Jonathan Winfield

Growth Equity Investor

📍 United States🔄 Updated September 2026💼 15 investments📅 11 years investing🗓 Last invested Nov 2025
VC🌍 United StatesInvested this year
15
Total investments
1
Early stage
1
Mid stage
6
Late stage
11y
Years active

Portfolio

10 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Board Observer
Nov 2025
Who is OVERWATCH? OVERWATCH (SDVOSB) is a professional service and veteran recruiting business that specializes in Construction Management & Project Management (Staff Augmentation) and Critical Facility Operations (Full Time Staff Placement) within the Digital Infrastructure industry. What do our customers PROVIDE US? Our customer provides us with a MISSION to support their continued success through talented military and industry veterans. What do WE PROVIDE our customers? We provide our customers the opportunity to solve their labor shortage with a meaningful PURPOSE. We offer our customers access to our leading-edge media platforms to highlight what they do and how they are making a positive impact on the veteran community. We also own and operate a long version podcast focused on data center industry thought leaders that is called Data Center Revolution. Our podcast ia available on Apple Podcast, Spotify, YouTube, and other platforms.
Investor (Argentum)
Feb 2025
JessCo Solutions is the leader in providing cutting-edge emission control equipment and services for the oil and gas industry. The company specializes in providing high-quality vapor recovery units, combustors, flares, and vapor recovery towers at competitive prices. Designed for durability and ease of maintenance, JessCo’s equipment ensures regulatory compliance while maximizing profitability for its customers. The company offers industry-leading preventative maintenance, repair services, and guidance to minimize downtime and optimize performance. With a reputation for reliability and customer satisfaction, JessCo is the trusted partner for emission control solutions. For more information, visit www.jesscosolutions.com.
late stageOil and Gas
Angel Investor
Apr 2024
Leni is an AI-powered reporting and decision-making system for real estate asset owners and operators. We automate aggregation data from multiple third-party managers, popular PMS systems, and teams to provide fast, transparent reporting and actionable insights using our AI layer. This helps organizations make better portfolio decisions and reach their goals faster. By leveraging advanced analytics and Artificial Intelligence, Leni provides actionable insights that enhance operational efficiency and drive strategic growth. Our platform is designed to streamline asset management processes, ensuring you stay ahead in a competitive market.
Angel Investor & Advisor
Oct 2023
Transformation Insights uses patented machine learning and artificial intelligence technologies to provide customers with digital enhancements for winning at change. Transformation Insights flagship products include - KTA Enterprise, the first Transformation Management Platform - The Kinetic Marketplace, the first superstore for change - Rozzy, the first cybernetic partner for change Transformation Insights solutions include use cases for - Banking and Capital Markets - Healthcare and Life Sciences - Manufacturing and Supply Chain - PE/M&A/Integration Learn more... www.transformationinsights.io
Angel Investor
May 2023
Sendspark is an AI-powered video platform to make personalized videos at scale. Over 50k sales & marketing folks at companies like Apollo, LinkedIn, Warmly, Clay, Canva and Salesforce use Sendspark to connect with prospective customers, book more meetings, and close more deals. Sendspark was voted #1 in video email (G2), #1 best feature set (TrustRadius), and #1 “product of the day” (Product Hunt).
Investor (Argentum)
Mar 2023
We increase car dealership profitability by revolutionizing warranty claims processing with our first-of-its-kind cloud technology, powered by advanced machine-learning. - Warranty revenue +10% - Up to 60% lower processing costs - Warranties processed 5x faster 📈 Curious how much your dealership could save? Get a free analysis at warrcloud.com
Investor (Argentum)
2023
SmartCommerce is a technology and data platform that transforms brands’ marketing touchpoints into e-commerce launch points. Our suite of solutions makes the carting process as simple and seamless as possible, driving sales via digital ads, social posts, video, email, and more. Real-time data and insights let clients manage campaigns, make changes, and meet their goals faster!
Investor (Argentum)
2022
Lender Price provides banks, lenders, credit unions, and IMBs with a trusted and configurable pricing platform that helps drive cost-reduction, improve profitability, and win more business in this market. Trusted by some of the largest financial institutions in the industry, we provide clients of all sizes with products and solutions that help them increase volume, benefit from workflow efficiencies, and improve their market competitiveness. Learn more at www.lenderprice.com.
Vice President of Investing
Sep 2015
