Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies – all online.
Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers – one that empowers their entrepreneurial spirits.
More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100), and Best Places to Work in Boston.
We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.
Product
Permanent
The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.
$81,500.00 - $134,500.00
1
The Mission
We’re rewriting the rules of insurance, and we need a Product Delivery Lead who lives for the "how." You’ll sit at the high-velocity intersection of commercial strategy and technical execution. Your mission? To turn ambitious product visions into airtight, shippable reality.
In this role, you are the connective tissue between our business partners and our development team. You aren’t just managing a list of tasks; you are the architect of our delivery pipeline, ensuring our platform remains compliant, optimized, and ahead of the curve. You’ll own the "now" while enabling the "next," balancing rapid-fire enhancements with long-term stability.
Architect the Pipeline: Own the end-to-day delivery engine. You’ll manage the intake of new ideas, compliance updates, and technical requirements, performing scenario planning to anticipate future demand. You’ll ruthlessly prioritize the backlog to ensure a constant flow of value while ensuring stakeholders understand our capacity constraints before they impact delivery.
Translate Vision to Velocity: Partner closely with developers during the refinement process to bridge business needs with technical logic. You’ll facilitate the vetting of requirements to ensure every ticket is "Ready for Dev," meaning zero ambiguity for the squad and maximum momentum.
Lead the Sprint: Orchestrate agile delivery cycles for the squad. You’ll manage external dependencies and unblock the development team by coordinating across the business to hit milestones, keeping the team focused on the highest-impact work.
Technical Discovery: Partner with the Product Architect and developers to de-risk large or high-complexity work. You’ll act as the investigative lead, surfacing the specific business rules and data requirements our technical experts need to validate feasibility and provide an accurate "ground truth" on what we can build and when.
Optimize the Machine: We hate friction. You’ll constantly refine our workflows by identifying and quantifying key bottlenecks in our delivery model. Using data-backed insights, you’ll improve team velocity and lead the shift away from ad-hoc fixes toward scalable, repeatable systems.
Own the Source of Truth: You’ll manage our project tracking (Jira) and act as the primary translator between technical execution and commercial value. By delivering regular data insights and performance feedback, you’ll demonstrate the team’s impact and provide workstream owners with a clear view of our output and success.
Insurance Savvy: You understand the mechanics of the industry like underwriting logic, rating structures, and policy lifecycles, and are excited to apply that expertise in a modern delivery environment.
A Precision Prioritizer: You thrive in fast-paced environments and can navigate complex backlogs without breaking a sweat. You know how to say "not now" to protect the "must-haves."
Technically Intuitive: You don’t need to code, but you speak the language. You intuitively understand technical constraints and can spot a gap in a requirement before it ever reaches a developer’s desk.
A Systems Thinker: You are outcome-oriented, prioritizing the "why" over a static list of tasks. You don't just follow a backlog; you understand the impact of delivery, allowing you to dynamically maintain portfolio balance and hit our commercial goals.
Bias for Action: You have a high sense of ownership. You don’t wait for permission to solve a problem; you identify the roadblock and clear it.
Composed and Confident: You are calm under pressure and thrive in the face of competing demands. You can navigate high-stakes stakeholder negotiations and "urgent" requests with grace, ensuring that external pressure is filtered through you and never disrupts the dev team’s focus or capacity.
Expert Communicator: You can translate a complex technical limitation into a clear business trade-off, building trust with partners while maintaining the discipline to negotiate timelines and protect the team's focus..
Detail-Obsessed: You have a keen eye for the "small stuff" that makes a big difference in data sets and product logic.
Experience: Typically 4–7 years of experience with a proven track record in product delivery, project management, or complex operational roles within Insurance, FinTech, or a high-growth SaaS environment.
Domain Expertise: A solid understanding of the insurance lifecycle, specifically how underwriting rules, rating logic, and policy documentation interconnect.
Agile Mindset: Practical experience with Agile methodologies and managing tools like Jira to maintain total transparency.
Stakeholder Management: Experience navigating competing priorities and the ability to negotiate timelines with commercial and technical partners to maintain a balanced delivery flow.
Collaboration: A love for working with diverse groups (from carriers to coders) to reach swift, smart decisions.
Curiosity: A genuine desire to dive deep into our platform’s mechanics to become a better facilitator and leader.
Here are some of the great benefits and perks that come from being a Simply Business employee:
Group plan for medical, dental, vision, and prescription drug coverage.
Short term disability, long term disability, and life insurance coverage.
Participation in the Company’s bonus program-Participation in 401(k) plan with a 5% employer match.
Commuter benefits to help cut down on parking and public transit costs.
25 days of vacation time plus 10 sick days and 10 company holidays.
A genuine investment in your learning and development-Regular team outings and volunteer opportunities.
An awesome office space.
A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.
Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture.