CIO Spotlight: Prasad Ramakrishnan, Freshworks

What roles or skills are you finding (or anticipate to be) the most difficult to fill? “… the role of the business analyst or IT product manager as it is being referred to nowadays, is very critical.”


Name: Prasad Ramakrishnan

Company: Freshworks

Job title: CIO and CISO

Date started current role: October 2018

Location: San Francisco, CA

Prasad Ramakrishnan is the Chief Information Officer (CIO) and Chief Information Security Officer (CISO) of Freshworks, leading the company’s IT vision, strategy and execution. Ramakrishnan is a seasoned IT professional, SaaS evangelist and go-to thought leader on all things cloud and security. His expertise is critical to the success of Freshworks products as well as global work culture. He spearheaded the company’s sustained connectivity in response to the pandemic despite weak internet infrastructure in India. Before Freshworks, Ramakrishnan was CIO at Veeva where he took a democratic approach to software adoption and empowered his employees - the would-be users - to decide on the software they would use. His team voted for Freshservice, Freshworks’ ITSM (IT service management) offering. Ramakrishnan became an early adopter, customer and advocate of Freshworks - and he liked it so much he joined the company.

What was your first job? My first job was as a product development engineer at Wipro, one of the major IT solutions companies in India.

Did you always want to work in IT? Growing up, I had a passion for math and science and wanted to become a mechanical engineer. I took a couple of programming classes during my undergrad years and found that I was very good with programming languages and computers. The personal computer era was just dawning at that time in the mid-80s. I pivoted from mechanical engineering to the world of computers. The rest, as they say, is history.

What was your education? Do you hold any certifications? What are they? I received my bachelor’s degree in mathematics and a diploma in business administration from Madras University in Chennai. I have a master’s in computer applications from Anna University in Chennai, and an MBA in global management from the University of Phoenix.

Explain your career path. Did you take any detours? If so, discuss. I started my career in product development and then moved into consulting, where I went on to head delivery and implementations. I found my “IT calling” when I joined Brocade in 2001. I decided within a year or so of moving into IT that this is where I want to be, and I worked my way through the corporate world to become a CIO and CISO.

As a consultant, you never really own the aftermath of the implementations and that always bothered me. I found that when you are in IT, you not only own transforming the business, but also own all the good and bad decisions you make along the way. This makes you a better leader and a better technologist. I love solving complex problems, and when you are in IT, you work with an ever-changing landscape - where the tech platforms around you are evolving AND the internal business processes landscape is also changing. This is a perfect recipe for innovation, akin to changing the wheels when the train is moving at 90 mph. That excitement and the ride is why I wanted to continue and build a career in IT.

What business or technology initiatives will be most significant in driving IT investments in your organisation in the coming year? In response to the pandemic and economic environment, we’re redefining and refining our business processes and systems to deepen our engagements with our customers. As such, we’re increasing investments in our customer engagement, analytics and security capabilities. Capacity planning and capacity expansion for virtual environments, as well as data exfiltration and data loss prevention (DLP) are additional key areas to stretch the value of our IT dollars in this new normal. Enhancing our overall security posture is vital to stay a step ahead of any potential new threats presented in the COVID era.

As a post-pandemic world continues to take shape, real estate investments, corporate network-related investments are being replaced by security-related investments. Security and data prevention are becoming a higher priority, and our team recognises that even in more challenging times, these investments will help us thrive economically through and after the pandemic.

In addition, the way we engage with customers and sustain the engagement is also changing. Investments in integrations to Chat, IM, Slack, WhatsApp will become even more critical. CIOs will need to invest in automation via artificial intelligence, machine learning and bots in order to handle the distributed business processes.

What are the CEO's top priorities for you in the coming year? How do you plan to support the business with IT? Our origins started in the cloud and that digital-first mindset enabled us to adapt quickly and continue our rapid growth, in spite of the pandemic. Our business starts and flourishes with great IT and our CEO is well aware. Our goal as a company is to help businesses delight their customers and employees. But unlike the legacy SaaS vendors, we do this in a way that is fast, simple and easy for our customers. Freshworks plans to continue building its IT infrastructure to continue our success with realising this mission.

The pandemic has amplified the need for cybersecurity protections. As a CISO and CIO, protecting data and information is my number one priority and the pandemic has increased that focus. Each product at Freshworks is created with security to the customer first. Throughout the pandemic and into 2021, we will continue strengthening our cybersecurity posture.

Does the conventional CIO role include responsibilities it should not hold? Should the role have additional responsibilities it does not currently include? The role of CIOs is ever-changing with new technologies and trends emerging constantly. In terms of responsibilities, I’m prepared and happy to wear many hats. I serve as both CISO and CIO of Freshworks, so it’s important for me to look at the roles holistically.

One trend I’m seeing is forward-thinking CIOs are recognising that software success is inextricably linked to end-user success. As such, they are abandoning the command-and-control approach to purchasing software for a more inclusive, democratic approach that includes administrators, managers and most importantly, end-users.

