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.

At Simply Business, our major competitive advantage is our people. As we continue to scale the business, we are looking for a Director of Underwriting who will support our efforts to provide small businesses with the appropriate insurance products. In this role you will be responsible for overseeing a team of experts that are passionate about serving the micro small business market (businesses with 0-5 employees, <~$5 million of revenue). You will be accountable for all underwriting operations within the MGA team including underwriting new classes and lines of business as needed, maintaining underwriting guidelines and investing in portfolio based underwriting tools including the use of AI/ML, where appropriate.

This role reports up to the VP, Commercial Strategy who has oversight of the MGA. You will be a key member of the MGA leadership team and enjoy interactions within the team and across the broader Simply Business functions (Insurance Product, Digital Product, Marketing, and the Customer Service Center) as well as externally with our fronting carrier partner(s), reinsurer(s) and key distribution partners. This is a newly established role that is designed to accelerate our business and to drive growth consistent with Simply Business’ long range strategy.

The right candidate will have a background in small business and/or program underwriting and will demonstrate an ability to manage a team of highly motivated and performing portfolio underwriters. We are looking for someone that is going to operate at depth, is customer obsessed and delivers results.

Key responsibilities:

Oversight of underwriting function and process across all insurance lines and products offered by Harborway Insurance including Business Owner’s Policies (BOP), Errors & Omissions (E&O), General Liability and Inland Marine.
Manage and maintain relationships with reinsurance providers to secure optimal coverage and terms for the company.
Monitor performance by line and marketing channels through assessment of key metrics against targets, takes action when necessary to improve results
Drive growth through underwriting actions including appetite expansion, product expansion and innovation and to support partnership initiatives, as needed.
Partner internally with actuarial & data/insights experts to drive rate, growth or improvement actions
Partner with Harborway Insurance Product Managers to continuously improve our product offering while executing on our underwriting strategy
Work closely with our Claim team to ensure we’re understanding our customers needs and taking actions as needed to reduce and mitigate losses
Ensure compliance within program guidelines and take corrective action as necessary
Review, evaluate, and recommend modifications to underwriting guidelines and workflows.
Ensures effective utilization of monitoring standards including audits, quality reviews and peer reviews to assess underwriting results and loss ratios
Implement a comprehensive training program to enhance underwriting capabilities, fostering ongoing skill development.
Oversight of an automated underwriting workbench tool equipped with anomaly detection capabilities to identify and flag accounts with potential issues.
Manage a team of underwriters providing guidance, mentorship and support.

What we are looking for:

Bachelor’s degree or its equivalent is required, along with a minimum of 8+ years of relevant portfolio underwriting experience, with increasing levels of responsibility.
Understanding of key small commercial P&C lines of insurance
2+ years of previous people management/supervisory experience.
Demonstrate an unwavering dedication to achieving Growth and Loss Ratio performance goals for the book of business.
Highly inspirational and disciplined leader who inspires and optimizes effectiveness among diverse teams while they embody our core Simply Business values
Skilled in combining action-oriented tactics with a commitment to fostering highly collaborative and effective working relationships within a cross-functional organizational structure.
A data-centric decision-maker, eager to test and refine strategies through iterative processes.
Additionally, the ideal candidate should possess excellent negotiation, analytical, and decision-making abilities.
Proficient in prioritizing business-critical activities, juggling multiple projects in an ever-changing environment, and continually exploring avenues to enhance underwriting effectiveness and efficiency.
Skilled at building strong relationships with team members, promoting unity, and fostering a sense of belonging
Proven ability to engage effectively with external stakeholders, strengthening partnerships and driving mutually beneficial outcomes

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: https://www.simplybusiness.com/careers/

Key responsibilities:

What we are looking for:

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