VC Principal @ Squadra Ventures in Baltimore, MD

Squadra Ventures

We are seeking an experienced professional to lead our cybersecurity investment efforts. The ideal candidate will have a strong background in cybersecurity and technology startups and a strong perspective on the future of this industry.

As a Principal, you will be involved in the entire lifecycle of the investment process, including sourcing investments, thesis-generation, diligence, and portfolio company support. You will work jointly with our deal and portfolio operations team, and directly with our Principal, National Security, and provide support to the Managing Partner and COO with other relevant business needs.

Your performance will be measured on four things:

  1. Our ability to make 2-3 great seed-stage cybersecurity investments every year;
  2. Provide excellent analysis and effort to enable our portfolio operations team for post-investment support to such companies;
  3. An activated, informed, and incented Venture Partner community, and
  4. The recognition of the Squadra brand as a top-tier investor in the cybersecurity ecosystem.

This is an exciting opportunity for someone interested in sourcing deals from the ground level, working with entrepreneurs, and being part of making investment decisions in the technologies and teams defining the future of cyber and national security.


  • Evaluate the relevance of the technology and the business value proposition to establish a realistic path to market for cybersecurity-related companies
  • Lead key efforts of the diligence process to include actual product usage & value, competitive analysis, market sizing and trends, and, future acquisition potential & economics,
  • Activate, manage, and grow our Cybersecurity Venture Partner Network
  • Manage and grow our network as it relates to cybersecurity including funds, angel investors, universities, accelerators, and incubators
  • Assist in the preparation of fundraising documents, investment memos, and investor updates
  • Build and maintain relationships across the enterprise ecosystem while tracking requirements and investment themes, and the later-stage and earlier, seed-stage, venture ecosystem for both deal in flow and follow-on financing for our companies
  • Corporate development with Fortune 1000 companies to identify pilot and business development opportunities for portfolio companies
  • Assist the Portfolio Operations team with leveraging relationships to identify new relationships for our existing portfolio companies
  • Be a brand ambassador and represent the Squadra brand positively in all settings including at industry events/conferences and support the local entrepreneurial community through active involvement

Required Industry Expertise

  • 5-15 years of professional experience in the cybersecurity industry
  • Fundamental understanding of cybersecurity landscape as it relates to technologies, enterprise cybersecurity budgets, and large public and private cybersecurity companies
  • Appreciation for industry-standard market research (i.e. Gartner magic quadrants, Forrester reports, 451 research, and investment banking cyber analysis)
  • Meaningful relationships that span cybersecurity customers, technologists, investors, and analysts

Required Skills & Experience

  • Entrepreneurial mentality with a worldview of cybersecurity
  • Exceptional interpersonal skills, with demonstrated experience of coaching and training team members
  • Credibility in a room of senior executives and operators
  • Analytical, data-driven problem solver
  • Collaborative, open, and transparent
  • Strong work ethic and low ego
  • High ethical standards, integrity, and authenticity
  • Extreme self-starting organizational skills and the ability to translate that to organizational and project management systems that influence the entire fund
  • Excellent written and verbal communication, project management and organizational skills
  • Ability to deal with ambiguity and be self-directed in a fast-paced, fluid environment
  • Ability to authentically and rapidly build trust
  • Experience in tech, venture, finance, or consulting
  • Operational experience in tech-related hyper-growths or start-ups preferred
  • Angel, scout or start-up investment experience preferred


  • This role is based out of Baltimore, Maryland with the expectation of weekly in-person meetings and work sessions
  • This role reports directly to the Managing Partner
  • This is a full-time position
  • We plan to fill this role by August 1, 2022 with a start date of no later than September 1, 2022.

About Us

  • Squadra Ventures is a venture capital firm led by founder-operators that invests in early-stage cyber and national security companies. We apply significant resources beyond the check, working hand-in-hand with our entrepreneurs to win and leave a lasting positive impact on the world. As investors we lead Seed to Series A rounds, work as active board members, invest $1-$3M and execute on an 18-month joint strategic plan.

Desired Skills and Experience

We may be looking for you…

  • If the first line of code you write when tackling a use case is @Test
  • If you think code really can have a smell
  • If your code serves as its own documentation
  • If you believe in leaving the campground cleaner than you found it
  • If you have a CI server for your pet projects
  • If you’ve ever plugged two keyboards and two mice into a computer during development
  • If lots of “new” statements in constructors makes you twitch
  • If you know all about advice, pointcuts, and weaving
  • If the best part of your resume is hosted at github, sourceforge, codehaus, or codeplex
  • If you get a rush out of pushing less lines of code than you pulled during a refactor
  • If your bookshelf is overflowing with technology books
  • If you can’t wait for some free time to learn Scala, Clojure, Groovy, or Haskell
  • If you have a blog
  • If you’ve always wanted to learn more about statistics/machine learning/data analysis