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Swapnil Jain of Observe.AI: “My recommendation is to be in touch with your people”

My recommendation is to be in touch with your people. As you grow as CEO, and add the next layer of management, it’s very easy to lose touch with your people because you are only hearing from managers. You don’t want to be a CEO who lives in a bubble of what you think is […]

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My recommendation is to be in touch with your people. As you grow as CEO, and add the next layer of management, it’s very easy to lose touch with your people because you are only hearing from managers. You don’t want to be a CEO who lives in a bubble of what you think is happening in your company, as opposed to what is actually happening in your company. Make sure you take the time every week to talk to people, understand what they are working on, hear them out, get feedback..your job is to listen.


As part of my series about the “How To Take Your Company From Good To Great”, I had the pleasure of interviewing Swapnil Jain.

Swapnil is CEO and co-founder of Observe.AI, a Contact Center AI leader that transforms customer experiences and improves agent performance by helping top brands analyze 100% of calls and streamline quality assurance workflows. During his time leading Observe.AI, the company has raised 88 million dollars in funding and added 150 customers. It has also been named as one of Forbes Top 50 Most Promising AI Companies, Gartner’s Top 25 Software Startups, and one of the fastest-growing startups in the Bay Area. Swapnil was Twitter’s first employee based in India, helping open the company’s offices there and spearheading its first India-based engineering teams. He is based in San Francisco, CA.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Thank you. My background is in technology and engineering. I graduated from the India Institute of Technology, Delhi. I worked as an engineer at Twitter (as the first employee based in India) before opening Twitter’s first engineering office as a technical team lead. I always wanted to lead my own company, and founded Observe.AI in 2017 with my two co-founders after doing extensive market research in India and the Philippines by walking the halls of contact centers.

Observe.AI helps companies to improve the performance of their contact center agents so that they can provide the best possible experience to their customers. We just announced our Series B financing that brings the company’s total funding to 88 million dollars, including 80 million dollars in the last 12 months.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

In 2016, I was exploring the idea of starting a company with two of my friends from IIT Delhi. We were young people with a lot of energy and hustle, and we were looking for the ideas and investors that would excite us. After four months of exploration together, both of them decided to not continue the entrepreneurial journey for personal reasons. I was alone in India without a job, and without any co-founders or an idea for a business. My friends were doing amazing jobs, and I was struggling.

What led me to continue when things were really hard was my sheer passion for wanting to start up a company. I knew this was going to be heard going on, but what kept me going was the whole concept of hustle and grit. I knew I really wanted to lead, and that kept me going as I continued to look for co-founders and ideas.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

One common mistake that I was avoiding, but knew I would end up making was to stop thinking strategically at the beginning of the process. When you are trying to start up, and you don’t have an idea, you sometimes run into the trap of thinking short-term and tactically because you want to show progress. I think of Mike Tyson’s famous saying that everyone has a plan until they get punched in the face. When you start up, you have an idealized vision of the kind of company you want and the kind of cofounder, and can easily get distracted by tactical thinking. My takeaway: Calm down and make sure that you write down your core principles and values so that when you get punched in the face, you don’t start making short-term decisions. We continue to follow this philosophy at Observe.AI today.

What do you think makes your company stand out? Can you share a story?

One thing that I believe stands out about Observe.AI is that we really understand the persona and culture we are building our company for. When people think about Silicon Valley, they tend to think of all the COOL stuff that people are building. We are building for a persona that many people in the Bay Area might not understand. Many people don’t even know what a call center is, or know a call center employee. We have a deep understanding of this persona based on all the background research we did in India and Manila. This makes us very unique. We believe that no one else in the Bay Area can match our depth of understanding of the people in the call centers and the problems they are facing.

Another thing that separates is that we do a very good job of taking care of our employees. Every company talks about culture, values, and people, but how can they show it? I personally believe that we are creating a place where everyone likes to work. This is evident from our Glassdoor reviews, what people say about us on LinkedIn and other social channels, as well as our attrition rates. You can verify that we are committed to our culture.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

The CEOs main responsibility to enable others to operate the company with them, and to really represent the company’s values and culture. Regarding burnout, as a leader, you have to be conscious about it. If you’re not aware of burnout, you are not going to be able to empathize or try to solve for it.

