A 1600% Improvement in Sales to Lead Conversion

The ServiceNow team is raising the bar by innovating on our own platform, taking an end-to-end agentic AI-first approach to running our business. We see this in a 16x improvement from lead-to-sale conversion & an over 86% deflection of the soul-crushing work people used to do themselves.

ServiceNow reported earnings yesterday alongside Google & many other companies. All the insights out of those reports were interesting, but this was the one that stood out the most to me.

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Rabbits on Firetrucks Redux

Two years ago I published an image of a rabbit on a fire truck to demonstrate how effective image generation was for blog posts.

The conclusion at the time : the images were unusable.

In 2025, the opposite is true - with one caveat.

Prompt: Coupa & Thoma Bravo logos each in front of a cloud with a plus sign between them.

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Two years has brought tremendous professionalism to new image. Corporate street art is now pixel-perfect professional. The clouds and the + sign are perfect, and the logos look the part.

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Integrations as Competitive Advantage

Software systems work best when they’re connected to each other. For years, incumbents use deep integrations as a competitive moat.

But AI upends this dynamic.

A few of our portfolio companies are starting to develop integrations with AI in a matter of hours, completely upending the two or three quarter timeframes of classic enterprise integration development.

This enables two important impacts to the sales cycle.

First, the integration a customer desires can be built during the sales cycle, demonstrating the startup’s technical agility.

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Social AI

I want to see how you use AI.

The biggest challenge to AI adoption is reimagining workflows, AI is best discovered socially.

Midjourney’s launch on Discord was brilliant. As a new user, I knew enough to ask for an image of a rabbit on a firetruck. But by watching others, I discovered I could create vector images, recast photos into Ghibli-style art, change aspect ratios, or convert photos to pencil-shaded drawings.

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Speed Running a 50 Year Old Software Category

We don’t often hear the words speed & ERP in the same sentence. But when researching Doss, we heard it again & again. We’ve always believed fast sales cycles create competitive advantage - nowhere is this more true than enterprise software.

Imagine purchasing software knowing there’s a 75% chance it won’t deliver value after a 12-month deployment. If selling software is the business of selling promotions, traditional ERP offers a ponderous path to career advancement.

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My Bottleneck with AI

I’ve been watching my behavior evolve as I use AI more.

Coding new projects, I started first by describing a big idea : generate a new website that ingests podcasts and transcribes them. But I quickly discovered this approach was like asking someone to build a skyscraper without blueprints—the AI choked on requests too broad & lacking structure.

So I broke the project down into smaller blocks. Write a function to download the list of podcasts in the last week from these sites. But I noticed how low-leverage that felt : I knew I was yoking a strong animal to pull along a child’s wagon.

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Beyond ARR: How Monte Carlo Reinvented Their Business with Daily Revenue

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Pricing is one of the most complex topics in software. Changing pricing is never simple. It is a company-wide evolution that has the potential to completely reshape your entire business & your customer relationships.

Few have executed this transition better than Barr Moses, Co-Founder & CEO of Monte Carlo.

Join us for a candid conversation with Barr as she shares how Monte Carlo transitioned from ARR to daily revenue as the core operating metric for the business.

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The Impact of Tariffs on Series As

With another tariff induced red-tinged day hammering markets, I wondered: Do private markets follow public ones? The data suggests yes—but with a delay & at a fraction of the magnitude.

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A 1% increase in Nasdaq’s (QQQ) quarterly return translates to a 0.47% rise in median Series A valuations—but only after a two-quarter delay.

The inverse holds true as well: when public markets contract, private valuations follow suit approximately six months later at roughly half the intensity.

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What do Tariffs Mean for Startupland?

The new tariffs have markets down broadly. What do they mean for startups?1

In terms of first order effects, tariffs can impact a startup in two ways : the input costs and consumers’ demand.

Most software companies don’t import or source critical components of the software from abroad so the COGS / gross margin structure of the company shouldn’t change unless they rely on significant hardware purchases, for example GPUs or robotics components.

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