Chief Customer and Revenue Officer

Company Details

Intrepid Direct Insurance (IDI) is a rapidly growing direct to consumer property and casualty insurance company. A member of the W. R. Berkley Corporation, a fortune 500 company, rated A+ (Superior) by A.M. Best, Intrepid Direct’s vision is to make life better for business . The insurance industry has not evolved with innovation like other major industries.We’re here to change that. We are making life better for our customers, shareholders, and our team members by leveraging data and technology as insurance experts for our targeted customers. You will be part of a highly collaborative team of talented and focused professionals. Join a group that enjoys working together, trusts each other, and takes pride in our hard-earned success.

The Company is an equal employment opportunity employer.

Responsibilities

The Chief Customer and Revenue Officer (CCRO) is a senior executive with enterprise accountability for revenue growth, customer acquisition, retention, and market execution across Agency, Sales, and Marketing. The CCRO leads through experienced functional leaders across Agency, Sales, and Marketing, setting strategy, creating alignment, and holding leaders accountable for coordinated execution and profitable growth and is responsible for building a durable, profitable growth engine aligned with Intrepid Direct’s underwriting appetite, customer promise, and strategic priorities.This executive will work in close partnership with the President and will increasingly represent the company in high-value customer and partner relationships. The CCRO is expected to personally visit, develop, negotiate with, and help close large and strategically important customers, expanding executive-level commercial leadership capacity while maintaining close alignment with the President on material opportunities.As a key member of the senior leadership team, the CCRO will help shape enterprise strategy, identify future verticals and partnerships, and translate market opportunities into disciplined execution, sustained revenue growth, strong retention, and profitable portfolio performance.

Key functions include but are not limited to:

Enterprise Revenue Ownership & Go-to-Market Strategy

• Own enterprise revenue strategy and results across Agency, Sales, and Marketing, including new business production, customer retention, revenue quality, and profitable growth.
• Define and execute an integrated go-to-market strategy for targeted franchise brands, verticals, geographies, national accounts, and strategic partnerships.
• Partner with underwriting, actuarial, product, and finance leaders to align growth objectives with risk appetite, pricing discipline, portfolio performance, and return on acquisition investment.
• Lead segmentation, targeting, pipeline, retention, and account-development strategies that create a predictable, high-quality book of business.
• Use market, customer, competitor, and performance insights to inform enterprise priorities and resource allocation.
• Work closely with the President to evaluate and launch future verticals, franchisor relationships, and strategic partnerships, with clear ownership and seamless handoffs into production and service.

Strategic Customer Leadership & Executive Market Presence

• Serve as the senior executive sponsor for the company’s largest, most complex, and most strategically important customers and partners.
• Personally lead or support customer visits, executive presentations, negotiations, relationship development, and closing strategies for large accounts.
• Assume primary executive responsibility for many strategic customer and partner interactions currently led by the President, while maintaining close communication and alignment with the President.
• Build trusted, long-term relationships with franchise systems, large operators, associations, vendors, and other market partners.
• Represent Intrepid Direct at customer meetings, industry events, conferences, and other external forums.
• Travel approximately 20% based on business needs, primarily for strategic customer, partner, and market-development activity.

Agency & Client Success Leadership

• Provide executive oversight of the Agency and client success organization through its functional leader, ensuring the function is aligned with Intrepid Direct’s revenue strategy, retention priorities, service standards, and customer experience expectations.
• Partner with the Agency leader to establish service standards, operating disciplines, governance, and performance measures that deliver a responsive, consultative, and best-in-class customer experience.
• Ensure the Agency is positioned as a strategic revenue and retention function, not solely a service operation.
• Align Agency, Sales, Marketing, Underwriting, Claims, and Operations around customer needs, franchise requirements, service trends, renewal strategy, and profitability drivers.
• Sponsor scalable process improvements and talent capability planning within Agency that support growth without sacrificing service quality or customer intimacy.

Sales Leadership

• Serve as the primary executive leader for the sales strategy and operating model, including prospect data acquisition, territory and vertical planning, pipeline discipline, forecasting, production expectations, strategic account development, and executive-level deal support.
• Provide executive oversight of the sales organization and hold leaders and team members accountable for production, pipeline quality, conversion, strategic account development, and growth results.
• Maintain active involvement in high-value opportunities, complex deals, and material account negotiations.
• Build a disciplined sales culture focused on preparation, customer insight, consultative selling, accountability, and profitable growth.

Marketing & Brand Leadership

• Provide executive oversight of Marketing, empowering the Marketing leader to execute brand, campaign, content, event, and demand-generation strategies while holding the function accountable for measurable commercial outcomes.
• Set enterprise commercial direction for positioning, customer acquisition priorities, market experiments, and growth campaigns, in partnership with the Marketing leader.
• Ensure consistent and differentiated expression of the Intrepid Direct brand and value proposition across every customer touchpoint.
• Establish clear performance expectations and analytics to evaluate marketing effectiveness and improve return on investment.

Cross-Functional Leadership

• Collaborate closely with the President and with underwriting, claims, operations, technology/data, actuarial, and finance leaders to align customer, risk, process, and enablement priorities.
• Lead cross-functional initiatives that improve revenue growth, retention, operating efficiency, customer experience, and market responsiveness.
• Create clear governance, decision rights, and handoffs across revenue-generating and customer-serving functions.
• Establish a consistent revenue operating cadence that provides the President and senior leadership team with transparent visibility into pipeline, retention, revenue quality, marketing effectiveness, customer opportunities, market conditions, and cross-functional execution risks.

Team Leadership & Organizational Capability

• Lead a high-performing team of functional leaders across Agency, Sales, and Marketing, creating shared priorities, clear accountabilities, and coordinated execution across the revenue organization.
• Evaluate and evolve the organizational structure, leadership roles, capabilities, and talent required to support Intrepid Direct’s growth strategy.
• Set measurable goals, KPIs, performance standards, and accountability mechanisms across all revenue functions.
• Coach and develop functional leaders, ensuring they have the clarity, resources, decision rights, accountability, succession plans, and talent pipelines needed to lead effectively and support continued growth.
• Develop a strong working knowledge of the CRM and related revenue technology to improve visibility, execution, and coordination across departments

Qualifications

• Bachelor’s degree in business, marketing, risk management, insurance, or a related field required.
• Advanced degree preferred.
• Relevant insurance or industry designations preferred
• 15+ years of progressively responsible leadership experience in commercial insurance, including significant experience in sales, distribution, agency operations, underwriting, marketing, or customer strategy; 20+ years preferred.
• Demonstrated success owning a broad revenue agenda and delivering sustained, profitable growth across multiple customer-facing functions.
• Experience leading through experienced functional managers, integrating Agency, Sales, and Marketing into a coordinated commercial organization, and creating accountability while enabling leaders to execute within their area of expertise.
• Demonstrated ability to develop executive relationships, visit and advise large customers, lead complex negotiations, and close strategic accounts or partnerships.
• Strong knowledge of commercial property and casualty products, underwriting dynamics, direct and intermediary distribution models, customer lifecycle management, and service operations.
• Demonstrated ability to translate strategy into execution, establish accountability, use data to support decisions, and build scalable processes.
• Executive presence, sound judgment, high personal accountability, and the ability to serve as a trusted partner to the President and senior leadership team.
• Ability and willingness to travel approximately 20% based on business needs.

Additional Company Details

We do not accept unsolicited resumes from third party recruiting agencies or firms. The company offers a competitive compensation plan and robust benefits package for full-time regular employees. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.

Sponsorship Details

Sponsorship not Offered for this Role