In Conversation With Sayantani Dutta on Advising Start-ups, Catering To A Growing Market, Entrepreneurship & More

With more than 3.5 years of experience working with 20+ startups, small businesses and proprietors, Sayantani Dutta has gained key exposure to unique legal issues faced by startups. With her undying passion for continuing to contribute to the startup ecosystem, StartUp Advisors is her latest venture to provide comprehensive legal services and advisory without the pocket pinch.

1. Your LinkedIn profile suggests a diverse professional journey. From being a legal expert to a startup advisor, could you share with us how your career trajectory evolved over time?

Sayantani: Absolutely, and I’m glad that you noticed the eclectic mix in my career- it’s been quite a ride! Even before I graduated, I started freelancing by writing blog articles for various kinds of websites while resorting to virtual internships due to the COVID-19 pandemic. But I soon found myself interested in drafting agreements. That is when I first reached out to some of my previous connections from Bangalore who were startup owners to offer them my services. My intention initially was to work on as many things as possible without being bothered about the pay. Well that surely did pay off, since from 2021; I have continued my legal freelancing journey. I transitioned from merely writing to actively helping businesses navigate the murky waters of legal compliance and contract management. My approach has always been hands-on helping clients understand the importance of solid legal foundations from shareholder agreements to SaaS contracts. Recognising a gap in the industry for providing a plethora of services dedicated only to startups, especially considering the booming startup economy in India: I founded “Startup Advisors” in March 2024. My aim is to combine my passion for law and business strategy to elevate startups from precarious to prepared, one contract at a time. It’s been a whirlwind, but who doesn’t love a good twist in the story! 

2. You describe yourself as “SaaS-y”, which is both catchy and intriguing. How does this playful moniker reflect your professional approach?

Sayantani: I have been a SaaS-enthusiast even before it became a term every entrepreneur wants to add to their resume. At the same time, I have always been known for quirky remarks and a straightforward approach in my professional realm. So the term “SaaS-y” isn’t just a fun play on words- it encapsulates my approach to the specialized field and my overall attitude towards legal services. 

SaaS contracts are often considered to be quite complex, multifaceted and absolutely crucial for a lot of my startup clients who operate in the tech space. I believe though that managing and understanding SaaS agreements shouldn’t be a daunting and boring task for entrepreneurs. Just like law doesn’t have to be so boring, stiff and formal. I strive to make the legal process as transparent and approachable as possible- from removing as much legalese as possible, discussing with the clients in detail the entirety of the agreement to ensure they understand the element of the agreement, and even add a touch of personality to it all. So being SaaS-y is all about embodying the spirit of the services I offer- smart, adaptable with a dash of fun! 

3. You’ve been dubbed the “legal contract drafting wizard”, which undoubtedly speaks volumes about your expertise in this domain. Could you share with us a particularly challenging or intricate contract drafting experience where your wizardry truly shone, and what strategies you employed to ensure its success?

Sayantani: Thank you for that! One of my most memorable contract drafting challenges involved a cross-border SaaS agreement between a startup client in India and a major European corporation. The stakes were high, and the complexities included differing legal frameworks, data protection laws like GDPR, and specific performance metrics crucial to both parties. The contract needed to balance the startup’s innovative flexibility with the corporate requirements of a MNC. This meant the contract should be able to navigate through the complex legal requirements without compromising on my client’s agility and growth potential. My “wizardry” came into play primarily in 3 areas: 

  • Cultural and Legal navigation: Understanding & respecting the legal and cultural nuances of both jurisdictions is crucial therefore a deep dive into the comparative law to ensure the agreement was robust and compliant at both ends was essential. 
  • Clarity and Precision: The agreement needed to be crystal clear, especially around IP rights and data handling, areas fraught with potential for conflict. I employed clear, precise language to ensure both parties were on the same page, avoiding any ambiguities that could lead to disputes later. 
  • Balancing interests: Perhaps the most critical of the 3, finding a middle ground that addressed the needs and concerns of both parties. This required several rounds of mediation ensuring both parties felt heard, accommodated, and valued. 

