Job Description

Hearst Connecticut Media Group

Chief Revenue Officer

Connecticut | 4 days in office | Full-time

Competitive base salary, performance-based bonus, and total compensation aligned with the scope and seniority of the role.

Connecticut’s largest and most diversified media company is seeking a Chief Revenue Officer to redefine how revenue is built, scaled, and sustained in a modern media organization.

This is a mandate for a leader who wants to rewrite the playbook, not operate within it—someone who sees AI not as a concept, but as a practical and immediate competitive advantage, and who has the experience and conviction to embed it across a complex, multi-channel revenue organization.

About Hearst Connecticut Media Group

Hearst Connecticut Media Group (HCMG) is the largest and most diversified media company in the state, anchored by CTInsider.com, Connecticut’s leading digital news destination. We connect businesses to audiences across a powerful, multi-channel platform spanning digital, print, sponsorships, and live events.

As part of Hearst—one of the most respected and enduring media companies globally—HCMG benefits from long-term investment, institutional strength, and a clear commitment to local journalism.

This is a business on the offensive: investing in growth, innovation, and market leadership.

The Role

As Chief Revenue Officer, you will own and architect the full commercial engine of HCMG, from initial market engagement through long-term client growth and retention.

You will lead a cross-functional organization spanning Sales, SDR, Revenue Operations, and Marketing, with direct accountability for revenue performance across all channels and customer segments.

This role extends beyond delivering near-term results. The mandate is to build a durable, future-ready revenue organization—one that is more intelligent, more efficient, and more client-centric than traditional local media models.

Key Responsibilities

Define and execute the enterprise go-to-market strategy, including segmentation, pricing, packaging, and channel mix across digital, print, sponsorships, and events
Lead, develop, and scale a high-performing leadership team, fostering a culture of accountability, performance, and continuous improvement
Drive revenue growth across SMB, regional, multi-location, and enterprise segments
Operationalize AI and automation across the revenue lifecycle—from prospecting and outreach to proposal development and client retention
Partner across Marketing and Revenue Operations to deliver a seamless, differentiated client experience
Establish rigorous pipeline management, forecasting, and performance analytics as core operating disciplines
Build and evolve a modern revenue technology stack, enabling real-time visibility and improved sales productivity
Serve as a senior external representative of HCMG, strengthening market presence and deepening relationships across the Connecticut business community

What Success Looks Like (12 Months)

Success in this role will be defined by both performance and transformation. Within the first year, you will have:

Implemented a clearly differentiated go-to-market strategy, with new segmentation, outreach approaches, and client engagement models
Embedded AI-driven workflows and automation into daily sales operations, materially increasing productivity and effectiveness
Delivered measurable revenue growth and market share gains, supported by clear examples of strategic client wins
Elevated the capability and performance of the leadership team and broader revenue organization
Positioned HCMG as the most forward-thinking and effective media partner in the Connecticut market

Candidate Profile

Required Experience

Proven senior revenue leadership experience within media, advertising, ad tech, SaaS, or closely related industries (required)
Demonstrated success building and scaling multi-channel revenue organizations, ideally within complex or evolving business models
Track record of driving growth through both strategy and execution, including go-to-market transformation

Core Capabilities

Deep understanding of modern revenue models, including digital advertising, performance marketing, and integrated client solutions
Strong perspective on the application of AI and automation within sales organizations, with evidence of practical implementation
Ability to operate at both strategic and operational levels—shaping direction while driving execution
Exceptional leadership presence, with a track record of attracting, developing, and retaining high-performing teams
Highly client-centric mindset, with a belief that sustainable revenue growth is driven by delivering measurable client value
Comfort operating in dynamic environments, with the ability to bring clarity and direction amid ambiguity

Additional Requirements

Based in Connecticut or willing to relocate
Commitment to being present in the market and with the team (4 days in office)

Why This Role, Why Now

There are CRO roles focused on optimization. This is a role focused on reinvention.

Hearst is one of the most iconic names in American media, with a long-term commitment to this market
CTInsider.com is an unmatched audience asset, reaching more Connecticut residents than any other local news source
You will have true authority to reshape the commercial model, not just incrementally improve it
The AI-enabled sales infrastructure is being built now—you will define how it works and how it wins
The outcomes of this role directly support local journalism and community impact

About The Team

You will lead 9 direct reports across four core functions:

Sales Directors overseeing key segments and client relationships
SDR team driving top-of-funnel activity
Revenue Operations managing systems, data, and performance infrastructure
Marketing leading brand, content, and demand generation

The foundation is strong. The opportunity is to elevate, align, and accelerate.

Ready to reshape local media in Connecticut?

We are looking for revenue leaders who are ready to move beyond legacy models and build what comes next.

If that is you, let’s talk.

About Hearst Newspapers:

With 2,500 employees across the nation, HNP represents a network of 24 daily and 52 weekly publications, including the San Francisco Chronicle, Houston Chronicle, San Antonio Express-News and Albany Times Union, several top digital-only news and lifestyle sites, marketing services businesses, and entertainment businesses such as King Features Syndicate. At HNP, we are investing in new and innovative ways to tell stories–growing newsrooms, diversifying tools, evolving platforms–to support the millions of people who trust us each month to help them make decisions, take action and be inspired.

Be a part of something bigger–Your Headline Awaits

Hearst Connecticut Media Group Jobs

Chief Revenue Officer