The RISE Podcast

In this episode, Sumit Johar, Chief Information Officer at BlackLine, shares insights from over two decades of experience in enterprise technology, automation, and AI.The conversation traces the evolution of enterprise systems—from early integration challenges and middleware to RPA and now AI-driven automation. Sumit highlights how what once felt like “magic” in connecting systems has evolved into intelligent, agent-based architectures that are redefining how businesses operate.A major theme is the transformation of the CIO role. Once predicted to become obsolete, it is now more critical than ever, especially as AI adoption accelerates. Sumit explains how CIOs are responsible for building cohesive enterprise-wide strategies and ensuring technology investments scale across the organization.The discussion also dives into deploying AI in high-stakes environments like finance, where near-perfect accuracy and trust are essential. He emphasizes human-in-the-loop systems and explainability as key to balancing innovation with risk.Finally, Sumit shares how organizations can unlock massive value—such as reducing deployment times by up to 75%—by combining AI adoption with cultural change, workforce enablement, and a thoughtful build-vs-buy strategy.📌 Key TopicsEvolution from system integration → RPA → AI agentsThe modern CIO’s role in enterprise-wide strategyAI in finance: balancing innovation with risk and accuracyHuman-in-the-loop systems and AI explainabilityBuild vs. buy vs. platform approaches in enterprise techDemocratizing AI adoption across the workforce🎯 Key TakeawayAI transformation isn’t just about deploying advanced technology—it’s about combining AI with human judgment, scaling it across the entire organization, and aligning it to real business outcomes.💬 Key Quote“99.9% is not good enough in finance—you need AI and humans working together to get to 100%.”🎬 Chapters00:00 – Introduction & Sumit Johar’s Background (CIO, BlackLine)02:00 – Evolution of Automation: From Integration to AI07:00 – The Changing Role of the CIO10:00 – AI in Finance: Accuracy, Trust & Risk14:30 – Human + AI: Explainability & Real-World Deployment17:00 – Startups, Agents & Enterprise AI Strategy21:00 – Build vs Buy vs Hybrid Approach24:00 – Democratizing AI Across the Organization29:00 – Real Use Case: 75% Faster Deployments32:00 – Hiring, Talent & Change Management in AI Era36:00 – Fun Segment: Personal Insights & Sci-Fi41:00 – Closing This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

In this episode of The Rise Podcast, Abhishek speaks with Rinki Sethi, a longtime cybersecurity leader who has led security programs at companies like Twitter, Bill.com, and Palo Alto Networks, about how startups can successfully sell to enterprises—and why relationships, trust, and real problem-solving matter more than technology alone.Rinki shares insights from both sides of the table: as a former enterprise buyer managing large security budgets and now as a founder and investor through Lockstep Ventures. She explains how founders can stand out when pitching security leaders, why many enterprise deals stall after strong demos, and how early-stage startups can find and work with the right design partners.They also discuss the realities of enterprise procurement, the importance of integrity when things go wrong with customers, and how community-driven investing is reshaping the cybersecurity startup ecosystem.Key topics include:- How startups should approach enterprise CISOs and security buyers- Why strong demos often fail to convert into real deals- Finding early adopters and design partners inside large organizations-Navigating enterprise stakeholders beyond the CISO-Handling customer failures with integrity and partnership-Why community and practitioner insight matter in venture investing-Lessons from early startup adoption inside large enterprises-A practical and candid conversation for founders building enterprise security startups and leaders navigating innovation inside large organizations.🔑 TakeawayEnterprise sales in cybersecurity isn’t about the best technology—it’s about understanding the buyer’s real problems, building trust across multiple stakeholders, and showing up as a partner when things go wrong. Startups that succeed in enterprise markets lead with empathy, credibility, and long-term relationships rather than product pitches.🎙️ Soundbite“Founders who succeed in enterprise sales don’t just sell technology—they understand the problem, the people, and the organization they’re selling into.”00:00 – Introduction to Rinki SethiHer cybersecurity leadership journey and transition into investing and strategy03:20 – What Startups Get Wrong When Pitching EnterprisesWhy understanding the buyer’s real problem matters more than technology07:40 – Breaking Through the Noise as a First-Time FounderHow founders can reach enterprise leaders and build meaningful relationships12:30 – Why Rinki Took Risks on Startup TechnologyLessons from adopting early security startups inside large companies16:45 – Why Great Security Demos Still Lose DealsEnterprise procurement, stakeholders, and internal objections21:30 – Navigating Legal, Risk, and Procurement in EnterprisesHow startups should manage momentum after the initial excitement26:15 – Finding Early Adopters and Champions Inside OrganizationsWhy innovation often starts with practitioners, not executives30:40 – When Startup Deployments Go WrongA story about early phishing testing and how strong partnerships recover trust34:10 – What Founders Should Do When Customers Are UpsetOwning mistakes, integrity, and long-term relationships37:00 – Why Rinki Started Lockstep VenturesBuilding a practitioner-driven investment model and cybersecurity community39:30 – Leadership, Work-Life Integration, and Final AdviceLessons on time management, career growth, and balancing priorities This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

