In the fast-moving world of tech, career trajectories can be anything but straightforward.
At Ontra, we recognize that true success lies in the ability to grow and evolve within an organization. Our commitment to nurturing talent means that our team members are empowered to not only excel in their roles but truly build dynamic careers that are as unique as they are.
Our culture is designed to support continuous growth, where employees have the freedom to thrive and expand their impact. In our latest blog, we highlight the stories of four individuals who’ve embraced the opportunities at Ontra and achieved significant milestones along the way. Their stories exemplify how a company’s investment in its people can lead to remarkable achievements.
Read on to learn more.
Miles Chan
VP/GM, Insight
NYC
“I didn’t even think I was the type of person who could be at a company for 10 years. I’ve always been someone who loves variety and needs to be having fun in what I’m doing. And that is exactly what Ontra has provided me.
My favorite thing about working at Ontra is that the sky’s the limit when it comes to growing your career. My story is a good example — I went from being a former practicing lawyer to an account manager to now leading a product at the forefront of the AI revolution. And I learned and grew more in that process than I ever thought possible. But I’m just one of many success stories at Ontra. Over the past decade, I’ve seen so many incredible people totally transform their professional trajectories — from former lawyers becoming global sales leaders to engineers becoming machine learning pioneers. There is no ceiling to what you can accomplish at Ontra.
But the one consistent trend I’ve noticed about successful people at Ontra is the willingness to embrace change. Change can be scary, sure. But I’ve always viewed change as an opportunity to learn really quickly, get comfortable with uncertainty, and ultimately grow both personally and professionally. As I prepare for my second decade at Ontra, I know that the company will continue to evolve and, in doing so, provide incredible opportunities for those willing to embrace the change. And that’s a lot of fun.”
Juliet Oskowsky
Senior Business Development Manager
NYC
“Ontra has truly been the perfect place for me to build my career, and that’s primarily due to two main factors: the people and the products.
When it comes to the people, working alongside such intelligent, motivated, and talented individuals has been an incredibly special experience. Each person contributes something unique and valuable, and together we work to make a substantial impact within the industry. Learning and growing with this group continues to inspire me, and our distinct culture and camaraderie really stand out. Engaging in cross-functional collaborations and working directly with senior leadership on various projects has further deepened my connection and involvement across the entire organization. The support, validation, and encouragement I have received over the years have played a pivotal role in my development from associate, to manager, to senior manager in just three years. I consider myself fortunate to report to a remarkable leader and mentor who trusts me to take ownership of my work and continuously guides me in the right direction.
When it comes to the products, supporting solutions that make a significant difference for our customers has been so rewarding. Our innovative solutions effectively reduce unnecessary expenses and save time for our customers. The opportunity to connect with world-class enterprises and witness firsthand how we’re improving people’s work lives has been fascinating and fulfilling.
Overall, working at a company with a great set of products alongside a great set of people has been such an invaluable experience. I look forward to continuing to advance my career at Ontra and make a positive impact on the industry.”
Jon Crandall
Managing Director, Customer Success
London
“After 11 years as a capital markets lawyer in New York, London, and Singapore, I knew I needed a change. The traditional law firm model was rewarding but rigid, leaving little room for creativity and innovation and making it difficult to find a work-life balance.
Joining Ontra in 2021 to lead our Asia-Pacific business was the fresh challenge I was looking for. It was effectively a startup within a startup, offering the perfect blend of strategic leadership and hands-on innovation. I found the opportunity to apply my legal expertise in new, impactful ways immensely satisfying — building our internal team, localizing our offerings for the diverse APAC markets, and expanding our global customer base into nine new countries.
As Ontra scaled, so did my role. I transitioned from leading the Asia-Pacific region to overseeing customer success for our entire international Contract Automation business. This shift allowed me to move back to London and lead a team across two continents, acting as the internal voice for our customers outside the United States. In this role, my team and I collaborate with many of the world’s most sophisticated private markets investors, helping them innovate legal processes, scale mission-critical functions globally, and fully leverage Ontra’s offerings.
For me, Ontra isn’t just a job — it’s where I’ve built a career on my own terms. The company’s culture of innovation, commitment to personal growth, and support for work-life balance has allowed me to achieve ambitious professional goals while prioritizing my family. I’m proud to be part of a high-functioning team that’s pushing the boundaries of what’s possible in the sophisticated legal markets we serve.”
Shiv Singh
Senior Business Development Manager
NYC
“My journey to Ontra has been anything but traditional. Before joining Ontra in 2021, I had just graduated from college with a degree in music performance and was on the pre-med track. Throughout college, I also ran a small handcrafted cosmetic company, where I discovered a love for business, entrepreneurship, and sales that ultimately led me to business development.
When I joined Ontra straight out of college, I was stepping into uncharted territory. My journey started as a business development associate building out a “New Markets” venture — bringing Ontra’s Contract Automation solution to the non-private markets space. It was an experience that challenged me to think creatively and strategically from the outset. A year later, I was promoted to business development manager, tasked with managing other top-of-funnel BDRs for our financial services work.
Being a manager at Ontra pushed me to refine my skills in sales and leadership, data-driven decision-making, and the art of relationship-building. Two years later, another opportunity came my way — senior business development manager, with a focus on new customer acquisition. This transition marked a significant milestone in my career, as it allowed me to specialize and dive deeper into the intricacies of scaling Ontra’s customer base.
In his book, The 5 Levels of Leadership, John Maxwell writes, “The challenge of leadership is to create change and facilitate growth.” Being a BDM at Ontra has been more than just managing BDRs — I’ve had the opportunity to be an internal advocate and coach for supporting BDRs’ career growth. Seeing my former BDRs grow their careers at Ontra into direct sales, customer success, operations, and implementation roles is one of the greatest pleasures of my professional life.
My background might seem unconventional, but Ontra saw potential in my diverse experiences. Ontra has been more than just a workplace — it’s been a place where I’ve been able to carve out a fulfilling career, one that I’m genuinely proud of. The support, mentorship, and opportunities here have made all the difference.”
