In a recent blog post by Ryan Monk and Gianna Santaniello of Primary Venture Partners, they highlight the best reasons for hiring (incl. where to find them, and when and how to hire) a Chief of Staff in early-stage startups. This piece resonated deeply with me, as I felt like it was written specifically about me, perfectly describing my own professional journey – 2x Chief of Staff, former VC, specializing in operations, strategy, marketing, community, and fundraising – a professional who excels in a wide range of tasks, adding immense value across various functions.

The article is a great and quick read, but I’ve condensed it here for you in a tldr version as I know you’re all busy people.

1. 𝐓𝐡𝐞 𝐄𝐬𝐬𝐞𝐧𝐜𝐞 𝐨𝐟 𝐚 𝐂𝐡𝐢𝐞𝐟 𝐨𝐟 𝐒𝐭𝐚𝐟𝐟:

Chiefs of Staff are crucial in startups, acting as the founder’s right hand and managing everything from internal KPIs to investor relations.

2. 𝐓𝐡𝐫𝐞𝐞 𝐓𝐲𝐩𝐞𝐬 𝐨𝐟 𝐂𝐨𝐒:

a. Operational Generalists: The Swiss Army knives who tackle diverse tasks, from setting up HR policies to organizing team offsite.

b. Functional Specialists: Experts in a specific area like product development, finance, or marketing, who also manage broader operations.

c. Versatilists: Similar to generalists who are capable in many areas, but also possess deep knowledge in one or more specific domains. (I added this one. For more info on versatilists, check out my Linked post.

Regardless of their type, a CoS spends over 75% of their time working closely with the CEO, building a relationship founded on trust.

3. 𝐖𝐡𝐞𝐧 𝐭𝐨 𝐇𝐢𝐫𝐞:

Timing is everything. Hire too early, and the CoS may have little to do; hire too late, and the founder could be too overwhelmed to make the most of the role. Typically, the best time to hire is around the Seed or Series A stage when the founder’s workload starts to hinder key activities like fundraising and product development.

4. 𝐊𝐞𝐲 𝐈𝐧𝐝𝐢𝐜𝐚𝐭𝐨𝐫𝐬 𝐘𝐨𝐮’𝐫𝐞 𝐑𝐞𝐚𝐝𝐲 𝐟𝐨𝐫 𝐚 𝐂𝐨𝐒:

– Delegatable tasks are piling up.

– Struggling to focus on core responsibilities.

– Increasing administrative complexity requires dedicated attention.

5. 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐭𝐡𝐞 𝐑𝐢𝐠𝐡𝐭 𝐅𝐢𝐭:

Look within your network and relevant communities. Strong candidates often transition from consulting or investment banking into startups. Primary’s Chief of Staff Mastermind Network, along with VC and startup communities, are excellent resources.

6. 𝐈𝐝𝐞𝐚𝐥 𝐂𝐚𝐧𝐝𝐢𝐝𝐚𝐭𝐞 𝐏𝐫𝐨𝐟𝐢𝐥𝐞:

– 2-3 years in top-tier consulting, investment banking, or private equity.

– Startup experience for a year or more.

– Proactive, self-starter with intellectual curiosity and strong executive presence.

7. 𝐌𝐢𝐧𝐝𝐬𝐞𝐭 𝐚𝐧𝐝 𝐁𝐞𝐡𝐚𝐯𝐢𝐨𝐫𝐚𝐥 𝐓𝐫𝐚𝐢𝐭𝐬:

– Comfort with ambiguity and a “get things done” attitude.

– Ability to build from scratch and research solutions to new problems.

– Strong organizational skills and attention to detail.

8. 𝐋𝐞𝐯𝐞𝐫𝐚𝐠𝐢𝐧𝐠 𝐚 𝐂𝐨𝐒:

Once hired, grant them trust and autonomy. Clearly define their responsibilities to maximize their impact, such as:

– Creating decks and financial models.

– Managing hiring processes.

– Setting up company-wide productivity tools.

– Handling contracts and agreements.

A successful CoS will ensure operations run smoothly, allowing the founder to focus on high-impact activities. Typically, they transition into a specialized role within 12 to 24 months, further contributing to the company’s growth.

𝐂𝐨𝐧𝐜𝐥𝐮𝐬𝐢𝐨𝐧:

The right Chief of Staff is transformative, enabling founders to focus on what they do best. They are capable of handling diverse challenges and driving results across various functions and acting as a force multiplier for their principal. So if you’re looking for someone like this in your startup, let’s connect!

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