Mark Roberge: If I Were 22

June 9, 2014


Ah, to be 22 again.  What would I do differently?

You know, I do get this question a lot from recent graduates.  “Mark, if you were me getting started today, what would you recommend I do?”   First, kudos to you for asking.  Here are the four pieces of advice I recommend to those starting out today.

Manage Your Career Like Your 401K.  Be Aggressive When You Are Starting Out

I remember picking my first mutual fund allocations for my 401K.  “I recommend allocating your money to aggressive funds” advised the 401K representative.  “You have 4 decades of work ahead of you with very little to lose.  Be aggressive.”

Good advice for early 401K disbursements.  Good advice for early career decisions as well.

You’re 22!  Now is a great time to take some big, smart risks with your career.  You probably do not have kids.  You probably do not have a mortgage.  Go for it.  Take the role that feels like it may be over your head.  Join a startup that may or may not make it. Heck, start a company!

Don’t play it safe.  In fact, playing it safe isn’t always as safe as it may seem.  Do you think the Spring 2008 graduates that joined Bear Sterns right before the financial crisis thought they were playing it safe?   When you join a big company, you are putting your destiny in the hands of others.

Put your destiny in your own hands.  Go somewhere you can make a big impact, learn a ton, and be pushed beyond your limits.

Obsess More Over the Industry You Choose, not the Company

Here are two graduates from 2009.  The first graduate joined the #1 publishing company in the world, based in New York City.  He spent the last 5 years slowly moving up the corporate ladder, accumulating his 4% annual raise, and getting experience in the world of publishing.  Having put in his 5 years, he has decided to make a change and look for a new company.

The second graduate bet on a new sector, social media.  In 2009 with social media on the rise but unproven, she took a chance on a startup in the industry.  With only 30 people at the company, she had to learn on the fly.  She accumulated a ton of unique experience building online communities, running social ad campaigns, and producing digital content.  Unfortunately, last month, the startup folded and she needs to find a new job.

Who would you rather be in this situation?  Who do you think is more marketable?  The first candidate that accumulated 5 years experience in a stagnant industry.  Or the second candidate that took a chance and, although the company failed, gained extraordinarily unique, valuable experience in the new world of social media and online marketing.

Focus less on the company and more on the industry.  Find a hot industry that you think will change the world.  Even if the company fails, you won’t.  The experience you gain will take you to extraordinary places.

Choose Mentors and Peer Groups over Formal Training Programs

When it comes to professional development, take things into your own hands.  Don’t rely on your company to train you.  I would much prefer a company that provides me with a training budget to utilize as I choose rather than be put through cookie-cutter training programs.

Here are a few specific ideas that worked for me.  Find a mentor.  It takes a long time and you need a little bit of luck.  However, invest the time to proactively look for one.  Identify people you look up to, preferably outside of your company.  Network your way to them.  Ask them to coffee.   Explore whether they are a good fit for you and you are a good fit for them.  The, ask them!

It took me a few years but I finally connected with John McMahon.  As a mentor, he was instrumental in helping me build out the HubSpot sales team.  In the early days, it was easier to see 6 months out and prepare for the obstacles ahead.  But as the team scaled to hundreds of people at a rapid pace, seeing that far ahead became difficult.  John was a huge help here.  As a guy who has run sales for a handful of public companies, it was great to bounce ideas off of him and here his war stories when he faced similar situations.   It was comforting to know there was someone to call when things got tough.

Another recommendation is to form a small group of peers from other organizations in similar roles.  Get together a few times a year and learn from each other.  When I first took the head of sales role at HubSpot, I had coffee with around 30 VPs of Sales.  I asked them every question in the book about scaling sales organizations.  There were a half dozen folks I really connected with.  I wanted to spend more time with them.  So, I asked the 6 of them if they would be interested in grabbing dinner once per quarter.  They all said yes.  So each quarter, we all showed up to dinner with a problem we were having or working on.  We spent approximately 20 minutes on each person’s issue.  7 years later, we still hold the quarterly dinners. It is amazing to see how much the attendees have grown in their careers.  I probably learned the most about scaling sales teams from the conversations at those dinners.

Lean Into Technology

Technology is everywhere today.   Lean into it, even if you are not an engineer or in the product division.

If you are passionate about sales, lean into technology.  Legacy sales people used to gain an edge with great sports tickets or exclusive country club memberships.   Today’s top performing sales people get an edge with technology, not exclusivity.  Use free tools like to make selling easier and create a better buying experience for your customers.

If you are passionate about marketing, lean into technology.  Align yourself with the principles of growth marketing that are taking the industry by storm.  Learn to code.  Learn design skills.  Learn quant skills.  You will be an extraordinarily valuable marketer.  One of our marketers, Anum Hussain, took a coding class on her weekends last month.  That is what you should do.

In closing, and this may sound strange coming from a guy that has preached a lot about data-driven management, don’t over think it.  It is life.  Things happen for a reason.  Figure out which natural gifts you have been blessed with and use those gifts to make the world a better place.