Scaling Finance Functions At High Growth Software Companies

Amartya Singh: Hello, everyone. I'm your host, Amartya Singh, co-founder and CEO of FinFloh—a product built by and for modern finance teams. We are back with the third episode of our podcast series, Inside the CFO Office, an exclusive channel for finance professionals to explore the journeys of finance leaders and trailblazers in the CFO office, delve into the challenges they’ve faced, and hear their perspectives on the future of finance.

In today’s episode, we are super excited to have Josh Troy as our guest to share his journey and his experience in building and scaling finance functions at high-growth software companies. Josh brings over 15 years of experience leading business and finance teams in diverse industries, including real estate, advertising, AI, and health tech. He has played pivotal roles in multiple growth stories and acquisitions. Currently, Josh serves as the CFO at PatchRx, a leading medication adherence platform. Prior to this, he co-founded Urbint, focusing on leveraging real-world data and AI to prevent critical incidents. Earlier, he held finance leadership roles at Spotad, CompStak, and StreetEasy, where he led the company’s $50M acquisition.

Josh, I’ve had some fascinating conversations with you about the evolution of finance leadership and technology at high-growth software companies. Your insights have been a revelation, and I’m thrilled to have you share your journey with our listeners. Welcome to the podcast, Josh!

Josh Troy: Thank you, Amartya. I appreciate the opportunity and am excited to be here.

Amartya Singh: Let’s dive right in. You’ve had such an exciting career across various industries and finance functions. That must have required a unique ability to adapt and context-switch between different tools and industries. Can you share more about your journey leading finance teams in industries ranging from real estate to advertising, all the way to AI and health tech?

Josh Troy: Absolutely, Amartya. My journey has been shaped by a strong foundational interest in business operations, models, and strategy. I’ve always been curious about what makes a business successful—how it markets itself, its positioning, and overall strategy. For me, accounting was the scorecard that tied everything together, which led me to study accounting in undergrad and earn my CPA in New York.

I started my career at KPMG, working in advisory and consulting. This gave me exposure to internal and external audit processes, which helped me understand financial operations and accurate reporting. While at KPMG, I worked with companies across different industries in the U.S. and Europe. However, I always knew I wanted to move to the operational side of businesses.

In 2013, I joined StreetEasy as their first finance hire. At the time, they were a post-Series A company with around 35 employees. They were looking to expand into new markets and mature their finance function. Within a few weeks of joining, the company received a term sheet from Zillow, leading to a $50M acquisition. That quick pivot taught me how rapidly things can change in the startup world and the importance of staying agile.

After StreetEasy, I held finance leadership roles at several companies, including CompStak, a commercial real estate data exchange platform, and Spotad, a mobile ad tech company leveraging AI for real-time bidding. Each role added a unique layer of experience, from managing venture debt to scaling international operations. Eventually, I co-founded Urbint, where we used AI to predict and prevent incidents for utilities and workers. Today, at PatchRx, I’m focused on scaling operations and driving financial strategy in the health tech space.

Amartya Singh: That’s an incredible journey, Josh. It’s fascinating how you’ve navigated such diverse industries. One common thread seems to be your ability to adapt and lead through change. Could you share some insights on how you’ve managed transitions, especially during critical moments like acquisitions or rapid scaling?

Josh Troy: Transitions are challenging, but they’re also exciting opportunities to learn and grow. During acquisitions, the finance team plays a strategic role in maximizing value. For example, when we sold StreetEasy to Zillow, I partnered closely with the CEO to create demand and negotiate the best deal. It required a balance of strategy and execution, from preparing the data room to aligning on the vision with potential buyers.

Navigating rapid scaling is equally complex. At Urbint, we started pre-revenue and grew into a leading AI company for utility safety. Scaling required constant focus on building the right team, aligning priorities, and adapting to market dynamics. The COVID-19 pandemic was a major challenge—it disrupted our fundraising plans, but we persevered by being transparent with the team, staying optimistic, and leveraging strategic opportunities.

Amartya Singh: Your ability to balance strategy with execution is impressive. Speaking of strategy, let’s talk about finance technology. You’ve seen the evolution of finance tech firsthand. How do you view the current landscape, and where do you think it’s heading?

Josh Troy: The finance tech landscape has evolved rapidly. Ten years ago, finance teams relied heavily on manual processes. Today, automation and AI have transformed how we work. Tools like NetSuite, Dynamics, and SAP S/4HANA are now integrating with modern solutions like Airbase, Ramp, and Brex to streamline workflows.

AI is playing an increasingly important role in automating back-office tasks like accounts payable and receivable. For example, machine learning can predict transaction categories and flag anomalies, significantly reducing manual intervention. Large language models like ChatGPT are also making an impact, offering quick answers to technical accounting questions and aiding in scenario analysis. The challenge for finance leaders is keeping up with the pace of innovation while ensuring new tools align with business goals.

Amartya Singh: That’s a great perspective. With AI and automation enabling leaner finance teams, what do you see as the future role of finance professionals?

Josh Troy: As routine tasks become automated, finance professionals will focus more on strategic initiatives. This includes scenario planning, investor relations, and partnering with other departments to drive business growth. The role will shift from being transactional to analytical, requiring a deep understanding of data and how to use it effectively.

Amartya Singh: Fascinating. Let’s wrap up with a personal question. For aspiring finance professionals, what are the top two pieces of advice you’d offer to help them grow into leadership roles?

Josh Troy: First, build strong relationships. Whether it’s networking with mentors or collaborating with colleagues, relationships are critical for career growth. Many challenges have already been solved by others, and leveraging those insights can save time and effort.

Second, focus on accuracy and diligence. As a finance leader, your credibility hinges on the reliability of the data you present. Always double-check your work and ensure it’s accurate. Taking pride in your work builds trust and sets the foundation for long-term success.

Amartya Singh: That’s excellent advice, Josh. Thank you so much for sharing your journey and insights. It’s been a pleasure having you on the podcast.

Josh Troy: Thank you, Amartya. I’ve enjoyed our conversation and appreciate the opportunity to share my story.

Amartya Singh: And with that, we conclude our third episode of Inside the CFO Office. Stay tuned for more inspiring conversations with finance leaders. Until next time!