Simply Business Project Manager interview questions & guide 2026

Preparing for an interview at Simply Business requires a balance of practical delivery skills and cultural alignment. The organization places a high premium on transparency, collaboration, and practical problem-solving. To stand out, you should approach your preparation with a focus on demonstrating how you lead projects through influence, structure, and clear communication.

Interviewers will assess your capabilities across several core evaluation criteria:

Role-Related Knowledge – You must demonstrate a deep understanding of project management methodologies, risk management, and delivery frameworks. For specialized roles like the US MGA Claims Program Manager, familiarity with insurance operations, claims workflows, and managing third-party administrators is highly valued.

Problem-Solving Ability – You will be evaluated on how you approach complex, ambiguous challenges. Interviewers want to see that you can break down large initiatives into manageable phases, anticipate bottlenecks, and make data-driven decisions to keep projects on track.

Leadership & Influence – As a Project Manager, you must be able to mobilize teams and drive alignment without relying on formal authority. Your ability to communicate clearly, resolve conflicts, and build trust across different departments is essential.

Culture Fit & Values – Simply Business prides itself on an approachable, supportive, and ego-free culture. You should be prepared to show how you collaborate with others, accept feedback openly, and contribute to a positive, inclusive team dynamic.

The interview process at Simply Business is designed to be transparent, collaborative, and highly structured, ensuring both you and the team can assess mutual alignment. Candidates consistently report a smooth, supportive experience managed by friendly and responsive talent acquisition professionals who provide constructive feedback at every stage.

The journey typically begins with an initial phone screen with a recruiter to discuss your background and high-level alignment with the role. This is followed by a video call with the hiring manager to dive deeper into your CV, your project management experience, and what you are looking for in your next role. The final stage is a comprehensive panel interview, which historically includes a practical project planning task and conversations with cross-functional team members.

The visual timeline above outlines the typical progression from the initial recruiter screen to the final decision. Candidates should use this timeline to pace their preparation, ensuring they allocate sufficient time to practice the hands-on project planning exercise before the final stage. While the exact steps may vary slightly depending on the specific team and location, the emphasis on practical skills and cultural fit remains consistent.

To succeed in the Simply Business interview process, you must understand the specific areas where the hiring team will focus their evaluation. The process combines conversational behavioral assessments with practical, hands-on tests.

Project Plan Design & Structure

This is one of the most critical practical components of the interview process. You will be asked to demonstrate how you take a high-level project objective and translate it into a structured, executable roadmap.

Be ready to go over:

• Visual Mapping – Drawing or presenting a clear, logical project plan that outlines phases, dependencies, and critical paths.
• Resource Allocation – Explaining how you identify resource constraints and allocate team members effectively.
• Risk Identification – Highlighting potential bottlenecks, technical risks, or external dependencies early in the planning phase.

Example scenarios:

• "Draw a comprehensive project plan to migrate a legacy claims handling system to a modern cloud-based platform."
• "Outline the steps, milestones, and key dependencies required to launch a new insurance product in a new geographic market."

Cross-Functional Collaboration

At Simply Business, projects involve close collaboration between technology, product, underwriting, and operations. You must prove you can navigate these diverse business units seamlessly.

Be ready to go over:

• Stakeholder Alignment – Techniques for managing conflicting priorities between commercial teams and technical delivery teams.
• Ego-Free Communication – Fostering an environment where team members feel heard and valued, regardless of their seniority or specialty.
• Third-Party Management – Coordinating with external carriers, vendors, or administrators to ensure delivery alignment.

Example scenarios:

• "How do you handle a situation where the engineering team reports a critical delay, but the underwriting team refuses to push back the launch date?"
• "Describe how you would establish a communication cadence for a project involving internal developers and external claims administrators."

Behavioral & Delivery Leadership

Your past experiences serve as the best indicator of your future success. Interviewers will use behavioral questions to explore your delivery track record and resilience.

Be ready to go over:

• Handling Ambiguity – How you establish structure when project requirements or business goals are poorly defined.
• Managing Failure – Your approach to diagnosing project setbacks, communicating them to stakeholders, and pivoting.
• Continuous Improvement – How you conduct retrospectives and implement process improvements within your project teams.

Example scenarios:

• "Tell me about a time when you had to manage a project with shifting priorities. How did you maintain team morale and delivery focus?"
• "Walk me through a project where you realized mid-way through that the initial plan was unviable. How did you address this with the stakeholders?"

As a Project Manager at Simply Business, your daily activities will focus on driving delivery, building alignment, and optimizing operational workflows. Your responsibilities will span the entire project lifecycle, requiring a balance of tactical execution and strategic oversight.

