Want a Chief of Staff job? Pitch the Role.

When speaking with people interested in landing a Chief of Staff role, I always give the same advice: pitch the Chief of Staff role to the Executive you want to work with.?

While I understand that getting in front of the right Executive is not the easiest task, I strongly believe that pitching the role is much more effective than cold applying or even applying with a referral. The Chief of Staff <> Executive relationship is unique - because of this, personal relationships and professional chemistry are often the winning factors.?

If you do have an opportunity to pitch an executive, keep reading on how you might best do this.?

1. Create Your Pitch

Paige Honeycomb , Chief of Staff at Puzzle ???? , landed her role by cold pitching to her now CEO. She recommends “answering the following questions in a concise email or message (followed with more details during an in-person meeting):

• What are the problems the company may be facing? (e.g. Industry-specific, current events, competitor related, etc)
• What makes your experience a perfect fit to be able to solve the identified problems?
• Why is the CoS role the right role to not only address those problems but also support other potential problems as the company grows?”

Create the role, yourself!

2. Find the Executive & Pitch

Existing Relationship: Sam Sterling from Minute Media was able to make an internal transition to Senior Director, Strategy & Business Operations by pitching the role. She recommends “pitching the role to someone with whom you have an existing relationship, because trust is such a strong foundation for the role.”

New Relationship: This strategy is a bit harder, but not at all impossible.?

• Get Connected: 1) Attend events where the Executives are (e.g. industry-specific events, VC summits). 2) Get connected to an Executive through a connection. 3) Send a direct message through LinkedIn or Twitter. There isn’t a perfect, one-size-fits-all strategy for getting connected so I would put on your hustle hat here.?
• Show Genuine Interest: Executives can smell a quick sell so don’t throw them off in the first interaction. Ease into your pitch by showing genuine interest. Ask questions about their life and business.?
• Don’t be Desperate: While you may be very excited to meet and potentially work with this Executive, stay cool and collected as you get to know them. Pitch the idea to them with confidence.

Note: A pitch might be successful after one conversation, but will likely take a few conversations to get real traction going.

3. Add Value with Your Follow-Up

Now that you’ve garnered some interest, you’ll likely have to wait a bit because Executives are busy. Rather than following up with a bland “Great chatting with you. I’d love to move the conversation forward” email, ADD VALUE with your follow-up. Samantha says: “Your future principal has a lot going on so taking this opportunity to drive the next steps forward shows initiative and gives them a tangible preview of the value you'll bring once you're in the role.” Some ideas on adding value:

• Share a draft job description. Write the job description based on what a Chief of Staff does, the information you gathered from the conversation, and your external research.?
• Provide relevant articles to continue carrying the topics of the conversation forward.?
• Share your ideas and recommendations on their business problems or how you might suggest moving the job process forward.

Pitching isn’t easy so go easy on yourself if it doesn’t happen immediately. I’ll leave you with an incredible insight from Paige: “I learned that hearing ‘no’ is not an end all be all. At the end of the day, this is not a widely understood role so that in itself makes it more difficult to pitch [Aarti here chiming in to say that a misunderstood role also generates opportunity!]. There are going to be times when you feel defeated, but it really just takes one person to give you that chance!”?

About the Author:

Aarti Bhatnagar is the Founder of Cadence Operators , a one-stop-shop serving Operating Leaders (individuals who oversee and manage the operations of a business) through Executive Coaching, Executive Search, and Facilitation + Training.?

The clients she supports are Chiefs of Staff, COOs, Early Stage Founders, Business Operations Leads, and Heads/VPs of Operations. Her clients come from places like Patreon, Airbnb, AgelessRx, Guild, KPMG, GitHub, Block, SandboxAQ, Fullscript, SF AIDS Foundation, Gigs, Crescent, and Kaizen Labs.

Learn more about her services here: https://cadence-operators.com/