May 2025’s Top Startup Events in Boston

May is all about empowering Boston’s entrepreneurs through both technology and personal growth. Events like EmTech AI 2025 and the Boston AI Executive Accelerator dive into essential conversations around AI, machine learning, data, and legal compliance. For those looking to build foundational business skills, Techstars Startup Weekend Boston offers hands-on learning. And Startup Boston’s Dealflow Mixer creates space for historically underserved founders to connect with investors.

Here are some May event highlights to check out:

Co-hosted with the Robotics Summit and Expo, MassRobotics Robotics Engineering Career Fair is being held on May 1st. Several notable robotic companies have announced they are hiring from this career fair, like Amazon Robotics, Cubiq, Raptor Maps, Asus, and many more! This career fair is a great opportunity for recent college graduates and seasoned professionals to find their next job.

The two-day AI & Machine Learning Summit, on May 14-15, gives technologists an immersion into an AI future where attendees can discuss and learn about AI and ML possibilities. The highlighted keynote presentations are Unlocking Your AI Potential With Real-Time Data Unification, Storytelling With Data, Get Your Business AI-Ready, and Transforming Analytics With AI: A Comprehensive Guide to an Advanced Tech Stack. 

Don’t forget about Maine and its potential in the startup ecosystem. Startup Maine is a week-long event where the organizers champion Maine’s entrepreneurial ecosystem. Go to Portland Maine on May 19-22 to see what opportunities lie there.

May 2025's Top Startup Events

AI Community Conference - AICO Boston

DATE: Thursday, May 1 at 10 AM and Friday, May 2 at 9 AM

LOCATION: Microsoft New England Research and Development Center, Boston, MA; Register Here

The AI Community Conference is divided into two days: Pre-Day Workshop on May 1st and the Main Event on May 2nd. The first day will feature developers, professionals, and enthusiasts working alongside industry experts on hands-on AI training, covering AI Agent Development and Practical AI Applications, and participating in a live demo. The main event will take place on May 2nd, where attendees can listen to keynote speakers and presentations, participate in thought-provoking discussions, and engage in sponsored showcases and networking opportunities. 

Startup Boston's Dealflow Mixer, Featuring CIC's Social Impact Cohort

DATE: Thursday, May 1, 9:30 AM – 11:30 AM ET

LOCATION: Cambridge, MA; Register Here

​Startup Boston is thrilled to welcome investors to meet CIC’s Social Impact Cohort - a powerhouse lineup of startups led by historically underserved entrepreneurs from Massachusetts. This is a targeted networking and matching event designed to connect complementary funders and founders, fostering meaningful relationships and potential investment opportunities.

MassRobotics Career Fair

DATE: Thursday, May 1, 3:30 PM – 5:30 PM ET

LOCATION: Boston Convention and Exhibition Center, 415 Summer St, Boston, MA; Register Here

This event is designed for technical industry job seekers, including both recent graduates and seasoned professionals in fields such as computer science, vision science, mechatronics, and AI. Companies, from start-ups to industry leaders, will be hosting information tables where candidates can learn more about the company, find out about available positions, and schedule interviews. Admission cost is $15.

AI Agent Building Hackathon for Biotech R&D

DATE: Saturday, May 3, 8:30 AM – 4:30 PM ET

LOCATION: Microsoft New England Research and Development Center, 1 Memorial Drive, Cambridge, MA; Register Here

​If you like building things, need to lead your company in choppy AI waters, whether you come from a biopharma wet lab background, love the computation/bioinformatics world, want to take an IT angle or just like coding up solutions, this Biotech Hackathon should be a great time as the promise of AI agents comes into resolution for the rest of the industry.

EmTech AI 2025

DATE: Monday, May 5 through Wednesday, May 7

LOCATION: Online and MIT Campus, Cambridge, MA; Register Here

For over a decade, EmTech AI (formerly EmTech Digital) has been the premier event for business and technology leaders, researchers, and policymakers seeking to translate AI breakthroughs into tangible impact. Curated by MIT Technology Review, one of the world's most respected science and technology news outlets, and backed by the technological expertise at MIT, EmTech AI is where business leaders come together in the same room to share their insights on harnessing the power of generative AI.

Start Up Tuesday – Sales for the Non-Salesperson: A Practical Guide to Driving Business Growth 

DATE: Tuesday, May 6, 8:30 AM – 10:30 AM ET

LOCATION: The Enterprise Center at Salem State University, 121 Loring Ave, Salem, MA; Register Here

This workshop is designed for entrepreneurs, freelancers, and professionals who do not consider themselves natural salespeople but need to boost their business success. Participants will learn how to create a simple yet effective sales plan tailored to their unique business needs. Key topics include identifying and understanding your target customers, crafting value-driven sales messages that resonate, overcoming common objections with confidence, building authentic customer relationships, and closing deals without coming across as overly salesy.

AI & Machine Learning Summit

DATE: Wednesday, May 14 through Thursday, May 15

LOCATION: Hyatt Regency, Boston, MA; Register Here

The AI & Machine Learning Summit offers a 2-day immersion into the possibilities inherent in an AI-driven future, providing the opportunity to harness the transformative potential of AI & ML. The AI & Machine Learning Summit is designed for chief information officers, chief data officers, data scientists, data engineers, enterprise architects, data analytics directors and managers, application developers, and tech-savvy business leaders. 

2025 Boston AI Executive Accelerator 

DATE: Monday, May 19, 10:00 AM – 5:30 PM ET

LOCATION: KPMG Boston Office, 60 South Street, Two Financial Center, Boston, MA; Register Here

Join KPMG as they explore responsible development, successful implementation, and effective use of this powerful technology. Their subject matter experts will cover hot topics such as agentic AI, data modernization, enterprise security, and global compliance, providing you with insights needed to drive better business outcomes. Their approach to learning involves in-depth exploration of how AI can transform your business. You’ll also have the chance to participate in small group industry roundtable discussions on AI use cases, aimed at creating pragmatic and practical next steps.

Startup Maine Week 2025

DATE: Monday, May 19 through Thursday, May 22

LOCATION: Portland, ME; Register Here

Startup Maine’s mission is to advance Maine's startup ecosystem. They believe in fostering connections among founders, investors, tech workers, and support organizations to create a thriving entrepreneurial landscape. Startup Maine supports the ecosystem through networking events, resource sharing, collaboration with entrepreneurial support organizations, and by hosting the annual Startup Maine conference.

Techstars Startup Weekend Boston

DATE: Friday, May 30, 5:00 PM - Jun 1, 8:00 PM ET

LOCATION: Suffolk University Law School, 120 Tremont St, Boston, MA; Register Here

Over three action-packed days, you’ll form cross-functional teams, turn ideas into viable products, and pitch your solution to an audience of experienced mentors, judges, and peers. Here’s how it works: Friday Night: Pitch your idea (or join someone else’s) and form teams with like-minded innovators.Saturday: Collaborate, brainstorm, and develop your business with the guidance of seasoned mentors. Sunday: Bring it all together—refine your pitch, present to a panel of judges, and compete for prizes.

About the author: Nicholas Ewing is a graduate of UMass Lowell in Business Administration: International Business. Today, he works as an implementation specialist for an electronic medical records company in Foxborough, MA. His hobbies include writing stories and going for walks in nature. You can connect with him here.