John Simon
Managing Director @ Sigma Prime Ventures
Boston, United States
John Simon is a Series A investor at Sigma Prime Ventures in Boston focused on Software and SaaS. John joined Sigma Prime in November of 2012 to help build the firm and help invest in great entrepreneurs. He focuses on software-based businesses and disruptive technology businesses, often getting involved in businesses at their formation or earliest stages.
- Total investments:
- 18
- Last investment:
- Lead investor:
- 33%
Last updated:
For AI agents: llms.txt
Industries John Simon invests in
Stages John Simon invests in
Countries John Simon invests in
Investment Focus
Industry
- Software 6 (33%)
- SaaS 5 (28%)
- Analytics 4 (22%)
- Marketing 3 (17%)
- Enterprise Software 3 (17%)
Stage
- Series A 7 (39%)
- Series B 4 (22%)
- Seed 2 (11%)
- Funding Round 2 (11%)
- Series C 1 (6%)
Country
- United States 10 (56%)
- United Kingdom 1 (6%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
RISA Labs
|
We exist for humanity 2Win. Pioneering BOSS [Business (Operating System) as Service]. Trusted by Top Oncologists, we serve mission critical enterprises. Transforming key operations with AI-driven discipline. Headquartered in Silicon Valley, RISA has offices across the globe. | $11.1M / Series A / Jan 13, 2026 | |
Phenom
|
Phenom is a purpose-driven company that delivers AI-powered talent experiences to global enterprises. Employers are using Phenom to hire employees faster develop them to their full potential, and retain them longer. The Phenom Intelligent Talent Experience platform seamlessly connects candidates, employees, recruiters, hiring managers, HR, andHRIS — empowering over 500 diverse and global enterprises with innovative products including Phenom Career Site, Chatbot, CMS, CRM, AI Scheduling, One-Way Interviews, Campaigns, University Recruiting, Talent Marketplace, Career Pathing, Gigs, Mentoring, and Referrals.With Phenom, candidates find and choose jobs faster, employees develop their skills and evolve, recruiters become wildly productive, managers build stronger-performing teams, HR aligns employee development with company goals, and HRIS creates a holistic tech infrastructure through seamless integrations. | $30M / Series C / Jan 16, 2020 | |
BlueConic
|
BlueConic is the operating system that puts data into action for marketing and growth doers. The industry-first solution empowers doers with an unmatched range of capabilities to access relevant customer data, create resonant customer experiences, and drive maximum returns for their business. More than 500 businesses worldwide rely on BlueConic tounlock their full customer data potential, including Forbes, Heineken, Mattel, Michelin, Telia Company, and VF Corp. | $12.8M / Series B / Jan 02, 2020 | |
|
Phenom
|
Phenom is a purpose-driven company that delivers AI-powered talent experiences to global enterprises. Employers are using Phenom to hire employees faster develop them to their full potential, and retain them longer. The Phenom Intelligent Talent Experience platform seamlessly connects candidates, employees, recruiters, hiring managers, HR, andHRIS — empowering over 500 diverse and global enterprises with innovative products including Phenom Career Site, Chatbot, CMS, CRM, AI Scheduling, One-Way Interviews, Campaigns, University Recruiting, Talent Marketplace, Career Pathing, Gigs, Mentoring, and Referrals.With Phenom, candidates find and choose jobs faster, employees develop their skills and evolve, recruiters become wildly productive, managers build stronger-performing teams, HR aligns employee development with company goals, and HRIS creates a holistic tech infrastructure through seamless integrations. | $22M / Series B / May 24, 2018 | |
Medallia Digital Experience Analytics
|
Decibel reveals exactly how users behave on websites and apps, making it easy for enterprise businesses to quantify and improve the customer experience at every digital touchpoint.Decibel is powered by machine learning, their award-winning technology processes hundreds of revolutionary behavioral metrics – from mouse movements and devicerotations, to pop-ups and errors – capturing an accurate picture of every user’s on-page experience.The world’s largest brands – including Lego, General Motors, British Airways, and AllState Insurance – use Decibel to pinpoint opportunities to improve the customer experience and collaborate across their organizations to put the customer first. | $9M / Series A / May 03, 2017 | |
|
BlueConic
|
