Pie Insurance’s cover photo
Pie Insurance

Pie Insurance

Insurance

Safety first, then Pie Insurance.

About us

At Pie Insurance, our mission is simple: make small business insurance affordable and as easy as pie. We specialize in workers' compensation and commercial auto insurance for small businesses across the U.S. With our data-driven approach, small businesses can get a workers’ comp quote in just three minutes and save up to 30% on premiums.* At Pie, culture isn’t just a buzzword; it’s what drives us. We’re obsessed with giving our customers the best experience, always curious, and never afraid to tackle challenges head-on. We believe that diversity fuels innovation and we aim to foster an inclusive environment where everyone has an opportunity for impact and growth. 🏆 Pie has been named to: Forbes’ America’s Best Startup Employers 2025, Purpose Jobs’ Best Places To Work Remote in 2025, BuiltIn's Best Places to Work in Colorado (2025), Best Remote Midsize Places to Work (2025), among others. ⚠️ Safety First ⚠️ Pie is committed to your security during the recruitment process. Verify the identity of recruiters before sharing personal or financial details. Protect yourself from job scams and report suspicious activity. * Individual savings and quote time may vary. Discounts and savings not available for workers’ compensation policies in Wisconsin.

Industry
Insurance
Company size
201-500 employees
Headquarters
Remote
Type
Privately Held
Founded
2017
Specialties
Insurance, InsureTech, workers'​ compensation, Small Business Insurance, and Commercial Auto

Locations

Employees at Pie Insurance

Updates

  • Most employees aren’t asking for big changes. They’re asking for small steps that show care. According to the 2025 Employee Voice on Workplace Safety Report, 73% of employees said some form of mental health support from their employer would make a meaningful difference. Here’s what they said they want most: 🤝 Flexible work hours or remote options (19%) 🕐 Mental health day allowances (17%) 💬 Confidential counseling or peer support (9%) 📚 Training on mental health awareness (8%) 💡 Stress management workshops (7%) These small actions can help teams feel more connected, valued, and safe, one conversation at a time. See what employees shared in the full survey: https://lnkd.in/gAN7C7ry _____________________ 🌾 Stay tuned and tap the 🔔 on our profile to join us all month long as we share insights from our Employee Voice Survey about mental health, safety, and what employees are really saying.

  • Stress doesn’t just affect how we feel, it can affect how we work, focus, and stay safe. In the 2025 Employee Voice on Workplace Safety Report, 36% of employees said workplace stress carries over into their personal lives. Among them: 🔥 63% experience burnout or reduced motivation 💭 62% report increased anxiety or depression 🌙 51% have difficulty sleeping or resting When fatigue, distraction, or exhaustion become routine, safety risks can rise. Employees said they want: 🤝 More flexibility to manage their workload 💬 Regular check-ins that show care 🕐 Time to rest and recharge Small steps like these can help everyone stay focused and supported. Safety first, then Pie Insurance 🥧 _____________________ 🌾 Stay tuned and tap the 🔔 on our profile to join us all month long as we share insights from our Employee Voice Survey about mental health, safety, and what employees are really saying.

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  • “I developed shingles from stress.” “I cried in my car before work.” “I didn’t want to say anything because I didn’t want to seem weak.” These aren’t isolated stories. They remind us that mental health challenges can appear in any workplace, across any industry, and at any level. According to the 2025 Employee Voice on Workplace Safety Report, 36% of employees said workplace stress affects their personal life, impacting their motivation, sleep, and relationships. Employees in the survey said actions like these can make a big difference: 💬 Regular check-ins 🤝 Open conversations about mental health 🕐 Flexibility to manage stress 🌟 Recognition for a job well done Building safer workplaces begins with awareness, empathy, and honest conversations about how people are really doing. Explore more insights: https://bit.ly/4nUkb0j _______________________ 🌾 Stay tuned and tap the 🔔 on our profile to join us all month long as we share insights from our Employee Voice Survey about mental health, safety, and what employees are really saying.

  • There’s a growing gap in how employers and employees see mental health at work. In our 2025 Employee Voice Report, 91% of employers said they feel confident supporting employee mental health. Only 62% of employees agreed. That divide grows wider when it comes to action. 52% of employers report having mental health protocols in place, but only 30% of employees say they’ve seen them. When asked what would make the biggest difference, employees shared they want: 💬 More open conversations about mental health 🤝 Genuine check-ins from managers 🕐 Flexibility to manage stress and recover 🌟 Recognition for the work they do These suggestions remind us that safety often starts with simple steps. Safety first, then Pie Insurance 🥧 _______________________ 🌾 Stay tuned and tap the 🔔 on our profile to join us all month long as we share insights from our Employee Voice Survey about mental health, safety, and what employees are really saying.

