Employee Spotlight

Employee Spotlight: Michael Gugliotti - Director of Sales Enablement

Michael Osakwe
May 1, 2023
Employee Spotlight: Michael Gugliotti - Director of Sales EnablementEmployee Spotlight: Michael Gugliotti - Director of Sales Enablement
Michael Osakwe
May 1, 2023
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Michael Gugliotti joins Nightfall as our Director of Sales Enablement. Mike's career has taken him on a rewarding journey that's combined his passion for education, with customer success, and sales. Given his very unique pathway to sales enablement and his roles at companies like Datadog and Forter, Mike brings a very detailed perspective on what it takes to build a world-class enablement function.

Can you share a little bit about your background? How would you describe your journey up until this point in your career?

My journey to this point in my career has certainly not been a straight line. When I graduated college, I didn’t really know what I wanted to do long-term, so I was a bartender for a few years while also pursuing passion projects on the side. I eventually moved to Boston where I was lucky enough to get a call center job at a medical software startup called athenahealth, which was 500 people at the time. While I originally intended that job to be a brief detour to something “bigger and better,” it actually ended up being the start of a ten year career.

I held multiple positions during my time at athenahealth, but long story short is that I went from CS, to Sales, to Enablement which taught me all about the customer lifecycle and how to educate people on that. After about ten years at athenahealth, the company grew to 5,000 employees. I think by nature I’m a builder, I’m someone who likes building systems and processes from scratch which is just not possible at a large company. That’s when I left to do the same thing at Datadog, which had coincidentally had about 500 people at the time. I stayed with Datadog for three years, helping provide world class enablement and onboarding for over 1,000 people. By the time I left, the company had grown to 2,500 employees.

At the time I was seeking more of a leadership position and landed at Forter as the Global Head of Sales Enablement. I started off as a team of one, but after my first year was able to bring someone else on. During that first year at Forter, I established not just an onboarding program but other programs for keeping the skills of current employees fresh. I won an employee achievement award for my efforts, giving me confidence that the enablement program was on the right track.

After about a year and a half at Forter, Mike Levy, Nightfall’s Director of Sales reached out to me about Nightfall. When I learned more about the technology, as well as the people and the agile nature of the team I’d be working with, I knew it was an opportunity I just couldn’t pass up. 

You spent 10 years as the director, creator, and owner of your own music marketing & management company. How was that experience and what made you leave that world?

In college, I enjoyed playing guitar, singing, and writing my own songs, but I admittedly wasn’t very good. I was, however, fortunate to be friends with a few really talented musicians. Over time I had the realization that I was better suited to help them book gigs and promote their music. In the first few years, I booked some shows and even attended a conference held by NACA (National Association For Campus Activities) to help one of my musicians book a college tour. I would put together press kits, attend lots of open mics, and become a regular at a few small music venues that artists I worked with would play at. One of the biggest accomplishments I achieved during that time was getting an artist a licensing deal with MTV to use her music on their reality shows The Real World and Road Rules. Over time, the company took on different forms, later on serving as more of a music blog that promoted new music than a management company.

While it was definitely fun to be so involved in the music scene, after ten years it felt more like a hobby, especially since I never really made any money off the business. Therefore, I decided to officially shut it down in 2017 and focus on my career in Sales Enablement instead.

Healthcare is a very specific niche, how did you end up there?

Purely by chance, at first. Over time, however, I found healthcare to be fascinating. There are a lot of issues with our healthcare system today. Information about how to read an EOB or just understanding your insurance coverage is often hard to come by or intentionally complex. So it was really exciting to work for a company that was trying to unravel some of the mysteries behind it and demystify what healthcare is.

Being part of a mission that focused on helping solve some of these problems was truly motivating. After a decade in the healthcare space, it was a bit difficult to walk away, which is why it feels quite serendipitous that what we do at Nightfall contributes to helping healthcare companies remain HIPAA compliant.

Partway through your time at athenahealth you switched from Sales to Enablement? What made you make the switch? Was this a logical and natural transition for you given your strengths and interests?

The short answer here is, yeah, it was a logical and natural transition in hindsight, but as I said in the beginning my career was not necessarily a straight line.

So after nine months in the call center role at athenahealth, I was offered a role as an Account Manager—what is basically a Customer Success role today. I spent three-and-a-half years in that role learning more about the company, the healthcare industry, SaaS applications, and managing customer relationships. It was also during this time that I decided to pursue a Master’s degree in Education because I had an interest in working for a college in Student Activities. However, when I began applying for jobs at colleges, they were quick to inform me that I would only make about half of what I was getting paid at the time. Having just racked up two years of loans from graduate school, that concept didn’t seem too appealing. 

So I pivoted to Sales, after being encouraged by friends. I tried it for a few years and discovered I really loved it. However, I wanted to find a path to leadership which brought me back to Customer Success as a Team Lead. Back in CS I found that a lot of reps there valued me for my sales knowledge and, in addition to managing a book of business, I was creating content and training to help educate them on how to sell and do referrals. This initially started out as a sort of side role working with Marketing and Channels, but I got noticed by some people who would go on to own the enablement function at athenahealth. When a role opened up on the Enablement team, I joined and began onboarding reps full time.

Looking back at everything - my move from CS to sales and back -  plus my Masters of Education, all led to me understanding the customer lifecycle fully. There are all the operations like knowing how we acquire customers, how we manage them, and how we help enable them. With what I had learned in my Masters program, I was able to take this and make lesson plans to educate and empower my teammates. So it was all a natural progression, just one I couldn’t predict at the time. Looking back now, though, it all makes so much sense.