The final product was not only a legal document but a testament of strategic foresight and collaborative negotiation. The process helped my client to gain an international exposure but also gave me a rewarding experience putting my contract drafting skills to test. 

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4. What sparked your interest in the startup ecosystem, and how did you transition from learning and practicing law to advising startups in particular?

Sayantani: My venture into the startup ecosystem is rooted in my inherent entrepreneurial spirit. Even before my legal career, I would often brainstorm business ideas and strategies. My passion naturally led to working with startups using law as the context. Initially I chose litigation after my graduation thinking it would offer more freedom than a corporate role. However I soon realized it wasn’t the right fit. The traditional path felt restrictive like being a “lonely candle with a burned wick in someone else’s shade.” I would rather shine on my own. This realization steered me to focus completely on my freelancing career. The shift was exhilarating – I wasn’t just applying legal principles but engaging directly with the vibrant, fast-paced startup world. It was here that I found my true calling. Transitioning to a startup advisor was a natural shift. I founded “Startup Advisors” to merge my legal expertise with my passion for business, creating a platform where I could offer both legal solutions and strategic advice. Here, I am more than a legal consultant; I am directly involved in helping the startups navigate the early challenges and grow. The role perfectly aligns with my legal skills and entrepreneurial spirit, making every day a new opportunity for growth and learning. 

5. As the founder of, could you walk us through the mission and vision behind the platform? 

Sayantani: Certainly! At, our mission is to ensure that the journey of every startup we partner with is as smooth and successful as possible. Recognizing the vibrant yet challenging landscape of the startup ecosystem, where a significant percentage of startups face obstacles early in their journey, we aim to provide the necessary legal help and strategic guidance to navigate these challenges effectively. 

Our vision encapsulates the 3R philosophy: Resilient, Reliant, Responsible. We pride ourselves on being resilient partners, capable of adapting and thriving in the face of business challenges. As reliant allies, we are there for our clients whenever they need us, ready to provide expert guidance and support. Being responsible means we’re committed to our clients’ success as deeply as our own; we stand by our service and the trust startups place in us. 

Our advisory is structured to provide a full-suite of services tailored specifically for startups making us a one-stop shop for all legal and strategic business needs. We handle everything from routine legal requirements to complex negotiations, emphasizing proactive risk management to safeguard our clients’ long-term interests. We are not just a provider of legal services but a co-navigator in the startup’s entrepreneurial journey, ensuring they have the support to overcome obstacles and seize opportunities effectively. 

6. How do you approach advising startups? Is there a general approach or is it domain specific? 

Sayantani: Certainly! When advising our startup clients, its a hands-on, personalized approach which is as unique as the startups themselves. It’s never a one-size-fits-all strategy; it’s bespoke, acknowledging that an ed-tech startup doesn’t grapple with the same issues as a fintech or a SaaS company. For instance, while a fintech startup might dive deep into compliance and regulatory compliance due to their technical and financial complexities, an ed-tech venture might focus more on content rights and data privacy, without needing the same level of precision in technical compliance. Our conversations with founders often start with understanding their vision and specific hurdles faced in the sector. This helps me tailor my advice to address the most critical areas of their business. For a SaaS startup, this might mean focusing on crafting watertight customer and vendor agreements, while for a fintech, the priority could be navigating the intricate maze of financial regulations and securing intellectual property. 

As mentioned previously, my aim has always been to make “legal” approachable and useful, stripping away the jargon and focusing on what will actually help the startup grow and secure its operations. The approach not only helps us build trust but also creates a partnership that evolves as the startup matures. 

