Powering Enterprise Innovation Through Advanced Software
We invest in B2B software companies building AI infrastructure, developer tools, and enterprise platforms that transform how businesses operate.
Powering Enterprise
Transformation
Investing in Intelligent
Software Stacks
Backing Visionary
SaaS & AI Founders
Our Enterprise Software Investment Focus
The engine of modern business runs on sophisticated software. Awesome Ventures invests at the forefront of enterprise innovation, backing B2B software companies whose new technologies are creating powerful market opportunities and fundamentally changing how organizations operate and compete. Our focus is on AI infrastructure, intelligent automation, developer tools, and next-generation enterprise platforms, including those that:
AI/ML Infrastructure & Applications
- Machine learning operations (MLOps) platforms (e.g., for model deployment and management).
- AI-driven automation and decision support (e.g., Zesty for cloud optimization, TrustPortal for hyperautomation).
- Data infrastructure, annotation, and processing tools for AI development (e.g., Waterplan's data foundation, Gradient Health's data curation - cross-portfolio example).
- Vertical AI applications solving specific enterprise challenges (e.g., Deep Sentinel for security).
Developer Tools & Platforms
- API development, management, and security.
- Cloud-native development tools and infrastructure-as-code.
- DevOps, CI/CD, and observability platforms.
- Next-generation database and data warehousing solutions.
Cybersecurity
- Zero-trust security architectures.
- Cloud security posture management (CSPM) and workload protection (CWPP).
- Advanced identity & access management (IAM).
- AI-powered threat detection, response (SOAR), and data security.
Enterprise Automation & Workflow
- Hyperautomation platforms orchestrating AI, RPA, and human workflows (e.g., TrustPortal).
- Intelligent business process management (iBPM) and optimization.
- No-code/low-code platforms for enterprise application development.
- Integration Platform as a Service (iPaaS) and API-led connectivity.
Enterprise Software Leaders We've Backed
Zesty
AI-powered cloud cost optimization platform that dynamically adapts resources to application demand in real-time, reducing cloud spend without human intervention.
Focus: Eliminating cloud waste and optimizing performance automatically for AWS, Azure, and GCP.
TrustPortal
HyperAutomation platform that orchestrates people, AI agents, and RPA bots in real-time to streamline complex enterprise processes.
Focus: Bridging automation gaps and enabling seamless human-robot collaboration for end-to-end process efficiency.
Waterplan
SaaS platform empowering companies to measure, respond to, report, and monitor their escalating climate-induced water risks.
Focus: Providing data-driven insights for proactive water stewardship and resilience in the face of climate change.
Deep Sentinel
AI-powered live video surveillance combining intelligent cameras with remote professional security guards for proactive property protection.
Focus: Transforming passive security monitoring into active, real-time crime prevention for businesses and high-value properties.
What We Look for in Enterprise Software
Technical Depth & Moat
- Proprietary algorithms, unique data sets, or a novel technical approach.
- Strong engineering team with relevant enterprise software experience.
- Scalable architecture designed for enterprise-grade reliability and security.
- Clear technical moats or emerging network effects.
Enterprise Focus & GTM
- Clear B2B sales model targeting mid-market or large enterprise customers.
- Understanding of enterprise procurement and long sales cycles.
- High customer lifetime value (LTV) and potential for expansion revenue.
- Sticky, mission-critical use cases that solve significant pain points.
Market Opportunity & Vision
- Addressing a large, growing enterprise software category or creating a new one.
- Multiple use cases and clear expansion opportunities.
- Path to becoming a platform or ecosystem player.
- Ambitious vision to redefine an enterprise function or workflow.
Founder FAQs
What kind of AI/ML companies are you most interested in within enterprise software?
We're particularly excited by companies building AI/ML infrastructure (like MLOps or data tools), as well as those applying AI to solve specific, high-value enterprise problems – for example, Zesty using AI for cloud cost optimization or Deep Sentinel for intelligent security. We look for a strong technical advantage and a clear path to enterprise adoption.
Do you invest in vertical SaaS or mostly horizontal platforms?
Both. We appreciate horizontal platforms like developer tools or cybersecurity solutions that have broad applicability. We also see great potential in vertical SaaS companies that embed deep domain expertise and AI to transform specific industries, similar to how Waterplan addresses water risk for enterprises.
How important is early revenue or paying customers for an enterprise software startup you'd consider?
While early revenue or paying pilot customers are strong validation points, especially for SaaS, we understand that deep tech enterprise software can have longer development cycles. For pre-revenue companies, we look for compelling technical proof-of-concept, strong founder-market fit, and clear evidence of demand from potential enterprise customers (e.g., LOIs, design partnerships).
Ready to Build the Future of Enterprise Software?
If you're a founder building breakthrough technology in Enterprise Software, we want to hear from you.
We typically respond to qualified applications within 48 hours and can move from first meeting to term sheet in 4 weeks.