Director, Customer Service and Operations

Pie | $140,000 - $180,000

Steph's Notes:

Pie's Careers page is very informative and their Values/How We Work statements seem pretty grounded. So far so good!

Identify gaps and needs for automation to create the best end to end experience. Create connectivity by collaborating cross-functionally within the direct functional areas as well as across other departments and functions that will influence direction, or could be impacted by strategy and direction within our departments.

I feel like there's gotta be a clearer way to say "will work cross-functionally with other applicable teams." Oh, look. I did it.

Accountable for the internal and external collection programs; managing through Managers and Analysts to maximize AR and reduce bad debt.

You can't see me, but I'm making a face because that's an odd duty for a Director of CS (though maybe not for Operations?). Actually, it's just hitting me how big a job running CS and Ops would be. Not sure those are functions I'd want to consolidate under one person.

(BJB Shitposting Board of Directors member Miles Goldstein said "CS = Chosen Scapegoat" and now I can't unsee it.)

There is just...a lot of words in this JD. So many words.

Works cross-functionally with UW, Product, Claims, Compliance, BD, Marketing, and Executives to deliver a best in class audit operation for our customer, partners, and internal team members to achieve Pie's financial goals.

I have been trying to figure out what this means for a good 2 minutes. Just staring at the words. The many, many words.

Data literacy is the ability to read, work with, analyze, and argue with data.

This is in the requirements section, apropos of nothing, and made me laugh right out loud.

Demonstrated experience working on projects involving redesigning how a company is structured, updating the technology everyone uses, or changing the way work gets done to be more efficient. Is comfortable making sure the organization is set up in the best way to meet its goals.

HOW IS THIS A CS ROLE (Miles: And now we're also the CIO?)

Overall organization support using planning skills, problem solving skills, communication skills and demonstrating adaptability while maintaining a results-focused approach to deliverables.

I'm curious how they expect the person in this role to have a "results-driven approach" when they seem to have all the deliverables.

Comfortable working in an agile-based workflow - working in a fast paced and flexible way of producing work and results. The need for collaboration, and continuous improvement, and supporting of the iterative process is essential here.

I really need to know who wrote this JD and then who approved it.

Demonstrated listening, and influence skills to build a culture of encouragement, and empowerment that cascades through the organization and other leaders.

Oooooooooof. Now they're also HR.

I mean, the comp is $140,000-$180,000, but that doesn't seem nearly enough for a role that's running CS, Ops, IT, HR, and maybe also the rest of the company?

Original Job Description: Director, Customer Service and 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.

As Director, Customer Service and Operations you oversee and manage end to end processes for all customer-facing policy support needs, policy changes and actions, as well as premium changes and audits. This role is accountable for Pie's customer service quality, audit effectiveness, and receivables management. From a leadership perspective, you manage all customer facing, operational functions at Pie. You are responsible for developing the strategy to ensure successful delivery in our day to day operations (service levels, resolution rates, quality) and will lead an organization through growth & scale by setting a service vision, developing strategies and driving continuous improvement.

The Director will lead all workforce management functions to optimize staffing efficiency and service levels. This role involves developing accurate forecasting models based on historical data and trend analysis, creating strategic scheduling frameworks that balance customer demand with agent availability, and implementing real-time adherence monitoring to ensure optimal coverage. The Director will oversee capacity planning for peak periods, manage intraday adjustments to address volume fluctuations, and collaborate with operations teams to minimize overstaffing and understaffing scenarios. 

How You’ll Do It

• Manage end to end partner & policyholder policy experiences
  • Identify gaps and needs for automation to create the best end to end experience. Create connectivity by collaborating cross-functionally within the direct functional areas as well as across other departments and functions that will influence direction, or could be impacted by strategy and direction within our departments.
  • Responsible for the overall compliance of the program; fulfilling state requirements and diverse premium audit accuracy programs (driven by NCCI and Departments of Insurance).
  • Accountable for the internal and external collection programs; managing through Managers and Analysts to maximize AR and reduce bad debt.
• Develop strategy for successful day to day deliverables
  • Leading in program strategies, and overall responsibility for successful delivery of processes and tools.
  • Responsible for overall scalability of programs success within functional areas.
  • Responsible for managing and implementing operational work processes including improvement, efficiency, and technology-driven solutions and achieving operational excellence. As the key decision maker, this position is responsible for making final decisions on implementation and ensuring operational effectiveness.
  • Uses Pie and CS data to inform and measure on the teams’ objectives, and track how the CS team influences Pie’s overarching OKRs.
• Drive efficiency at scale
  • Works cross-functionally with UW, Product, Claims, Compliance, BD, Marketing, and Executives to deliver a best in class audit operation for our customer, partners, and internal team members to achieve Pie's financial goals.
  • Oversee the development of processes that prioritize value added interactions or work while automating and reducing manual tasks.
  • Partnering across the org to eliminate the need for help or service or enable automated resolutions.
• Build quality based programs that lead to retention
  • Responsible for continuous improvement processes and encouraging the test and learn approach.
  • Establish KPIs and managing to performance expectations
  • Uses quality insights to drive improvement and push strategy on both people and processes within the organization.

The Right Stuff

• A Bachelor’s degree is required. Graduate’s Degree is preferred.
• 12 years of related experience in insurance, Insurtech, customer service, premium audit or other service based organization set up is required.
• 6  years leading leaders or team management responsibilities is required.
• Data literacy is the ability to read, work with, analyze, and argue with data. 
• Specifically, need to be able to: 
  • Understand Data - knowing what data is and the ways it can be used. 
  • Critical Thinking: Asking the right questions about the data you see.
  • Evaluating Data: Deciding if the data is good quality and useful for what you need.
  • Using Data: Being able to use tools and methods to do something with the data.
  • Ethical Considerations: Understanding the right and wrong ways to use data.
• Demonstrated  experience working on projects involving redesigning how a company is structured, updating the technology everyone uses, or changing the way work gets done to be more efficient. Is comfortable making sure the organization is set up in the best way to meet its goals.
• Overall organization support using planning skills, problem solving skills, communication skills and demonstrating adaptability while maintaining a results-focused approach to deliverables.
• Comfortable working in an agile-based workflow - working in a fast paced and flexible way of producing work and results. The need for collaboration, and continuous improvement, and supporting of the iterative process is essential here.
• Highly advanced leadership skills with demonstrated ability to create productive and positive work environments. Experience building career progression programs is highly desired.
• Demonstrated listening, and influence skills to build a culture of encouragement, and empowerment that cascades through the organization and other leaders.

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range
$140,000 - $180,000 USD

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 is remote. 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.

Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.

Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy.  

Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

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