7. What are some of the most valuable lessons you’ve learned throughout your journey in the startup ecosystem?

Sayantani: I have learned quite a few things throughout this eclectic journey of mine. But I think the following are the most memorable ones: 

  1. Flexibility is the key: One of the key lessons I have learned is being flexible. Startups are dynamic, never knowing what tomorrow brings for them. This requires quick pivots not just in business strategy but also handling legal matters. Being adaptable has allowed me to effectively support startups and navigate various shifts and challenges. 
  2. Understanding over Instruction: One needs to truly understand a startup’s vision, market and challenges in order to decide the correct strategy. It is essential to understand rather than merely dishing out instructions. More listening and less talking and always asking the right questions is the right approach. 
  3. Preparation Prevents Pitfalls: Proactive preparation is far more effective than reactive solutions. Most startups delay legal services until it is absolutely necessary or things have already gone awry. This is why we always are on the lookout for startups just starting out and providing the most affordable legal services to ensure legal and strategic frameworks are already in place to avoid common pitfalls. 
  4. Relationships are Everything: I’ve learned that relationships champions everything. Building genuine, long-lasting, trust-based relationships with founders and their teams is the most rewarding part of working with startups. We thrive on such networks and connections which is why once we welcome a startup, they become our partners growing together. 
Also Read:  In Conversation With Pradhhnyaa Deshmukh on a Career in Legal Business Development, Emerging Trends in the Legal Marketing Industry & More

8. Who or what inspires you the most in your professional journey, and why?

Sayantani: In my professional journey, I draw a great deal of inspiration from the startup founders I work with. Their passion, resilience, and relentless pursuit of innovation keep me motivated and energized. Each founder brings a unique vision and a commitment to solving real-world problems, and being part of their journey—from ideation to realization and beyond—is incredibly inspiring.

Beyond individuals, the very nature of the startup ecosystem itself is a source of inspiration. It’s a space where creativity meets practicality, where every day presents new challenges and opportunities to learn and grow. The ecosystem’s dynamism pushes me to stay on top of legal and business trends, ensuring I can provide the best advice and support possible.

Lastly, the impact of our work together is profoundly motivating. Seeing a startup overcome initial hurdles and flourish, particularly when I’ve helped navigate some of those early challenges, reinforces the value of what I do. It’s not just about drafting contracts or advising on IP strategy—it’s about empowering these visionaries to build something great, knowing that I had a part in their success. This connection to a larger purpose is what drives me every day.

9. With the ever-changing landscape of technology and entrepreneurship, how do you envision the future of startups in India, particularly in terms of compliance and profitability?

Sayantani: The future of startups in India looks incredibly vibrant but equally challenging, especially given the rapid evolution of technology and shifting market dynamics. As we move forward, I foresee compliance becoming even more critical, not just as a regulatory requirement but as a competitive advantage. Startups that proactively manage compliance—from data protection and privacy to financial regulations—will not only avoid the pitfalls of non-compliance but will also build greater trust with customers and investors, which is crucial for long-term success.

Profitability, while always a key goal, will likely hinge on how well startups can leverage technology to streamline operations, enhance customer experiences, and innovate their offerings. With digital transformation accelerating across sectors, startups that can effectively use new technologies to improve efficiency and open up new revenue streams are likely to outperform their peers.

Moreover, the increasing support from the government in terms of startup-friendly policies and the growing ecosystem of investors and mentors also play a significant role in shaping a conducive environment for startups. The focus will likely shift towards sustainable growth and building scalable models that prioritize not just market capture but also responsible entrepreneurship.

Ultimately, the startups that are able to adopt a balanced approach by combining strong compliance frameworks with agile business practices will be able to navigate the complexities of the Indian market and seize the abundant opportunities that lie ahead. 

10. Lastly, what advice would you give to aspiring entrepreneurs and startup enthusiasts who are just starting their journey?

Sayantani: To aspiring entrepreneurs and startup enthusiasts stepping into this thrilling journey, my top advice is: Stay curious, be adaptable, and never underestimate the power of a well-drafted contract. The road to startup success is paved with challenges, but it’s your resilience and willingness to learn that will set you apart. Equip yourself with a solid legal and business foundation, surround yourself with a strong support network, and always be prepared to pivot and embrace new opportunities.

SaaSy-ness signing off: “Entrepreneurship is not just about building a business—it’s about crafting a thrilling story. So make sure yours is worth binge-reading!”


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