Meet Rajiv Ramanan, a person who began his journey with a noble thought. “I want to touch a million lives! I am not a doctor to save lives, but I want to build businesses that can help me touch a million lives”, said he.
With his great learnings, he is on a mission to scale Spendflo -A SaaS buying and management platform that can reduce 30% of SaaS spending.
Even after reaching a stage where most people begin to relax, his thirst for learning remained insatiable, and he continued to seek out more.
Let us read through his amazing journey of passion and persistence…
YC: Hi Rajiv, welcome to Yellow Chapter. We believe that a person is deeply influenced by the upbringing he or she received. So can we start your journey from the very beginning?
Rajiv: 1984! I was born and brought up in Chennai, in a typical lower-middle-class family. Both my parents were working and struggled a lot to come up in life. I grew up with my grandmother. I’ve even acquired some of her characteristics!
My grandmother was a bold woman. She was widowed within two years of marriage and had a child to look after (my father). With no educational background, she struggled her way through and enrolled on a teachers training program. Finally got a job as a teacher in a government school in a remote village – Devakottai.
My father too struggled for a few years to become a CA. My mother was in a central government job. Both of my parents started their career journeys together and worked out things together.
There was never a month when they didn’t have an advance salary to help them make ends meet. But as children, we never felt it. Until I matured and gained a better understanding of things on my own.

@ Family
The Early Lessons of childhood:
1. Live with what you have and make the best use of what you have.
2. If you want something in life, you have to go and get it, nobody will provide for you.
3. You have to fend for yourself, you should have the drive to solve your own problem. Be hardworking and creative enough to deal with problems.
Both our parents retired at quite senior positions from their respective organisations. My sister and I have seen them grow step by step. We love them and at the same time respect them a lot!
YC: Can we talk about what options you were exploring post class 10th? Engineering or Medical?
The Base
Rajiv: Trust me, I had no clue of what to do. I thought I would do whatever my friends were doing.
Till class 10th, I studied in Padma Seshadri Bala Bhavan, Chennai. Cricket was everything for me. I used to spend 6-7 hours a day in the field. I hardly used to study. I still remember I watched the movie- The Mummy, before board exams (laughs). But I was always a very attentive child during class hours. I managed to clear 10th with good grades.

@ PSBB Group
The Change
After 10th, my sister knew I needed a more focused environment conducive to studies to get into a good university post 12th. I was moved to Ahobila Math Oriental Higher Secondary School. It was a huge cultural change for me. There were no fans in classes, and we used to wear veshti as uniforms. We used to do Vedas daily, a very strict and disciplined religious institution. It was like the gurukul of old times.
The school fundamentally believed in practice. Our 12th class syllabus was fully covered before the annual holidays of class X1. All through the academic year of class 12th, we were just practising.
Though from a learning perspective it is not the best method to learn, understand concepts or go deeper into anything, it showed the importance of how practice helps to perform better.
I met a completely different set of people there, and we grew very close to each other. Even today, some of my closest friends are from school. I had made great friends during my education, Ashwin, Alags, Navin, Deepak and my Ahobs group (Swami, Arun, Niranjan, Suri, Kaka and 2 Ramyas).

