Chief of Staff

Cowboy Ventures

Palo Alto, CA, US / New York City, NY, US
  • Job Type: Full-Time
  • Function: Administration
  • Industry: Venture Capital
  • Post Date: 04/16/2024
  • Website:
  • Company Address: 525 Lytton Ave, Palo Alto, CA 94301 US
  • Salary Range: $100,000 - $200,000

About Cowboy Ventures

Cowboy Ventures is a seed-focused venture capital firm dedicated to supporting extraordinary founders building legendary technology companies.

Job Description

This special person will power a number of functions including evaluation of new ventures; portfolio company support; community building; firm operations; strategic planning; and selective support for LP relationships.

This is an incredible apprenticeship opportunity to be part of a fast-paced, close-knit and fun-loving team, while gaining extraordinary exposure to all facets of venture capital. You'll work closely with a curated group of early-stage startups, build your network, and play a valued role in the growth and success of a world-class venture firm.

This role has three main areas of focus:

  1. Support our Managing Partner as a dedicated venture associate, helping provide world class support to our portfolio companies and identifying and diligencing new technologies and venture opportunities

  2. Support Cowboy Ventures’ strategic planning, programming, and firm operations 

  3. Provide leverage to our Managing Partner 


1. Support our Managing Partner as a dedicated venture associate, helping provide world class support to our portfolio companies and identifying and diligencing new technologies and venture opportunities

Cowboy Ventures is fortunate to receive a high volume of inbound opportunities to evaluate, in addition to proactively learning about important technology and societal trends. In this role, you’ll support our Managing Partner in: 

  • Evaluating a broad array of technology driven startups and trends, escalating promising companies and trends to dive deeper on

  • Performing outstanding and efficient strategic due diligence (including financial analysis, financial modeling, market research, customer interviews)

  • Executing investment decisions (including drafting investment memos, working on term sheets, and helping oversee financial and legal processes for new investments)

We also aim to deliver best-in-class strategic and operational support to accelerate portfolio company success. You’ll understand and contribute to achieving their strategic priorities including: 

  • Helping make connections across our network

  • Recruiting

  • Financial planning

  • Customer and advisor introductions

  • Product road mapping

  • Competitive intelligence

  • Helping with successful follow on financings

2. Support Cowboy Ventures’ strategic planning, programming, and firm operations

In this role, you'll collaborate cross-functionally with other team members to drive projects to completion, with a "no task too big or too small" demeanor. Projects and ongoing responsibilities will include: 

  • Enhancing Cowboy Ventures’ operations by identifying opportunities to continually improve how we do our work; identifying and implementing process improvements

  • Helping our team define firm-wide priorities

  • Planning strategic offsites

  • Cultivating and managing our relationships & CRM

  • Supporting on firm programs (e.g., scout program, events)

  • Devising and executing improvements to our brand and website

  • Supporting our Head of Finance & Operations in LP communications and financial processes 

3. Provide leverage to our Managing Partner

In this role, you’ll have the opportunity to be the “right hand” to our Managing Partner, ensuring we are well prepared and follow through on our most important commitments and relationships, including by: 

  • Establishing processes and operations that support in all day-to-day operational activities

  • Playing a support role at meetings (proactively drive meeting preparation, ensure flawless quality of follow-through, etc.) 

  • Supporting on preparation for board meetings and follow-up on board commitments, including non-profit commitments

  • Providing excellent preparation for all speaking engagements and events

  • Collaborating on research and writing 

  • Managing and processing email communication 

Qualifications, Skills & Characteristics

Cowboy Ventures values a mix of incisive thinking, hustle, humility, humor, creativity, proactivity, emotional intelligence, results and inclusion. These values must shine through in all the Chief of Staff at Cowboy Ventures does. We are looking for: 

  • 3+ years prior full time work experience, preferably in an operating role at a VC-backed tech company, management consulting, investment banking, venture capital, or a blend of prior work experiences. 

  • Digital fluency and strong quantitative skills are musts. Prior exposure to tech and/or the tech investing ecosystem is preferred.

  • Outstanding and concise written and verbal communication skills to successfully collaborate with executive-level operators

  • Action driven with a high sense of urgency, balanced with strong attention to detail, quality orientation and exceptional organizational skills

  • Someone who thrives on keeping the trains running on time with little oversight, and who is able to juggle multiple high visibility projects simultaneously. A true blend of process orientation and creative thinking and problem solving. 

  • A track record of thriving in an unstructured environment through resourcefulness, high efficiency, judgment and work ethic. Someone who is comfortable executing with little direction and/or structure, and who will proactively ask for clarification or direction when needed

  • Outstanding EQ (emotional intelligence) and the ability to anticipate needs and expectations

  • A natural collaborator, true team-player with low ego and a proactive disposition.  

  • A sense of humor, empathy for others, and confidence with humility

  • The ability to collaborate with the utmost integrity, and to maintain trusted confidences, with all internal and external partners

Other position specifications

  • This role will report to our Managing Partner, Aileen Lee

  • This role is an in-person role based in the Bay Area 

  • This is a full time role with salary, medical benefits, and 401k 

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.