In 1914, Lawrence Sperry stepped out of the cockpit of a Curtiss C-2 flying boat and walked onto the wing. Mid-flight. In front of a crowd in Paris.The plane kept flying. The world's first autopilot demonstration.But autopilot alone didn't make aviation safe. Checklists did. Simple, repeatable protocols that ensured nothing got missed. Later, fighter pilot John Boyd added OODA loops (Observe, Orient, Decide, Act) for rapid decision-making in dogfights.Autopilot gave planes autonomy. Checklists gave them reliability. OODA loops gave pilots adaptability.Now swap "planes" with "AI agents" and you've got the enterprise playbook.I sat down with Brian Danaher on the latest episode. Brian spent nearly two decades at VMware leading CTO services across Ireland and held senior leadership at NetApp directing global technical strategy.His take: your documentation and culture matter more than your tech stack.He shared how hundreds of policy documents at VMware were treated as shelfware. In the agentic world, those same documents become the instruction manual agents use to make decisions. Your most valuable asset was gathering dust the whole time.Agents need to observe their environment, orient to your policies, make decisions based on your knowledge, and act within guardrails. Then loop back and improve.Here are two of my favorite books on this topic. 📖 The Checklist Manifesto by Atul Gawande 📖 Science, Strategy and War - The strategic theory of James Boyd This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

SummaryIn this conversation, Abhishek Dubey and Abhilash Garimella discuss the evolution of AI, particularly in the context of cybersecurity and Bolster's innovative approach. They explore the importance of human oversight in AI systems, the transition from traditional models to language models, and the significance of automation in enhancing operational efficiency. Abhilash shares his unconventional journey into AI leadership, the challenges of team sentiment towards automation, and strategies for building a strong AI team. The discussion concludes with rapid-fire questions that reveal personal insights and opinions on the future of AI.TakeawaysAbhilash has been a pioneer in productionizing AI agents.Bolster protects numerous brands from phishing and scams.False positives in cybersecurity can have severe consequences.Human oversight is essential in AI systems.Problem-solving and impact creation are key to success in AI.Shadow deployment helps in testing models before full deployment.Automation in the loop reduces risks in critical processes.Upskilling analysts is vital for successful AI integration.Hiring for mindset is more important than just skills.The trend of replacing human workers with AI is a significant concern.titlesAI Evolution in CybersecurityBolster's Innovative AI ApproachSound Bites"Humans are needed to guide the entire system.""Shadow deployment is key to our model testing.""Hire for mindset, not just skills."Chapters00:00Introduction to AI and Bolster02:59Understanding Bolster's Unique Approach to Cybersecurity05:50The Role of AI in Cybersecurity08:59The Evolution of Phishing Tactics11:56Abhilash's Journey to AI Leadership16:00Transitioning from CNN to Language Models18:56Shadow Deployment and Automation in AI19:15Automation in the Loop: A New Framework21:00Identifying Quick Wins in Automation23:11Managing Team Sentiment Towards Automation24:33Co-Building AI Systems with Domain Experts25:47Collaborating with Customers for Effective Solutions27:37The Challenge of Signal Noise in Automation28:39The Role of Domain Expertise in AI30:15Building AI Systems as an Outsider31:23Upskilling Employees Amid Automation32:38Retaining Talent in a Competitive Market35:38Hiring Passionate AI Talent37:05Rapid Fire Questions: Insights into Abhilash's Preferences This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

