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.’”

How does your team stay ahead of emerging technology trends while scaling fast?

Our engineering organization does a really great job of encouraging us to use new tools and technologies like Microsoft Copilot/LLMs for development work. We have a dedicated Slack channel to talk about our experiences with AI native development. I personally have started tinkering with OpenCode and exploring how it can refine and refactor code that I’ve written, and even help me bypass blockers that I run into along the way. I do believe that collaboration between engineers will be the best way to adopt these new technologies, even as “vibe coding” increases in its commonality. 

Communication across development teams can’t boil down into “Claude did it” or “I just listened to Copilot” because that’s how we lose the craft of being software engineers. Discourse that starts with “Why did Copilot output this?” and continues across teams will lead us down a path of using these tools to their maximum potential by more efficiently crafting prompts and tickets to write readable and maintainable code. I’m encouraged by the care that our leadership has taken in rolling out these tools and giving engineers an open platform to discuss the insights gleaned from a very exciting technology.

What recent product or feature are you most proud of — and what impact has it had?

Our team recently launched a new insurer on our general liability panel, and while our team is no stranger to onboarding new carriers, a big focus of this implementation was the data and tracking point of view. We launched it as an A/B test because we wanted to be able to see how the new carrier would perform against the current panel of insurers for the general liability product. The process of implementing the test required heavy collaboration and learning between engineering, product and data engineering/analytics to make sure that everyone had what they needed to deliver a successful product launch. I’m really proud of the effort the team and I put in over the course of the project, which ended up being completed in a shorter time than originally estimated, leading to hundreds of new customers buying insurance through our platform that otherwise wouldn’t have been able to. We’ve recently had our biggest sales day in the U.S. market in large part due to this project.

How do you create a culture where innovation and experimentation are encouraged daily?

Simply Business does a really great job of encouraging engineers to take time out of their weeks to learn a new skill, level up their current skills, or expand features outside of the scope of refined feature work. This dedicated learning time gives engineers the opportunity to take advantage of tools that the company offers such as Spark courses to improve technical skills, or use the time to collaborate across the engineering organization with others who have different skills, experiences and perspectives. 

Since Simply Business has a lot of moving parts, I’ve been able to meet with and gain knowledge from more senior engineers and develop relationships with people that I wouldn’t typically work with during my day-to-day work. I believe that the best way to level up is through that collaboration and relationship-building; it builds a culture of asking questions and development of ideas with people that have entirely different contexts around their work. I’m happy to work at a company with people that I know are willing to answer questions and assist on projects, even if it isn’t directly related to their team’s work.