Your primary responsibilities will include:

• Leading the planning, execution, and delivery of business-critical initiatives, such as the US MGA Claims Program, ensuring alignment with strategic organizational goals.
• Collaborating closely with product managers, engineers, underwriters, and external partners to define project scope, requirements, and success metrics.
• Creating and maintaining robust project documentation, including project plans, risk registers, and status reports, to ensure high visibility across all stakeholder groups.
• Proactively identifying, tracking, and mitigating risks and dependencies that could impact project timelines or delivery quality.
• Facilitating key project meetings, including kick-offs, stand-ups, stakeholder reviews, and retrospectives, to foster continuous improvement and open communication.
• Managing relationships with external vendors, third-party administrators, and carriers to ensure external deliverables align with internal timelines and standards.

To be competitive for a Project Manager position at Simply Business, you should possess a strong blend of delivery expertise, domain knowledge, and interpersonal skills. The hiring team looks for candidates who can demonstrate immediate value while aligning with the company's collaborative culture.

• Technical and Methodology Skills – Strong proficiency in project management frameworks (such as Agile, Scrum, or hybrid methodologies) and delivery tools (such as Jira, Confluence, or Trello).
• Domain Experience – Previous experience working in insurance, insurtech, or financial services is highly advantageous, particularly for roles focused on MGA operations or claims management.
• Experience Level – Typically, candidates should have 3 to 5+ years of experience managing complex, cross-functional projects in a fast-paced environment.
• Soft Skills – Exceptional active listening, clear presentation skills, a proactive attitude, and a proven ability to lead and influence without formal authority.

Must-have qualifications:

• Proven track record of successfully delivering cross-functional business or technology projects from inception to completion.
• Demonstrated experience in stakeholder management, with the ability to build relationships across diverse professional backgrounds.
• Strong practical capability in project planning, milestone tracking, and risk mitigation.

Nice-to-have qualifications:

• Professional project management certifications (such as PMP, PRINCE2, or Certified ScrumMaster).
• Experience working with Managing General Agent (MGA) structures, claims administration, or digital insurance platforms.

Q: How difficult is the interview process for a Project Manager at Simply Business? A: Candidates generally describe the process as average to easy in terms of technical difficulty, but highly thorough regarding behavioral alignment and practical planning skills. The focus is on practical, real-world application rather than academic theory or "gotcha" questions.

Q: What should I expect during the project planning task? A: You will likely be asked to draw or map out a project plan for a realistic scenario. The interviewers want to see how you structure your thoughts, identify dependencies, manage risks, and present your plan logically. They value clarity, simplicity, and realistic timelines over overly complex charts.

Q: How long does the entire hiring process typically take? A: The process is known for being smooth and transparent, usually wrapping up within three to five weeks from the initial recruiter screen to the final decision, depending on scheduling availability.

Q: Is there a strong emphasis on specific project management methodologies? A: While familiarity with Agile and hybrid frameworks is expected, Simply Business values practical delivery over rigid adherence to any single methodology. They look for project managers who can adapt their approach to suit the needs of the team and the project.

To maximize your chances of success during the Simply Business interview process, keep these practical tips in mind:

• Leave your ego at the door: The company culture is highly collaborative and approachable. Frame your achievements around team success, and demonstrate a willingness to listen, learn, and adapt.
• Focus on clear communication: Whether you are walking through your CV or presenting a project plan, keep your explanations clear, concise, and structured. Avoid overly dense jargon.
• Prepare real-world examples: Use the STAR method (Situation, Task, Action, Result) to structure your behavioral answers, ensuring you highlight your personal contribution and the business impact of your work.

• Show curiosity about the business: Ask thoughtful questions about the company's growth, how teams collaborate, and the specific challenges the department is currently tackling. This demonstrates genuine interest and engagement.

The Project Manager role at Simply Business offers an exceptional opportunity to drive meaningful impact within a leading insurtech company. By combining your structured delivery expertise with a collaborative, customer-centric mindset, you can help shape the future of small business insurance. The interview process is designed to highlight your practical skills and ensure a strong cultural fit, making thorough preparation of both your technical planning capabilities and behavioral stories essential.

As you prepare, focus on mastering the project planning exercise, refining your cross-functional communication examples, and aligning your personal values with the company's supportive, ego-free environment. Taking the time to structure your thoughts and practice your delivery will significantly build your confidence and help you stand out to the hiring team.

The salary range shown above reflects the competitive compensation structure at Simply Business for this role. When evaluating the offer, consider the overall package, including the company's commitment to professional development, collaborative work environment, and the impact you will have on scaling their digital platform. For more detailed interview insights, community feedback, and preparation resources, you can explore additional guides on Dataford to help you put your best foot forward.