@ My Ahobs group
Learnings –
1. One institution in my school life helped me learn to think freely and focus on multiple things. It taught me to be confident in what I am doing, and have faith in myself.
2. Another taught the importance of practice. If you focus on something for a short duration and practice around it for a long period, you can perfect it.
After the 12th, Medical was not even an option. Visual communication or Engineering were my two choices. My dad was not convinced with Viscom and all my friends were going for engineering, so engineering was an obvious choice. I got into KCG College of Technology – Electronics and Communications Engineering.
YC: What were your College days like? Suggestions for young B.Tech students out there?
Little things matter!
Rajiv: I used to be in every extra-curricular activity and enjoyed those more than sitting in classes. I grabbed each opportunity that came my way. I still remember I printed my college’s first campus placement brochure.
Suggestions:
An engineering student should focus on two things.
1. Get exposure to multiple fields. Apart from the curriculum, you need to explore the maximum options available. For me, it was the extra-curricular, which helped me hone my program management skills.
While organising placement sessions, I imbibed the lessons of whom to reach out to, how to reach out, and how to ensure companies come to the campus. Basically, I learned how to get things done. It was almost as if I had built my own CRM in Excel. It wasn’t a conscious effort, but that is the result when you expose yourselves to diverse opportunities.
Gopi and I used to arrange field visits and ensured a smooth experience for everyone. I was never hesitant to take the initiative and would suggest the same to other students as well. While ‘managing’ my college music team I met my wife Janani. Right from the time we met, we had a strong friendship built up. We spent a lot of time together travelling to different cities, colleges and performing. That friendship, that implicit trust in each other formed the foundation for our love story and we got married right after college… I was 24 and she was 22!
2. If you think you can create an impact by doing something, be fearless and go for it! If you genuinely have an idea and believe that it has a purpose, then definitely try to work it out regardless of the odds. Also remember it’s ok to fail!
Learning – Books and education are all inevitable, but Life skills are also equally (and at times more) important. I cleared most of my exams by studying notes prepared by my friends Ruby, Ramya and Praga. Madam Sumathi Poobal, our then HOD and now VP, really helped me shape my college days with the right guidance.
YC: Now that we have heard about your college days, can we talk a bit about how you started your career and how it progressed?
Rajiv: 2006 – I started working at Infosys as a Software Engineer. The early training I received at Infosys shaped my professional journey to a large extent. The facilities in Mysore were mind-boggling, and rather than being very creative or largely out of the box, they focused on the basics. Simple things in practice, some codes to follow, and very strict evaluation were all that they stood for, and it made an impact. It made us into strong professionals.
The major takeaways there were:
- Play your strength – Be upfront about what you know and what you don’t. There are various departments, and many roles in any organisation, explore and try to find your strengths.
- Build good relations with your managers – Though I understood tech very well, I was never a coder by heart. My manager, Duraisamy Rajan Palani, realised the same and moved me to the system analyst role. Within 1.5 years I moved to the UK and got huge international exposure which shaped my career to a very large extent. Raj, my friend and manager in the UK, was instrumental in my phase there.
- Build domain knowledge – In consulting, domain knowledge is the key. You have to work hard and deep. I still remember we used to work with clients during the day and reverse engineer through the night time.
- Things are learnable – Treat everyone with respect, no one is above or below anyone. If you don’t know anything today, it’s ok. Put some amount of concentrated effort and you will eventually pick it. All you need is a hustle mindset to grow and excel in your career. Working in a hostile environment, and appreciating different cultures, are all I learned from my Infosys days.

@ Mr. Durai
YC – Why MBA?
Rajiv – Very relevant question, being in Infosys for almost 5+ years, I realised the business side of things is more exciting for me. During my Infosys days, I used to provide data for business decisions. But now I wanted to be on the other side of it.
I wanted to know how decisions were made and what influence those decisions had on businesses. I was always very curious about strategy and marketing. I decided I wanted to be a business guy!
2012 – I decided to join a premium B-School. I applied for a sabbatical. It took me three attempts to clear the GMAT, but I was certain that I would go for the premium institutions. I am a very strong believer in a powerful learning environment with a good peer group.
I joined The Indian School of Business (ISB) – Mohali
Learning –
1. Powerhouse of a great network. My friends at ISB, Saravanan – CEO of TrusTrace especially, are a pillar of support in entrepreneurship and life in general.
2. Exposure to a very fast-paced working environment.

