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Michael Massad Headshot

Michael MassadVice President

Elsewhere Operating Advisor Spotlight: Sanjay Castelino

Sanjay Castelino Headshot

Welcome back to our OA Spotlight series. Elsewhere operating advisors (OAs) are accomplished software executives who partner closely with portfolio companies to accelerate their growth. This is a unique differentiator about Elsewhere — we provide strategic support to all of our portfolio companies through the guidance of our Operating Advisors. Advisors may serve as board representatives, fractional resources, or executive officers, depending on the unique needs of each portfolio company.

Recently, we spoke with Sanjay Castelino, Chief Product Officer at Snow Software and Elsewhere’s board representative at Sellers Shield. Sanjay has held a variety of different positions during his near three decade tenure in the technology industry. During our conversation, he offered valuable takeaways about communication strategies and measuring success for himself and his teams.

Tell us more about the variety of roles you’ve held in the technology industry.

I started off as an engineer, dabbled in management consulting, and have since held roles in product and engineering, marketing, revenue operations, and business development at traditional software and SaaS companies. In terms of titles, I’ve served in every role from software engineer to product marketer, vice president of business development, Chief Marketing Officer, Chief Product Officer, and more.

Though some may see this varied background as almost sporadic, the variety has actually been really valuable to me. I’ve had the opportunity to see how companies operate from a number of unique perspectives, and learn how different financial models work for those businesses.

What is your role as an Operating Advisor with Sellers Shield?

I serve as a board director for Sellers Shield and provide guidance on the go-to-market strategy. In terms of product development, I help the team think about the value of the products they are selling and what’s most competitive and appealing about their offering. My goal is to help position the company for sustainable long-term growth. I have a unique perspective based on my work experience that can help guide the team to make decisions that benefit them in the long run, instead of just providing a Band-Aid solution in the moment.

How do you measure success for yourself and your teams?

Measuring success is really a personal metric. For me, success stems from asking myself if I’m solving interesting problems and helping the people around me move forward. Especially in my director-level roles and above, I place a lot of value in the accomplishments of those who are on my teams. I love to measure success by thinking about what the people on my teams have gone on to accomplish after their time with me.

I think another good measure of success is the scalability and sustainability of solutions. Finding a point solution is great, but implementing meaningful change that provides long-term value is significantly more fulfilling.

There are also measures of success in the outcomes of the product and the team, of course. I like to measure the value we’re delivering to our customers. With modern feedback loops, you can get that information so much faster; you don’t have to wait and see if a customer purchases a second time — there are so many other ways to quickly measure value.

How do you manage stress and prevent burnout?

The impact of the COVID-19 pandemic has been interesting because so many people are forced to integrate their personal and professional lives into one. I think acknowledging that integration is the key to managing this change without burning out.

Think about what you need to do to effectively integrate your work and home life. I’ve personally found that taking a break in the middle of the day, instead of jamming everything into a 9-5 schedule, works best for me. It allows me to communicate with team members in all time zones, while still carving out a chunk of time for myself so I can recharge.

I also enjoy hobbies outside of work. I’ve been flying airplanes for many years. I think it’s important to find and do things you love outside of work, and make time for that, as well.

Have you picked up any new hobbies during the COVID-19 pandemic?

I took up photography. It’s a nice excuse to get outside and it’s something you can easily do by yourself. I’ve been learning new things about photography and spending a lot of time taking pictures and editing photos.

What’s something you always keep on your desk?

These aren’t on my desk necessarily, but I rotate wearing watches from my dad and my grandfather. They are sentimental to me, so I bring the two watches with me when I go into the office or when I travel.

What are you reading about and excited about right now?

I’m very interested in all the different challenges that are coming into play as everyone moves into the cloud. Companies are pushing the boundaries and they aren’t quite sure how to tackle certain issues, and it’s putting providers in a position where they aren’t quite sure what solutions to offer.

In my role at Snow Software, I’m really excited about how quickly our space is evolving. Companies have historically looked at their technology in silos, but we’re bringing new capabilities to market that significantly increase the visibility and manageability within IT and help organizations look across their technology stack. With greater visibility, IT teams can accelerate analysis of their usage and spend, allowing them and their stakeholders to make more strategic decisions about their technology.

What advice do you have for founders who are building and scaling a business?

There are always a million different things you can do when you're starting or scaling a business. Because of that, there’s a lot of noise out there. My best piece of advice is to focus. Get and stay clear on what your strategy is and make sure others are clear about that strategy, as well.

In my experience, the best way to get and stay clear on strategy stems from communication. Sometimes we think we’ve said one thing, but the people we are talking to hear something completely different. It’s important to ask what others heard and clarify that everyone on your team is on the same page. This is especially important for the executive team because more junior team members may be hesitant to ask questions if they assume they should already know something. As an executive, you need to proactively seek out ways to ensure everyone is on the same page. Honestly, this may be some of the best advice I personally received early in my career.

To that point, it’s great to have different people with different ideas and skills on a team, but it can become a problem if you don’t all know how to communicate with each other effectively. What’s worse, sometimes simple communication problems are tough to spot right away. I’ve been in situations where my team is 30, 60, or 90 days into something only to realize that we’re not hitting our goals or getting to our desired end state because of simple communication issues that occurred early on. In these situations, it’s hard not to kick yourself and think “it was totally in my control to fix this months ago.”

We’re always on the lookout for strategic advisors who can help our portfolio companies take their businesses to the next level. Interested in becoming an Operating Advisor with Elsewhere? Contact us today.

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About the Author

Michael Massad

Michael is a software investor at Elsewhere Partners where he co-leads all sourcing and diligence efforts in the IT infrastructure and cybersecurity sectors. Michael strives to connect capital and operational expertise with growing software companies across industries that are located outside of traditional VC hubs.