Digi Pro

Fractional Chief Marketing Officer (CMO)

Location: Remote (United States)

Commitment: Approximately 5 hours per week

Employment Type: Fractional / Contract

About the Companies

InsurePro is a specialized insurance operations partner delivering underwriting support, policy servicing, claims administration, payroll audits, analytics, and back-office services for carriers, MGAs, PEOs, wholesalers, and brokerages. The company combines deep Workers' Compensation expertise with scalable operations and AI-enabled workflows.

InsureComp is an AI-enabled underwriting and pricing platform that helps insurers, MGAs, and PEOs automate eligibility, underwriting, pricing, and analytics to make faster and more informed underwriting decisions.

Together, our mission is to modernize insurance operations through a combination of technology, domain expertise, and operational excellence.

Position Overview

We are looking for an experienced Fractional Chief Marketing Officer to serve as a strategic marketing advisor for both InsurePro and InsureComp.

This is an executive-level strategy role, not a hands-on marketing execution position. You'll work directly with the founders to refine our market positioning, accelerate growth in the US insurance market, build thought leadership, and create scalable go-to-market strategies.

The ideal candidate has significant experience marketing within the Property & Casualty (P&C) insurance industry, with strong relationships and knowledge across carriers, MGAs, PEOs, brokers, TPAs, and InsurTech companies.

Key Responsibilities

• Work with the digital marketing agency to come up with the overall marketing strategy for both companies.
• Define clear positioning for InsurePro (outsourced insurance operations) and InsureComp (underwriting technology).
• Build a scalable US go-to-market strategy.
• Advise on brand positioning and messaging.
• Guide account-based marketing (ABM) initiatives targeting enterprise insurance organizations.
• Review website messaging, sales decks, case studies, and collateral.
• Recommend demand generation strategies for enterprise sales.
• Build thought leadership initiatives including webinars, industry content, whitepapers, and speaking opportunities.
• Advise on conference strategy (WSIA, TMPAA, NAPEO, InsurTech events, etc.).
• Mentor the internal marketing team.
• Help establish KPIs and marketing dashboards.
• Identify strategic partnerships and channel opportunities.
• Recommend AI tools and marketing automation to improve efficiency.
• Participate in a weekly leadership strategy meeting.

Required Experience

• 15+ years of B2B marketing leadership.
• Previous experience as a CMO, VP Marketing, or Head of Marketing.
• Deep knowledge of the US Property & Casualty insurance market.
• Experience working with one or more of:
  • Insurance Carriers
  • Managing General Agents (MGAs)
  • Program Administrators
  • PEOs
  • Retail Brokers
  • Wholesalers
  • InsurTech companies
• Strong understanding of the insurance buying cycle.
• Experience supporting long enterprise sales cycles.

Preferred Qualifications

Experience marketing solutions related to:

• Workers' Compensation
• Policy Administration
• Insurance Operations Outsourcing
• AI in Insurance
• Insurance Data & Analytics
• SaaS Platforms

Success Measures

Within the first 6-12 months, the Fractional CMO will help us achieve:

• Stronger market positioning for both InsurePro and InsureComp.
• Increased brand visibility across the US insurance industry.
• A predictable enterprise lead generation strategy.
• Higher-quality marketing assets and sales enablement content.
• A structured content and thought leadership program.
• Improved marketing ROI and executive reporting.
• Better alignment between sales, marketing, and product strategy.

Time Commitment

• Approximately 5 hours per week
• Monthly marketing review
• Available for strategic consultation as needed

Compensation

Competitive hourly rate or monthly retainer, based on experience.

Ideal Candidate Profile

We are looking for someone who has already built and scaled marketing for an insurance, InsurTech, or insurance technology company. This individual should understand the buying behavior of carriers, MGAs, PEOs, brokers, and enterprise insurance organizations, and be able to translate that experience into practical strategies that accelerate growth for both InsurePro and InsureComp. Experience with executive networking, industry events, analyst relations, and AI-driven B2B marketing will be a significant advantage.