Drive Growth with Fractional CMOs & CSOs for Financial Services
and Revenue Growth
Chief Outsiders provides experienced fractional CMOs and CSOs who help financial services companies develop and execute marketing and sales strategies that attract new clients, strengthen relationships, expand market opportunities, and accelerate profitable growth.
Why Financial Services Companies Choose Chief Outsiders
- Access proven marketing and sales leadership without the cost of a full-time executive hire
- Develop and execute growth strategies tailored to financial services markets
- Improve client acquisition, retention, business development, and revenue performance
- Build stronger marketing and sales capabilities, processes, and teams for sustainable growth
Our "Big-Company" Experience Will Help You Grow
How Chief Outsiders Helps Financial Services Companies
Growth opportunities look different across financial services. A wealth management firm may need to attract high-net-worth clients, while a regional bank focuses on expanding commercial relationships or an insurance provider looks to strengthen its distribution network. Chief Outsiders helps organizations identify the priorities that matter most to their business and put the marketing and sales leadership, strategies, and resources in place to pursue them.
Marketing Strategy & Execution
Our fractional CMOs help financial services companies turn marketing into a more effective driver of business growth. They develop and execute strategies that differentiate your brand, reach high-value prospects, and improve client acquisition while aligning marketing investments with business priorities and measurable outcomes.
Sales Strategy & Execution
Our fractional CSOs bring structure, accountability, and proven leadership to financial services sales organizations. They evaluate existing sales processes, identify obstacles to performance, and implement improvements that strengthen pipeline management, increase sales team effectiveness, and turn business development opportunities into closed deals.
What Financial Services Firms Are Up Against Right Now
Financial services firms face mounting pressure to compete in crowded markets, adapt to changing customer expectations, and deliver consistent growth while navigating complex regulatory requirements. From traditional banks and insurance providers to wealth management firms and fintech companies, business growth increasingly depends on building trust, demonstrating value, and creating stronger connections with customers and prospects.
Marketing Challenges
Intense Competition & Differentiation
Standing out in markets where competing financial products and services often appear similar, making it difficult to communicate a compelling value proposition.
Rising Client Acquisition Costs
Attracting qualified prospects and converting them into clients while managing increasing competition for attention and marketing investment.
Regulatory & Compliance Constraints
Developing effective financial services marketing campaigns while navigating industry regulations, disclosure requirements, and advertising restrictions.
Changing Customer Expectations
Meeting growing demand for personalized experiences, digital convenience, transparency, and consistent communication across channels.
Digital Transformation & Marketing Effectiveness
Modernizing outdated marketing approaches, integrating customer data, and demonstrating measurable returns on marketing investments.
Client Retention & Loyalty
Maintaining meaningful customer relationships, building long-term trust, and preventing attrition as competitors introduce new offerings.
Sales Challenges
Complex Buying Decisions & Longer Sales Cycles
Navigating multiple decision-makers, extensive due diligence, and trust-driven purchasing decisions that can delay new business.
Inconsistent Business Development
Building reliable pipelines of qualified opportunities rather than depending heavily on personal networks, referrals, or individual producers.
Recruiting & Retaining Advisory & Sales Talent
Attracting, developing, and retaining financial advisors, relationship managers, insurance agents, and sales professionals who bring in new clients, grow existing relationships, and generate revenue.
Sales Process & Pipeline Visibility
Overcoming fragmented sales processes, inconsistent CRM adoption, and limited visibility into opportunities, forecasts, and team performance.
Cross-Selling & Relationship Expansion
Identifying opportunities to introduce additional financial products and services while maintaining customer trust and delivering meaningful value.
Scaling Sales Performance
Expanding into new markets, improving sales productivity, and building repeatable processes without sacrificing service quality or compliance.
Our Methodology
Our Growth Gears® framework is a proven methodology, validated by research and thousands of client engagements, for helping mid-market companies identify growth opportunities, align marketing and sales, and accelerate results.
