Current Vacancies

Senior Product Manager

Boston, MA • Product – US Product • Permanent • US Product
Simply Business is more than our name. It’s how we approach insurance: Make it clear. Make it simple. Make it affordable. By combining exceptional talent, technology, data, and knowledge, Simply Business is the go-to online insurance brokerage that protects small businesses and the entrepreneurs who work hard to build them. 
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.
We are looking for a Senior Product Manager to join our Digital Product team in Boston, MA.
As a Digital Product Management team we are responsible for…
Ideating and delivering innovative digital experiences and solutions for customers to research, buy, and manage business insurance online. Harnessing customer insights and new technologies to strengthen our competitive advantage and unlock hyper-growth in the online small business insurance space.

Here’s what you’ll be doing:

  • You will be embedded in our Online Sales Journey Value Stream and leading a cross-functional team (and reporting into our Direct-to-Customer Head of Product) through the full life­-cycle of product development, from ideation to delivery to measuring success, seeking outcomes that support our ambitious company growth plans. 
  • Shape the approach to solve critical customer problems and business challenges in collaboration with cross-functional stakeholders, you seek to find product solutions that strike the right balance of stakeholder needs.
  • Evolve our online sales journey with novel technologies (such as AI and GenAI) to be more personalized, flexible, and component-based, so that it can cater to different customer segments.
  • Formulate the roadmap for your area, including a discovery and delivery backlog, and ensuring alignment to strategic priorities, broader team, and company goals. You understand how to make trade-off decisions that maximize value. You define a clear vision for your product area.
  • Proactively engage stakeholders to keep them abreast of the latest learnings and results.
  • Champion Build Measure Learn, creating a culture of innovation and continuous improvement within the product management discipline, especially in discovery methodologies.
  • Accountable for delivery against Value Stream OKRs (primarily conversion-to-purchase metrics).

We’re looking for:

  • Customer-focus. Improve the online purchase experience for complex, misunderstood products and to make finding and buying small business insurance as hassle free for customers as possible.
  • Familiar with using frameworks to ensure a steady flow of work/delivery, learnings, and value (experience with agile/lean/value streams is a plus).
  • Influence. Able to align people with different objectives/agendas to a common goal.
  • Collaboration. Iterate a product and strikes the right balance between technical, design, and commercial trade-offs.
  • Data-driven and evidence-based. Supports decisions and prioritisation with an objective point-of-view and evidence.
  • Experience in owning, measuring and reporting on key product metrics.
  • Experience with analytics tools (Amplitude, Mixpanel, Looker, Tableau) and ensuring we’re capturing the right data to help prioritise what customer pain points to solve and to build a roadmap.
  • From a product or startup background, can demonstrate experience of managing multiple stakeholders in a fast-paced competitive environment.
  • Has a track record with iterative product development from discovery to launch to continual optimisation and innovation. You understand technical and design trade-offs, and can work with your team to find creative solutions that strike the right balance between speed and quality. You know how to motivate your team to push through challenges, and do whatever it takes to ship a better product for the customer.
  • Inspirational leadership. Can lead by example and create passion for others to level-up their product management practice.
  • Experience and desire to leverage new, novel technologies (such as AI and Gen AI) to provide a better experience for our customers.
  • Nice-to-have: part of a scale-up in Fintech or other related industry.
What are the benefits?
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. And that commitment starts with our interview process. 
Once you apply, your info will be reviewed in a committee with employees from different levels, teams, and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!
Most of our first round interviews will take place over Zoom; however, further through the process there may be the opportunity/expectation to meet members of the team in-person. 
If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].
Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above.
Want more info on working at Simply Business? Check out our careers page: 

Get Our Newsletter

We’ll deliver tips and tools to grow your business right to your inbox