Three Secrets to Impressing Your CEO Right Now

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To alumni, I hope today finds you safe and well. To students and recent graduates, while I cannot truly understand what you are going through right now, I can relate to it to some degree and attempt to offer a bit of encouragement.

I graduated during a crisis, too.

As a 2007 graduate of Endicott College, with a bachelor’s degree in International Business and Marketing, little did I know the steps waiting ahead of me. Leaving a small, intimate campus where I was fortunate to make lifelong friends—leaping into a world unknown—seemed both exciting and scary. While the world wasn’t suffering from COVID-19, it was going through one of the world’s worst worldwide economic crisis in history which sparked a global recession economists compared to the great depression at the time. I remember thinking “well here goes nothing” and I started applying to jobs. Graduating Endicott of course had pros and cons as I sought out my first job. On the one hand, I was competing against students from local Ivy League schools and universities with widely respected credentials. On the other hand, I had the Endicott ace up my sleeve which included three internships at UBS, JP Morgan, and Beth Israel Lahey Clinic. I also had been uniquely lucky to have had the opportunity to study and learn from Professor or Business, Dr. Aron Viner. For an eager marketing enthusiast like myself, his classes were far and away the highlight of my learning over the course of my four years.

Dan Slagen - InsetEventually, I took my first role at CSN Stores, or as most people know it today, Wayfair. It was an entry level marketing role that paid $28,000 per year and consisted of essentially doing data entry to get products to show up on Google searches. The very first assignment I was given upon joining was for a product line of toilet seats. Yes, you read that correctly, that’s what it was. I spent my days writing descriptions of toilet seats. Regular. Elongated. Porcelain. Green. Blue. Glamorous to say the least. I loved that job, and upon joining the company had instant access to some of the best and brightest people in the Boston start-up community to learn from and I’ve never looked back. Fast forward 13 years later and here we are. I’ve been fortunate enough to work at a number of start-ups including Wayfair and HubSpot, that have managed through billion dollar mergers, acquisitions, and I currently work as the CMO for an incredible company, ClimaCell, which is transforming the weather technology industry. It’s truly an amazing company with a moonshot mission.

The Three Secrets

Given the current global economic situation, a number of companies have already frozen hiring/budgets, reduced headcount, and will likely continue to do so depending on the next few months. What this means for employees is—make sure you’re doing everything in your power to make yourself indispensable to your boss, your company, and ultimately your CEO. While some circumstances may be out of your control, it never hurts to do everything in your power to set yourself up for success. Over the course of my career to date, I’ve worked directly for a number of CEOs and have advised countless others including their executive teams. While it’s true that it’s difficult to understand and predict the behavior of individuals during a single event, it’s much clearer over time through multiple experiences, and that’s what brings us here today.

I recently finished writing my first book, Understanding Start-Up CEOs (and the mindset you need to successfully work for one), which was published in early May, 2020. The book details three strategies that will help you deal with any of the following work situations:

  • Your first job
  • You’re rising in the ranks, quickly becoming a shining star
  • You’re an executive reporting into the CEO for the first time
  • You’re an executive reporting into the CEO for the Nth time
  • You’re the CEO interested in better understanding your team
1. Understanding The Mindset of Your CEO

Having an understanding of what’s going on in the mind of your CEO is a near impossible task; however, the mere act of trying to think about what’s running through your CEO’s mind on a consistent basis puts you one step ahead. So often at work you can get caught up in your own struggles and tasks, which is okay, but you must remember to pick your head up and look around, especially up at your CEO to make sure you’re spending your time wisely.

Coming in each day and reporting to a start-up CEO especially for the first time (and almost every time after that) is a transformational process for most. Working directly for someone whose life is as connected to the success of the business as the CEO’s is, to some degree, a crazy task to have accepted. Your CEO is obsessed with winning and will avoid losing at all costs, and there’s always more going on than you think. But even with all the chaos, what do most start-up CEOs do? Do they come in each day wearing their emotions on their sleeve and letting their direct reports know these kinds of pressures are building up? Not usually. Most days they come in and focus on moving the business forward, and you are none the wiser. It’s an impressive character trait and one you should be alert to as a direct report. The truth is, being a start-up CEO is a lonely job. Having a little compassion for your CEO is a good idea and can improve your working relationship.

Odds are you’ll never fully penetrate the mind of your start-up CEO. They’re a rare breed of people and uniquely built to withstand pressure. Although you shouldn’t overstress yourself trying to figure out what your CEO is thinking, there are things you should know and can do to make your CEO’s life and your own easier. Below are just a few examples of things you can focus on (all explained in the book) which include:

  • Practice process and frameworks to show consistency
  • Do what you can to take work off your CEO’s plate
  • Be alert to reduce cultural friction and ensure teams are working well together
2. Focusing on Performance Outputs

The truth is, you need to perform—and your team needs to perform. Your CEO needs to look at your performance at the end of each week, month, quarter and year to get a crystal-clear understanding of your impact on the business. You need to be comfortable reporting on numbers and outcomes. You need to align your input directly with the strategic growth of the business in order to maximize the outputs of your efforts.

You also need to have a crystal-clear communication plan with your CEO and not shy away from the hard discussions. Your role is to manage your CEO much more than it is the CEO’s job to manage you. If your CEO is telling you what your department should be doing next, then something is wrong.  It’s your job to bring them along for the development and growth of your department and team in accordance with the overall vision for the company. Share what your vision is for your area of ownership, how it aligns with the company vision, how it syncs with the other departments and how you’re going to get there.

Do the legwork, but allow room for your CEO to add value. Show plans that are 80% baked so the CEO can provide input and debate key points. Most important, stay one step ahead and continually connect and build the pieces to advance your department.

3. Managing Yourself

Your CEO will provide as much guidance and vision as possible, but you must be an owner. Ultimately, you must hold yourself accountable for putting forth the best possible effort to help the business succeed. Your CEO often will be distracted, and you’ll be left to manage yourself and your team. This means keeping yourself healthy from a physical and mental standpoint. A few of the key components to managing yourself include:

  • Don’t lose steam on anything you directly own
  • Understand that reporting into the CEO will be mentally tough
  • Be open to change
  • Don’t ignore your life outside of work
  • GSD (Get stuff done)—this is especially important during an economic crisis
  • Ask for help. It’s always better to ask for help early on than fake it and get caught later
  • Show up and compete every day.

While this might sound like a lot, if you can continually focus on these areas on a weekly basis you’ll be putting yourself in the best possible position for success. The most important part is to keep these things top of mind consistently, so use this post and information as your guidebook more than anything else. Stay humble, stay creative, put people first, keep an unrelenting drive, and everything will work out just fine.

About Dan:

Author of the recently released book, Understanding Start-Up CEOs, and current CMO at ClimaCell, Dan Slagen is a four time start-up executive specializing in scaling global go-to-market functions from early stage to $100M+ in ARR. With experience in both B2B and B2C at companies such as HubSpot and Wayfair, Dan has built teams across marketing, growth, sales, customer success, business development, and also founded and sold his own video tech start-up.

A frequent contributor and advisor to the start-up community, Dan has spoken at more than 50 conferences and has been featured in The New York Times, The Wall Street Journal, Forbes, CNBC, TechCrunch, and Bloomberg TV among others.

Above all else, Dan believes in creativity, drive, and a people first mentality.


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