Juniper Square

When we first hit the functional singularity moment in Dec/Jan with Opus 4.5 + Claude Code, I'll admit that I became a doomer for a few months. We employ hundreds of accountants at Juniper Square , so the question of what AI does to that job is something I think about a lot. It seemed like AI was going to be able to do anything that a human sitting in front of a computer typing on a keyboard could do, only better. Then I thought about the arrival of spreadsheet software and how despite the automation of calculations we still need accountants more than ever today. I looked at the data, here's the conclusion: Spreadsheets didn't kill accounting jobs, they created more of them. (Yes correlation vs. causation, but you get my point.) There are roughly 2.6x more accountants and auditors today than in 1970, before any commercial spreadsheet existed--and the field grew straight through every spreadsheet launch. If you define a job by the execution of the tasks, like "calculation" for an accountant, then yes those tasks get automated with new technologies like spreadsheets. But if you define the job as "making sure the numbers are right", then the job is really about overseeing the systems that do the calculation. As new technologies like spreadsheets then, and AI now, let you do more calculations, you need more accountants--not fewer. This is Jevons' Paradox in action. Now that we have several more months of experience with current AI technologies, I've gone from being a doomer to an optimist. I think it will go just like it did with spreadsheets and accountants. Now AI systems will enable accountants (and every knowledge worker job) to up-level to a higher level of abstraction and do even more. Yes the tasks will change, and we won't be using spreadsheets as the primary tool anymore, but we'll still need accountants to steer the AIs and do the job of "making sure the numbers are right". While I'm so optimistic for the expansion of human potential and the productivity boom ahead, a final point is to talk about what happened to bookkeepers, as indeed there was a collapse in those jobs and there are fewer accountant + bookkeeper jobs today than there were at peak employment in 1990. We have to be honest about the fact that there will be job displacement as a result of AI, even if there is an explosion in overall employment and economic productivity. The key will be creating the systems of support to allow people to retrain, re-skill, and move to the new shape of the economy. I feel like this is a point that gets lost in the doomer vs. optimist debate when people take binary positions. Both can be true at once. Yes, AI will drive explosive economic activity, enable many jobs to be 10x more productive, and create tons of new jobs we can't even imagine today (per MIT's David Autor, 6 / 10 jobs today didn't exist in 1940). And yes, it will *also* displace a lot of jobs. We need to make sure we help those affected make the transition.

148 private markets leaders across 3 events, 3 podcast and a lot of new knowledge gained this week. So much to share but it's a reminder about the power of relationships. Every meeting, every conversation, every side discussion was about relationships and how they impacted individuals, opportunities and investments. Each one was made possible due to the power of relationships. From PE to CRE to VC - from debt to equity - from primary to secondaries - it's all about relationships. I'm greateful to be a part of these conversation and to be able to learn and share with all of you. The events: 1. Virtual INVITE ONLY PE Roundtable co-hosted with Chris Brimsek and Juniper Square 2. Beyond the Hype: AI and private markets co-hosted with Institutional Real Estate, Inc. (IREI) - Virtual 3. Venture Secondaries Summit in Healdsburg, CA with Industry Ventures and Revelation Partners Podcast Recordings this week - will be dropping soon: 1. Hessam Nadji - President & CEO of Marcus & Millichap does his journey from Iran to the USA and his outlook on the CRE markets from the lens of one of the most active CRE brokerage and advisory firms. 2. Aaron Gershenberg - CEO and Managing Partner of Pinegrove Venture Partners discuss the evolution of Venture and why it's never been a more exciting time to be alive and investing 3. Lowell Baron , CEO - Real Estate at Brookfield and I discuss how persistence pays off personally and patience pays off professionally and the benefits of operational alpha... at scale ...and 3 client meetings + 1 prospect meeting and 1 partner meeting in 24 hours.

Looking for a rockstar PM to reshape the private markets in a very AI-native role. Juniper Square is growing like crazy and it's a fun time to build - come join my team! 🚀 https://lnkd.in/g2v44eBX

This is a awesome role for a dynamic leader that is parsinonate about building community, connecting dots and making connections across the private market ecosystem. Juniper Square is burning for a Partner Relatiinship Manager based in NYC! DM if you are interested or reach out to Derek directly.

Big news from Juniper Square — we just acquired Sightglass, an AI-native DDQ automation company built specifically for private markets. 🎉 IR teams are spending 40–60 hours per DDQ response. That's not a workflow problem — it's a structural one. Now those teams can start with an AI-generated first draft, built from their own knowledge base, with every answer source-cited. Proud to be part of a company that continues to modernize the private markets.

Big news at Juniper Square today! We are officially bringing Sightglass in. The private markets have hit a breaking point with DDQs. The volume of these requests has shifted from a routine task to a massive bottleneck for IR teams. While the industry has tried to solve this with generic AI tools, the reality is that DDQs require more than just a chatbot... THEY REQUIRE CONTEXT. We’re creating a closed-loop system that already understands a firm’s history and compliance needs. 👉 Full article and Demo: https://lnkd.in/d5e8EfHG #JuniperSquare #FundAdmin #PrivateMarkets #AI

Incredibly excited to see Sightglass join the Juniper Square ecosystem! This is exactly the kind of value we’re building in private markets—less time chasing documents, more time closing relationships and capital.

Another top shelf tool being weaved into the Juniper Square fabric ensuring our GPs have the best, scalable Operating Partner in the private markets. GPs who raise capital from institutional LPs know the struggle in responding to DDQs with velocity, accuracy and depth. Whether fielding these requests during fundraising or recurring questionnaires there hasn’t been a great solution that’s connected to a true operational source of truth… until today. Comment “DDQ” for more information or feel free to DM!

Excited to announce that Juniper Square has acquired Sightglass , a AI-first DDQ automation platform. Post-Covid, DDQ requests have skyrocketed and it has quickly moved to a top pain point for private markets IR teams. It's a perfect scenario for AI leverage: DDQ requests are inherently unstructured and come in all forms, yet GPs are continually recycling the same responses to similar questions. But it also has deterministic elements too: responses need to go through official approval and compliance workflows, and golden response data sets must be maintained. With our ability to pair the DDQ capabilities of Sightglass with the investor and fund data already inside Juniper Square, we are building something no horizontal AI tool can replicate: an AI layer with the full context of a firm's LP relationships, fund history, and data narrative already embedded. I'm very excited for this new product capability added to our suite, and thrilled to welcome Thomas Buley and team to Juniper Square!