YC – What were the options post MBA?
Rajiv – 2013! I wanted to join Flipkart but was not able to make it through as I was lacking consulting experience they were looking for. Infosys was very keen on taking me but did not find a suitable role for me to join. So I joined as a consultant with Cognizant Business Consulting and moved to the UK again within a few years.
A Twist.
2015 – I had kind of settled in the UK, and my wife also had a job there. It was very comfortable, just 5-6 hours of working. But this comfort was gradually becoming quite frustrating for me. I realised I wanted to do more. My role had certain restrictions too. I was hustling around trying to figure out what else I could do.
Here I met my professional mentor, Ananthakrishnan Sankaranarayanan, who was one of the early employees of Satyam and grew very fast to be one of their youngest VPs and led a consulting business in Europe. He told me that he was joining as the president of a startup in India, in the enterprise mobility space and invited me to join him. He told me that SMAC is going to be the next big stack and I joined – IVY Mobility Solutions Ltd.
We were building Salesforce automation products for large enterprise FMCG and Pharma clients. I got great exposure, I built out a couple of products there. But a year down I realised:
1. In large enterprises, the gap between products and services was blurred. You cannot deliver a pure SaaS product to large enterprises. The amount of customization these companies need is immense and you will eventually need dedicated teams to service them. So if your bandwidth goes in all these things you will not be able to build just products and scale them.
I realised this was not the kind of space I wanted to be in. It worked well for the business but not for me. So I decided to quit!
Interestingly at that time, SaaS was picking up in India. I still remember, it was one of those days, and I was eating in a canteen when I saw a board which read Freshdesk. I Googled a bit about it. I had a friend working there. He invited me to come over, so I went there. That day changed my life!
The Game Changer!
The amount of energy at Freshdesk was unbelievable! All young people around 22-23 years old, doing sales, customer support, product development… was crazy. It was buzzing and you could feel that vibe! They were even serving free lunch😜!
I learned they were hiring for a Product Manager position. I gave the interview, got selected, and joined the company.
2016 – Freshworks– Ganesh Ram Natarajan was my first mentor at Freshworks. Ganesh liked my energy, he knew I was raw with product skills but had confidence in me. My first three weeks were horrible. Ganesh and Rohit Reddy helped me in orienting my thoughts, getting me more organised. Once the base was set, I started picking up quickly.
Within 2 years, 2018 – I became the Head of Marketplace Business and Tech Partnerships. In another 2 years, 2020 I was the Director of Startup Programs and Technology Alliances.
It wouldn’t have been possible without my stellar teams (Marketplace, ISV, GSI, Startups and Channel Teams), who really worked hard, motivated me every day and helped me become a better version of myself on this journey.
The amount of exposure was phenomenal. I had built in so many zeros to ones at Freshworks. Freshworks for me was the perfect platform to learn, explore and practise a lot of diverse professional areas. All the credit here goes to Freshworks CEO Girish, Siddharth Malik our ex CRO, and my boss Anand Venkataraman, for setting up and scaling such a great culture to promote strong ideas and trust people to execute.
I always wanted to be an entrepreneur. I shifted from the UK to India primarily because of this reason. I wanted to learn in India and build from India. Initially, I was lacking the required skills and confidence to be an entrepreneur. Freshworks gave me the skills and the confidence to startup.
The major takeaways for a startup founder from Freshworks were:
- The safety net of not being penalised for trying out new things – Give psychological safety to your employees + Provide them with enough ammunition to experiment. My bosses Ganesh and Anand Venkatraman always gave me the freedom to experiment and execute. Not a single time has I been shut down for something that has potential.
They both were very pragmatic in their approach. They told me whatever I wanted to explore had to be above and beyond what I was currently supposed to do. But at the same time, they gave me the safety net of not being penalised for trying out new things and evening failing at times.

@ with Anand – Freshworks
- Keep employees first. If the employees are taken care of, they will take care of the customers and the business. The culture that we set up at a company defines the company’s as well as the people’s progression in future. Create that openness, create that willingness to work for everybody. Make your employees play as a single team.
- Hire for potential and not for experience – Freshworks has this great ability to identify talent and groom them. Freshworks always brings in people with similar thought processes, people who can learn, adapt and execute.

