SIERRA Ventures

SIERRA's Ashish Kakran was in PitchBook today discussing GPT-5. Did OpenAI’s much-anticipated Summer Update feel more like a maintenance release than a leap forward? Many said the launch was marred by confusing performance charts, a basic physics flub, and a missing sense of "wow" that past unveilings carried. The real story of GPT-5 may be in code. OpenAI leaned heavily into software development use cases—code completion, application generation, and developer tooling—which many in the ecosystem see as the core battleground. Software on demand will be a defining characteristic of the GPT-5 era,” Sam Altman.

We signed the term sheet on a pizza box at 12:06am. A few weeks later, ProductNow officially closed our Seed — led by the phenomenal Tim Guleri at SIERRA Ventures, and followed by believers - seasoned execs in MAANG/Frontier model companies. We’re building agents that give ANYONE (including developers) the power of a full-stack product org — strategy, planning, and execution, all in flow. AI teammates that turn docs, decks, and status calls into structured, shippable output. Since closing: → Super early pilots with product-forward teams — from XXL tech companies to breakout startups → Real usage in the wild, real feedback loops → Growing momentum from design partners and GTM leaders Thank you to Tim and Sierra for recognizing the shift we’re building toward — and backing it when it was just starting to spark. We’re just getting started!! 🌐 productnow.ai

AI isn’t just changing how we build products. It’s changing how we define the markets. For years, TAM was a vague estimate—a slide that looked good on paper but often didn’t hold up under scrutiny. That’s no longer enough. In today’s AI-native world, where data is more readily available and much easier to model, the best founders are turning TAM into a dynamic, data-driven model that informs GTM strategy, pricing, and product direction. It’s not about chasing a big number. It’s about clarity—understanding your ideal customer, how that expands over time, and where you can build long-term advantage. 1️⃣ Use firmographics to define your real market 2️⃣ Combine top-down, bottom-up, and value-based models 3️⃣ Build layered TAM views: core, expanded, and future 4️⃣ Leverage AI for ICP scoring, what-if modeling, and clustering 5️⃣ Feed your model with first-party data and real-time signals If your TAM slide hasn’t evolved with your company, now’s the time to rethink it. Read more on SIERRA Ventures' blog: https://xmrrwallet.com/cmx.plnkd.in/g-ziMKbp #AI #TAM #B2B #GTM #Startups #Founders #GTM #ProductStrategy #VentureCapital

Tript Singh Lamba and I were introduced by a friend earlier this year, and a few things stood out as his key traits a) incredibly accomplished [MSFT, GOOG, Expedia] yet humble b) very networked but always willing to play it forward c) hungry to build in the age of AI d) speed. SIERRA Ventures and my partners did a full court press on getting him to join us as an EIR. He accepted and as he worked with us (and as I'd predicted) the entire partnership fell in love with him ! We ideated for a few months, talked to prospects and customers on the various ideas/ threads and then it hit him (and me) on the face......a 1T market staring us in the face...the 2 million "product practitioner" [a.k.a Product Manager, Technical Product Manager etc]. As coding was getting faster / more efficient with AI, the pressure was being felt by the product teams that had to move faster as well and they were bottlenecked. Enter ProductNow ! I am beyond thrilled to announce our leading ProductNow's $6M Seed and more importantly investing in a great entrepreneur like Tript Singh Lamba. Company is based in PaloAlto and is hiring ! Let's build More details on our thinking behind this investment. https://xmrrwallet.com/cmx.plnkd.in/gTSNrZJX

Ashish Kakran is a Partner at SIERRA Ventures, where he leads early-stage investments in AI, cloud infrastructure, and cybersecurity. ~~~~~ This episode is brought to you by Verivend. If you’re a GP or LP looking to simplify the capital raising and deployment process, Verivend is here to help. Trusted by over 800 funds and managing more than $2 billion in transactions, Verivend offers a secure, streamlined payments platform designed specifically for private capital markets. Say goodbye to manual reconciliation and repeated follow-ups - raise and deploy capital faster and with greater transparency. Ready to make your fund operations smoother? Visit https://xmrrwallet.com/cmx.pbit.ly/3GrB4Qj and see how easy it can be.  ~~~~~ Before Sierra, Ashish spent seven years in venture, most recently as a Partner at Thomvest Ventures, where he invested in companies including Cohere, Harness, Isovalent (acquired by Cisco), Opaque, and Exaforce. Ashish is known for working closely with technical founders. Prior to venture, he spent nearly a decade in engineering and product leadership roles at early-stage infrastructure startups, giving him firsthand insight into company building from the ground up. He holds a BS in Computer Science from IIT and an MBA from the Kellogg School of Management. Ashish has been recognized by VC Journal’s “40 Under 40” and Business Insider’s “Rising Stars in VC.” Topics: - The current AI infrastructure stack - Evaluating AI companies: technical differentiation vs. go-to-market execution - Security in the age of AI #VCPodcast #AIInfrastructure #CloudNative #Cybersecurity #TechnicalFounders

