Director, Payroll Operations

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.
Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.
Reporting directly into our VP of Sales, Payroll, and New Lines, our Director of Payroll Operations is responsible for the Payroll channel including sales, distribution, underwriting and service. They will be accountable for leading the cross-functional payroll team which includes underwriting associates, underwriters, customer success, and admin. The Director of Payroll Operations will manage all aspects of payroll partnerships including contracts, sales, and ongoing support while also owning the relationship and management of pay-as-you-go vendor partners. In this highly collaborative role, you will work cross functionally with other stakeholders like premium audit, underwriting, and other teams at Pie to provide payroll-specific needs and support.
How You'll Do It

• Direct expansion of new Payroll partners (agency based)
• Guides the Manager, National Accounts and Client Relationship Managers in business development activities related to current new payroll partners
• Provide strategic leadership for the channel
• Design and negotiate commission structures as well as other incentives for the channel
• Direct the product team on new payroll integration requirements
• Manage Payroll underwriting
• Provide management of payroll operations team including underwriters and underwriting associates
• Ensure underwriters are meeting or exceeding target service levels, and that underwriting guidelines are consistently applied
• Propose new underwriting and underwriting associate processes or changes to improve operations. Work with Pie underwriting department to make changes as appropriate
• Guarantee that the team is trained and authorized, and that skills are up to date
• Manage Payroll services and administration
• Manage a team of customer success individuals responsible for policy issuance, service and renewals
• Manage the overall remittance operations, including guaranteeing that remittance is processed monthly
• Ensure that the team is trained and authorized, and that skills are up to date
• Drive overall business performance
• Monitor loss ratio, retention, audit, premium and other metrics on a regular basis. Own the overall performance of the business. Make or propose changes to improve where possible
• Work with other departments to improve processes wherever possible
• Develop workforce staffing models and while ensuring that the team is appropriately staffed
• Manage compensation and incentives for all team associates
• Develop forecasts for payroll channel on a regular basis

The Right Stuff

• • A High School Diploma or GED is required.
  • 6+ years of related professional experience working with payroll partners or underwriting is required.
  • 6+ years of leadership experience, with the ability to develop individual skill sets and general experience leading working groups to deliver on specific tasks, is required.
  • Advanced sales skills with a previous consistent track record in achieving/exceeding targets in a closing role; relevant experience in developing new business relationships, overcoming objectives, and exceeding quota.
  • Exceptional analytical skills and natural curiosity for how data impacts our sales and business development efforts.
  • The ability to manage complex situations with multiple layers, and resolve to anticipate needs now and into the future.
  • Comfortable with ambiguity and can navigate complexity; able to direct work and provide analysis even when limited information or inputs are available.
  • Demonstrated ability to multitask and meet strict deadlines in a fast-paced environment.
  • Consistent experience juggling multiple deliverables simultaneously.
  • The ability to work well under pressure and problem solve, with the advanced ability to plan and execute strategically.
  • Strong communication (written and verbal) and organizational skills while maintaining a strong attention to detail. Requires the ability to deliver complex information effectively.
  • Advanced Microsoft Office, Google Suite skills, Salesforce, and Looker skills, with the ability to quickly learn new systems and technology, is strongly preferred.
  • Regional travel to and from partners, around 20%. This time will be spent visiting partners across the US and to our Denver and DC offices.

Base Compensation Range for position: $150,000
This is an incentive pay based position and as such, there is no guaranteed commission amount. The on-target earnings (OTE) is approximately $215,000, and is based on successfully meeting standard metrics and key productivity indicators.
Compensation & Benefits

• Competitive cash compensation
• A piece of the pie (in the form of equity)
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Our core values are more than just a poster on the wall; they're tangibly reflected in our work

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we've identified a talented individual who we'd like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidate's knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges.
Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.
Location Information
Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver or DC office and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet.
Additional Information
Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.
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