SummaryIn this conversation, Abhishek Dubey and Aaksha Meghawat discuss the challenges and opportunities in deploying AI in enterprise settings. Aaksha shares insights from his experience at Moveworks and his transition to founding Kashikoi, focusing on the importance of verification systems in AI. They explore the differences between traditional automation and LLMs, the need for a new approach to verification, and the concept of minimum viable intelligence. The discussion also touches on customer expectations, the future of AI, and the importance of adapting to new technologies.takeawaysAaksha transitioned from Moveworks to focus on verification systems in AI.There is a significant gap in the market for effective verification tools.LLMs require a different approach compared to traditional software development.Organizations need to segment their problems to effectively implement AI solutions.The burden of verification often falls on the seller, but it should be a shared responsibility.Understanding customer expectations is crucial for AI product success.Minimum viable intelligence is a key concept in evaluating AI performance.Verification is essential even in non-mission critical applications.The AI landscape is rapidly evolving, necessitating continuous adaptation.Companies must measure the impact of AI failures on customer satisfaction.Sound Bites“Everybody wants best of both worlds.”“We need to start thinking in those terms.”“I think it should lie with the customer.”Chapters00:00Introduction and Background02:07Transitioning from Moveworks to Kashikoi04:53Challenges in AI Deployment and Verification10:05The Role of LLMs in Automation13:59Verification in Hardware and Software Systems17:58Defining Minimum Viable Intelligence20:37The Cost of Perfection in AI21:32Quality Assurance vs. Real-World Performance23:49Business Pressures and AI Efficiency25:55Mission-Critical Software and Verification Needs27:49The Burden of Verification in AI29:49Empowering Customers in AI Verification32:09The Challenge of AI Talent in Enterprises34:12The Overrated Trend of Replacing Humans with AI36:40Favorite Christmas Movie and Closing Thoughts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

SummaryIn this conversation, Shyam Bhojwani shares his extensive experience in automation across various industries, discussing the challenges and strategies involved in scaling automation efforts. He emphasizes the importance of a balanced approach between in-house development and outsourcing, the need for proper expertise in AI, and how to quantify the success of automation initiatives through Experience Level Agreements (XLA). The discussion also touches on the evolving role of CIOs in driving automation and the long-term planning required to achieve meaningful impact. In this conversation, Abhishek Dubey and Shyam Bhojwani discuss the critical aspects of implementing automation in organizations, emphasizing the importance of understanding organizational needs, being a good listener, and leveraging data for decision-making. They explore the role of stakeholders, the significance of building trust, and the challenges faced by non-tech companies in adopting automation. The discussion also touches on the value of vendor partnerships, forward deployed engineering, and the need for resources in automation projects. They conclude with insights for CIOs and a candid reflection on the perceived hype surrounding agentic automation.takeawaysAutomation is a real problem that companies face.A balanced approach is essential for effective automation.Automation is a business problem, not just an IT issue.The right talent is crucial for successful automation.XLA focuses on reducing context switching for users.Costs may initially rise with new automation tools.Long-term planning is necessary for automation success.CIOs are increasingly involved in automation discussions.ROI should be a key focus in automation initiatives.Learning from automation experiences is vital for growth. Be a good listener, especially in the automation era.Think about Experience Level Agreements (XLA) across your lines of business.Understanding processes is crucial before implementing automation.Start with basic problems and aim for six wins in the first year.Building trust with stakeholders is essential for successful initiatives.Data-driven decision-making is key to understanding organizational needs.Vendor partnerships can accelerate the automation journey.Forward deployed engineering can provide quick impact and ROI.Automation should not be seen as a threat to jobs but as a means to enhance productivity.Read your audience and tailor your approach to their needs.titlesThe Future of Automation: Insights from a CIOBalancing In-House and Outsourced Automation StrategiesUnderstanding the Role of AI in Business AutomationSound Bites"Automation is still a real problem.""You need a balanced approach.""It's a business problem, not just IT.""Costs may go up before they go down.""It's a learning game.""Data is a very good story.""Start with very basic problems."Chapters00:00Introduction to Automation Passion02:59Scaling Automation Across Different Companies05:56In-House vs Outsourcing Automation09:02Building Expertise in AI and Automation12:04Quantifying Automation Success with XLA14:59Long-Term Planning for Automation Impact17:49Understanding Organizational Needs for Automation18:03The Importance of Listening in IT19:00Data-Driven Decision Making20:14Building Trust with Stakeholders21:14Experience Across Different Industries22:39Approaching Automation in Non-Tech Companies24:00The Role of Vendors in Automation25:44Forward Deployed Engineering and Its Benefits27:51The Need for Resources in Automation28:54Convincing Organizations to Embrace Automation30:30Actionable Insights for CIOs31:51The Overrated Nature of Agentic Automation33:39Companies Leading in Automation Practices34:36Personal Favorites and Guilty Pleasures This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

