Three tips from the top tech CEOs in Boston

CFOs take care of the finances, CMOs do the marketing, CTOs do the tech. So what does the CEO do? Often times it’s a little bit of everything, but after meeting with the top tech CEOs in Boston at an Underscore VC Core Community Dinner, I came away with a couple tips on how to be a top CEO, whether you’re a 15 person startup or a 300 person corporation.

1. Get on the same page

As a CEO, if you assume everyone in your company can read your mind, think again. While the CEO defines the vision and molds the strategy, they also hold the responsibility to be able to effectively communicate it to their team. Employees need to have a crystal clear understanding on the core mission of a company, what defines success, where the company is going, and what numbers matter. This translation of vision into organizational action is hard, but 100% necessary.

Ken Rugg, former CEO of Tesora says the key is to “use the right vocabulary”. A CEO needs to define a centralized sense of success with a common vocabulary that can be adopted throughout the entire company. Then, they need to make the effort to be constantly conveying this meaning to employees in a way that forms meaningful ambition. The group recommended to frequently hold company meetings to discuss your mission and strategy so your vision is aligned with reality as the company scales.

2. Know your data

We talked a lot about data, and I mean a lot. Sandra Richter, CEO of Soofa, and Jennifer Lum, founder of Adelphic Mobile, preached the importance of data transparency at the executive level using a corporate dashboard like Related IQ. These tools allow visibility into company data to keep vision and strategy aligned. Matt Johnston, CEO of Mautic, also made an important point:

“If data from the product isn’t getting to lead generators then you are missing a whole dimension”

The quote parallels a piece of advice from the evening — when mining data, companies need to “go behind the log in” to ensure visibility into critical product data coming straight from consumers. Companies need to measure more than just the basic metrics (i.e. usage/download rates or qualified leads) and start analyzing user behavior and interactions to create effective KPI’s that drive progress. The CEOs in the room suggested filling management roles with data-driven and systems-focused talent. These employees acquire and analyze the data and report it to the C-level who translate it to big-picture strategy.

3. Hire A+ talent that fits

The biggest question of the night was “how to hire the best people”. In Startup Secrets: Hiring A+ Talent, Michael Skok says that it’s not finding quality talent that’s the problem, the real challenge is finding the fit. Every hire needs to have emotional, cultural, and intellectual fit. This fit is also a dynamic concept — your first employee may not be the best fit for the company ten years down the road. Ignorance to this evolution of employee-stage fit results in catastrophe.

A CEO needs to hire and fire with the next stage in mind to keep his/her organization lean and evolving. For hiring, Raj Aggarwal, CEO of Localytics, recommended the book The Hard Thing About Hard Things by Ben Horowitz. It advises to try to find someone who will be good for the next 18 months of your company’s growth because in 18 months, you’ll be a completely different company. For firing, CEOs Stefania Mallett of EzCater and Susan Hunt of WeSpire, suggest looking through Patty McCord’s infamous Netflix Culture: Freedom and Responsibility presentation and to start employing the “Keeper Test”. The test requires to ask yourself the question:

“Which of my people, if they told me they were leaving for a similar job at a peer company, would I fight hard to keep at my company?”

Use these tips and be constantly reflecting on the fit of your employees as your company changes and grows.

Although this advice is extremely valuable, it’s important to mention that the overarching theme of the night was that there is no formula to being a great CEO. Every company is different and as CEO you need to make it your #1 priority to understand every thread of your company so you can align your growth with your vision.

It was a privilege to be in the room with some of Underscore VC’s Core Members at this month’s Community Dinner. I am excited to announce that I will be joining the Underscore team this coming July as an Associate for my next co-op at Northeastern University. I can’t wait to keep learning and engaging with the Underscore Core community.




Solving people’s problems. EIR + Head of Strategy at Onward Labs | Former @UnderscoreVC | Star Wars Thought Leader | @abbey_ellis

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Abbey Titcomb

Abbey Titcomb

Solving people’s problems. EIR + Head of Strategy at Onward Labs | Former @UnderscoreVC | Star Wars Thought Leader | @abbey_ellis

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