When you left athenahealth, you moved on to a startup in Datadog. How was that transition? What made you seek out a startup?

When I first started at athenahealth, there were about 500 people working for the company. By the time I left, there were over 5000. The size of the company definitely correlates to the way the culture is. For example, how much red tape is there?

When you see a company 10x over the course of ten years, a lot of things change. Culture for one, but also the nature of roles and the direction of certain departments. While I credit my time at athenahealth as a testament to where I am today, I felt that I had outgrown the company and wanted to go back to a smaller startup where I could have a bigger impact. I was lucky enough to be recruited by Datadog and the challenge of taking on the onboarding program was exciting to me.

At the time, I couldn't tell you what cloud infrastructure was, and it took a long time for me to get up to speed and understand it all. Luckily, a lot of sales skills translate over—the discovery process, sales motions, etc. - making what I knew about Sales applicable in any industry. The idea here is just how do you make it fit with your industry? You have to learn the product to understand the nuisances of the industry and your solution.

Over at Datadog I ran world class training programs, both remotely and in person. Besides the onboarding program, which I ran for 23 weeks every year for three years, I did lots of internal certification programs and QSRs.

After three years at Datadog, I was trying to really figure out how I could get to the point where I was a true leader. I loved the people I worked with at Datadog. Loved the person I reported to, loved my team, but there wasn't a clear path forward. So when the role at Forter to be the Global Head of Sales Enablement became available, I decided to take go for the opportunity.

What brought you to Nightfall?

Startups are exciting and are where ingenuity lies. It's where people go to try new things and ideas. If you're looking to grow your career, it's a great place, as well. It's really hard to progress when there are layers upon layers upon layers of blockers at a company and they have a very set, regimented way they want to do things.

If you're at a large enterprise style company, they might not be open to just creating new roles, creating new opportunities or, kind of shifting away from the way they're working today because they have that blueprint of success already. Unless you give them a very compelling reason to do otherwise they're going to stick to that. Whereas if you go to a startup, you get to try on a lot of hats. However, it's definitely a double-edged sword. It's an exhausting thing to work at startups because you're taking on so many different roles and responsibilities.

With that in mind, the prospect of being able to build a world-class enablement program is exciting. I want to take on more responsibility. I want to take on more challenges. I also then want to hire more people to help manage that program so I can think of what other things we can do from a strategic position.

Beyond that, the product is amazing; it's exciting! I found cloud DLP to be a very approachable subject. It made sense. What I also love is the fact that I had worked in healthcare for ten years, cloud monitoring for three years, and fraud prevention and protection for a little under two years. All those industries are applicable to what we're doing here at Nightfall. All those companies I've worked at had the same problem. Sensitive data is everywhere and a lot of times you don't know where it is or it's where it shouldn't be, so I intuitively understand what Nightfall is trying to accomplish.  

What’s the most important lesson you’ve learned about enablement through your career (something that could have helped you at the beginning of your career)?

Be patient, believe in what you already know, and don’t be afraid to ask for help. I’m someone who can’t always see the light at the end of the tunnel from the outset, which is why I love routines and predictability. Knowing what steps to take next make the hard choices easier. It’s why I love building mutual action plans. 

However, when I first started in Sales Enablement, I regularly felt like I was unsure of myself or my abilities. I also felt like I couldn’t necessarily tell anyone that I wasn’t sure what I was doing, so I struggled for a while before I was willing to ask for help. I’ve been lucky enough to work alongside some incredibly talented people along the way who not only supported my growth but showed me that I don’t have to take on every burden by myself. Asking for help isn’t a sign of weakness, but rather the faster way to get things done. No one can be a master of everything, so when in doubt, look to those around you for a helping hand.

Do you have advice for anyone starting a career in your field? How would you recommend building out a career path that mixes your passions like you have?

My recommendation is to familiarize yourself with a few Sales Methodologies. I'm a bit bias considering I’ve spent the last ten years using Command of the Message, but it also helps to know what else is out there (i.e. Challenger, Sandler, Value Selling, SPIN, etc.). No need to be an expert, just know the basics concepts.

I would also recommend learning about how to build a lesson. It's one thing to understand a topic, but it can be difficult to convey that knowledge to others. I generally look at a lesson first by determining what the key takeaways should be and then building it out from there. It also helps to use analogies when discussing challenging topics/concepts.

Lastly, patience is key. No one becomes a master of anything overnight. It takes months, if not years, of practice and learning. I can honestly say that I’m still learning new things all the time. You should always be trying to get better.

Not that any of this is ever easy. It’s all really about understanding your limitations, knowing what you can accomplish, and then setting realistic goals so you don't feel that you're stretching yourself too thin.

Are you reading, listening to, or watching anything interesting? Could be industry related or not.

I listen to podcasts every day, usually while walking my dog. Some of my favorites are Freakonomics, The Audible Ready Podcast, Revenue Builders, Science Vs and, more recently, The CISO Series podcast. Some of my favorite books are Never Split the Difference by Chris Voss and The Qualified Sales Leader by John McMahon. While I don’t get to read as much as I’d like, I’m currently reading This is What It Sounds Like. Considering my background and interest in music, it was right up my alley. My sister was kind enough to send it over as a “thinking about you” gift.


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