My recommendation is to be in touch with your people. As you grow as CEO, and add the next layer of management, it’s very easy to lose touch with your people because you are only hearing from managers. You don’t want to be a CEO who lives in a bubble of what you think is happening in your company, as opposed to what is actually happening in your company. Make sure you take the time every week to talk to people, understand what they are working on, hear them out, get feedback..your job is to listen.

Ok thank you for all that. Now let’s shift to the main focus of this interview. The title of this series is “How to take your company from good to great”. Let’s start with defining our terms. How would you define a “good” company, what does that look like? How would you define a “great” company, what does that look like?

I have never thought about good vs. great, because I always thought about wanting to be the best. I want to push the boundaries from a customer experience and from an employee experience, so it’s very hard for me to talk about where to compromise, where to be just good.

A good company is one which is not pushing boundaries and not trying to innovate. It will be okay with 30% attrition rate or a 4.0 Glassdoor rating, 40% YOY growth. A great company is not going to be okay with that.

Another example of a good company is one that sells products that buyers like buying, but users don’t like using. A great company will try and do both.

A good company settles, but a great company is building for the future.

Great companies will have CEOs, founders, leaders who don’t think of the company as their job. Great company leaders will feel the pain if the company doesn’t do well. They won’t sleep at night if the company isn’t growing fast enough or employees are unhappy, and a great leader will take ownership of these issues too. Great companies are always striving to be the best.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. Can you help articulate for our readers a few reasons why a business should consider becoming a purpose driven business, or consider having a social impact angle?

I 100% agree. If you look at what defines people, it is never about money or materialistic things. Country is an amorphous concept that will get millions of people thinking in the same way. Religion, sports fans… a lot of these are concepts. What binds people together are the stories and purposes behind those concepts.

This happens at a company. You can’t motivate people with salary and short term goals alone. You need to connect with them on a deeper level — what is their purpose and why are they at this company? What problems do they want to solve? As a CEO, you want everyone to have the same mission and vision, and you have to have a purpose to align everyone in the same direction.

What would you advise to a business leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth and “restart their engines”?

From a leadership perspective, always be learning. As a leader, your job is to listen more and speak less. My job is not to explain things to people. If you are stuck, go on calls and keep learning, understand their problems, talk to other CEOs and learn from them — the only way forward is to continue growing. That is the only way to scale. Look at Observe.AI. We went from 15 people to more than 120 this year. With that kind of growth, the meaning of leadership, how to organize the company, establish processes, and establish culture changes. You have to evolve.

From a business perspective, it’s important to get a philosophical understanding of why you are stuck. As the company grows, people have a hard time getting to the root of problems. Understand the why. Ask the questions.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

A business is solving a problem a client has. With changes of economy, people’s needs change and evolve. You have to keep adapting to the clients’ needs. The buyer will always have needs. Either you will capture them or someone else will. When the market changes, needs change — can you cater to that? Does your product satisfy the new buyer needs? How soon can you adapt strategies, your go-to-market plan, product? For large companies, it takes a lot of time to adapt and realign. Startups are used to doing shorter-term planning, so surviving change is much easier.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Goals and alignment. If you can design goals for the leadership team and managers, in a way that aligns really well with the company goals, you can create an amazing growth engine with everyone working in the same direction. This can create so much momentum. It’s a simple concept, but very hard to execute because it requires having a company goal. How do you set a big goal and then roll it out to every single person in the company? Even after 1.5 years of trying to do goal setting and alignment, we are still working on this at Observe.AI. This is important because if you aren’t doing it, then you have people driving the company in different directions. Think of a car where the steering wheel and tires are going in a different direction. Will this car function? No. It’s the same with companies.

As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies a business should use to increase conversion rates?

You have to think about the entire customer journey. Let’s use a simple example of website conversions. What does the buyer need at this stage of the customer journey? The customer comes to your website with a need so you should talk about your solution in the customer’s language. You only have to solve for one problem at this point. You don’t have to solve every possible problem .

