Top 5 VC Deals of the Week in AI (5/30/25)

By Christopher Robbins · May 29, 2025 Views: 5

Our Top 5 VC Deals of the Week in AI featured funding announcements from AwardCo, LMArena, Siro, Pallet & CloudSEK

This week we continue our series on the top 5 VC-funded deals in AI.

This week our announcements are led by two deals exceeding the $100 million threshold.

The top reported deal, per FinSMEs, came from Lindon, Utah-based Awardco, an employee rewards platform, which raised a $165 million Series B in part to "broaden its rewards and recognition platform with additional solutions for employee engagement and performance, leverage AI to drive deeper employee insights and automations, enhance HRIS and partner integrations, and scale its global infrastructure," according to its announcement. The next biggest announcement came from the AI benchmarking space, where San Francisco-based LMArena got off to a blazing start by bringing in a whopping $100 million seed round. The top five also included companies in the logistics, cybersecurity and sales spaces.

Smaller funding raises that did not quite make our top 5 this week included announcements from the fintech, security and software development sectors.

Below, we highlight the top five venture capital deals, ranked from the highest to the lowest funding amounts, showcasing the companies at the forefront of the AI revolution...

Top 5 Venture Capital Deals from May 22-May 28

1. Awardco

Location: Lindon, UT
Description: Awardco is an employee rewards, recognition, and engagement platform helping companies foster workplace culture through scalable, customizable incentive programs. The company is now valued at over $1 billion.
Funding Amount: $165M
Funding Round: Series B

2. LMArena

Location: San Francisco, CA
Description: LMArena provides an open community platform for benchmarking and evaluating the best AI models, fostering transparency, collaboration, and trust in the AI ecosystem.
Funding Amount: $100M
Funding Round: Seed funding

3. Siro

Location: New York City, NY
Description: Siro offers an AI-powered conversation intelligence platform specifically for in-person sales teams, enabling real-time coaching, analysis, and performance optimization.
Funding Amount: $50M
Funding Round: Series B

4. Pallet

Location: San Francisco, CA
Description: Pallet is the company behind CoPallet, an AI workforce solution designed to optimize logistics operations through automated task management and workforce coordination.
Funding Amount: $27M
Funding Round: Series B

5. CloudSEK

Location: Bangalore, India
Description: CloudSEK is an AI-powered cyber threat prediction and intelligence platform that helps enterprises proactively identify and mitigate digital security risks.
Funding Amount: $19M
Funding Round: Series A2 and B1

Make sure to check out our Top 5 VC Deals of the Week in AI right here!

Written & Researched by DWN Staff

VC Deals Synopsized by ChatGPT Research Source: FinSMEs