Our proprietary, AI-powered operating system, GrowthGears® OS, brings this methodology to life, harnessing the learnings and best practices from hundreds of growth executives and thousands of engagements to accelerate impact and reduce risk.
| INSIGHT | STRATEGY | EXECUTION | ||
| Market | Company | Offering | Marketing | Sales |
| Market Assessment & Opportunity Analysis | Market Alignment Strategy | Product / Service Branding | Organization Audit, Planning & Development | Sales Audit & Process |
| SWOT & Gap Analysis | Brand Assessment | Product / Service Planning | Marketing Mix Optimization | Funnel Conversion Analysis, Metrics & Reporting |
| Customer Experience | Value Proposition | Product / Service Positioning | Digital Marketing & Social Media | Partner & Channel Strategy |
| Profitability Analysis | Positioning & Messaging | Packaging & Delivery | Technology Systems & Process | Demand/Lead Generation |
| Sales & Marketing Alignment | Market Segmentation | Pricing | Key Account Strategies | Sales Ops & Compensation |
| Competitive Analysis | Go-To-Market Strategy | Launch Planning | Communications & PR | Sales Enablement |
| Company Perspective | Innovation Process | Marketing Metrics, Reporting & ROI | Marketing Sales Alignment | |
Success Spotlight
Proven Results for Financial Service Companies and Organizations
Reducing Customer Acquisition Costs by 40%
Following an unexpected CMO departure, a digital insurance brokerage needed to stabilize its marketing team and improve growth efficiency. Chief Outsiders strengthened the marketing organization, reduced customer acquisition costs by 40%, and launched the company's first national brand campaign.
Case Studies
Increasing Customer Value by 150% While Cutting Acquisition Costs in Half
Seeking more profitable growth, a tax advisory firm partnered with Chief Outsiders to sharpen its go-to-market strategy, modernize its marketing systems, and increase average revenue per customer by 150% while reducing acquisition costs by more than 50%.
“We’ve increased our average revenue per sale by 150%, while lowering our cost per sale by over 50%, and we built out better systems that help us forecast and track the financial results of our marketing and sales spending. All of those things translate into better business results and a better customer experience.”

Building a Scalable Growth Engine for a Fintech Company
Following a private equity acquisition, a fintech company partnered with Chief Outsiders to build a repeatable go-to-market strategy, expand into new markets, and establish the marketing discipline needed to support sustainable growth.
“Chris and Chief Outsiders put in place the process that allows us to get to market much quicker than before. It's money well spent to bring in a person with experience who builds confidence and spends the time to understand your business.”

Opening New Markets for a Financial Technology Company
To move beyond its traditional direct sales model, a financial technology company partnered with Chief Outsiders to identify new growth opportunities, strengthen its market positioning, and build a sales pipeline that secured customers for new products in new markets.
“With a goal to double the customers and revenue of First Rate, we knew that we needed to consult with experts that knew how to orient our marketing strategies to our strengths. Chief Outsiders took a different approach than other firms we had met with – they wanted to understand our business goals and drivers first and foremost.”

Fractional Chief Marketing Officers for Financial Services Companies
Financial services companies need marketing leadership that understands the importance of trust, regulatory requirements, complex customer relationships, and long-term business growth. Chief Outsiders provides experienced fractional CMOs who bring executive-level expertise to financial firms without the cost or commitment of hiring a full-time chief marketing officer.
Our fractional CMOs work alongside executive teams to establish marketing priorities, identify untapped growth opportunities, and build the strategies, teams, and capabilities needed to compete more effectively. Whether your company is entering new markets, launching financial products, modernizing its marketing operations, or struggling to generate qualified demand, our executives provide the leadership and accountability to move initiatives forward.
CMOs Supporting Financial Services Growth
Anne-Flore Goldsberry
Partner & CMO
Juli Bark
CMO & CSO
Stephen Cassell
CMO & CGO
R. Scott Harris
CMO
Tom Arduino
CMO
Matt Benner
Partner & CMO
Vickie Sherman
CMO
Tom McCrary
Partner & CMO
Dawn Werry
President, Partner & CMO
Beth Brady
Partner & CMO
Anka Twum-Baah
Area Managing Partner & CMO
Carol Eversen
Area Managing Partner, CMO & CRO
Tom McCarty
Partner & CMO
William Collins
Partner & CMO
Slade Kobran
Managing Partner
Paul Eppen
Partner & CGO
Bill DeWitt
Partner & CMO
Grant Johnson
Partner & CMO
Ken Murray
Partner & CMO
Michael Morrison
Partner & CMO
Gary Stockman
General Manager, Team Outsiders™
Kelly Megel
CMO & Executive Coach/Advisor
Chris Wallner
Partner & CMO
Anil Singh
Partner & CMO
Robin Liebowitz
Partner & CMO
Fractional Chief Sales Officers for Financial Services Companies
Financial services companies face unique sales challenges, from managing complex buying cycles and building trusted client relationships to improving business development performance and expanding into new markets. Chief Outsiders provides experienced fractional CSOs who bring proven sales leadership and industry expertise without the cost or commitment of hiring a full-time chief sales officer.
