Do I need a Chief of Staff as a Venture Capital GP?

Max Fleitmann
Founder of VC Stack
Do I need a Chief of Staff as a Venture Capital GP?
Ajey Bhasker
VC Stack Expert

A General Partner (GP) in a venture capital firm has a myriad of responsibilities ranging from day-to-day operations to fundraising and deal sourcing. A Chief of Staff can support the GP in managing their daily workload by acting as their right hand, helping implement the firm’s overall strategy. We connected with two superstars who currently hold a Chief of Staff role to get their thoughts on this topic. Rylie Jennings from Behind Genius Ventures (BGV) and Michael Amar from Diagram Ventures share their views in this deep dive on the multi-faceted role of a Chief of Staff at re. Together, we explore the role of a Chief of Staff at a VC firm, the benefits of having one, the factors that GPs should consider before hiring, and how to equip a Chief of Staff for success. 


Why would a General Partner need a Chief of Staff? 

Broadly, the role of the Chief of Staff is to provide operational and strategic support to the GP. The Chief of Staff acts as the GP’s right hand, managing the day-to-day operations and implementing the firm's overall strategy. The specific responsibilities of a Chief of Staff vary depending on the size and structure of the firm. Rylie notes that at BGV: 

As a solo-GP having that additional person to assist with the backend operations of the fund helps mitigate being a single person. My role as a Chief of Staff shifts depending on the priorities of the fund, and that’s extremely helpful to have to continue moving towards our strategic goals” 

Similar responsibilities are identified by Michael at Diagram Ventures - a mid-sized firm. While they remain fluid, they have a more defined scope, reflective of the organizational structure in which the role is performed: 

The Chief of Staff ultimately acts as an extension of the Partner, and serves to increase their capacity, facilitate coordination and help streamline processes for improved efficiency.

Michael echoes the Chief of Staff role description provided by a Harvard Business Review article. The responsibilities include: 

  • “Acting as an air traffic controller for the leader and senior team
  • Connecting work streams that would otherwise remain siloed
  • Communicating and linking leadership with the broader organization
  • Acting as an honest broker and truth-teller
  • Acting as a confidant without an organizational agenda.”

What is not the role of a Chief of Staff?

As mentioned above, this varies depending on the firm and what was negotiated as part of the scope of the role, but generally, the Chief of Staff is not:

  • An associate position or a partner-track role. 
  • An executive assistant role. While both roles work closely with the GP, the Chief of Staff is focused on optimizing the strategic initiatives that the GP is driving, while the executive assistant manages the day-to-day schedule to maximize the GP’s time for the best use.
  • Expected to source companies or to be directly entrepreneur-facing. However, the Chief of Staff can be involved in reviewing, analyzing, and prioritizing existing deal flow to support the firm’s portfolio.
  • Expected to make investment decisions. While a Chief of Staff may provide support in due diligence and term sheet negotiation, the GP will make the final decision.
  • Expected to manage portfolio companies. The Chief of Staff may help the GP in monitoring the performance of the firm's portfolio companies, but they would not typically be responsible for managing the day-to-day operations of these companies.

When is the right time to get a Chief of Staff? 

While there are no hard and fast rules on this, there are many questions you can ask to make that decision:  

  • Are you having difficulty managing the firm’s operations? 
  • Are you finding it difficult to scale your business? 
  • Do you lack time for strategic activities? 
  • Do you have a growing list of strategic initiatives without an owner?
  • Are these strategic initiatives cross-functional and, therefore, not within a specific functional lead’s scope?

As Rylie notes: 

Hard to say the exact right time [for hiring a Chief of Staff], but when fund activities are scaling up, then that’s the right time to look into hiring additional personnel

Michael adds that the opportune time is: 

as the firm grows, workload increases and the partner feels drained rather than energized by the day-to-day demands. [A Chief of Staff’s] primary goal is to enable the partner to focus on more strategic tasks. In my case, I was brought in as the firm was in the process of raising two additional funds, had a portfolio of 18 companies, and the partner had four functions reporting to him (Investing, Legal, Accounting, and Talent). The partner was concerned about his productivity, poor information flow, and too much time spent on follow-ups and slow decision-making.” 

What are the characteristics of a strong Chief of Staff?

Each Chief of Staff is different because the best ones share a complementary skillset to the GP to fill in the gaps. For example, if the GP has a technical background, they would benefit from hiring a Chief of Staff with a financial background to help manage the go-to-market side of the business.

Additional key characteristics of a strong Chief of Staff include: 

  • Relationship-building skills to connect with people in the firm and external stakeholders.
  • Comfort operating in ambiguous situations and capable of adjusting to changes in the internal or external environments
  • An ability to understand a business at a ten thousand-foot view and dive deep into specific challenges and problem-solve at a tactical level.
  • Organizational skills to simultaneously manage multiple projects and prioritize workloads to meet deadlines.
  • Strong verbal and written communication skills. 
  • Analytical skills to evaluate data and think strategically to input into the firm's overall strategy.
  • Leadership skills to manage teams, inspire others, delegate responsibilities, and provide guidance.

