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    LightSight was thrilled to sponsor the annual Catch Meaning golf outing at Sand Ridge Club.

    LightSight was thrilled to sponsor the annual Catch Meaning golf outing at Sand Ridge Club.

    It was a gorgeous day for the outing. There were a number of friends of LightSight attending, including Joe Kubic, Chip Chaikin, Andrew Greiff, Larry Oscar, Chuck Grossman, Matt Weil, Jeffrey Cristal, Brett O'Brien, Rob Miller, and of course, Michael Weil and Meredith Weil. Thank you to Catch Meaning for hosting a lovely event.

    LightSight AI

    LightSight AI

    October 15, 2026

    Story
    Yesterday, Jackson Rudd had the pleasure of presenting at Blue Point Capital Partners' CEO and OEG Forum.

    Yesterday, Jackson Rudd had the pleasure of presenting at Blue Point Capital Partners' CEO and OEG Forum.

    We discussed why the biggest returns from AI come from bringing it to the core of a business, both its core capabilities and its core systems. We want to extend our gratitude to the Blue Point team for hosting us, and look forward to continuing to collaborate in the future!

    LightSight AI

    LightSight AI

    October 7, 2026

    Story
    A good look at how we work with client teams: objectives first, process second, prototypes in the room.

    A good look at how we work with client teams: objectives first, process second, prototypes in the room.

    Nice write-up from Jalen Brown

    LightSight AI

    LightSight AI

    August 15, 2026

    Story
    Watch the Startup Builder™ Q&A Live Stream with William Callaway, CEO & Co-Founder of LightSight AI.

    Watch the Startup Builder™ Q&A Live Stream with William Callaway, CEO & Co-Founder of LightSight AI.

    Will helps private equity and mid-market companies adopt AI through leadership education, organisational training and custom software development. We talked about: ✅ Where companies should begin investing in AI ✅ How the buy-versus-build decision is changing ✅ What to consider before developing a custom AI solution ✅ Where an AI investment should start and where it should end ✅ How software engineering teams may change as AI adoption grows

    Kirk Drage

    July 17, 2026

    Story

    Remember Agile? I do. I spent years of my career preaching it, practicing it, believing in it.

    As CEO of SolutionsIQ, we used to say our mission was bringing humanity to the workplace. Agile wasn't a methodology to us. It was a movement. Then AI showed up and everyone stopped talking about Agile. Here's what I think most people are missing: this isn't an out with the old, in with the new moment. The core premise of Agile, that markets had become too volatile for waterfall planning to work, is now proving true faster than anyone predicted. Innovation cycles that took years now take weeks. One popular AI tool was built and shipped in 10 days. Below is the first post in a new series on Agile in the age of AI. I'll be revisiting the practices, asking the hard questions (are two week iterations too long? are two pizza teams over with agentic coding?), and pulling in real examples from our client work. Full post in the comments. #Agile #AI #BusinessAgility #Leadership

    John Rudd

    John Rudd

    July 7, 2026

    Story
    Last week, our team had the pleasure of joining North Coast Ventures and their incredible...

    Last week, our team had the pleasure of joining North Coast Ventures and their incredible...

    Last week, our team had the pleasure of joining North Coast Ventures and their incredible portfolio community for an evening of meaningful conversations around AI and what's next for mid-market companies. A huge thank you to the North Coast Ventures team for having us as a sponsor, and for bringing together such a thoughtful, energized group of leaders at your April Member Meeting. Our CEO and founders had a wonderful time sharing their perspectives and, more importantly, listening and learning from everyone in the room. Events like this remind us why we do what we do. The mid-market is full of companies ready to move boldly on AI alongside the right partners, frameworks, and community. Looking forward to the conversations that continue from here!

    LightSight AI

    LightSight AI

    May 7, 2026

    Story

    "Are restaurants dead because you can cook at home?"

    My friend hit me with this when we were discussing the whole “Is SaaS dead?” debate. It was meant as a gotcha (an admittedly good one), but it’s a great way to think about why and what you should build. Why do you go to a restaurant? You don't have the right ingredients, skills, or time to cook at home. For businesses: ingredients (your core products and services) and time (or lack thereof) hasn’t changed. But agentic coding has fundamentally changed the skill variable. SMBs can cook a lot more in-house than they realize. Read more about the why and what in the full blog. Link below in the comments.

    William Callaway

    William Callaway

    April 13, 2026

    Story

    I’m pretty skeptical about using an LLM to generate validation or tests for applications.

    If you aren’t highly aware/involved in validating your application, it reserves the right to behave in unpredictable ways. However, I’ve been using DeepEval as our internal evaluation framework and am impressed with the ease-of-use and efficacy of the synthesizer. The speed of synthesizing test cases means we get much higher coverage across our internal LLM powered tools, while still manually writing cases for important scenarios. See the comments for my retrospective blog on DeepEval, and how its adversarial dynamics allow me to put a lot of trust into our current evaluation system.

    Beau Dekker

    Beau Dekker

    March 24, 2026

    Story
    The second blog in my Ready, Aim, Fire series is titled "The Good News Is: We Have All the Answers."

    The second blog in my Ready, Aim, Fire series is titled "The Good News Is: We Have All the Answers."

    In this post, I look to lessons from the pulpit for clues about innovation. Find the link in the comments. #AI #Innovation #Strategy

    John Rudd

    John Rudd

    March 20, 2026

    Story

    There is a $3,800 per employee SaaS tax sitting in your tech stack.

    I've been talking with business leaders lately, and a major theme is clear: SaaS is in trouble. The "Buy vs Build" equation has been rewritten and for most SMBs, the new reality is: You should probably build. Math (Pendo & Zylo) - $4,800: The average company spend per employee, per year on SaaS - 80%: Features in that software that go completely unused = $3,800: Amount spent on wasted features every single year, per person If coding is "largely solved" (Boris Cherny, head of Claude Code), the competitive advantage shifts from who buys then best tailors generic apps to who builds the best custom workflows. It's time to get the pitchforks. I'm going to dive into how to prioritize these solutions. (Hint: Start where the friction is highest and the judgement needed is lowest. If your team groans about a repetitive, time-consuming task, that's your first automation. Then build custom tools that drive competitive advantage). Which SaaS apps are you ditching first? What custom tools are you building? Let's talk 👇 Link to the full blog in the first comment

    William Callaway

    William Callaway

    March 12, 2026

    Story
    Channeling George Costanza as a great leadership anti-pattern to kick off my blog series, Ready, Aim, Fire!

    Channeling George Costanza as a great leadership anti-pattern to kick off my blog series, Ready, Aim, Fire!

    Find the link in my comments to read my first post. #AI #Leadership #Strategy

    John Rudd

    John Rudd

    March 10, 2026

    Story
    After nearly a decade of stagnation, U.S. productivity is climbing again.

    After nearly a decade of stagnation, U.S. productivity is climbing again.

    Stanford economist Erik Brynjolfsson argues this reflects businesses finally learning how to leverage AI effectively. His research across 10,000 firms reveals how individual companies can capture those gains and avoid the costly transition period that holds many back. Read more about my take on Brynjolfsson's research, and its implications for mid-market firms via the link in the comments.

    Jackson Rudd

    Jackson Rudd

    February 18, 2026

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