Issue 41: Pitching Yourself as a Chief of Staff
How one generalist successfully created her own role
Welcome back, aspiring and current Chiefs of Staff 👋🏼
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🧘🏻♀️ Optional morning yoga for anyone who wants to get a morning stretch in
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In this week's issue, Ciara Dinneen, an operations generalist and the current Chief of Staff at Optimize IS, shares her experience pitching herself for a Chief of Staff role after leaving her previous job.
Known for her profound commitment, keen listening skills, and action-oriented mindset, Ciara is adept at navigating the complexities of fast-paced and ambiguous environments to support visionary leaders in achieving their goals. With a combination of high emotional intelligence and analytical strategy, she is able to understand and act on complex issues with clarity and precision.
As someone who had taken on strategic operations responsibilities across various domains, Ciara realized that the Chief of Staff role could be the perfect fit to leverage her diverse skill set. We hope her journey provides some helpful insights and inspiration for those exploring Chief of Staff opportunities or aiming to pitch themselves for a similar role. ✨
In November 2023, I left what was my favorite job to date (at the time) because of a misalignment with leadership. It was a tough decision, but one I don’t regret.
A little backstory: I was the first People Operations hire at the company (Series B) and quickly grew to take on general operations in addition to the people side of things. I supported the leadership and broader team through significant layoffs, an entire product rebuild, and a company rebrand.
In this and previous roles, I naturally became a strategic partner to leadership. This proximity, exposure, and influence are my favorite things about what I do–being the person behind the scenes who helps make it all happen.
🧭 Figuring Out My Next Move
In the weeks after I left, I spent time sound-boarding my next steps with mentors, trying to figure out what I should and want to do. I heard a lot of advice around getting specific (e.g., it helps only to need one version of your resume), but as a generalist with skills and a genuine interest in many areas, narrowing down on the role itself can be difficult.
I explored multiple roles, including technical customer success (I know SQL and invested some of my "time off" in learning basic computer programming with Python), people and culture manager (the role I had been in most recently), executive assistant (I've been this de facto alongside main roles), and even event manager (having learned some things about pulling off purposeful events from the all-company retreats and team offsites I'd done).
What I did get specific on was what was most important to me outside of the role itself.
I learned that I’m less concerned about what I’m doing day-to-day as long as a few things beyond the role itself are aligned with me, which are:
1⃣ Who I work with
2⃣ How much I learn and how quickly I learn it
3⃣ What we are working on (the mission)
🔎 Exploring the Chief of Staff Role
I often think about what it might be like to have specialized in something. Sometimes I feel the fact that I’m a generalist works against me. It feels this way, especially when looking for a new role.
While I was aware of the “Chief of Staff” title, I hadn’t seriously considered it as a role for me until a mentor suggested that I look into it. After telling this mentor what was most important to me and what I enjoy, they thought a Chief of Staff role would be perfect.
I did a deep dive and felt both excited and seen. Turns out, there’s a role and title, an actual named thing, for what I love doing. It became a job “North Star,” pointing me toward a role I could strive for–a role that views the fact that I'm a generalist as a strength.
📝 Pitching My Role
With this job search goal more clearly defined, I started looking more into who I’d want to work with and where I’d want to work. I was connected to one of the co-founders of an Airtable consulting agency through a no-code ops community I’m part of. Someone had kindly posted about me looking for my next thing, and the co-founder asked for an introduction. I met with them, and over a few weeks, we discussed everything they needed help with, such as sales, customer success, internal operations, and more.
After weeks of discussion with enthusiastic co-founders but no formal offer, I understood it was up to me–I would need to pitch my role.
As I was putting together a proposal with an adaptable, versatile job description and a few compensation packages for them to choose from, I realized that what they needed was a Chief of Staff. So, I pitched them Chief of Staff, and they said, “Yes, please.”
In my proposal, I shared how, through a collaborative and adaptable approach based on their needs and priorities, I could contribute across various domains such as sales, customer success, strategic planning, and internal SOP development during a pivotal growth phase. My suggestion of stepping into the Chief of Staff role was an offer to leverage my broad experience supporting the co-founders' vision. It was an opportunity to apply my diverse skill set towards fostering team cohesion, enhancing operational efficiencies, and supporting the company's ambitious goals.
This pitch was as much about finding a place where I could add value as it was about joining a team where working closely with leadership (1), learning (2), and mission alignment (3) were valued.
For anyone considering pitching themselves for a Chief of Staff opportunity, I encourage you to reflect on what truly matters to you beyond the day-to-day responsibilities. Identifying your core values, learning goals, and vision for the type of team you want to be a part of can help clarify your path. Don't be afraid to propose a role that genuinely aligns with your strengths and aspirations—you may be surprised by the positive reception.
Want to take a look at the proposal Ciara used to successfully pitch herself as a Chief of Staff? The template is FREE for Ask a Chief of Staff community members.
Here's a sneak peek at what this premium template includes:
✨ A customizable structure to craft a compelling proposal tailored to the company's needs and your unique qualifications
🔑 Insights on how to position the multifaceted Chief of Staff role and its value to the organization
💼 Examples of how to showcase your relevant experience and unique selling points (USP)
💰 Guidance on proposing compensation plans, including various options like fixed salary, commission-based, or a combination
📈 An appendix section with tips for providing context, research, and rationale behind your proposal
⚡ And much more to help you stand out, negotiate effectively, and secure your dream Chief of Staff opportunity!
Members of the Ask a Chief of Staff Community get access to this and 50+ other templates in the Resource Library.
🎥 Upcoming Events and Workshops:
May 2nd: Designing Engaging and Impactful Offsites
May 7th: Top 5 Tech Mistakes Startups Make When Scaling
May 9th: The Chief of Staff Role for Future Entrepreneurs
May 10th: Volunteering at Battery Park City (NYC, in-person, free for all to attend)
August 7th-9th: First Ever Ask a Chief of Staff Summit 📣 📣 📣
As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.
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