Chief of Staff

2026 Chief of Staff Job Description

About Cowboy Ventures

Cowboy Ventures is a seed-stage venture capital firm investing in exceptional founders to build customer-loved tech companies that scale with sustained success. We work closely with our portfolio founders and companies to deliver best-in-class support, as a small but mighty team based in Palo Alto.

About the Role

This special person will provide leverage to our Managing Partner, Aileen Lee, and to our firm by powering a number of functions, including: driving firm-wide processes and our rhythm of business; evaluation of new ventures; portfolio company support; community building; firm operations; strategic planning;  fundraising and LP relations.

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. Work with our Managing Partner to help achieve key priorities for our firm including with team building, LP relations, and community building 
2. Drive excellence for Cowboy Ventures’ firm operations. This will include leverage of AI to drive firm-wide intelligence, automation, efficiency and collaboration, and driving successful  ‘rhythm of business’ activities.
3. Support our Managing Partner as a dedicated venture associate, helping provide world class support to our portfolio companies and to identify and diligence new technologies and venture opportunities

This is an in-person role in the Bay Area and regularly working in our Palo Alto office. It is full time, with salary, benefits, and 401K.

Responsibilities:

Work with our Managing Partner to achieve key priorities

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 activities
• Driving meeting preparation and ensuring flawless quality of follow-through
• Supporting preparation for board meetings and follow-up on board commitments, including non-profit commitments
• Collaborating on research and writing 
• Providing excellent preparation for speaking engagements and events
• Managing and processing email communication 
• Tracking and helping nurture key and emerging relationships across the tech and venture ecosystem 

Drive Cowboy Ventures’ strategic planning, AI leverage, 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: 

• Be an in-house driver to leverage AI; creating,implementing, and continually improving processes to enable us to effectively source, diligence, win and support the most promising startups each year.
• Helping our team define firm-wide priorities
• Planning strategic offsites
• Cultivating and managing our relationships & CRM
• Supporting  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 reporting

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 building new relationships and 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: 

• Making connections across our network
• Recruiting
• Financial planning
• Product road mapping
• Competitive intelligence
• Helping with successful follow on financings

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: 

• 2+ 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. Prior exposure to tech and/or the tech investing ecosystem is preferred
• AI fluency is a must. You enjoy using AI-native products whether in customizing your Claude Cowork environment, building in a current role, or personally. You are well versed in tools like Claude Code, Codex, Vercel, and Replit.
• Strong quantitative skills and detail orientation
• 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
• 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 and communicate 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
• High integrity, with ability to maintain trusted confidences with all internal and external partners.

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.