Our fractional CSOs work alongside executive teams to evaluate sales performance, identify barriers to growth, and implement strategies that improve sales effectiveness and revenue generation. Whether your company needs to strengthen financial advisor and insurance agent performance, build a more predictable sales pipeline, expand distribution channels, or improve coordination between sales and marketing, our executives bring the experience and accountability to drive meaningful improvements.
With Chief Outsiders, financial services companies gain hands-on sales leadership that strengthens teams, improves execution, and builds the processes and capabilities needed for sustainable revenue growth.
CSOs Supporting Financial Services Growth
When Should Financial Services Companies Deploy Our Growth Executives?
Financial services companies face important strategic decisions as they expand into new markets, introduce financial products, navigate acquisitions, and adapt to changing competitive and regulatory conditions. These situations often require specialized marketing and sales leadership to evaluate opportunities, manage organizational change, and execute growth initiatives effectively.
Consider bringing in a growth executive when your company is:
Entering New Markets or
Expanding Geographic Reach
A bank, insurance provider, or wealth management firm is expanding into new regions or customer segments and needs a market entry strategy, differentiated positioning, and coordinated sales execution.
Growing an RIA or Wealth
Management Practice
Your firm needs to attract high-net-worth clients, expand assets under management, strengthen referral networks, or build a more systematic approach to client acquisition.
Expanding an Insurance Agency
or Distribution Network
Your organization is recruiting insurance agents and brokers, expanding into new territories, strengthening distribution partnerships, or looking to improve policyholder acquisition and retention.
Launching New Financial
Products or Fintech Solutions
Your company is introducing lending products, investment services, insurance offerings, or financial technology solutions and needs stronger go-to-market planning, market education, and customer adoption.
Navigating Mergers, Acquisitions,
or Consolidation
Your financial services organization needs to unify brands, integrate marketing and sales teams, retain valuable client relationships, or identify cross-selling opportunities following an acquisition.
Modernizing Marketing and
Sales Operations
Your firm is investing in CRM, marketing automation, digital acquisition, or sales technology but lacks the executive leadership needed to align systems, processes, and teams.
Addressing Stalled Client
Acquisition or Revenue Growth
Your financial services company is struggling to generate qualified opportunities, convert prospects, improve advisor productivity, or create consistent business development performance.
Bridging a Marketing or Sales
Leadership Gap
Your organization needs experienced executive leadership to guide growth initiatives, strengthen internal teams, or maintain momentum while evaluating a permanent executive hire.
Financial Services Marketing Services
Marketing financial products and services requires understanding how individuals and businesses make financial decisions, what builds confidence in a provider, and how to reach prospective clients across increasingly competitive markets. Chief Outsiders helps financial services companies identify market opportunities, understand customer needs, differentiate their offerings, and develop marketing strategies that attract qualified prospects and strengthen long-term relationships.
Our financial services marketing executives bring firsthand experience leading marketing organizations, managing budgets, and delivering measurable business results. Whether the priority is attracting wealth management clients, increasing bank customer acquisition, expanding insurance distribution, launching fintech solutions, or improving digital marketing performance, we help translate market insight into focused strategies and effective execution.
Areas of focus include:
Financial Services Sales Services
Growing revenue in financial services requires strong client relationships, effective business development, and sales teams that understand how to navigate complex financial decisions.
Banks, wealth management firms, insurance providers, and fintech companies must navigate relationship-driven buying decisions, complex financial products, regulatory requirements, and diverse distribution channels. Chief Outsiders helps financial services organizations strengthen business development, improve sales effectiveness, and build more consistent approaches to acquiring clients and expanding revenue.
Our financial services sales executives bring practical experience leading sales organizations, developing high-performing teams, and implementing strategies that deliver measurable results. Whether the priority is increasing assets under management, improving advisor productivity, expanding insurance distribution networks, strengthening institutional sales, or accelerating fintech adoption, we help translate revenue objectives into actionable sales plans, effective processes, and stronger execution.
