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The Venture Codex

Webb Investment Network

785 Market Street, Suite 700, San Francisco, CA, 94103, United States

Overview

Webb Investment Network is an investment firm that particularly in mobile, consumer Internet, and cloud applications. With its Affiliate Network, the firm draws not only from Maynard’s experience and insight but from those CEOs, CTOs, founders, and investors who make up the WIN Affiliate Network to provide our portfolio companies with on-demand advice and support.

Total investments
70
Lead investments
2
Investments · 12mo
1
Active investors
8

Sector focus

  • Finance
  • Financial Services
  • Venture Capital
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Investment portfolio

  • Code Four

    Participated · Seed · Nov 2025

    Code Four is a policing-technology startup founded by George Cheng and Dylan Nguyen that leverages artificial intelligence to turn body-camera video into preliminary incident reports officers can edit and submit in court or for record keeping. The platform also auto-generates transcriptions, interview summaries, and can redact both video and written materials for public-records requests. By automating these processes, the company aims to cut down on administrative workload and return officers to field duties more quickly. The product is sold on a subscription basis starting at $30 per officer per month, and the company says it is already serving 25 police departments. Code Four currently employs four people split between engineering and sales. The founders are alumni of Y Combinator and are slated to join the second cohort of the Palantir Startup Fellowship. While the system drafts reports with AI, final review and edits are performed by officers to address accuracy and ethical concerns.

  • System Two Security

    Participated · Equity · Dec 2024

    System Two Security develops purpose-built GenAI models and role-based agents trained on detection and security data to automate detection engineering. The company says its models and agents enable detection engineers to generate actionable detections in minutes and outperform human counterparts in speed and accuracy. Its platform is designed to work across major enterprise security systems, including Splunk, Microsoft Sentinel and CrowdStrike’s Next-Gen SIEM. Led by CEO Robert Fly and CTO Prasanth Ganesan, the company focuses on integrating its agents into existing security stacks. System Two intends to use the new funding to scale its team and accelerate product development. No operating metrics or prior funding rounds were disclosed in the article.

  • Legion Technologies

    Participated · Equity · May 2024

    Legion Technologies develops an AI-native workforce management (WFM) platform focused on optimizing schedules, improving employee engagement, and increasing labor efficiency for hourly workforces. In 2024 the company launched 70 product features — including employee productivity‑based scheduling, a generative AI Time and Attendance Workbench, enhanced shift offers, schedule scoring, and increased extensibility — and advanced its Generative AI assistants for conversational schedule and timesheet analysis. Legion reported strong revenue growth, expanded its customer footprint into new regions, and claims the platform delivers 13x ROI through schedule optimization, reduced attrition, and increased productivity. The company has been repeatedly recognized on the Inc. 5000 and Deloitte Fast 500 lists and has grown an average of 374% over the past three years. Legion is using the new financing to continue product development and to scale operations and market expansion. Legion builds a workforce management platform that automates scheduling, demand forecasting and labor optimization for hourly and gig workforces. Its platform uses customer and third-party data to generate schedules that match business demand with employee preferences via a mobile app. The company is adding generative AI features (Copilot) to answer work questions and, soon, summarize schedules and handle shift-change requests. Legion also offers InstantPay, an earned-wage-access product that charges $2.99 (capped at about $30) for instant transfers while next-day transfers are free. Legion sells subscriptions priced by the number of hourly workers and counts customers such as Cinemark, Dollar General, Five Below and Panda Express. The business reported revenue growth of 55% and bookings growth of 125% in the past year and employs about 200 staffers. Planned uses of new capital include expanding R&D and customer-facing teams and launching go-to-market efforts in Europe. Legion offers an AI-powered workforce management (WFM) platform that provides demand forecasting, labor optimization, automated scheduling, and time-and-attendance alongside a mobile app for shift preferences and swaps. The platform targets hourly workforces across retail, distribution, manufacturing, hospitality, food services, and healthcare, and is used by customers in more than 38 countries. Legion says its product improves labor efficiency, reduces compliance risk, and boosts employee engagement by matching schedules to employee preferences and offering gig-like flexibility. The company reported 391% year-over-year growth after surging demand driven in part by the COVID-19 pandemic. Legion plans to use the new funding to increase hiring and accelerate product innovation. The company is headquartered in Redwood City, Calif., and was founded by Sanish Mondkar. Legion provides an artificial intelligence-driven platform that automates decisions about labor deployment and scheduling by combining demand forecasting, labor optimization and employee preferences. The product generates schedules that aim to match worker preferences (hours, shift lengths, store locations) with business needs. Legion has adapted its machine-learning forecasting to be hyper-localized for pandemic-era scenarios and added COVID-specific features such as contact tracing, identification of healthy versus quarantined workers, and streamlined employee communications. The company sells to mid-sized and larger enterprise customers, naming SoulCycle, Philz and Dollar General among its customers, and reports its largest customer has more than 100,000 employees on the platform. Since April the company has onboarded more than 18,000 new locations. Legion says customers can expect at least a 10x return on investment and that it has reduced churn for many customers by 30–50%. Legion uses large amounts of data — down to local weather and point-of-sale/traffic counters — and machine learning to predict customer traffic and produce optimized employee schedules. The product aims to give hourly workers a spectrum of options, from predictable full-time hours to gig-like flexible shifts. Legion has begun deploying as a proof-of-concept with Philz to validate its approach and prove impact on workforce retention and customer experience. The company integrates with HR tools today (e.g., Zenefits) and may expand its data integrations to better model employees over time. Legion faces competitors offering simpler scheduling apps (such as When I Work) but positions itself on richer data and ML-driven forecasts. To fund expansion beyond pilot accounts, the company raised a $10.5M Series A.

