusses critical considerations for entering new geographies, leveraging local partnerships, and using payments infrastructure as a growth lever. Packed with actionable insights, this episode is a must-listen for SaaS leaders navigating the complexities of international growth.

Key Takeaways:

1. Market Expansion Strategy
   • Market size and access are key to identifying expansion opportunities.
   • Operational challenges, like legal and regulatory barriers, need thorough evaluation.
   • Localizing for cultural norms and customer expectations is crucial for success.
2. Leveraging Payments as a Growth Lever
   • Offering region-specific payment methods boosts conversions significantly.
   • Partner with payment platforms like Paddle to simplify tax compliance and payment localization.
   • Missteps in payment infrastructure can result in high drop-off rates despite strong intent to purchase.
3. Tactical Entry into New Markets
   • Conduct roadshows and spend time on the ground to understand the local ecosystem.
   • Leverage accelerators, incubators, and local networks for insights and partnerships.
   • Hiring local talent provides essential market expertise and operational efficiency.
4. Balancing Global Consistency with Local Flexibility
   • Use foundational playbooks but adapt pricing, messaging, and distribution strategies to local markets.
   • Understand cultural nuances, such as Germany’s data consciousness or the business formality in Europe.
   • Localization isn't just about language; it’s also about tone, style, and relevance.

Lightning Round Insights:

• Work-Life Balance Tip: Set boundaries with notification management to avoid work distractions during personal time.
• Advice to Past Self: You learn best by doing—don’t hesitate to dive in and experiment.
• Book Recommendation: Good Strategy, Bad Strategy by Richard Rumelt for mastering strategic thinking.

About Paddle: Paddle simplifies payment infrastructure for SaaS businesses, enabling global expansion by handling tax compliance, payment localization, and more. Their platform helps companies turn operational complexities into growth opportunities.

Connect with Lucas Lovell: LinkedIn | Paddle

Chapters:
00:10 – Introduction
01:00 – Lucas’s Journey in SaaS
06:30 – Choosing France for Market Expansion
10:00 – Operational Barriers to Entering New Markets
15:00 – Using Payments as a Growth Lever
20:00 – Localization Strategies for Success
25:30 – Building Partnerships for Distribution
30:00 – First Principles GTM Strategies for New Geographies
35:00 – Lightning Round Insights

Visit our website - https://saassessions.com/
Connect with me on LinkedIn - https://www.linkedin.com/in/sunilneurgaonkar/

Episode Summary

In this insightful episode of the SaaS Sessions Podcast, we down with Satya Ganni, the CEO and Founder of Userflow and Beamer. Satya shares his journey as a serial entrepreneur, having founded six companies before leading Userflow and Beamer, two innovative platforms revolutionizing user onboarding and product engagement. We dive into how AI is reshaping Product-Led Growth (PLG), strategies for leveraging data effectively, and the future of PLG and Product-Led Sales (PLS).

Key Takeaways

• Satya’s Journey in SaaS:
  • Over two decades of experience in SaaS as a founder, operator, and executive.
  • The mindset of a problem solver is the driving force behind his entrepreneurial success.
• AI's Role in PLG:
  • AI influences every stage of the PLG funnel, from acquisition to engagement.
  • Personalization powered by AI can reduce CAC and improve time-to-value.
  • Examples of effective AI use in PLG include content generation, user segmentation, and in-app personalization.
• The Importance of Data in PLG:
  • PLG's success relies heavily on combining formographic, behavioral, and in-app data.
  • Tools like product analytics, session replays, and experimentation platforms are key to unlocking actionable insights.
  • Challenges arise with inaccurate or incomplete data, but the right systems can mitigate these issues.
• Challenges and Misconceptions in PLG:
  • PLG requires a massive market and some elements of virality to thrive.
  • Many SaaS companies are in the early stages of adopting personalization and leveraging AI to its full potential.
  • Integration of data-driven tools and workflows is critical for success.
• Future of PLG:
  • Hybrid models combining PLG and PLS (Product-Led Sales) will dominate.
  • AI-driven precision will empower sales teams to nudge users toward upgrades and drive conversions.
  • PLG will evolve to emulate the personalization seen in B2C platforms like Instagram and Amazon.

Lightning Round Insights

1. Biggest Lesson: The value of having a mentor or coach early in his career to accelerate growth.
2. Book Recommendation: Thinking, Fast and Slow by Daniel Kahneman—a must-read for understanding decision-making.

About Userflow and Beamer

• Userflow: A user onboarding and guides platform that simplifies the journey for SaaS and digital-first businesses.
• Beamer: A product adoption and engagement platform designed for product leaders and marketers to drive engagement.

Connect with Satya

• Website: Userflow | Beamer
• LinkedIn: Satya Ganni

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