Simply Business Innovation & Technology Culture

What practices does your team employ to foster innovation, and how have these practices led to more creative, out-of-the-box thinking?

In the dynamic realm of digital product innovation, particularly within the insurance sector, understanding the customer journey is paramount. At Simply Business, our customer lifecycle team has transcended data collection, transforming it into the foundation of our strategic advocacy for small businesses. We’re not just insuring small businesses; we’re building a dynamic, tech-driven ecosystem that fuels their growth. 

Our approach to discovery and innovation is grounded in a continuous stream of data deep dives with our analytical partners. Each reporting and analytics request is a targeted exploration, designed to extract actionable intelligence on customer pain points and behavioral patterns, allowing us to provide digital-first self-service support where and when our customers need it. The product team has weekly data review sessions, allowing us to rapidly iterate to enhance customer experience or lay the groundwork for innovative projects. We bring that data to collaborative sessions with product, analytics, customer experience and engineering to define our vision. By grounding our tech efforts in solid data around customer behavior, we’ve seen a boost in creative, out-of-the-box thinking. 

How has a focus on innovation increased the quality of your team’s work?

At Simply Business, we’ve learned that reliable innovation lies in de-risking assumptions through iterative prototyping rather than immediately pursuing complex, resource-intensive implementations. This approach allows us to validate the efficacy of potential solutions with minimal investment, ensuring we’re solving real problems and seeking validation from our customers along the way.

Instead of launching fully-fledged, feature-rich products, we prioritize “demand testing” through prototypes. This might involve A/B testing, “fake door” experiments to gauge interest or even manually-supported solutions that lay the groundwork for future AI automation. This strategy allows us to gather concrete user feedback and data, enabling us to refine our solutions before scaling them. Our focus on innovation has fostered a culture of continuous improvement, where we prioritize data-driven experimentation and customer-centric solutions. This has resulted in higher-quality work, increased efficiency and a more impactful customer experience.

How has a focus on innovation bolstered your team’s culture?

Before immersing myself in this data-driven product management approach, I wouldn’t have believed that data could be a powerful catalyst for team cohesion and enrichment. Yet our team’s relentless pursuit of innovation, fueled by high-velocity data analysis and collaborative opportunity mapping, has proven me wrong.

These sessions have established a predictable cadence of thought-provoking discussions that consistently yield unexpected insights. It’s become a dynamic, almost gamified process, where each team member is a detective, piecing together data clues to unlock the “next level” of customer understanding and solution development. The thrill of uncovering hidden patterns and identifying impactful opportunities has created a shared sense of purpose and excitement.

In essence, our focus on innovation has transformed our team into a highly collaborative, intellectually engaged and genuinely connected group. We’ve found that the pursuit of data-driven solutions is not just about building better products — it’s about building a better team.

How does innovation show up in your company culture?

At Simply Business, innovation is reflected in how our teams operate on the day-to-day. We’ve focused on using the benefits of AI to work more effectively and free up headspace for solving tough problems.

What’s one recent innovation that improved user or employee experience?

Small business insurance is notoriously complex. To lower the barrier to understanding coverage, we launched our AI-powered advisor, which provides personalized guidance on coverage details and limits in real time. For the small business owner, this means they can ask the questions that matter to them 24/7. If the chat experience cannot answer a specific nuance, we escalate the conversation to our team of licensed agents. By leveraging the benefits of generative AI, we are empowering business owners to make confident, informed decisions when selecting the right insurance for their business.

How do you balance experimentation with stability?

In the highly regulated insurance industry, we can’t afford recklessness with our use of new technologies, but we also can’t afford to stand still. We balance these needs with informed urgency, moving quickly while maintaining rigorous safety guardrails.

Our AI-powered advisor chat experience already leverages AWS Bedrock guardrails to keep the LLM outputs within strict operational boundaries. For nuanced inquiries, we have a human-in-the-loop approach in place today, providing a seamless transition to our licensed agents whenever a human expert is best suited to help.

To further accelerate our deployment speed, we are actively building out LLM evaluations that monitor for accuracy before updates reach production. We are also refining our LLM-as-a-judge architecture to critique our LLM outputs in real time. This ensures that any response failing our internal criteria is intercepted before it ever reaches the customer. 

Ultimately, these methods serve a simple purpose: ensuring that every interaction remains reliable and helpful, providing the dependable experience our customers need and expect to protect the business they’ve built.

Simply Business’ Innovative Culture in Action

• “CX Insights: Our CX team uses Gemini’s Audio Overview feature to transform research decks into podcast-style formats. By lowering the barrier to entry, more team members can quickly level up on key insights and identify areas for deeper discovery.”
• “Engineering Efficiency: I recently sat with a senior engineer to audit code against our requirements with incredible speed using Cursor. A task that would have been a grueling afternoon of vertical lookups was finished in just 20 minutes.”
• “Workflow Automation: We use Atlassian Rovo to instantly turn messy Slack threads into clean, organized Jira tickets.”
• “Rapid Prototyping: To bring an idea to life quickly, I use the voice feature to explain concepts to Gemini Canvas. This shifts the focus from manual documentation to immediate validation, allowing us to accelerate the transition from ‘concept’ to ‘build.’”