  • PeerDB

    Participated · Seed · Apr 2024

    PeerDB builds a data-movement platform specialized for PostgreSQL, implementing techniques like parallel snapshotting, native Postgres data-type replication, and infrastructure cost optimizations. It offers open-source, a fully managed cloud service, and a self-hosted enterprise offering and targets use cases such as replication to Snowflake/BigQuery/ClickHouse, real-time streaming to Kafka and other queues, database migrations, HA/backups, and vector ETL for LLM workflows. The company claims up to 10x faster data movement and up to five times lower cost compared with incumbent ETL tools, and reports revenue is doubling every two months. Named customers include Harmonic AI (saved $80,000 yearly), Expedock (replicates 700M rows monthly to Snowflake with under one-minute latency), Fiber AI (real-time terabyte replication to ClickHouse), and Flatiron Health (migrated 35,000 tables to Snowflake in a week). Co-founders Sai Krishna Srirampur and Kaushik Iska, both IIIT Hyderabad alumni, previously worked at Citus Data/Microsoft Azure, Google, SafeGraph, and Palantir and emphasize deep Postgres expertise. PeerDB plans to use new funding to grow its engineering team, accelerate go-to-market and client acquisition, and extend its infrastructure to support mission-critical Postgres use cases at scale.

  • Reach Security

    Participated · Series A · Mar 2024

    Reach Security builds an AI-powered assistant that turns security intent into enforcement, helping teams detect and remediate configuration drift and exposures across SaaS and on-prem products. The platform leverages domain-specific language models (DSLM) and operational automation to drive adoption and remediation workflows. Reach recently launched ConfigIQ Drift™, enabling customers to author drift-detection rules and monitor deviations from a single centralized location. The company previewed an upcoming Asset Intelligence capability to provide continuous context across identities, devices, and workloads to improve prioritization and remediation. Reach emphasizes use cases including Zero Trust implementation, CMMC mapping and monitoring, and Microsoft 365 E3-to-E5 optimization. Financially, the company announced a $10 million strategic investment led by M12 with support from existing investors. Reach Security offers an AI purpose-built platform that reprograms an organization’s security infrastructure based on who it is and how it is being attacked. The platform works across the entire security estate, interrogates each tool, and gathers data on who is being targeted and how attacks work without requiring sensors, infrastructure, or attack simulations. Reach’s product takes seconds to set up and minutes to carry out actions. Co-founders Garrett Hamilton (CEO) and Colt Blackmore (CTO) spent over a decade building detection and prevention products at Palo Alto Networks, Proofpoint, and Cylance. The company emphasizes helping security teams use existing solutions effectively instead of buying more point products, a message echoed by investors and customers quoted in the announcement. Financially, Reach announced a $20 million Series A financing led by Ballistic Ventures.

Team