July 24, 2018

Career Path - Chris Rossignol, Sales Director - UK & Ireland at ObserveIT

Ever wonder what a day-in-the-life of a Sales Director - UK & Ireland at ObserveIT looks like? We asked Chris Rossignol to find out!

Also, ObserveIT is hiring! Visit their BIZZpage for the latest job openings!

Where did you grow up?  What did your parents do for work?  What was your very first job (before any internships)?

I grew up in Hudson, Massachusetts. My dad is a consultant in the psychiatric healthcare space and my mom teaches ESL. My first job was as a lifeguard at our local country food and golf, best job ever.

Where did you go to college?  What did you study and what were some of your initial jobs out of school?

I graduated from Northeastern University with a dual concentration in Finance and Marketing. Upon graduation, I joined a fellow NU alum at a company called CollegeWeekLive where we ran the marketing team. I was in marketing for almost two years before deciding to join the “dark side” as an Account Executive on the CWL sales team. Not long after, I joined my first Bain-backed company called Stackdriver, which was acquired by Google only 8 months after I started. That’s when I came over to ObserveIT.

How did you make the transition into sales?

Working in marketing gave me a huge appreciation for how hard the demand generation process is (not to mention managing marketing operations, event planning, social media, etc...) as well as understanding and improving the key elements in the lead conversion process. But the more leads we passed over to the sales reps, the more I wanted to be the one following up with them. I have a background in improvisational comedy, and I wanted to use my skills from the “limelight” to represent the company and bring in new customers. I wanted to have a direct impact on the revenue target, which proved difficult to do in the marketing space with our small team, but I will always have a deep respect for marketing and the relationship with sales.

Chris Rossignol
Chris Rossignol's first sale at ObserveIT ($79.34, which set the record for smallest company deal).

Can you share the high-level responsibilities of your current position as Director - UKI at ObserveIT?

Since I joined back in 2014, ObserveIT struggled to build a strong presence in the UK...out of our 1,800 customers, only about 50 are spread across England and Ireland. At the highest level, my job is to increase our customer footprint with a 200% growth rate target by the end of 2018. This includes helping to build and train our UK team, develop our customer success initiatives, and most importantly outperform our quarterly revenue goals by signing on net new customers and expanding installations within our current customer base.

Since joining ObserveIT, it looks like you have held a variety of positions and have received multiple promotions.  What would you say has helped contribute to your success?

I think the key to my success has been that I like solving problems, both large and small. Every role I’ve had at OIT was because we had a “burning fire” in a certain area, and I decided to try and fix it. Being able to identify issues and challenges is important, but you become much more valuable if you are able to fix them as well. For every problem I would run into, I would also come up with a proposed solution and then go figure out how to implement it, because in my mind it wasn’t going to be accomplished by anyone else. This inherently provided an opportunity for me to try new things out, take risks, and build credibility.

Any tips for someone considering a career in sales?

Many people get into sales for the earning potential, but the majority of first-time sales reps burn out or never meet that income level if it’s their only driver. Sales is difficult because it’s a craft...something that you never fully master and always need to keep improving. But that’s also what makes it fun, and keeps things interesting every day. I’ve always been competitive, so I love the idea of earning business from a company who chose me instead of the tens of thousands of other salespeople who are also trying to break in. If you are a good listener, have a natural curiosity in the industry, and believe the technology or product solves a real problem, it turns every day into a game you want to win.

Chris Rossignol During Cold Call Hour
 Chris Rossignol after a sales "power hour".  "My coworkers tried to distract me during a “power hour” cold call blitz...I still booked 2 demos."

Day in the Life

Coffee, tea, or nothing?

Coffee, usually two cups. 

What time do you get into the office?

Chris Rossignol and team members at Boston Best Places to Work Awards
Chris Rossignol (Bottom Far Right) and team members the first time they won the Boston Business Journal's Best Place to Work Award. 

7:15 am.

Every day is different, but can you outline what a typical day looks like for you?

Usually my early mornings and late afternoons consist of prospecting activities (sourcing / company research / cold calling). In between those times, I schedule meetings to move opportunities through the pipeline. But on any given day there are additional time slots dedicated to training and development of the other UK team members, troubleshooting customer issues, or conducting industry research.

What time do you head out of the office?

Usually 6:00 pm, but never a guarantee...

Do you log back in at night or do you shut it down completely?  

I check emails for anything urgent, but try not to fully log back in.

Any productivity hacks?

Block off specific hours on your calendar for an activity you want to accomplish, and stick to it. Doesn’t matter if they are daily, weekly, or ad-hoc projects. During that specific hour, everything else gets put on hold. This helps maintain focus and stay task-oriented.

What are the 3 apps that you can’t live without?

Salesforce, LinkedIn, and Outreach.

What professional accomplishment are you proudest of?

Running the largest deal in ObserveIT history (to date), which took 2.5 years to complete.

Who do you admire or call upon for professional advice?

I have one professor from Northeastern that I always go back to for guidance and advice, and am also lucky to have a mentor from each of the companies I have worked for (CWL, Stackdriver, and ObserveIT). These mentors have been instrumental to my success.

Alyssa Oxner is a Customer Success Specialist at VentureFizz.  Follow her on Twitter: @Aoxner23.

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