On your website, customers are asking if your product is worth a demo. Satisfy that need, and then solve for other needs at additional points in the sales funnel. To increase conversion rates, solve for the buyer needs at that particular stage of the customer journey, that will then lead them to the next stage.

Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that a business can earn a reputation as a trusted and beloved brand?

If you try to link this to human psychology, when you are trying to buy something you usually buy from someone you know or from someone who comes highly recommended from someone you trust. If you trust me, you are likely to trust my recommendation. If I come to a website and see a lot of good references and testimonials from people like me, I can trust that brand. If I see that no one has recommended this product on the website, how can I trust this company? Convince your customer that their peers in the industry have trusted you, and you create trust in the buyer’s mind.

Great customer service and great customer experience are essential to build a beloved brand and essential to be successful in general. In your experience what are a few of the most important things a business leader should know in order to create a Wow! Customer Experience?

A lot of people confuse customer experience with customer service. Customer experience is not just the service you provide when the customer has a pain point. It’s about the experience the customer has every single time the customer interacts with any property of the company — sales, renewals, talking to the CEO, LinkedIn — every single touchpoint with a brand is customer experience. A very good example of this is Apple. Everything from launching a product, how they talk about it, the sales process, the in-store experience all ties back to their brand.

You can’t think about customer experience in silos. It is not just customer service. You should think of customer experience as a fabric that overlays every single touch point customers have with your brand. Use the framework of customer experience in every single interaction and not just customer service.

What are your thoughts about how a company should be engaged on Social Media? For example, the advisory firm EisnerAmper conducted 6 yearly surveys of United States corporate boards, and directors reported that one of their most pressing concerns was reputational risk as a result of social media. Do you share this concern? We’d love to hear your thoughts about this.

Social media reputation is one part of creating a trusted and reputable brand — it’s all part of your reputation. We are not a reactive brand on social media. We are more of a proactive brand, and we control our messaging and our brand identity. We believe this allows us to be more forthcoming. You need a social strategy, but as a company, Observe.AI doesn’t view this as a risk.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

If you are a product founder, you like to focus on building a great product. If you are a go-to-market(GTM) founder, you focus on selling, sometimes before your product is ready. Both have huge flaws. With product founders, you might lose a lot of time if you don’t test the market — you could be building something in a silo. If you are a GTM founder, you might be selling things you don’t have or you will never build, essentially vaporware.

It’s a challenge as CEO to bridge the gap between both. There’s a great saying by Reid Hoffman that essentially says, “If you are not ashamed of your first product, then you are late to market.” Make sure you are testing your assumptions with customers.

In terms of advice, I would advise you to hire as needed, but not too early. One challenge with building teams is that the more you build and add on, the more dissolution of alignment you get. If you are bloated, the vision, alignment and execution gets harder. Align quickly and move fast.

It’s also important to understand your market really really well. Either you start with the idea that you want to start a company and need a market and an idea, or you are deeply in a market and want to use that insight to start a company. With the former, you have a hammer and are looking for a nail — it’s very easy to get excited about ideas. Do your research and your learning, and make sure you -understand the market and the problems and the personas before you commit.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

If I tried to extrapolate what we are doing at Observe, I think a movement could be how corporations and business leaders can think about their employees and their workplace. Large corporations have a tendency to treat employees as people who are there to get a task done. If you use this framework, you will always look at people as resources and as resource optimization problems. I’m strongly against this. People spend a big part of their life in workplaces. If you are treated as a resource, this will not lead to a satisfactory or happy life. The movement I would like to push is around how corporations can start treating their people as people. How do we create an environment where these people can have a happy, satisfactory life? How can CEOs stop thinking of people as task masters? When you look at it through this lens, people say you are not thinking about profits or shareholders. I don’t think this is true. When people are happy, they are more productive, happier, more involved. They care more about the company, and they want to drive it’s growth.

How can our readers further follow you online?

You can learn more about Observe.AI on our website, or follow us on Twitter and LinkedIn.

This was very inspiring. Thank you so much for the time you spent with this!


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