When priorities shift, strategies evolve, and organizations transform, execution depends on how well people understand what’s changing and what happens next.
Odessa Strategic Advisors partners with executives to reduce execution risk, accelerate adoption, and strengthen alignment during pivotal transformations.
THE COST OF COMMUNICATION BREAKDOWNS IS MEASURABLE
70%
of integrations fail to achieve their intended outcomes.
Deloitte & McKinsey
75%
of leaders spend time fixing communication breakdowns.
Deloitte
47%
of key employees leave within the first year of a merger.
Deloitte
27%
of employees believe organizations manage change effectively.
Deloitte
When a transition is underway, the margin for error is small. We partner to reduce execution risk by turning communications into an operational lever that accelerates employee adoption, strengthens alignment, and stabilizes stakeholder confidence.
High-Stakes Transitions Demand an Embedded Strategic Communications System
M&A Integrations
Post-merger alignment failures are costly. We stabilize executive messaging, stakeholder confidence, and build the strategic communications system that extends beyond Day 1 and moves integration forward without confusion or resistance.
Leadership Transitions
Leadership changes create credibility gaps if left unmanaged. We protect the narrative, maintain board and employee confidence, and build continuity into the corporate strategic narrative.
Regulatory Events
When regulators are watching, every message carries risk. We provide discipline and independence to ensure communications are consistent, defensible, and board-safe throughout heightened scrutiny.
Enterprise Restructurings
Restructuring without an embedded, strategic communications system creates conditions for turnover, productivity loss, and missed deadlines. We build the infrastructure that keeps people aligned and executing effectively.
Artificial Intelligence & Technology Rollouts
AI and technology adoptions often cause employee unrest and uncertainty, which leads to lost productivity. We develop the communication strategy that reduces employee resistance and accelerates adoption from day one.
Crisis Communications
Crises are manageable when you have a plan in place. We develop your issues management plan, assess organizational readiness, and provide executive-level counsel to protect your reputation, stakeholder trust, and leadership credibility.
Strategic initiatives gain traction faster because employees, managers, and teams have the clarity they need to execute.
Talent + Adoption Readiness
Strengthened alignment.
We help employees move through adoption curves quickly by lessening ambiguity and operational friction.
Stabilized Confidence
Trust maintained under pressure.
Employees, boards, regulators, customers, and partners maintain trust in leadership direction even during uncertainty, keeping the work on track and on budget.
The Framework
Communication as Leadership™
OSA believes that communications is more than a “soft skill.” Through our Communication as Leadership™ methodology, we help leaders use communication as their primary tool for clarity, alignment, readiness, culture, and execution.
No matter the size of the company, we deploy and customize the Communication as Leadership™ Transition Alignment System™ to ensure each engagement receives the same structured support.
Not Sure Where You Stand
Start with the Communications Readiness Assessment.
A free diagnostic that identifies where communication gaps are creating execution risk in your organization. Results in minutes. No commitment required.
What Executives Say
In their words.
"Sherrii was a vital strategic partner during our time working together. Her ability to align communications strategy with talent acquisition priorities was instrumental in strengthening our employer brand across targeted populations. Through strategic partnerships, conference visibility, and stakeholder engagement, her work directly contributed to a 3x increase in candidate applications and significant gains in click-through rates. She is a trusted advisor who understands how to translate business objectives into meaningful, measurable impact."
Vice President, Human Resources, Fortune 100 Organization
"Sherrii has been phenomenal to work with. She consistently delivered results with confidence, clarity, and precision. Her ability to lead with both authority and authenticity pushed me to raise my standards and sharpen my strategic thinking."
"I had the privilege of working closely with Sherrii where she played a critical role in advancing our employer branding strategy. She consistently demonstrated the ability to build trusted relationships with key partners, align messaging to target audiences, and elevate our brand through conferences, speaking engagements, and executive stakeholder communications. Sherrii is the kind of communications leader who delivers both clarity and results."
Senior Director, Fortune 100 Company
"Sherrii was a trusted partner on our most sensitive, high-stakes initiatives. She has a rare ability to translate complex, emotionally charged decisions into clear, grounded communication that brings leaders into alignment while meeting the needs of diverse audiences. She is a steady presence when risk is elevated and precision truly matters."
Project Management Office Leader, Fortune 100 Company
If your organization is navigating a critical transition, let’s talk.
A Reflective Insights Session is the starting point. It’s a conversation about where you are and what execution risk looks like in your situation.
What OSA Delivers
Communications strategy built for moments that cannot afford to fail.
OSA delivers organizational communications strategy. Not marketing, public relations, or brand work. This is the operational infrastructure that allows leaders to move organizations through change without losing alignment, trust, or momentum.
Communications Audit
Most Common Starting Point
A structured assessment of the organization's current communication infrastructure, channel effectiveness, message consistency, and stakeholder reach. Identifies gaps, misalignments, and execution risk points before they become budget-busting problems. Delivers a prioritized risk register and recommended path forward. Available as a standalone project or as the entry point into a broader engagement.
Executive Communication Strategy
Develop and maintain the strategic messaging architecture that guides how executives communicate during transformation. Includes narrative development, message hierarchy, and executive messaging frameworks aligned to business objectives and stakeholder needs across boards, regulators, employees, and partners.
