---
title: 'Regional Sales Manager, Broker Sales (Tampa) at Sidecar Health'
canonical: 'https://feeny.ai/job/regional-sales-manager-broker-sales-tampa-sidecar-health-remote-sthcxrvz5kd3'
type: 'job'
last_seen: '2026-10-29'
---

# Regional Sales Manager, Broker Sales (Tampa) at Sidecar Health

- **Company:** Sidecar Health
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-10-23
- **Last confirmed live:** 2026-10-29
- **Apply:** https://job-boards.greenhouse.io/sidecarhealth/jobs/6233384004

## Job description

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

## About the Role

Sidecar Health is looking for a Regional Sales Manager based in Tampa, FL to own broker relationships across a territory spanning Tampa to Naples and Lakeland. This is a channel sales role — your job is to be so embedded in the local broker community that Sidecar is the first call brokers make when a client is frustrated with their legacy insurance bill or heading into renewal. You won't knock on employer doors; you'll build the trust with brokers and consultants that makes the business come to you.

## What You’ll Do

- Map your existing broker and consultant relationships across the Tampa Bay to Naples corridor and identify the 20 who can move business in the next 90 days
- Meet with Sidecar's sales leadership and internal teams to understand how the Benefit Amount model works and how to position it against legacy insurance in broker conversations
- Establish a regular presence in the Tampa, St. Petersburg, and Clearwater broker community through meetings, events, and informal touchpoints
- Begin qualifying and prioritizing employer group opportunities in the 100–2,000 employee range surfaced through broker partners
- Deepen relationships with general agencies and regional brokerages so Sidecar becomes a default recommendation at renewal
- Collaborate with underwriting and product teams to develop competitive proposals tailored to employer groups whose members want more choice and the ability to get money back
- Build a repeatable pipeline cadence across the full territory, covering Tampa north to Lakeland and south to Naples, within your 40% travel footprint

## What You Bring

- Established broker and consultant relationships in the Tampa Bay market that you could activate this week, not someday
- 5 or more years in group benefits channel sales — carrier, GA, or TPA side — with a track record built on trust rather than transaction volume
- Deep fluency in self-funded or level-funded plan design and the ability to explain why legacy insurance leaves money on the table for employers and their employees
- A relationship-first sales style: brokers call you with problems, you don't have to chase them for meetings
- Active Florida Life and Health license or ability to obtain one quickly

## Nice to have

- Experience at a general agency such as BenefitMall or a regional benefits distributor, where broker distribution was the core of your daily work
- Familiarity with presenting the Benefit Amount concept — fixed, transparent reimbursement tied to local cost of care — to brokers and employer HR or CFO audiences
- Exposure to employer groups ranging from 100 to 2,000 lives with demonstrated ability to manage cases start to finish
- History of finishing at or near the top of a regional leaderboard in a broker-distributed benefits product

## What You’ll Get

- Competitive base salary with uncapped performance-based commission and an equity package
- Medical coverage from day one, with 100% of the premium paid by Sidecar for you and your dependents. Choose an HSA-eligible plan or a $0 deductible plan
- Dental and vision coverage from day one, with 100% of your premium covered, and 80% covered for your dependents
- A 401(k) retirement plan
- Paid vacation, company holidays, and paid parental leave
- Stay connected: $50 a month toward your internet and $50 a month toward your phone, reimbursed through expenses
- The opportunity to make an impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.

## About Sidecar Health

## Company Overview
- **One-liner**: Sidecar Health is a health insurance company that provides ACA-compliant, employer-sponsored major medical plans with transparent pricing and no provider networks.
- **Entity Type**: Private (Series D)
- **Headquarters**: Manhattan Beach, California, USA
- **Founded**: 2018
- **Founders**: Patrick Quigley (CEO) and Veronica Osetinsky (COO)

## Core Business
- **Primary industry**: Health Insurance / Healthcare Technology
- **Target customers**: B2B — Large employers (fully insured and self-funded/ASO groups); previously served individuals
- **Mission**: To make quality healthcare affordable and accessible for all by bringing price transparency and consumer choice to health insurance

## Products & Services
- **Sidecar Health Employer Plans**: ACA-compliant major medical coverage for large employers. The model provides members with transparent, upfront pricing on care, allows them to shop for services, and shares savings when they choose lower-cost providers. Members keep 50% of the difference between the plan’s typical local cost and what they actually spend. The company covers members in 46 states and partners with employers across 50 industries. Plans are available as fully insured and administrative services only (ASO) for self-funded employers. [sidecarhealth.com](https://www.sidecarhealth.com/)

