Jenny Lefcourt
General Partner @ Freestyle Capital
San Francisco, United States
Jenny Lefcourt is a General Partner at Freestyle. Jenny earned her B.S. in economics from The Wharton School at the University of Pennsylvania, and attended the Stanford Graduate School of Business. In 1998 she left Stanford to found Wedding Channel.com (sold: XOXO). In 2003 she co-founded Bella Pictures (sold: CPI). In 2014 Jenny joined Freestyle,and was promoted to GP in 2015. Some of Jenny’s notable investments include BetterUp, Crexi, Daily.co, Embark, Ridwell, Narvar and WELL Health. She is also a founding member and board member of All Raise. Jenny is an angel investor in Discord, MainStreetHub and Minted.
- Total investments:
- 106
- Last investment:
- Lead investor:
- 20%
Last updated:
For AI agents: llms.txt
Industries Jenny Lefcourt invests in
Stages Jenny Lefcourt invests in
Countries Jenny Lefcourt invests in
Round sizes
Contacts
| Type | Contact | Validation |
|---|---|---|
| Work email | ||
| Personal email | ||
| Work phone | ||
| Personal phone | ||
| Socials |
Round size
- Seed
- $2M–$6M
- Series A
- $6M–$16M
- Series B
- $7.1M–$40M
Investment Focus
Industry
- Software 11 (10%)
- SaaS 9 (8%)
- Artificial Intelligence 8 (8%)
- Internet 7 (7%)
- Enterprise Software 6 (6%)
Stage
- Seed 35 (33%)
- Series A 19 (18%)
- Series B 9 (8%)
- Angel 3 (3%)
- Pre-Seed 3 (3%)
Country
- United States 40 (38%)
- Italy 1 (1%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| Upside is the only nationally scalable housing stability platform purpose-built for healthcare. The company partners with health plans and employers to identify and stabilize members and employees experiencing housing instability, connecting them to safe, supportive housing while reducing avoidable emergency utilization and improving healthoutcomes. Upside pairs dedicated Care Guides with AI-supported housing orchestration to deliver measurable results at scale. The platform serves Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations across the full housing continuum, from crisis intervention to long-term tenancy support. Founded in 2020 and headquartered in Fort Lauderdale, FL, Upside is redefining how healthcare addresses housing as a foundation of care. | $20M / Series A / Jun 25, 2026 | ||
| AI-Enabled Coding for Medical Billing Teams | $16M / Series A / Apr 15, 2026 | ||
| AI-Enabled Coding for Medical Billing Teams | $6M / Seed / Feb 18, 2025 | ||
| Fulfilld is an AI-powered location-aware (digital twin) warehouse management software focused on driving higher warehousing productivity more efficiently. Our AI is essential in orchestrating how products, people, and automation flow and work from the movement products arrive in the warehouse to when they are loaded onto delivery trucks. Our AI isthe brains and engine optimizing warehousing operations enabling our customers’ warehouses to run faster, smoother, leaner, and with fewer errors.Get Fulfilld. | $2.5M / Seed / May 08, 2024 | ||
| Deduce protects businesses and their customers from unauthorized account access, data leakage, and identity fraud. We eliminate fraud in real-time using risk algorithms and behavioral analytics across the most comprehensive network of consumer identity data. This empowers any organization to harness the value of collective identity-based threatintelligence and cybersecurity. | $9M / Series B / Sep 13, 2023 | ||
| BurnerPage is an AI and machine learning platform that automatically optimizes web page conversion performance. | $2M / Pre-Seed / May 08, 2023 | ||
| Vital Interaction is a software provider specialized in automating complex communication workflows. Their premier product, the Automated Patient Interaction System, enables healthcare organizations to communicate more effectively with patients using text messaging, automated voice, and email.This automated system helps both patients and healthcare providers connect quickly through technology to remind patients of appointments, fill open slots and request patient feedback. | $5M / Series A / Feb 23, 2023 | ||
| Arkive is building the people’s museum: a collection of art and culture curated by a global community of members and displayed around the world. | $9.7M / Seed / Jul 13, 2022 | ||
| CHANGE is a platform that powers the giving economy. Brands add a button to checkout, and we do the rest. With CHANGE, brands eliminate the time and resources spent on connecting, vetting, and integrating with nonprofits. The platform streamlines corporate giving, provides real-time analytics, and actively engages the most coveted demographic withshareable content. | $5M / Seed / Jul 11, 2022 | ||
| Inspectiv is an application security testing company. We help customers find and fix vulnerabilities in their applications before threat actors can. We provide an innovative platform that seamlessly combines manual and automated application security testing, empowering teams with actionable insights to prioritize risks, optimize remediationefforts, and secure applications at scale. | $10.7M / Series A / Jun 30, 2022 | ||
| See all 106 investments → | |||
Co-Investors
About Freestyle Capital
Freestyle Capital is an early-stage venture capital firm that invests in technology companies at the seed stage. Founded by serial entrepreneurs, the firm leverages its extensive experience to support market leaders and enhance diversity in the investment landscape.
Freestyle Capital Contacts
| Name | Phone | Socials | |
|---|---|---|---|
David Bill
CTO
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David Samuel
Founding General Partner
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Jenny Lefcourt
General Partner
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Josh Felser
Co-Founder and Board Partner
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Joyce Kim
Principal
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FAQ
What does Jenny Lefcourt invest in?
Jenny Lefcourt invests primarily in Software, SaaS and Artificial Intelligence startups, most often at Seed and Series A stage. Most of the 106 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What is Jenny Lefcourt's check size?
Jenny Lefcourt typically joins rounds of $2M–$6M at Seed, $6M–$16M at Series A and $7.1M–$40M at Series B. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Jenny Lefcourt participates in.
How do I contact Jenny Lefcourt?
Public channels for Jenny Lefcourt include LinkedIn, X (Twitter) and Facebook. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Jenny Lefcourt last invest?
The most recent investment recorded for Jenny Lefcourt closed in Jun 2026. Shizune tracks 106 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 Oct 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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