Mara Reiff and FreshBooks – Driving Change for SMB Accounting Technology

Embedded Partners
accounting technology for SMBs

Welcome to the SMB Tech Innovators podcast, powered by Gusto, where we explore the intersection of financial services and vertical SaaS strategy and discuss how software combats the rising complexity of running a business. We aim to share stories, advice, and best practices from the leaders and investors behind today’s cutting-edge platforms. In this episode, Mara Reiff, Chief Customer Officer and Interim Co-CEO of FreshBooks discusses the journey from traditional invoicing to innovative, cloud-based accounting technology that prioritizes ease of use and customer engagement for small and medium-sized businesses (SMBs).

Highlights include:

  • Mara’s journey to FreshBooks and her diverse career background.
  • FreshBooks’ unique owner-first approach to accounting software.
  • The evolution from a simple invoicing platform to comprehensive accounting services.
  • Introduction of collaborative accounting in FreshBooks.
  • FreshBooks’ strategy in technology partnerships and embedded technologies.
  • The impactful role of AI for small businesses, according to FreshBooks’ study.
  • The significance of actionable insights over ‘dinner-party data.’
  • Strategies to enhance customer experience through effortless interactions.


From Engineering to Customer-Centric Leadership

Mara’s journey started with an engineering degree, which sparked her interest in the relationship between human behavior and technology. This passion continued to grow during her consulting career, where she specialized in blending human behavior with technological advancements. She later joined Canada’s biggest telecommunications company and took on various roles, such as managing excellent customer experiences and leading data teams, demonstrating her diverse expertise. She eventually became a support leader, where she focused on customer-centric solutions. During the pandemic, Mara transitioned to FreshBooks, where she initially worked in data-focused positions before moving into support operations. Her main goal is to improve customer experiences and offer customer-oriented solutions.

The Evolution of FreshBooks Accounting Technology for SMBs

FreshBooks is an accounting technology that offers unique features specially designed for SMBs and accountants. As a cloud-based platform, it prioritizes simplicity and user-friendly design, allowing users to navigate accounting easily. While initially intended to be an invoicing tool, FreshBooks has evolved into a comprehensive accounting solution that includes collaborative accounting. This evolution enables business owners to manage their operations efficiently while working seamlessly with accountants.

FreshBooks’ core value focuses on providing excellent customer service, which is evident in its award-winning support and commitment to the ‘4E mantra.’ This mantra emphasizes their dedication to executing extraordinary experiences for their customers every day. This customer-focused philosophy highlights FreshBooks’ commitment to delivering exceptional service and user experiences, positioning itself as a reliable ally for small business owners who need help navigating the complexities of accounting.

Vertical SaaS and Customer Growth

FreshBooks’ remarkable growth is a testament to its unwavering commitment to helping its customers grow in the Vertical SaaS landscape. The company’s journey from basic invoicing to comprehensive accounting and the upcoming integration of payroll services reflect its dedication to meeting the ever-changing needs of its customer base. By adopting a niche focus catering to service-based businesses, FreshBooks has successfully adapted its products to align with the expanding demands of its customers. This dedication to understanding and addressing specific industry requirements has played a crucial role in FreshBooks’ growth, positioning it as a vital player in providing tailored solutions to a diverse range of service-oriented enterprises.

Build vs. Buy Framework in Embedded Technologies

When companies need to implement new technology solutions, they must decide whether to build them in-house or outsource them. This decision-making process considers the benefits of building internal capabilities versus buying specialized solutions from external providers. Factors like resource allocation, regulatory compliance, time-to-market, and overall business objectives are taken into account. Integrating AI technology has become essential for improving customer experiences. Using AI, tasks like expense categorization can be streamlined, giving customers a more efficient and user-friendly platform. However, while AI can enhance support systems, it’s essential to ensure that customers can easily transition to human interaction when needed. This way, the support ecosystem remains balanced and effective.

Data-Driven Customer Insights and Support

At FreshBooks, the fusion of data-driven customer insights and dedicated customer support is at the heart of their service philosophy. Central to this approach is the “Effortless Team,” an internal unit dedicated to discerning and addressing customer pain points. This team acts as a pivot, meticulously analyzing support queries, gathering valuable feedback, and collaborating with other departments to enhance the overall customer experience.

Embracing AI in customer support, FreshBooks aims for a harmonious balance between AI-driven assistance and human intervention. While leveraging AI for efficient initial queries and rapid issue resolution, they emphasize the seamless transition to human agents when customers require more personalized or complex assistance. This strategy ensures that customers receive efficient, tech-driven support while maintaining the accessibility and comfort of human interaction when needed.

Insights on AI and Its Impact on SMBs

According to recent research, SMBs are increasingly turning to generative AI tools, particularly for marketing initiatives and customer support. This growing trend suggests a keen interest among SMBs in harnessing AI’s capabilities to streamline tasks and enhance customer interactions. However, while SMBs recognize AI’s potential to bolster efficiency and scalability, they view it as something other than a replacement for human roles within their organizations. Instead, they anticipate AI as a catalyst for growth, enabling them to achieve more without diminishing the importance of human expertise and personalized customer engagement.

Leveraging Data for Actionable Insights

Mara is an advocate for leveraging data for actionable insights, steering clear of what she calls “Dinner Party Data.” Her approach prioritizes actionable changes over superficial information, aiming for insights directly influencing business strategies and outcomes. By advocating for business-driven analytics, she emphasizes the crucial role of analytics and AI initiatives in aligning with business goals, ensuring that data insights translate into tangible actions and shaping and driving the trajectory of the organization toward growth and success.

Elevating the Customer Experience

Mara’s emphasis on elevating customer experience centers around pursuing a seamless and effortless journey for FreshBooks users. Her vision aligns with the imperative need to minimize hurdles and complexities, streamlining operations for businesses utilizing the platform. By prioritizing simplicity, FreshBooks aims to empower users, enabling them to concentrate on their core operations while ensuring that the platform provides comprehensive support throughout their business endeavors. This commitment to an intuitive and hassle-free experience embodies FreshBooks’ dedication to enhancing customer satisfaction and fostering long-term relationships built on trust and efficiency.

Mara’s insights into FreshBooks’ growth journey, customer-centric approach, AI adoption, and leveraging data offer valuable perspectives for SMB-focused SaaS leaders navigating the evolving accounting technology landscape for SMBs. Her leadership at FreshBooks is helping drive innovative strategies in embracing adaptability, customer-centricity, and AI integration within the SMB accounting technology domain.

Listen to the From invoices to innovation with Mara Reiff podcast.

Learn more about Freshbooks and connect with Mara on LinkedIn.

Updated: January 17, 2024

Brian Busch Brian is currently Head of Marketing at Gusto Embedded; the only payroll API with 10 years of experience and actionable data behind it. Before joining Gusto, Brian held leadership positions at Cloud Elements, Kapost, and Captricity. He holds a BS in finance and a BA in philosophy from Boston College and an MBA from the Cal Berkeley Haas School of Business.
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