The sheer volume of solutions on the market continues to explode. It’s the CIO’s job to analyse all of these solutions and discern what will give their company a differentiated edge. Correctly assessing the value of these solutions will become increasingly important as more companies move into the cloud.

Are you leading a digital transformation? If so, does it emphasise customer experience and revenue growth or operational efficiency? If both, how do you balance the two? Digital transformation for any company should encompass a balance of both customer experience, revenue growth and operational efficiency. At Freshworks, we are empowering our customers by making sure their customer experience is at the forefront of our mission. The operational efficiency for our customers helps them succeed through rapid acceleration to cloud and SaaS-based platforms. Internally, our operational efficiency (including cybersecurity needs) helps our employees work more productively, and we've also invested in tools that allow online collaboration and work from anywhere, including Workplace, Zoom and Slack.

Implementing any kind of technology transformation requires leadership and direction from the top. Leaders need to make communication a focus — there must be a clear articulation of why, when and how you are doing what you are doing. In addition, championing from the CEO needs to clearly communicate not only why things are changing, but also drive adoption of those changes. Most importantly, developing a continuous feedback loop allows you to make adjustments as needed to respond to the shifting landscape.

Describe the maturity of your digital business. For example, do you have KPIs to quantify the value of IT? We are a fast growing product company that was born in the cloud. As with any fast growing business, the systems and processes always play catch up with the growth. We use a method which I refer to as ‘metrics that matter” to drive metrics and analytics in the organisation. We use metrics such as “project timeline - planned vs. actual”, budget vs. actual expenses, first call resolution, time taken for onboarding, trend with false positives in our security alerts, etc. to measure how IT supports the business.

What does good culture fit look like in your organisation? How do you cultivate it? Freshworks is a heart-driven business - we treat each other like Kudumba (family) and this has been key to our successes. By encompassing Kudumba in everything that we do, we enable our customers to feel comfortable and at ease with a company they can trust.

For many tech companies, building a culture is usually not top of mind nor purposeful, but I have found it to be foundational – the difference between success and failure. Without the feeling of family, companies can lose sight of their goals and ultimately, lose customers.

Our wellness as individuals is not taken lightly by the company and as a leader on the executive team, we are constantly discussing how we can give our employees a sense of belonging even when we are working in thousands of “home offices” around the globe.

It is vital for employees to keep a healthy work-life balance and we make that a priority by allowing necessary downtime, including mental health days and impromptu company holidays, encouraging micro meetings to save time and workload, and offering “No Meeting Days.” Culture retention and appreciation is another important aspect of strong work-life balance - we prioritise recognising and celebrating our employees virtually for their hard work.

The pandemic has given companies a unique opportunity to listen to employees and recognise the necessary tools that individuals need to succeed while ensuring their mental and physical wellness. At Freshworks, we launched a powerful photo campaign #AndItsOkay to give a voice to employees struggling with the effects of COVID-19 and shine a light on mental health.

What roles or skills are you finding (or anticipate to be) the most difficult to fill? We have a 100% cloud and SaaS-based technology stack. The industry at large is still moving from a traditional on-prem based tech landscape to a cloud and all SaaS footprint. In this new world, the role of the business analyst or IT product manager as it is being referred to nowadays, is very critical.

Analytics environments have evolved to a model where we are not just looking at the rear view mirror, but are looking at a model of predictive and future looking analytics. These roles are hard to fill.

Cybersecurity roles have always been hard to fill and will continue to be in the future. The threat landscape is more complex now than ever before and will continue to be a challenge.

What's the best career advice you ever received? One of my mentors said “If you don’t enjoy what you are doing, don’t do it here.” The journey will be more bitter for you and for everyone around you if you do not enjoy what you are doing. 

When I moved into IT and realised that I enjoy being in IT, I went to my CIO and told him that I wanted to be a CIO someday. His advice to me (which he was fully supportive of) was to rotate between different roles within IT to get an appreciation for the various functions and business areas. Doing this has enabled me to gain first hand experience in various business processes in sales, marketing, finance, SOX, infrastructure, etc.

That is one of the reasons why I encourage my team members to explore different roles within the team and to bounce between IT and other organisations, such as Product / Engineering, to give them a rich perspective of what is out there. This will enable them to find their ultimate passion and help them achieve their career goals.

Do you have a succession plan? If so, discuss the importance of and challenges with training up high-performing staff. Employee development is an art and a science. The greatest engineers don’t necessarily have to be great leaders. It is important to define the various roles that are required to run the business at the different stages of evolution, and map the “right” people into these roles. It is important to acknowledge that we will, in some cases, not be able to find someone internally who is operating at the level we want them to operate - in which case we have to go outside for the right talent. The key to success is to provide an environment where talent can thrive. As a leader, it is your responsibility to constantly look for key talent, and invest in their potential. Provide opportunities, whether internal or external to your team, to keep high achievers motivated.

What advice would you give to aspiring IT leaders? Aspiring IT leaders should know that honesty and integrity are often overlooked in competitive workplaces, but will ultimately be the key to success. It’s also important to always continue learning and adapting to the shifting industry around us. As it always has been with IT, putting yourself in the shoes of the end user will lead to a better, more successful software or product.

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