@ Freshworks Partnerships Team
YC: How did Spendflo happen?
Rajiv: 2022! I have had a wonderful journey at Freshworks. I saw them starting small around $20 million and growing into the IPO stage – $300 million. By this time I realised it was time for me to apply my learnings to a startup + my entrepreneurial itch was also slowly coming back.
I’ve always wanted to build something in the cost space. I have seen the growth of SaaS first-hand and realised that shortly, there will be a requirement to limit spending.
I met Sidharth and Ajay, the co-founders of Spendflo. I spoke to them and wanted to onboard them to Freshworks. But it happened the other way. (He laughs big time!)
I learned about Sid and Ajay’s vision of building out an actual product on the buy-side. I’ve seen how broken the buying products of SaaS are, so I was indeed sure that this will work out well. We realised we could actually build a full-fledged buying stack for SaaS. I knew I had an opportunity there. Our visions aligned, our skills were complementary and we joined hands.
YC: So who is the ideal customer for Spendflo?
Rajiv: We are going after startups which are:
1. Funded, Series-A, B and above.
2. Employee strength should be 100+.
3. Annual SaaS spend should be around $250,000.
Sectors we are targeting at the moment are – Edtech, Fintech, SaaS, Technology, Consumer and E-commerce verticals. We are going for the global market since it is a global problem.
YC – Can we talk about some numbers like TAM? Also, how is the competition?
Rajiv – In 2021, $330 billion SaaS was bought, and its expected growth is 20-25% YOY. We are expecting SaaS to hit about $800 billion by 2027. We want to help people buy SaaS better, faster, and cheaper. Some of the fastest-growing companies are our customers in India, APAC & US – Wingify, Airmeet, CrownPeak etc. We are growing steadily month on month.
Our major competitor is Vendr.com – a very inspirational and fantastic company. Others are Tropic.io, SaaStrify in Europe, Zluri in India, Ramp, Quolum etc.
In my honest opinion, the CFO community has been quite underserved with the right kind of tool all these years. We are focusing on building the CFO stack and gradually moving into other adjacent spaces which are top spending areas for CFOs.
YC: What is the Sales and Marketing approach of Spendflo right now?
Rajiv: Sales and Marketing:
1. Multi-channel Outbound approach and sales., though Email and LinkedIn are the most effective channels.
2. Content – In our category there is not enough search volume for inbound content, so we are trying to penetrate through good thought leadership content and support our outbound engine with that content.
3. The next in line is a brand-driven marketing engine, though it will take time to set up.
4. We are also investing in building good partnerships, to deliver our messages faster to our potential audience.
5. Talks, interviews, events. We are participating in all these to generate awareness.
YC: What is that one thing which keeps you going in tough times?
Rajiv: My dream, “I want to touch a million lives!”
I lost my dad to cancer around 13 years ago. Now, I cannot be a doctor, but I want to help people with incurable diseases. I will build a successful business and will figure out a meaningful way to support people fighting this terrible disease.
Secondly, building a product with a lot of smart people is fun! That urge to create a long-lasting impact for my TEAM is what keeps me going every day.
Want to call out the support of my family here, especially my wife Janani Padmanabhan, for giving me the confidence to take the plunge. She is managing a lot of things – home, my 2 fast-growing daughters, her full-time work and her passion projects (She is a Silk Saree Connoisseur). Without her hustle, I would not have the strength and time to build Spendflo.

@ with Janani
Rajiv, I am sure this interview will be a great read for my readers. We wish you all the very best in your future endeavours!
Thank You!
Congratulations Rajiv. You have described your journey beautifully. It will motivate millions of youth. I wish you all success..May all your dreams come true. May God bless you. You are a great achiever and rolemodel for others.
Congratulations Rajiv. Got to know more about your tough and challenging journey. Wish you good luck.
Truly amazing and inspiring journey! The youth has a lesson to learn and be inspired in every bit of this extensive exchange. Thank you for sharing and you will definitely touch millions and millions of life for sure!