My First 100 Days As An AI Startup COO

If you’re interested in my origin story with the founders at Sectorflow Inc., a startup building an AI platform for business, you can read more on this LinkedIn post.

Here’s the quick version: I got a call from my former engineering team that they were quitting their jobs to start their own company and they wanted me on board as their COO. It was a hard yes from me — then I got pregnant soon after. Should I back out? I asked myself. I might be doing a lot of sitting around the next few months…

“No problem. You can take all the time you need when the baby comes. We don’t envision doing this without you.”

Cool - locked in - anxiety subsides. As a first-time COO, I thought I should probably figure out what this role actually entails. I had over a decade of experience in agile methodology, technical project management, product management, and business development but I had never served in this type of leadership capacity before. A search yielded several “First 100 Days as COO” articles with some solid advice, usually around setting goals and fostering relationships with the C-suite. Great stuff but I found it was pretty conventional whereas startup life and our team history is anything but that. Thus those well-meaning and unhelpful articles are the inspiration for this blog. I’ll discuss some of what I actually did in my first 100 days as a COO at an AI startup and cover tool selection, initiatives, research, and some general insights.

Tool Selection

The very first thing I was asked to do was pick project management and issue-tracking tools. With everyone in their own lane, communication was only happening via Slack or the daily standup. I estimated that searching for information, duplicating tasks, miscommunications (or overcommunication trying to avoid miscommunication), and progress updates were costing us around 10 hours per week across the team, maybe more. Simply, it was time to get organized.

Our application for Notion For Startups had just been approved (this gives you 6 free months of the Notion Plus Plan) but we weren’t sure exactly how we would use it and the biggest question was, would engineering use it? A quick pros and cons analysis led me to recommend using Notion for company matters and JIRA and Confluence for engineering (see analysis below). And that’s almost exactly what we did.

I started building out our first Notion workspace with the Data Room template, a good starting point if you’re going in fresh. Not every section was relevant to us but I left them all in there just in case. For example, we didn’t use the Fundraising Tracker table right away but a couple of months in - it was a ready-made interim CRM solution for our CEO. Overall, Notion is excellent for keeping track of everything non-engineering related.

As for engineering and development, the team has experience with Atlassian tools so it was an easy ramp-up to creating sprints and managing tickets. What I didn’t expect was that we would completely disregard Confluence as our documentation tool and instead went with ReadMe.

ReadMe is marketed as a doc hub for developers and our CEO (with an engineering background, of course) fell in love with it after a test drive. I admit I was concerned I wouldn’t be able to self-serve my way through some release notes but that wasn’t the case at all.

I’m not a developer but I love ReadMe because it brings us value in several ways:

• So easy even a non-technical COO can use it
• Branded experience which keeps our doc hub consistent with our public image
• A dedicated location for us to nurture this key piece of our customer experience
• Internal accountability for the team, promotes discussion and decisions

Sectorflow Tool Selection Analysis: Notion v. Atlassian

💡 Key Considerations:

• Need for specialized engineering tools.

• Preference for unified vs. specialized platforms.

• Long-term scalability and integration.

  
  

Here's why:

1. Flexibility & Scalability: This option seems better suited for our growth and scaling needs. I'm anticipating the need for DevOps and sustaining engineering tools here.
2. Distinct Project Management Needs: Development project management differs significantly from other business areas. Specialized Atlassian tools will better serve these requirements.
3. Future Planning: Anticipating a PMO to handle project management down the line, having distinct tools will facilitate easier transition and separation of duties.

Some final thoughts on tools. I’d like to give two other shoutouts here to customer.io for marketing automation and TrustPilot for SOC2 compliance. Like Notion, these SaaS companies approved us for their startup program. If you’re a startup trying to gain efficiencies on a budget, always check if the tool you’re vetting offers a freebie before signing on. Gotta hold on to that precious runway.

Initiatives

The most important thing I did in my first 100 days was lead the market research, ICP (Ideal Customer Profile), and messaging efforts for the startup. The reasons for doing these activities are easy to grasp - we wanted to engineer a sustainable growth and communication strategy for the company. What’s not so easy is the homework you have to do to get somewhere with your market positioning (there are levels to this).

With no clear first step for market research, I had to work with what we did have. Thankfully, my CEO was having tons of conversations with everyone we knew (existing investors, previous clients, and connections that the team had made over the years) so I gathered a list from him of all the contacts within our network. We then compiled this information into a table, along with some data about each contact's company. This initial research helped us identify consistencies or patterns, to give us some sort of insight into problems, trends, and use cases.

Another key piece to this process was engaging in numerous deep discussions with our founding team. We shared our knowledge and experiences, while also continuing to gather valuable information from the network. It raised several questions and uncertainties about our market fit and positioning. Were we an AIOps platform? A BI tool? To answer these questions, I took to Gartner, GigaOm, and Forrester reports to understand these industries better. By analyzing the players, their solutions, and the problems they were solving, we were able to determine that - well, we did not fit into any existing categories. Discussions continued. Research continued. This research and analysis process took several weeks, but ultimately, we developed a v1 ICP based on the research I did, the team’s limitations, and the team’s industry experience.

In grad school, I learned about strategic communication plans and how they’re a great tool before putting out any communication on behalf of a company. It’s something I had done for companies before and intended to do for Sectorflow to get alignment on our messaging.

However, as we were already in the process of identifying our ICP and having conversations about what we stood for and who we are, I came across this video and realized a manifesto is essentially the SaaS startup version of a strategic communication plan. This seemed a better framework to follow given where we were at as a young company. This was an easier part of the process for me, since waxing poetic about our philosophy reminds you why you’re doing all this crazy stuff in the first place. More importantly, the manifesto will now inform our go-to-market strategy and marketing efforts moving forward, setting the tone for our external communications.

What I’ve learned

Finally, I’ll leave you with the biggest lessons I’ve learned in my first 100 days as a COO:

• While you must understand what is going on in the product and engineering world, your main job is to be a business leader.

  
  

• Come in every day with an idea of what you should be doing and the expectation that you will not be working on that. As COO, I realized the need for extreme adaptability and pivoting based on what’s needed.

  
  

• You are the CEO’s support system. This is easier if you have a good relationship and thankfully, that’s the case at Sectorflow!

  
  

• Read. Learn. Repeat. Become a business student. Become an (AI)* student. It’s easy to go heads down in work (especially at a startup when there’s so much to do) but you can bring value just by knowing what’s going on. I carve out 1-2 hours per weekday for reading reports, news, and social posts to level up on artificial intelligence concepts and startup business practices [ Insert your industry here ]

If you thought this peek into my first 100 days as a new COO was helpful, please connect with me on LinkedIn or follow Sectorflow as I continue sharing our startup journey. I welcome feedback and post ideas around fundraising, validation, or anything else you'd like to hear about.

Additionally, I'm currently researching AI explainability and ethics. If anyone works in AIOps/MLOps and wants to exchange ideas on responsible AI principles, as we build out the Sectorflow platform, I'd love to connect. 💙

— never finished, Deborah