Your Self-Appointed Chief of Staff Checklist

Running a startup is like driving a car while fixing the engine. There is a constant juxtaposition of keeping your long-term goals and exit strategies within your line of sight as you put out fires that only seem to just barely move the needle. As a 2x Chief of Staff and multi-time startup operator, my job is to provide the leverage for my principal to focus on the most critical levers of the business and set them on auto-pilot (or at least keep the gears from sticking). Here’s what I'm thinking about at the start of the year.

Agility as the North Star: In the early days of your venture, your business plan cannot be a static document. It’s a living, breathing roadmap that should reflect the market you operate infrom industry dynamics to customer behavior. Fun Fact: YouTube was created as a dating site. The founders original vision for the platform was for users to create and upload videos describing their perfect match (cringey in retrospect). Being able to successfully pivot is predicated on keeping an active pulse on market trends, understanding the underlying shifts and infusing flexibility and agility into your planning process.  

If you’re looking resources on this, I suggest this strategic planning template from Asana.   

Data (and Tech Stack) Optimization: Manual processes are not only laborious but also act as a blind spot. Regardless of stage, you want to ensure you’re capturing and synthesizing data across your business and for most manual processes, you’re not collecting all the data you need. In optimizing your processing through your tech stack, you’re not only improving your company’s overall efficiency but also building the foundation for data-oriented strategic decisions which is especially vital for go-to-market. All your sales, marketing and customer success efforts should be measurable to better meet and serve your customers.  

Having data around on the drivers of your business and how/why each lever affects your business is also a helpful tool to have under your belt in fundraising (and let’s be honest, we’re always fundraising) in proving traction and product market fit.  

Some new tooling I’ve been looking into:  

Legal Compliance: In my first month as CoS at my previous startup, I was tasked with leading our California Consumer Privacy Act (CCPA) compliance efforts and I’ve been hyperaware of the everchanging legal landscape for online businesses (sadly, you’re not exempt simply because you aren’t a “tech”company) and the importance of staying on top of your legal responsibilities as you grow.  This means understanding the full legal implications of key decisions as you expand into new product lines (trademarks, IP), hire and fire (“Do you have to pay severance to an employee you caught embezzling?” “Is this contractor legally considered an employee?” “What are the guidelines regarding unpaid interns in my state?” all questions I’ve had to navigate) and enter into new agreements.  Please please please review your contracts with a fine tooth comb. I've had the unfortunate experience of being grandfathered into an ongoing dispute that cost the company tens of thousands of dollars and months of time because someone at the company was unaware of the full terms of an agreement they signed.

My unbiased legal recommendation: All Places.

As you settle into the first few weeks of the New Year and finalize your Q1 roadmaps, keep us in the loop and feel free to use me as a resource—I'm always happy to help.  

-- Erica Akitani-Bob 

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