Areas of focus include:
Why Financial Services Firms Choose Chief Outsiders
Financial services organizations need executive leaders who understand their markets, recognize the commercial implications of regulatory requirements, and know how to build growth strategies around trust, relationships, and measurable performance. Chief Outsiders combines experienced marketing and sales leadership, financial services expertise, and hands-on execution to help firms make better strategic decisions and turn business priorities into results.
Proven Financial Services Experience
Our executives bring experience across banking, wealth management, investment management, insurance, fintech, and other specialized financial services markets. They understand the distinct customer expectations, distribution channels, competitive dynamics, and regulatory considerations that influence marketing and sales performance across these sectors.
Executives Who Have Done the Job
Our fractional CMOs and CSOs are proven operators who have led marketing and sales organizations, managed teams and budgets, launched financial products, expanded into new markets, and developed revenue-generating partnerships. They bring practical leadership informed by firsthand experience and accountability for business results, not just strategic recommendations.
The Right Executive for Your Organization
A wealth management firm, regional bank, insurance provider, and fintech company have very different commercial needs. Our executive matching process connects your organization with a fractional CMO or CSO whose industry experience, functional expertise, leadership approach, and track record align with your specific business priorities.
Strategy + Execution
Our executives do more than develop strategic plans. They work alongside your leadership and internal teams to establish priorities, coordinate resources, guide implementation, and create accountability for marketing and sales initiatives that support client acquisition, business development, and revenue growth.
On-Demand Execution Resources
When specialized capabilities are needed, Chief Outsiders can provide access to additional marketing execution talent to support initiatives such as digital acquisition, financial services content development, marketing technology implementation, and campaign execution without requiring your organization to build every capability internally.
A Proven, Technology-Powered Approach
Our engagements are powered by GrowthGears® OS, our proprietary AI-enabled platform that brings together proven best practices from over 2,500 client engagements. It helps keep teams aligned, priorities focused, and progress transparent, accelerating execution and creating a clearer path to measurable growth.
The Strength of a Team
Your organization gains more than the experience of a single fractional executive. Chief Outsiders' CMOs and CSOs can draw on the collective knowledge and specialized capabilities of a broader team of seasoned marketing and sales leaders, including experience across different financial services markets and business models.
Flexible Expertise Without the Full-Time Commitment
Access senior financial services marketing and sales leadership when your business needs it, without the time, cost, or long-term commitment required to recruit and hire a full-time executive.
Frequently Asked Questions About Fractional Marketing & Sales Leadership for Financial Services
What does a financial services fractional CMO do?
A financial services fractional CMO provides experienced marketing leadership on a flexible, part-time basis, helping organizations develop marketing strategies, establish priorities, lead teams, and improve performance. Responsibilities may include brand positioning, client acquisition, financial services lead generation, digital marketing, customer retention, product launches, and marketing ROI. Unlike a full-time executive, a fractional CMO provides senior-level expertise without requiring a permanent leadership hire.
What does a financial services fractional CSO do?
A financial services fractional CSO leads sales strategy and execution, helping organizations strengthen business development, improve sales processes, and increase revenue performance. Depending on the business, responsibilities may include improving advisor productivity, developing referral networks, optimizing sales pipelines, expanding distribution channels, strengthening sales teams, and identifying opportunities to grow existing client relationships.
When should a financial services company hire a fractional CMO or CSO?
Financial services companies often benefit from fractional executive leadership when entering new markets, launching financial products, navigating acquisitions, addressing stalled growth, or strengthening marketing and sales operations. A fractional CMO or CSO can also provide experienced leadership during executive transitions or when an organization needs specialized expertise without committing to a full-time hire.
Can a fractional CMO or CSO work with our existing financial services marketing and sales teams?
Yes. Chief Outsiders' fractional executives work directly with existing leadership, marketing, sales, and business development teams. They help establish priorities, improve processes, strengthen team capabilities, and guide execution while coordinating with internal compliance, legal, product, and operations stakeholders as needed.
How can a fractional CMO improve client acquisition for financial services companies?
