Unusual Ventures

The move towards outcome-based pricing for AI products (where you pay for success vs. usage) requires a rethinking of pricing as an engineering issue. In the latest episode of the Startup Field Guide podcast, Dor Sasson (CEO and co-founder of Stigg) chats with Unusual's Scott Schwarzhoff about how pricing, now more than ever with AI, is increasingly an engineering problem instead of a billing problem. Check out the entire episode to learn more about Stigg's approach to pricing and packaging! https://lnkd.in/dJDZDQnb

AI isn't just disrupting knowledge workflows, it's disrupting business models. Outcome-based pricing, where you pay for success vs. usage, is rapidly accelerating AI adoption because the risk of purchasing a product shifts from buyer to vendor, and expectations of value delivery increase dramatically. See Salesforce and Zendesk resolution-based pricing as mainstream examples. Hot on the heels of his Series A funding round, Dor and I sat down in our latest Startup Field Guide Podcast to discuss how pricing, now more than ever with AI, is increasingly an engineering problem vs. a billing problem. Stigg's self-service monetization platform enables engineering teams to easily manage entitlements at the feature level, which is essential when measuring the complexities of outcomes vs. activities to determine the price someone pays. Watch the episode below to learn more about Dor Sasson's journey founding Stigg and how his team is helping companies like Webflow, Miro, and PagerDuty ship groundbreaking pricing and packaging changes quickly. There are a lot of great tips for how founders can really embrace early adopters as their North Star during product development, particularly when working on cutting edge problems like AI monetization. Link to full episode in the comments!

We are excited to announce our investment in GovSignals — the first AI platform to automate the full process of finding and bidding on government contracts. In their latest blog post, Unusual investors Lars Albright and Tyler Crown explain how GovSignals is poised to transform the government contracting space using AI. GovSignals removes much of the time and complexity of government contracting with its AI engine that constantly scans for new opportunities, flags relevant projects for users, and helps companies create compliant proposals with just a few clicks. Read the entire post to learn more! We are excited to partner with co-founders Derek Hoyt, Conner Aldrich, Ethan Aldrich, and Jeremy Doochin!

What's the secret to creating "sticky" ideas? How do you create ideas that are memorable, impactful, and capable of changing opinions and behaviors? This month, our team read "Made to Stick" by Chip Heath and Dan Heath to understand the six principles behind successful ideas (captured by the acronym SUCCESs): 1. Simple 2. Unexpected 3. Concrete 4. Credible 5. Emotional 6. Story Ready to learn more? Check out our entire review!

🧟 The Billing Monolith is Dead: Build for Flexibility I’m really excited to announce that Stigg has raised $17.5M Series A funding, led by Red Dot Capital Partners and supported by incredible partners like Unusual Ventures, Emerge Ventures, Redseed, and Cerca Partners. This milestone allows us to double down on building the first unified monetization platform for engineers. At Stigg, we started with one belief: monetization infrastructure should empower growth—not block it. Traditional billing systems are rigid and slow to adapt to modern needs, leaving engineering teams stuck building complex, one-off solutions. With Stigg’s flexible, API-first platform, companies can: ✔️ Model dynamic catalogs ✔️ Track usage ✔️ Manage entitlements ✔️ Adapt pricing models in real-time —all without overhauling their stack. For developers, it’s a seamless, modular approach to solving monetization challenges—freeing your team to focus on revenue instead. Huge thanks to our investors, customers like Miro, Webflow, AI21 Labs, and PagerDuty, and our amazing team. Together, we’re creating tools that make engineering a key enabler of growth. And we’re hiring globally—join us to build the future of SaaS monetization. (links in comments) #API #DeveloperTools #SaaS #Monetization

What should sales leaders consider before joining an early-stage startup? When we posed this question to Hector Hernandez, the founding head of GTM at Speakeasy, he listed the following: 1️⃣ Look for founders who you can have open and passionate disagreements with, and still respect and trust each other. 2️⃣ The partnership between sales leaders and founders should be mutually beneficial, with a good fit in terms of personality, ambition, and the decision-making process. 3️⃣ It is crucial for the sales leader to feel like they want to be in a foxhole with the founders, forming a strong and enduring partnership. For more insights from Hector, listen to his entire chat with Penny Mares on the latest episode of the Startup Field Guide podcast. Link in the comments!

🚀 BREAKING NEWS: Axios broke the story this morning. We are excited to announce a raise of $5.5 million led by Unusual Ventures! The funds will help scale our already robust full acqusition software. 💪 No other AI-first software goes end-to-end from taking companies before an RFI drops to AI-matched capture, compliant proposals built in as little as 15 minutes, and supercharging govcon teams with AI knowledge management. 👏 No other founding team has the experience between govcon & AI expertise as co-founders Derek Hoyt, Ethan A., Jeremy Doochin, Conner Aldrich. 🤩 And backed by one of the most venerable venture capital firms in the industry, Unusual Ventures. 🎖️ GovSignals has aready helped hundreds of executives to 3X their team's capabilities, and now we're excited to roll this out across the entire industry! 👉 Want to see more? Schedule a 30 minute demo at: https://lnkd.in/gqUeVbwM Follow along as we take GovSignals to the next level! Let’s win together. #GovTech #AI #Innovation #Fundraising #GovSignals #UnusualVentures #VentureCapital

I've had the opportunity to participate in a number of panels and keynotes this year and there are a couple of things I always share when I'm speaking to new/aspiring entrepreneurs. Here are 3 lessons I've learned from a decade of building companies: 1) Starting a company requires a deep sense of purpose. I often ask new entrepreneurs: "Are you willing to commit 10 years of your life to this idea?" If the answer is anything less than yes, then maybe it's not the right idea. 2) Don't overcomplicate it — success is one milestone at a time. Entrepreneurship can feel overwhelming, but it doesn’t have to be. Take things one milestone at a time. For AppDynamics, our goal wasn’t to build a billion-dollar company overnight—it was about reaching one goal after another: launching the product, signing early customers, expanding the team, etc. By focusing on one milestone at a time, you can create a sense of progress and build momentum. Small steps, consistently taken, lead to big achievements. 3) Grit and perseverance are essential. When I started my first company, I didn't completely understand the power of grit. But after over a decade spent building companies, I now know it's the factor that makes all the difference. Setbacks are inevitable. Founders face their share of obstacles — competition, product challenges, and moments when success feels out of reach. But what kept us moving was a refusal to give up. In my experience, this willingness to keep going is more powerful than any strategy or resource. Every entrepreneur's journey is unique, but I've found that these principles have helped me stay the course.

Thank you Penny Mares and the Unusual Ventures team for having me on the Startup Field Guide Podcast! I loved talking through the $0 to $100M journey and diving deep into the early days of company building. BTW, all of these episodes are amazing - I also highly recommend watching the conversation with Denis Yarats of Perplexity and Barr Moses from Monte Carlo. 💥

➡️ When should founders bring on their first sales hire? ➡️ What should sales leaders look for in an early-stage startup? ➡️ How does your ICP shift as your company grows? We covered these questions and more in an all-new episode of the Startup Field Guide podcast featuring Hector Hernandez, founding head of GTM at Speakeasy. An early GTM leader at companies like LaunchDarkly, Traceable, and Teleport, Hector has a wealth of experience scaling revenue orgs and creating hyper-growth. Listen to his entire conversation with Unusual's director of sales Penny Mares! Link in the comments!