BlueConic is the operating system that puts data into action for marketing and growth doers. The industry-first solution empowers doers with an unmatched range of capabilities to access relevant customer data, create resonant customer experiences, and drive maximum returns for their business. More than 500 businesses worldwide rely on BlueConic tounlock their full customer data potential, including Forbes, Heineken, Mattel, Michelin, Telia Company, and VF Corp. | $6.3M / Series A / Jul 28, 2016 | |
Codeship
|
Codeship's continuous integration platform operates B2D portal that delivers hosted continuous integration and deployment for web applications. It shortens the development cycles thus reducing the risk of bugs and increasing innovation. It helps software companies to develop a better product faster by taking care of the testing and releaseprocess.Codeship automates software deployment and all the necessary tasks involved with it. | $7M / Series A / Jul 26, 2016 | |
|
Codeship
|
Codeship's continuous integration platform operates B2D portal that delivers hosted continuous integration and deployment for web applications. It shortens the development cycles thus reducing the risk of bugs and increasing innovation. It helps software companies to develop a better product faster by taking care of the testing and releaseprocess.Codeship automates software deployment and all the necessary tasks involved with it. | $1.5M / Dec 03, 2015 | |
|
Phenom
|
Phenom is a purpose-driven company that delivers AI-powered talent experiences to global enterprises. Employers are using Phenom to hire employees faster develop them to their full potential, and retain them longer. The Phenom Intelligent Talent Experience platform seamlessly connects candidates, employees, recruiters, hiring managers, HR, andHRIS — empowering over 500 diverse and global enterprises with innovative products including Phenom Career Site, Chatbot, CMS, CRM, AI Scheduling, One-Way Interviews, Campaigns, University Recruiting, Talent Marketplace, Career Pathing, Gigs, Mentoring, and Referrals.With Phenom, candidates find and choose jobs faster, employees develop their skills and evolve, recruiters become wildly productive, managers build stronger-performing teams, HR aligns employee development with company goals, and HRIS creates a holistic tech infrastructure through seamless integrations. | $7M / Series A / Oct 20, 2015 | |
N Toggle
|
nToggle delivers heightened efficiency and transparency for buyers and sellers amidst the rapid rise of programmatic advertising. nToggle's proprietary algorithm-driven software platform helps supply and demand partners manage the ever expanding bid stream. nToggle's big data platform “toggles” real time bidding requests across alldigital media utilizing the latest analytical and machine learning techniques to optimally match supply and demand. | $5.6M / Series A / Feb 03, 2015 | |
| See all 18 investments → | |||
Co-Investors
About Sigma Prime Ventures
Sigma Prime Ventures invests in early stage technology companies focusing on SaaS, Cloud, Mobile, disruptive technologies and technology-enabled service companies. Sigma Prime Ventures primarily cover the East Coast, focusing on Boston, New York and Atlanta.Their first-hand experience allows us to give early-stage companies both tacticaland strategic guidance and access to a powerful business network. Their team has founded or cofounded 10 companies, helped run 10 companies, and collectively been responsible for exits worth over $4.2B in companies where they were operators.
Sigma Prime Ventures Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Donna Sears
Investor Relations & Operations
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John Simon
Managing Director
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Jere Doyle
Managing Director
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John Mandile
Managing Director
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Paul Flanagan
Co-Founder & Managing Director
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FAQ
What does John Simon invest in?
John Simon invests primarily in Software, SaaS and Analytics startups, most often at Series A and Series B stage. Most of the 18 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
When did John Simon last invest?
The most recent investment recorded for John Simon closed in Jan 2026. Shizune tracks 18 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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