Second in Command: The Chief Behind the Chief with Cameron Herold
Episode 494: Rina Jariwala - Bold Moves and Personal Evolution in the World of Fintech
Release Date: July 22, 2025

In Episode 494 of the “Second in Command” podcast, host Cameron Herold engages in an insightful conversation with Reena Jarwala, the Chief Operating Officer (COO) of Fundbox. Reena brings over two decades of experience in financial services, coupled with a profound sense of empathy for both customers and employees. This episode delves into her journey, leadership philosophies, and the transformative strategies she employs to steer Fundbox toward sustained growth and profitability.

Balancing Career and Family

[02:50] Reena Jarwala:
Reena begins by addressing the often-discussed challenge of balancing a demanding career with family responsibilities. She emphasizes the importance of having a supportive partner, stating:

"The secret I think to my success is I have an amazing partner in crime and the two of us just figure out how to make it work."

Reena highlights the complementary dynamics between her and her husband, which have been instrumental in managing both personal and professional spheres. This partnership allows her the flexibility to dedicate quality time to her children while effectively leading her team at Fundbox.

Empathy in Leadership

Cameron probes deeper into how motherhood has influenced Reena's executive capabilities. Reena passionately explains:

[05:22] Reena Jarwala:

"My kids have taught me so much about life. They show me a different perspective, which really balances things out."

She underscores the role of empathy in her leadership style, conveying that understanding and connecting with her team on a personal level fosters a motivated and cohesive workforce. Reena believes that Emotional Intelligence (EQ) is crucial for rallying teams and driving organizational success.

Understanding Fundbox's Mission

Reena provides a comprehensive overview of Fundbox, articulating its mission to simplify access to working capital for small businesses. She explains:

[08:51] Reena Jarwala:

"Fundbox is really the pioneer of embedded working capital for small businesses... We've unlocked over $6 billion in working capital since our inception."

Fundbox integrates seamlessly into the ecosystems where small businesses operate, leveraging data from platforms like Intuit to offer swift and frictionless financing solutions. This embedded approach allows Fundbox to underwrite loans quickly, often within minutes, providing same-day access to capital through real-time payments.

Regulatory Framework and Operations

Cameron seeks clarity on Fundbox's operational structure, particularly regarding its banking status. Reena clarifies:

[10:17] Reena Jarwala:

"We actually work with two bank partners here at Fundbox... we are the ones doing the underwriting, making the lending decisions, distributing the money to the SMBs."

Fundbox operates in conjunction with banking partners, originating loans under their names while handling the underwriting and repayment processes independently. This hybrid model enables Fundbox to provide efficient financing without functioning as a traditional bank.

Growth Strategies and Partnerships

A significant portion of the discussion revolves around Fundbox's growth strategies. Reena attributes their success to strategic partnerships with platforms that serve large swaths of small businesses. She states:

[15:14] Reena Jarwala:

"Finding those platform and distribution partners that serve a multitude of SMBs... has created this flywheel for us."

By collaborating with established platforms like QuickBooks and FreshBooks, Fundbox leverages existing customer bases and data insights to offer tailored financing products. These partnerships not only enhance Fundbox's reach but also ensure customer retention through integrated financial solutions.

Navigating Financial Pressures and Achieving Profitability

Reena shares the challenges Fundbox faced in 2022 when rapid growth began exposing vulnerabilities in their business model. She reflects on the strategic shift toward profitability:

[19:53] Reena Jarwala:

"We had to narrow in on our focus... by Q3 of 2024, we had our first profitable quarter."

This pivot involved streamlining operations, enhancing execution precision, and concentrating efforts on high-impact partnerships. Reena credits the leadership team's transparency and clear communication of key metrics (OKRs) as pivotal in maintaining organizational morale and focus during this transformative period.

Cultivating a Thriving Company Culture

Maintaining a positive and resilient company culture amidst significant changes was another focal point. Reena discusses the importance of transparent communication and fostering a sense of ownership among employees:

[26:23] Reena Jarwala:

"We shared our key metrics with the entire company and said... you can make the choice to stay or leave."

This approach ensured that the team remained aligned with Fundbox's mission and empowered individuals to take control of their roles within the organization. Reena emphasizes the familial atmosphere at Fundbox, where collaboration and mutual respect are paramount.

Leadership Development and Executive Coaching

The conversation shifts to leadership development, where Reena elaborates on her pursuit of an MBA with a focus on coaching and leadership:

[32:41] Reena Jarwala:

"This program has made me a better mother, a better leader, a better partner, because it's opened my eyes to a different way of doing things."

Reena distinguishes between mentoring and coaching, advocating for the Socratic method of leadership that encourages self-reflection and independent problem-solving among team members. This philosophy aligns with Fundbox's emphasis on empowering employees to develop confidence and trust in their capabilities.

Personal Growth and Future Aspirations

Reflecting on personal growth, Reena shares the advice she would offer her younger self:

[40:01] Reena Jarwala:

"Everything's going to work out and be just fine. Marry the right guy."

This perspective highlights her journey from a fear-driven approach to leadership to a more confident and trust-based methodology. Reena's commitment to continuous learning and personal development remains a cornerstone of her leadership style.

Notable Quotes

• Reena Jarwala on Empathy:

  "EQ is what's so critical to rally the masses and get them going in the direction you need them to go in."
  [08:13]

• On Fundbox's Mission:

  "We are really that embedded financial partner in the ecosystem where our small businesses live and work every single day."
  [08:51]

• Leadership Through Transformation:

  "We are transparently going to share these [key metrics] with you every single month in our all hands meeting... you can make the choice."
  [28:37]

• On Coaching vs. Mentoring:

  "Coaching is the Socratic method... it's about asking the hows and the what's."
  [37:14]

• Personal Advice to Younger Self:

  "Everything's going to work out and be just fine."
  [40:01]

Conclusion

Reena Jarwala's episode on the “Second in Command” podcast offers a compelling glimpse into the intricacies of leading a fintech company through periods of rapid growth and transformation. Her emphasis on empathy, strategic partnerships, and transparent leadership provides valuable lessons for current and aspiring COOs. Reena's journey underscores the importance of balancing personal life with professional responsibilities, fostering a positive company culture, and continuously evolving as a leader. Listeners gain profound insights into the operational strategies that drive Fundbox's success and the personal philosophies that sustain Reena's impactful leadership.