IIT AI weekend charcha: 3 takeaways for AI founders in 2025 Vikram Chatterji co-founded and runs Galileo, an AI reliability and Eval platform. He was early member of the Google Android team and joined the Transformers/BERT team in 2018. Thanks for sharing your journey, and advice for founders! 💡Ideation: Don't wait for the perfect idea, it doesn't exist. Start with a theme/thesis and talk to customers before starting the company. Galileo stared with a simple observation that 80% of world's data is unstructured and AI will eventually deal with this problem. From a 'deep learning startup' the company evolved into inference/monitoring and focuses on multi-agent observability/guardrails today. With advances in AI, the tech stack is changing so rapidly, nimble teams that adapt quickly to market changes will have an advantage. 💡 Product-market fit: spent 3-4 months talking to data scientists about workflows. Identified 5-6 pain points, starting with most painful. Constant outbound (3-4 hours daily as founder/SDR). When messaging stopped working, completely changed approach. For technical founders, this is one of the key skills to learn. Hiring sales leaders early won't solve the product-market fit problem. It has to come from founders through founder-led sales. Founder must be the first salesperson till 4-5 deals are closed. 💡 Picking investors: choose hungry investors who will 'roll up sleeves' and won't be at the golf course after making an investment. When constructing the Board, optimize for diverse opinions/expertise. Get domain experts on the cap table instead of unknown investors. If he were to do it all over again, compared to bootstrapping, he would still choose the VC route for the capital++ value they bring to the table. As an investor, helping founders bring their vision to life adds meaning to my work. If you are are an ambitious technical founder with an idea you can't stop thinking about, I can't wait to hear from you. There has never been a better time to start a company. Just DM me and I will make time for you! #ai #founder SIERRA Ventures

Congrats to Shashank Saxena, Somesh Saxena, and the Pantomath team on raising their $30M Series B led by Quentin Clark at General Catalyst. You couldn't have found a better partner for this next phase of growth. SIERRA Ventures is excited to have been part of this journey from the very early days. https://xmrrwallet.com/cmx.plnkd.in/gDWJ9sqa

Pantomath raises a $30M Series B led by General Catalyst. Congrats, Somesh Saxena, Shashank Saxena, Narayana Surabhi, and the Pantomath team! Pantomath is redefining how enterprises manage data operations—moving from reactive troubleshooting to proactive, AI-powered resolution. With the rise of complex analytics pipelines and the pressure on data teams to deliver trusted insights fast, Pantomath’s AI DRE agents represent a step-change in productivity and reliability. This is what the future of data ops looks like: → Real-time monitoring → Automated root-cause analysis → AI agents that resolve incidents, not just detect them SIERRA Ventures' Mark Fernandes led the Series A in 2023. #AI #DataOps #EnterpriseAI #SierraVentures #Pantomath #StartupFunding #AIInfrastructure #EnterpriseSoftware

🎉 Exciting News: Pantomath has raised $30 million in Series B funding Led by General Catalyst alongside SIERRA Ventures, Bowery Capital, EPIC Ventures, Hitachi Ventures, Foster Ventures, & Cintrifuse Capital. The funding accelerates our mission to eliminate manual data operations by combining real-time monitoring, traceability and agentic AI to boost enterprise data reliability at scale. Stay tuned! To our employees, customers, investors, and partners - thank you 💙 Read the full announcement → https://xmrrwallet.com/cmx.plnkd.in/gbhBqpRi #dataoperations #fundingraise #ai

The Cloud is going 𝘀𝗲𝗹𝗳-𝗱𝗿𝗶𝘃𝗶𝗻𝗴. At Sedai, we’re not just automating—we’re making the cloud autonomous. with AI. We’ve moved beyond recommendations, alerts and dashboards. Now, the platform learns, decides, and acts—continuously optimizing cost, performance, and availability without manual intervention. And it’s not just a vision—𝗶𝘁’𝘀 𝗹𝗶𝘃𝗲 𝗶𝗻 𝗽𝗿𝗼𝗱𝘂𝗰𝘁𝗶𝗼𝗻 𝘁𝗼𝗱𝗮𝘆. The best in the world run on Sedai: 𝗣𝗮𝗹𝗼 𝗔𝗹𝘁𝗼 𝗡𝗲𝘁𝘄𝗼𝗿𝗸𝘀, 𝗖𝗮𝗽𝗶𝘁𝗮𝗹 𝗢𝗻𝗲, 𝗛𝗣, 𝗘𝘅𝗽𝗲𝗱𝗶𝗮, 𝗘𝘅𝗽𝗲𝗿𝗶𝗮𝗻, 𝗚𝗦𝗞, 𝗚𝗲𝗼𝗱𝗶𝘀, 𝗞𝗻𝗼𝘄𝗕𝗲𝟰, 𝗠𝗰𝗚𝗿𝗮𝘄 𝗛𝗶𝗹𝗹, 𝗙𝗹𝗲𝘅, 𝗢𝗮𝗸 𝗥𝗶𝗱𝗴𝗲 𝗟𝗮𝗯𝘀, 𝗚𝘂𝗶𝗱𝗲𝘄𝗶𝗿𝗲 𝗮𝗻𝗱 𝗺𝗼𝗿𝗲... (Category leaders in security, e-commerce, financial services, pharma, logistics, learning science and more) 𝗧𝗵𝗲𝘆’𝗿𝗲 𝗻𝗼𝘁 𝗷𝘂𝘀𝘁 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿𝘀—𝘁𝗵𝗲𝘆’𝗿𝗲 𝗽𝗿𝗼𝗼𝗳. The future of cloud isn’t manual. It isn’t automated either. It’s autonomous... And it's self-driving...