A fractional CMO can improve client acquisition by identifying high-value customer segments, strengthening competitive positioning, developing targeted marketing campaigns, and optimizing lead generation and conversion strategies. For banks, wealth management firms, insurance providers, and fintech companies, this may include improving digital acquisition, building referral programs, and aligning marketing with the financial decisions and needs of prospective clients.
How can a fractional CSO improve business development and revenue growth?
A fractional CSO helps financial services companies build more effective business development operations by improving sales processes, strengthening pipeline management, coaching sales teams, and expanding referral and distribution networks. They also help identify opportunities to deepen client relationships, increase cross-selling, and improve sales productivity across advisors, relationship managers, agents, and other revenue-generating professionals.
What types of financial services companies does Chief Outsiders work with?
Chief Outsiders serves financial services organizations across banking, wealth management, investment management, insurance, fintech, and related markets. Our fractional CMOs and CSOs bring executive leadership tailored to different business models, customer audiences, regulatory environments, and growth priorities.
Does Chief Outsiders work with RIAs and wealth management firms?
Yes. Chief Outsiders works with registered investment advisors (RIAs), wealth management firms, and financial advisory organizations to help them attract new clients, grow assets under management, and build stronger referral networks. Our executives also help firms improve advisor performance, retain valuable client relationships, and pursue growth opportunities through acquisitions or expansion into new markets.
Does Chief Outsiders work with banks and financial institutions?
Yes. Our fractional executives help banks and other financial institutions improve customer acquisition, strengthen competitive differentiation, introduce new financial products, expand business and commercial banking relationships, and improve marketing and sales effectiveness. Engagements can address both consumer and business banking growth priorities.
Does Chief Outsiders work with insurance companies and agencies?
Yes. Chief Outsiders supports insurance carriers, agencies, brokerages, and related businesses with marketing and sales leadership focused on customer acquisition, policyholder retention, distribution channel development, agent and broker relationships, and market expansion. Our executives help align marketing and sales initiatives with the organization's business model and growth priorities.
Does Chief Outsiders work with fintech companies?
Yes. Chief Outsiders helps fintech companies develop go-to-market strategies, strengthen product positioning, build demand, and accelerate customer acquisition. Fractional CMOs and CSOs can also support new product launches, strategic partnerships, sales team development, and expansion into new financial services markets.
How long do fractional CMO or CSO engagements typically last in financial services?
Engagement length depends on the organization's needs, priorities, and scope of work. Some financial services companies engage fractional executives to address specific initiatives, such as launching a product or entering a new market, while others retain ongoing leadership to guide marketing and sales transformation, team development, and revenue growth.
How quickly can a fractional CMO or CSO begin working with our financial services company?
Chief Outsiders' executive matching process is designed to connect organizations with experienced leaders whose industry backgrounds and capabilities align with their needs. The timeline depends on executive availability, the organization's requirements, and the engagement scope, but fractional leadership can often be deployed more quickly than recruiting a permanent executive.
What should we expect during the first 90 days with a financial services fractional CMO or CSO?
We start by solving immediately, getting to the root of what is holding growth back and acting on opportunities right away. We stop what’s not delivering, sharpen what is, and invest more into what’s actually driving results. Depending on the engagement, the executive may assess customer segments, sales pipelines, marketing investments, team capabilities, and competitive positioning while beginning to implement high-priority improvements.
How do we know whether we need a fractional CMO, fractional CSO, or full-time executive?
A fractional CMO is typically the right choice when marketing strategy, brand positioning, demand generation, or client acquisition needs executive leadership. A fractional CSO is better suited to challenges involving sales execution, business development, team productivity, and revenue performance. A full-time executive may be appropriate when the organization requires continuous, dedicated leadership. Chief Outsiders helps companies evaluate their needs and identify the right leadership approach.
What results can financial services companies expect from fractional marketing and sales leadership?
Results depend on the organization's starting point and growth priorities. Potential outcomes include stronger client acquisition, improved marketing ROI, higher sales productivity, more qualified opportunities, better customer retention, and increased revenue. Chief Outsiders' executives establish performance metrics and accountability to connect marketing and sales initiatives with measurable business results.
Ready to Accelerate Your Financial Services Marketing & Sales Performance?
Put experienced financial services marketing and sales leadership to work on your most important growth priorities. Connect with Chief Outsiders to find a fractional CMO or CSO who understands your industry and can help you attract new clients, improve sales performance, and accelerate revenue growth.