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  • “Small businesses thrive when their people feel genuinely supported.” - John Swigart, CEO, Pie Insurance In our 2025 Employee Voice on Workplace Safety Report, we surveyed more than 1,000 small business employees and found a clear perception gap around mental health at work: 🧠 91 percent of employers said they feel confident supporting mental health 🧠 62 percent of employees agreed 📉 More than one third said workplace stress affects their personal lives 🧩 73 percent said some form of mental health support from their employer would make a meaningful difference Safety+Health Magazine covered these findings in a recent article. Read it here: https://lnkd.in/gtiG2XK6

  • As fall winds down, now’s the time to prep your crews and vehicles for cold-weather safety. Here’s how to keep things running smoothly: ✅ Inspect vehicles before the first freeze. A quick look at tire tread, fluids, and battery strength can help prevent breakdowns and costly repairs when temperatures drop. ✅ Warm up your safety checks. Cold weather brings slippery floors and icy entryways. Encourage quick walk-throughs to keep high-traffic areas clear and safe. Fall may be wrapping up, but staying safe is always in season. 🍁 Safety first. Then Pie Insurance. 🥧

  • Fleet safety isn’t just about vehicles. It’s about visibility. Commercial auto coverage is more than a box to check. For agents, it’s a chance to help small business clients protect one of their biggest operational risks: the vehicles that keep their businesses running. According to Pie’s 2025 Workplace Safety Report: 🚚 67% of small businesses rely on commercial vehicles to deliver goods, transport employees, or provide services. ⚠️ 42% experienced an auto-related incident in the past year. 💰 The average out-of-pocket cost per incident was around $5,700, but total annual costs, including downtime and legal fees, can climb much higher. Here’s how agents can help clients strengthen fleet safety and reduce exposure: ✅ Encourage structured safety programs. Many small businesses recognize the importance of safety but do not have formal protocols in place. Establishing clear policies for vehicle inspections, driver training, and maintenance can help reduce incident frequency. ✅ Promote technology adoption. Telematics and GPS systems are no longer just for large fleets. About 62% of small businesses using these tools report improvements in efficiency and risk management. ✅ Highlight the value of documentation. Encourage clients to record inspections, training, and maintenance checks. It supports claims, renewals, and underwriting accuracy. ✅ Start safety conversations early. Regular check-ins about vehicle usage and driver behavior build trust, improve coverage accuracy, and help clients make proactive adjustments before incidents happen. Share this post to help more agents start the fleet safety conversation and keep small businesses moving safely forward. Safety first. Then Pie Insurance. 🥧

  • Helping clients prepare for renewal starts early. If you missed this quarter’s Monthly Slice webinar on renewals, one question came up again and again: “What’s the best way for agents to help their clients get ready?” Renewals work best when communication starts early and information is accurate. Here are a few practical steps agents can take to help their clients prepare: ✅ Encourage clients to review their operations. If the business has changed, such as adding employees, new work locations, or updated equipment, those details help ensure an accurate renewal. ✅ Check payroll and class codes. Accurate payroll reporting and classification prevent surprises during the audit and help keep premiums aligned with actual exposure. ✅ Confirm contact information. Simple but important. Up-to-date email addresses and contacts help ensure all renewal documents reach the right people. ✅ Ask about changes in subcontractors or coverage needs. These updates can affect both premium and underwriting decisions, so the earlier Pie knows, the better. Renewals are not just a date on the calendar. They are an opportunity to strengthen relationships, reinforce trust, and set clients up for a smooth year ahead. Watch the full Monthly Slice replay: https://bit.ly/4p8Hm8e Safety first. Then Pie Insurance. 🥧

  • Carrier relationships aren’t built in a day. But they’re worth the work. The strongest agency and carrier partnerships are built on consistency, communication, and trust. Not just renewals or new business. When collaboration is proactive, agencies can write more business, solve problems faster, and build lasting client trust. Here are eight ways to get more out of your carrier partnerships: 1️⃣ Be willing to let go of relationships that no longer work. Focus on a few core carrier partners that align with your goals and client base. 2️⃣ Prioritize communication. Consistent, two-way communication helps you bind business and resolve issues faster. 3️⃣ Assign a relationship manager. A single point of contact keeps things clear and consistent. 4️⃣ Schedule regular check-ins. Review performance, share updates, and plan what’s next. 5️⃣ Use value-added services. Ask about training, client education, or financing tools. 6️⃣ Ask for feedback. Understand how your agency performs and where you can improve. 7️⃣ Know your carrier’s comfort level with risk. Align submissions with each carrier’s appetite to reduce friction. 8️⃣ Respect the underwriter’s role. Be transparent and collaborative, even when you don’t agree on the outcome. If strong carrier relationships help you win business, share this post and start the conversation with your network. Safety first. Then Pie Insurance. 🥧

  • The workplace safety conversation is changing. Nearly 1 in 3 employees surveyed say mental health is their top workplace safety concern, according to our 2025 Employee Voice on Workplace Safety Report. Stress and fatigue can affect focus, awareness, and overall well-being. Mental health is one of the most overlooked safety risks, according to our Employee Voice on Workplace Safety Report. Addressing it can helps create safer, more resilient teams. This November, we’re exploring what employees are really saying about stress, safety, and support at work. Explore the full 2025 Employee Voice Report: https://bit.ly/49PMgCt _______________________ 🌾 Stay tuned and tap the 🔔 on our profile to join us all month long as we share insights from our Employee Voice Survey about mental health, safety, and what employees are really saying.

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