Sandeep Jain

Sandeep Jain is the CEO & Co-Founder of MonetizeNow. The company offers a first-of-its-kind solution that unifies CPQ, billing and usage monitoring for B2B SaaS companies. Sandeep began his career at Juniper Networks as an Engineering Manager before moving to Palo Alto Networks as a Product Manager for Threat Prevention, and then to Cisco Systems as a Manager of Product Line Management. Seeking a new challenge, he joined InMobi as VP of Business Development, and then became the Director of Mobile Publishing Business Development. He later moved to Plume Design, Inc. as Sr. Director of Product and in 2021, before co-founding MonetizeNow — where he currently serves as CEO.
Sandeep received a BTech in Computer Science & Engineering from the Indian Institute of Technology, Kanpur and a Masters in Computer Science at Purdue University. He earned an MBA in Business Administration from both Columbia Business School and the University of California, Berkeley.

What is your typical day, and how do you make it productive?

As a CEO, there is no such thing as a typical day. Each day I have a mental map of must-do tasks that I keep at the forefront of my mind in order to remain productive.

There is always some new problem or opportunity that needs attention, which keeps things exciting. Of course there are plenty of meetings, decisions to make, and admin tasks to take care of, but my favorite activity is definitely writing for our blog. It gives me the much-needed opportunity to clear my head and crystalize ideas and strategies I’ve been thinking about.

Throughout the day, I try to preserve some time to think. When possible, I will end meetings five minutes before the top of the hour, sneak a walk at lunchtime, and close my laptop when the work day is over to spend quality time with my wife and two kids in the evening.

How do you bring ideas to life?

I like to do my own type of crowdsourcing rather than deciding what to do in a vacuum. When it was time for me to start a company of my own, I felt it was important to be clear on what problem we should solve to provide the most market value. I immersed myself in the problem, researching all the details, shared that with others for their input, and then built the business around the issues I discovered. Before we built anything for MonetizeNow, I actually spoke with over 100 people to get their thoughts on the (quote to cash) Q2C systems landscape. Most of them mentioned their challenges moving from generating a sales quote to accepting money from the customer and recording the transaction in the ledger. Those conversations helped me to realize that the right way to solve the problem was not to build yet another individual solution, but to build and bundle a first-of-its-kind collection of solutions for the whole C2Q pipeline.

What’s one trend that excites you?

I am excited by the potential for automation in the sales pipeline to empower team members to do more fulfilling and important work. It is more cost-efficient to free sales and support teams to have time to speak with clients with the most complex needs while others use the self-service options for simple queries. This means that team members are spending less time doing admin tasks, and more time applying their time and effort to selling.

What is one habit that helps you be productive?

As an entrepreneur, my to-do list is filled with priority tasks, and it can be almost impossible to find the time to focus one’s brain on strategic development of the organization. To help me deliberate, I always share my ideas with as many people as possible. As a result, I can utilize their brain power and experience to develop ideas. Often their experience leads me to new ideas, and helps me to identify pain points that our product should be addressing. I find it extremely useful to receive input from a cross-section of sources for the hard task of thinking

What advice would you give your younger self?

Any future entrepreneur should learn all the roles they can before starting a company. That’s going to require you to get far outside of your comfort zone. When I started out I was focused on engineering roles, but I knew that I’d have to learn sales in order to be successful as a CEO. So, I found a business development role at a mobile advertising company. I learned empathy-driven selling, and gained a real understanding for how to execute the sales process. I am able to use the knowledge to connect with existing and potential clients and close deals. Many CEOs are not effective sellers. They can talk about their product and why they developed it, but to sell they need to put themselves in the customer’s mindset. CEOs can talk about how great their product is but not specifically about how it can solve pain points for the client, which goes back to the empathetic approach. You can be animated and passionate about what you are selling but must work from the customer’s frame of reference. I never would have learned an effective sales style had I not pushed myself early on.

Tell us something you believe almost nobody agrees with you.

