From 160 “No’s” to Global Growth: Ilia Bovkunov on Building Sendforsign and Simplifying B2B Contracts

In this insightful interview, Ilia Bovkunov—product designer turned founder—shares how he launched Sendforsign, a B2B eSign and contract automation startup, after years in design leadership. From moving countries to facing 160 investor rejections, Ilia gets candid about what it really takes to build something simple, scalable, and global.

Can you share a brief note about yourself?

I’m Ilia Bovkunov, a product designer and manager turned entrepreneur with over a decade of experience in digital product design. I started in IT, initially trained as a programmer, but quickly pivoted to design because I was drawn to understanding why and how people use products, rather than just coding them. I’ve worked in various roles—designer, manager, product design director—and spent time at several startups, where I helped shape design teams and processes. I’ve moved frequently, from city to city and country to country, chasing opportunities and growth. Each move taught me how to integrate, adapt, and build meaningful connections.

Right now, I’m the CEO and founder of Sendforsign, a B2B startup focused on embedded eSign API and AI-powered contract management solutions. We’re building tools that make contract workflows seamless, from creation to signing, with AI assistants that save time and reduce complexity. Our product is live in markets like Europe, the US, India, and China. Outside of work, I’m passionate about sharing practical insights on startups, team-building, and product design through my social media. I believe in simplicity, honest communication, and learning from failures as much as successes.

Why did you choose to start a business?

I started Sendforsign because, while working for my previous company, I saw a gap in how digital contracts were handled—tools like Docusign made things digital, but not simple or intuitive. I wanted to solve real problems for businesses with a product that’s easy to integrate and saves time, especially with AI to handle the heavy lifting. But honestly, it’s deeper than that. I’ve always been driven by creating something meaningful, not just consuming what’s around me. Starting a business was a way to take ownership of my ideas, build something that reflects my values, and work with a team that’s as fired up as I am. It’s not just about the product—it’s about the freedom to shape my own path and make a dent in how things are done. Plus, after years of moving and adapting, I knew I could handle the uncertainty of entrepreneurship.

How did you start your business?

The early days of Sendforsign were a mix of excitement and chaos. I was still at my previous company, transitioning out, when I decided to launch my own venture. I had an idea for an embedded eSign API solution and starting capital for about eight months of development. I chose Europe for its access to early-stage capital and startup-friendly programs, despite the challenges of navigating bureaucracy with a Russian passport during a tough geopolitical period.

I started by researching startup visa programs in Portugal, Spain, and France, diving into the nitty-gritty of applications, pitch decks, and accelerator requirements. I applied to nine accelerators in Portugal, and three expressed interest. It was a lot of paperwork—motivational letters, CVs, tax clearances, and bank statements showing I could survive a year. Meanwhile, I was building the initial product, focusing on a narrow use case: a simple eSign API that platforms could integrate quickly. My approach was to bootstrap minimally, validate the idea with a working version, and then seek external investment for network and mentorship.

Navigation was hands-on and scrappy. I leaned on my experience in product design to prototype fast, talk to potential users to refine the idea, and keep the team small but passionate. There were tons of rejections—160 “no’s” from investors in total—but each one sharpened my pitch and focus. I also used my social media channels to document the journey, which helped me stay accountable and connect with others for feedback.

What do you wish you’d known before you started your business?

Looking back, I wish I’d fully grasped how simplicity is key to survival. I got caught up in trying to build a “spaceship”—a product with too many features—early on, which diluted our focus. I wish I’d known to stick to one clear, solvable problem and nail it before expanding. Also, I underestimated how emotionally taxing the founder’s journey would be. I wish I’d prepared for the mental marathon of constant “firsts” and rejections and sought out more advisors—people to offer fresh perspectives—earlier. Lastly, I wish I’d realized that failure is the default, not the exception. Knowing that 90% of experiments don’t work out would’ve made me less hard on myself when things didn’t click.

Did you have any support in your journey?

Yes, support was critical, though it often came in unexpected ways—my team, external advisors, and other founders. I also leaned on my network from past roles, connecting with designers, developers, and founders for advice. My social media became a surprising source of support—readers offered feedback, asked questions, and even volunteered as guest posters, creating a two-way dialogue that kept me grounded. Books like No Rules Rules shaped my approach to team-building, emphasizing mentorship over hierarchy. I also drew on online resources, like Y Combinator’s Startup Library, for crafting pitch decks. Most importantly, my small but dedicated team—starting with our “ninja members,” as we called ourselves—shared the vision and helped turn ideas into reality.

What is your greatest challenge as a business owner?

The greatest challenge is balancing the need for speed with the reality of long-term progress. As a founder, there’s constant pressure to deliver results now—new features, more users, investor traction—but meaningful wins, like retention or market fit, take months or years. This creates a mental tug-of-war: the urge to rush versus the need to build thoughtfully. Another big challenge is the emotional weight of rejection and failure. I’ve faced 160 “no’s” from investors and countless experiments that flopped. Staying resilient while maintaining team morale and my own sanity is tough. Finally, communicating our value clearly—especially when juggling three product blocks (eSign API, contract management, AI assistant)—is a constant struggle. Simplifying that message without losing the vision is a daily battle.

What advice would you give to your past self before opening your own business?\

I’d tell my past self: “Stop chasing status and perfection—focus on progress over ego.” I’d urge myself to embrace junior roles or small wins without shame. I’d also say, “Find your advisors early”—people who can offer fresh perspectives when you’re stuck. And critically, I’d hammer in: “Simplify ruthlessly.” Don’t build a complex product or team too soon. Start narrow, solve one problem well, and let the rest evolve. Lastly, I’d remind myself that failure is the norm—those 160 rejections aren’t a verdict on your worth, just part of the game.

Reflecting on your path to entrepreneurship, what key piece of advice would you offer to aspiring founders ?

The key advice I’d offer aspiring founders is: Embrace simplicity and resilience, because the journey is a marathon of failures. Complexity is a startup killer—keep your product, team, and message as simple as possible to stay agile and focused. Expect rejection—whether it’s 160 “no’s” from investors or failed experiments—and treat each one as a lesson, not a defeat. Surround yourself with a small, passionate team and a few trusted advisors to challenge your blind spots. Above all, build something that solves a real problem and communicate its value clearly, because even a mediocre product with great sales beats a perfect one nobody understands. Stay human, stay curious, and keep moving forward, even when it feels lonely.