The GP should also ensure that the Chief of Staff is a good fit with the firm's culture, values, and goals.

Rylie notes that: 

For me, the best preparation is the mental stamina of learning how to do new things on any given day. Truly embrace the information that can come from each day. That way, when it comes to improving systems and processes, you already understand the deeper context of how all these different systems support each other and therefore learn how to make them better. This can be within communication practices, the tech stack your team uses, workflows, etc.”  

What does a typical day look like as a Chief of Staff? 

At the most fundamental level, a GP can implement parallel strategic initiatives with a Chief of Staff. From Rylie’s perspective at BGV, it varies based on the day, but broadly, it is managing operations, content creation, and LP and founder relations: 

I help produce [the GP’s] podcast, Seed To Harvest, so oftentimes I’ll conduct research and meet with our editor to finalize details of upcoming episodes. I manage capital calls, help write LP updates, and plan events across Miami, SF, New York, and LA for our founders and LPs. 

We have a part-time analyst focused on research-driven written pieces, so I enjoy brainstorming new ideas, and iterations focused on our investment thesis of the future of work and play. 

We’ve recently opened an office in San Diego, so this week I’m focused on setting up the property for official move-in. In summary, it depends on the day.” 

Rylie’s typical day at BGV has evolved as the firm has grown but the best part of the role is “being able to touch base with each team member and have a part in just about every area of BGV’s activities.

Likewise, Michael notes that his day to day at Diagram Ventures is extremely varied but that his “role is to provide additional leverage and capacity to the Partner, making sure that the firm runs smoothly and efficiently”. Tasks over Michael’s day include: 

  • Acting as a quarterback for strategic and operational initiatives
  • Managing day-to-day operations, such as scheduling meetings, communicating with different teams, and handling ad-hoc administrative tasks
  • Overseeing the firm's budgets and expenses
  • Assisting with marketing, PR, communications, and branding efforts
  • Preparing for, attending, and following up on meetings with internal and external stakeholders
  • Supporting the partner in leading teams efficiently and fostering collaboration
  • Creating key presentations and financial analyses in the context of fundraising, strategy, and portfolio management
  • Interacting with portfolio company CEOs and providing ad-hoc functional support
  • Monitoring key metrics, returns, and developments for portfolio companies
  • Facilitating investor and stakeholder relations.

How do you equip a Chief of Staff for success?

From Michael’s experience at Diagram Ventures, three key factors stand out:

  • Aligning Expectations: The role of a Chief of Staff can vary significantly, from junior administrative tasks to senior leadership responsibilities. It is essential for the Chief of Staff and their partner to align on the responsibilities and expectations of the role, as well as establish clear priorities and timelines.
  • Facilitating Relationships: A Chief of Staff may face skepticism from direct reports and other senior leaders, who may see them as an obstacle or an extra layer to navigate. To overcome this, the Chief of Staff and their partner should clearly communicate the role and responsibilities of the Chief of Staff, as well as how the Chief of Staff's role benefits the larger organization.
  • Building Trust: Trust is a crucial component of the Chief of Staff role. The Chief of Staff's partner should provide them with access to necessary information and decision-makers within the organization early on and allow them to serve as an extension of themselves. This will enable the Chief of Staff to effectively support their partner and the organization.

Rylie adds that: 

The Chief of Staff role is ambiguous. Every role has a different need and every Chief of Staff has their own way of onboarding. It depends on the team you join.” 

Additional success factors for the Chief of Staff role include: 

  • Establishing clear communication channels: The GP and Chief of Staff should establish clear communication channels, to ensure that the Chief of Staff is kept informed about the firm's activities and can provide input into strategic decisions.
  • Providing opportunities for growth by encouraging the Chief of Staff to take on new challenges to develop their skills and in turn become more valuable to the firm over time.
  • Providing constructive feedback regularly to help the Chief of Staff understand their strengths and weaknesses and to identify areas for improvement.

That said, equipping a Chief of Staff for success is an ongoing process, and the GP should work closely with the Chief of Staff to enable them to perform their role effectively.

Concluding thoughts

The decision to hire a Chief of Staff is a complex one. While a Chief of Staff can provide valuable operational and strategic support, the key to unlocking the benefits will be correctly timing the hire and having a defined list of responsibilities for the role. Given the role’s ambiguous nature, it is important the Chief of Staff is adaptable with strong people and problem-solving skills and is aligned with the firm’s culture. Once hired, it is an ongoing process to ensure that the Chief of Staff is equipped for success. If executed well, the Chief of Staff is a force multiplier for the GP’s strategic value.

If you are thinking about hiring a Chief of Staff (or want to become one) make sure to check out our job board at Startup&VC.