Most founders I meet do not agree with my decision to build in public and crowdsource feedback. Usually that “stealth startup” point of view is driven either by a fear that someone will steal your ideas, or a feeling that a revolutionary founder and CEO should “go with their gut” because they know more than their prospective clients. I genuinely believe that the insights I have derived from all those open conversations has borne fruit for us, and we have a better company today than we ever would have if I had focused on being stealth.

What is the one thing you repeatedly do and recommend everyone else do?

Set aside some time to think. It can be during a mundane activity that you do – walking, driving or even while showering. Otherwise, the day gets filled with tasks which will only help you make incremental progress. For exponential progress, you need great ideas and they need some organic thinking time.

When you feel overwhelmed or unfocused, what do you do?

I take deep breaths or do a quick walk or run outside. Deep breathing is a proven biological way to calm oneself. Other than that, I tend to focus on the root cause of the problem and figure out three things–is it completely under my control, partially under my control or not in my control? Just bucketing an issue this way gives me a lot of clarity and mental peace in resolving the issue.

What is one strategy that has helped you grow your business or advance in your career?

My ongoing and recommended strategy is to cultivate a sense of empathy. Empathy is a powerful tool and, I believe, a predictor of future revenues. We build relationships with customers by learning about and understanding their individual issues. I strongly believe if you do right by your customers, they will return the love 10x.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

I experienced one particularly educational failure with my previous startup, which (retrospectively) was set up for failure. The problem was that I picked a space with a very small B2C market with a high degree of variability, and a very broadly defined customer (all podcast listeners). This made it difficult to raise capital, making it hard to scale. I might have been able to build a lifestyle business in the space, but it just couldn’t work as a venture business. What I learned from that experience was that as a founder/CEO, your job is to minimize risks so you must select your business idea carefully and be very intentional about it.

What is one business idea you’re willing to give away to our readers?

One of the problems that I’d like to see solved is the ability to hire training experts for a business on any topic with ease – sort of Yelp for trainers. For example, if I need to hire a management coach for my managers, or someone to run a workshop to help my employees practice better mental health or improve their written communication, I could go to a single marketplace to compare options and select a coach.

What is one piece of software that helps you be productive? How do you use it?

ChatGPT is on everyone’s mind right now — including mine. While ChatGPT cannot replace the empathy and relationship building skills of the sales staff, it can help coders to increase productivity, generate messages for social media, or quick responses to customer inquiries. ChatGPT will never substitute face-to-face interaction, but like other forms of automation, it will free people from more mundane tasks and enable them to focus on big picture thinking.

What is the best $100 you recently spent?

It was more than $100, but I recently got a personal training coach. They helped me to be consistent with my exercise and made it more focused and efficient.

Do you have a favorite book or podcast from which you’ve received much value?

An episode of the a16z podcast changed my life. It was an episode from Andreessen Horowitz on online marketplaces. The VC invested in and out in this podcast space, and was offering a framework for an early stage founder like me. It made me realize what a valuable, free source of information podcasts can be and it inspired me to start a podcast app that curates podcasts by subject matter to increase accessibility. This lead to my finding a co-founder and starting Leela Labs and Leela Kids, which organizes podcasts for children three to 15 years old and packages them in a kid-friendly interface.

What’s a movie or series you recently enjoyed and why?

It is a French series called The Bureau – it is about the French equivalent of the CIA. I really liked it because I think it shows the true workings of an “intelligence” officer with more focus on strategy and negotiations than guns. They also show different countries that you typically don’t see in an American program e.g., Iran, Azerbaijan, Russia etc. If you appreciate fine direction and characters with depth, this is the one for you.

Key learnings:

• Before starting a business, founders must immerse themselves in the problem, researching all the details clearly, share them with others for their input, and then built the business around the issues
• Empathy is a powerful emotion and predictor of future revenues. We build relationships with customers by learning about and understanding their individual issues.
• It’s time we let the idea of the stealth startup die. It hurts founders when they do not share what they are building and what problem they are solving.