TAMID Group is a nonprofit organization that develops the professional skills of undergraduate students through hands-on interaction with Israeli business. TAMID integrates the next generation of entrepreneurs and business professionals with Israel through a comprehensive education curriculum, pro-bono consulting for Israeli startups, capital market investment research, and a summer internship program in Israel. TAMID has no political or religious affiliations. TAMID Consulting provides pro-bono consulting for the most exciting and innovative companies coming out of Israel. TAMID members engage in projects during the academic year that build skills in market research, competitive analysis, US market entry strategy, beta testing/product development and design, and more. The TAMID Fund leverages a partnership with Seeking Alpha to develop strong equity research skills while the chapters compete in a national simulated fund competition. TAMID is currently on 57 campuses around North America, China and Israel and is rapidly expanding.
Experience · 17 entries
All (17)
Investments (15)
Board (1)
2025
Board Observer
Nov 2025
Who is OVERWATCH? OVERWATCH (SDVOSB) is a professional service and veteran recruiting business that specializes in Construction Management & Project Management (Staff Augmentation) and Critical Facility Operations (Full Time Staff Placement) within the Digital Infrastructure industry. What do our customers PROVIDE US? Our customer provides us with a MISSION to support their continued success through talented military and industry veterans. What do WE PROVIDE our customers? We provide our customers the opportunity to solve their labor shortage with a meaningful PURPOSE. We offer our customers access to our leading-edge media platforms to highlight what they do and how they are making a positive impact on the veteran community. We also own and operate a long version podcast focused on data center industry thought leaders that is called Data Center Revolution. Our podcast ia available on Apple Podcast, Spotify, YouTube, and other platforms.
Investor (Argentum)
Feb 2025
JessCo Solutions is the leader in providing cutting-edge emission control equipment and services for the oil and gas industry. The company specializes in providing high-quality vapor recovery units, combustors, flares, and vapor recovery towers at competitive prices. Designed for durability and ease of maintenance, JessCo’s equipment ensures regulatory compliance while maximizing profitability for its customers. The company offers industry-leading preventative maintenance, repair services, and guidance to minimize downtime and optimize performance. With a reputation for reliability and customer satisfaction, JessCo is the trusted partner for emission control solutions. For more information, visit www.jesscosolutions.com.
late stageOil and Gas
Investor (Argentum)
2025
Insellerate transforms the Borrower Journey from transaction to relationship creating customers for life. We help you accomplish this through our Customer Experience Platform which delivers Lead Management, Sales Enablement, Engagement Automation, a Mortgage Specific Content Library, Data Intelligence and Customer For Life Campaigns all in one comprehensive and highly scalable platform. This dynamic solution seamlessly fits into your tech stack and allows you to communicate through multiple channels: text, social media, email, Direct mail, phone, ringless voicemail, and retargeting. Providing you with the ability to give your customers and referral partners timely, relevant information based off of data intelligence to build repeatable outcomes at each stage of the customer’s journey. - Close More Loans - Improve Borrower Conversions - Enhance Customer Retention - Transform Your Customer Acquisition Lifecycle - Create Customers for Life
2024
Angel Investor
Apr 2024
Leni is an AI-powered reporting and decision-making system for real estate asset owners and operators. We automate aggregation data from multiple third-party managers, popular PMS systems, and teams to provide fast, transparent reporting and actionable insights using our AI layer. This helps organizations make better portfolio decisions and reach their goals faster. By leveraging advanced analytics and Artificial Intelligence, Leni provides actionable insights that enhance operational efficiency and drive strategic growth. Our platform is designed to streamline asset management processes, ensuring you stay ahead in a competitive market.
2023
Angel Investor & Advisor
Oct 2023
Transformation Insights uses patented machine learning and artificial intelligence technologies to provide customers with digital enhancements for winning at change. Transformation Insights flagship products include - KTA Enterprise, the first Transformation Management Platform - The Kinetic Marketplace, the first superstore for change - Rozzy, the first cybernetic partner for change Transformation Insights solutions include use cases for - Banking and Capital Markets - Healthcare and Life Sciences - Manufacturing and Supply Chain - PE/M&A/Integration Learn more... www.transformationinsights.io
Show all 17 entries ↓
Investment activity
2015–2025 · 15 investments
2015120225202352024120253
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