## Market Standing
- **Valuation**: Not publicly disclosed
- **Key Metric – Total Funding**: $328M (across 4 rounds)
- **Annual Revenue**: $50M (estimated, per LinkedIn data) [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Notable Investors**: Koch Disruptive Technologies (led Series D), Drive Capital (led Series C), Cathay Innovation (led Series B), GreatPoint Ventures, Morpheus Ventures [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Notable Advisors/Board Members**: Anne Wojcicki (CEO & Co-Founder, 23andMe), Andrew Liveris (President, Brisbane 2032 Olympic Committee), The Honorable David J. Shulkin, M.D. (Former Secretary of Veterans Affairs), Adam Stavisky (Former Walmart SVP, US Benefits) [sidecarhealth.com](https://www.sidecarhealth.com/about-us)
- **Growth Signals**: Headcount grew 18.7% YoY to 202 employees; active job postings surged 466.7% monthly and 1600% quarterly; expanded large group employer plans from Ohio to Georgia (2023) and Florida (2024); launched ASO capabilities for self-funded national employers in 2025. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Competitive Advantages
- **No provider networks**: Members can see any doctor or use any facility, removing the limitations of traditional narrow networks.
- **Transparent pricing engine**: The company shows guaranteed, local costs for care upfront, enabling members to shop and compare.
- **Shared savings model**: A behavioral economics approach that incentivizes members to be cost-conscious, which the company claims lowers overall costs for the entire group.
- **Carrier ownership**: Sidecar Health established its own insurance carrier (Sidecar Health Insurance Company) in 2021, allowing it to underwrite its own products and control the full insurance stack.
- **High claims approval rate**: The company reports approving over 99% of claims. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Strategic Focus
- **Shift to employer market**: After proving the model with individual plans, the company pivoted exclusively to employer-sponsored coverage, targeting large national employers.
- **Geographic expansion**: After launching in Ohio, the company expanded to Georgia and Florida, with a stated goal of covering members in 46 states.
- **Product breadth**: Offering both fully insured and ASO (self-funded) plans to capture different segments of the large employer market.
- **AI investment**: Actively hiring a Lead Product Manager, AI, signaling an investment in AI-powered capabilities. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)

## Why Work Here
- **Mission-driven work**: The company is explicitly focused on fixing a broken healthcare system, which attracts talent from tech, policy, and healthcare backgrounds.
- **Remote-first culture**: All current open positions (engineering, product, marketing, sales, member care) are listed as remote. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)
- **Strong ratings**: 4.2/5.0 on LinkedIn (117 reviews), with Culture rated 4.4 and Career rated 4.1. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Growth trajectory**: With a recent $165M Series D, rapid job posting growth, and a headcount expansion of nearly 19% YoY, the company is in a scaling phase — offering advancement opportunities.
- **Diverse team composition**: Team members come from backgrounds as tech leaders, policymakers, and healthcare professionals. The company is an Equal Opportunity employer. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)
- **Open roles (as of mid-2026)**: 17 active job postings including Senior Software Engineer (Backend/Full Stack), VP of Marketing, VP of Strategic Accounts, Director of Account Management, Lead Product Manager (AI), and more. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Sources
1. [sidecarhealth.com - About Us](https://www.sidecarhealth.com/about-us)
2. [sidecarhealth.com - Homepage](https://www.sidecarhealth.com/)
3. [job-boards.greenhouse.io - Sidecar Health Careers](https://job-boards.greenhouse.io/sidecarhealth)
4. [linkedin.com - Sidecar Health Company Profile](https://www.linkedin.com/company/sidecarhealth)

## Other roles at Sidecar Health

- [Lead Product Manager, Member Experience](https://feeny.ai/job/lead-product-manager-member-experience-sidecar-health-remote-xth7g6803rf1)
- [Senior Software Engineer, Full Stack (Member Experience)](https://feeny.ai/job/senior-software-engineer-full-stack-member-experience-sidecar-health-remote-bzkw41b5tnap)
- [Staff Data Analytics Engineer](https://feeny.ai/job/staff-data-analytics-engineer-sidecar-health-remote-ty366nskbbn3)
- [Staff Software Engineer, Full Stack (Member Benefits)](https://feeny.ai/job/staff-software-engineer-full-stack-member-benefits-sidecar-health-remote-jed2cz2vjnqa)
- [Lead Product Manager, Claims Automation](https://feeny.ai/job/lead-product-manager-claims-automation-sidecar-health-remote-gekn6t8k2qvg)
- [VP of Finance](https://feeny.ai/job/vp-of-finance-sidecar-health-remote-svc5b8sd95fr)