SummaryIn this conversation, Abhishek Dubey and Zain discuss their long-standing connection and delve into various topics surrounding angel investing, the impact of AI on enterprise solutions, and the challenges faced by startups in the current landscape. They explore the nuances of buyer behavior in security, the importance of understanding market needs, and the complexities of building AI solutions. Zain shares insights on navigating AI fatigue, the significance of niche solutions, and the realities of enterprise software development. The discussion culminates in rapid-fire questions that reveal personal insights and reflections.takeawaysZain emphasizes the importance of thoughtful investing and learning from founders.AI is creating opportunities for automation in enterprise sectors.Understanding buyer behavior is crucial for startups in security.The application of AI in enterprise is still evolving and requires careful consideration.Startups should focus on solving existing problems with better solutions.Building AI solutions comes with significant challenges and complexities.The incentives of enterprise buyers play a critical role in decision-making.Niche solutions can provide a competitive edge in the market.The journey of a startup is often more complex than it appears from the outside.There is no one-size-fits-all playbook for success in the AI space.Sound Bites"There's no playbook for building with AI.""The future of AI in enterprises is bright.""You have to start with a very tough problem."Chapters00:00Introduction and Background01:51Angel Investing Insights04:40Navigating AI Fatigue in Enterprise09:46Understanding Buyer Behavior in Security14:44The Role of AI in Enterprise Solutions19:32Building vs. Buying AI Solutions21:53The Future of AI in Enterprises27:19Challenges of Implementing AI Solutions30:03Navigating Data Privacy Concerns33:26Building Trust with Enterprise Clients36:33The Reality of Startup Growth Expectations38:51Personal Insights and Reflections This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

summaryIn this episode, Sangram Dash shares his journey from hands-on cybersecurity roles to becoming a CISO and VP of IT. He discusses the pivotal lessons learned along the way, the importance of building trust and influence, and the evolving role of CIOs in the age of AI. Sangram emphasizes the need for confidence, clarity, and the ability to simplify complex information to effectively lead and support organizations. He also highlights the balance between operational efficiency and the implementation of AI technologies, providing insights for aspiring leaders in the cybersecurity and IT fields.TakeawaysBeing at the right place at the right time can shape your career.Building trust requires producing results over time.Confidence stems from knowledge and clarity of thought.Simplifying complex information is key to effective communication.Transitioning from practitioner to leader requires understanding customer needs.CIOs will increasingly need to manage budgets and justify spending.AI is becoming integral to business operations and decision-making.Practicing clarity of thought can enhance leadership effectiveness.Understanding the needs of various departments is crucial for IT leaders.Continuous learning and adaptation are essential in a rapidly changing tech landscape. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

SummaryThe conversation focuses on the importance of transforming raw data into meaningful insights, particularly in the context of HR and user activity. It highlights how data can be interpreted differently depending on the perspective of the stakeholders involved.takeawaysData transformation is crucial for meaningful insights.HR focuses on specific data points that matter.User activity can be simplified into key metrics.Understanding data from different perspectives is essential.Transforming data requires a shift in thinking.Meaningful data can drive better decision-making.The context of data matters in its interpretation.Data points should align with organizational goals.Effective data transformation enhances user experience.Collaboration between departments improves data utility. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com

SummaryIn this conversation, Steve Januario, Deputy CIO at build.com, shares insights on the evolving role of IT in business, emphasizing the importance of simplicity, customer service, and strategic partnerships in technology. He discusses the balance between operational needs and the implementation of AI, the challenges of building versus buying AI solutions, and the significance of customization in enterprise environments. Steve also highlights the importance of leadership, team building, and staying updated in a rapidly changing tech landscape.TakeawaysIT's role has evolved from just running systems to shaping business productivity.Simplicity in tool selection is crucial for effective IT management.Customer service within IT is essential for employee satisfaction.AI implementation requires a balance between operational demands and strategic goals.Building AI solutions can be resource-intensive; partnerships may be more effective.Customization is key to meeting unique enterprise needs.Design partnerships can lead to better outcomes in AI projects.Unstructured data can now be leveraged for actionable insights.Leadership in IT requires empathy and understanding of team dynamics.Staying updated on technology trends is vital for IT leaders.TitlesTransforming IT: From Operations to Strategic PartnerThe Future of AI in Business: Build vs. BuySound bites"Simplicity is key in IT management.""No smart a-holes in my team.""Leverage AI to stay updated on trends."Chapters00:00 Introduction to Steve's Background and Role02:03 The Evolution of IT's Role in Business03:50 Strategic Priorities in IT Management05:58 Balancing Operational Needs with Strategic AI Implementation07:50 Build vs. Buy in AI Solutions10:01 Navigating the AI Talent Landscape11:59 The Importance of Customization in AI Solutions14:00 Design Partnerships and Collaboration15:50 Customer Service in AI Development17:55 Leadership and Team Building in IT19:50 Staying Updated in a Rapidly Changing Tech Landscape21:54 Quickfire Questions and Personal Insights This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit risepodcast.substack.com