Internal Communication Operating Systems
Design and build the internal communication infrastructure that keeps employees informed, aligned, and prepared during change. Includes communication cadence design, channel strategy, manager communication toolkits, and message templates that leaders can sustain after the engagement ends.
Change & Transformation Communications
Strategic communication planning and execution for enterprise restructurings, M&A integrations, leadership transitions, technology rollouts, and regulatory events. Covers stakeholder analysis, message sequencing, cascade planning, and readiness measurement from day one through adoption.
Crisis Communications Readiness
Assess organizational readiness to communicate during a crisis or high-scrutiny event. Develop crisis protocols, holding statement frameworks, stakeholder response playbooks, and spokesperson preparation. Delivered as a standalone engagement or embedded within a fractional CCO relationship.
Leadership Alignment Workshops
Facilitated sessions that bring executive and cross-functional leadership teams into alignment on narrative, priorities, and communication responsibilities during transformation. The Communication as Leadership™ workshop is available in half-day and full-day formats, prescribed beginning at Tier 2 engagements.
Stakeholder Communication Planning
Develop audience-specific communication plans for boards, regulators, investors, employees, customers, and partners. Ensures each group receives consistent, appropriately tailored messaging that maintains confidence during transition.
Initiative & Technology Rollout Communications
Communication strategy and execution for AI and technology implementations, policy changes, and new operating model introductions. Reduces adoption lag, employee resistance, and the productivity disruptions that compound when change is poorly communicated.
Not sure which service fits your situation?
Most engagements begin with a conversation. We will help you identify the right scope and starting point.
Engagement Models
Senior communications leadership structured around your situation.
OSA embeds at the executive level through three engagement models designed for different durations, scopes, and risk profiles. Every engagement follows the Odessa Method™.
The Framework
The Odessa Method™
Every OSA engagement follows a disciplined four-phase approach grounded in accurate diagnosis, not assumptions, so every deliverable advances organizational readiness in a measurable way.
01
Assess
Rapid review of communication infrastructure, stakeholder alignment, message consistency, and execution risk. Where most organizations discover the gap between what leadership believes is happening and what is actually landing.
02
Align
Establish a shared narrative and communication architecture across executive and functional leadership. Resolve misalignment before it reaches employees, boards, or external stakeholders as conflicting signals.
03
Activate
Execute the communications plan. Build the infrastructure, deploy the messages, and equip leaders and managers to carry the strategy forward with consistency and confidence.
04
Amplify
Measure impact, refine the approach, and transfer capability so the organization sustains communication discipline and realizes the full value of what was built.
How We Engage
Three models. One standard of work.
Ongoing
Fractional CCO
Executive-level communications leadership embedded on a recurring monthly basis. The right model when your organization needs sustained strategic oversight without a permanent hire.
Monthly retainer structure
Strategic communications leadership
Executive advisory and messaging
Board and stakeholder-level support
Change and transformation guidance
Crisis readiness and response
Defined Duration
Interim CCO
Full-scope executive communications leadership for a defined period. The right model when you are post-acquisition, in a leadership transition, or facing a high-urgency event.
90-day or defined-term scope
Full executive communications authority
Rapid assessment and stabilization
Board and sponsor-ready reporting
Leadership messaging and alignment
Transition planning built in
Defined Scope
Project-Based
Focused, high-impact engagement tied to a specific deliverable. The right model for a communications audit, an integration plan, a workshop, or a crisis readiness assessment.
Scoped to a defined deliverable
Communications audits
M&A integration communications
Initiative and technology rollouts
Leadership alignment workshops
Crisis communications readiness
Ready to discuss which model fits your situation?
A Reflective Insights Session is all it takes to determine the right engagement structure.
Client Results
What executives say and what the work has delivered.
Client names may be withheld by agreement. Industry, transformation type, and outcomes are accurate.
What Executives Say
In their words.
"Sherrii has been phenomenal to work with. She consistently delivered results with confidence, clarity, and precision. Her ability to lead with both authority and authenticity pushed me to raise my standards and sharpen my strategic thinking."
"Sherrii was a trusted partner on our most sensitive, high-stakes initiatives. She has a rare ability to translate complex, emotionally charged decisions into clear, grounded communication that brings leaders into alignment while meeting the needs of diverse audiences. She is a steady presence when risk is elevated and precision truly matters."
Project Management Office Leader, Fortune 100 Company
"Sherrii was a vital strategic partner during our time working together. Her ability to align communications strategy with talent acquisition priorities was instrumental in strengthening our employer brand across targeted populations. Through strategic partnerships, conference visibility, and stakeholder engagement, her work directly contributed to a 3x increase in candidate applications and significant gains in click-through rates. She is a trusted advisor who understands how to translate business objectives into meaningful, measurable impact."
Vice President, Human Resources, Fortune 100 Organization
"I had the privilege of working closely with Sherrii where she played a critical role in advancing our employer branding strategy. She consistently demonstrated the ability to build trusted relationships with key partners, align messaging to target audiences, and elevate our brand through conferences, speaking engagements, and executive stakeholder communications. Sherrii is the kind of communications leader who delivers both clarity and results."
Senior Director, Fortune 100 Company
What Leaders Say
In their words.
Case Studies
The situation. The work. The outcome.
Client case studies available upon request.
Ready to discuss your situation?
Schedule a Reflective Insights Session. No commitment. Just a direct conversation about where you are.
About the Founder
Built on the belief that communication is a leadership discipline, not a support function.
📷
Professional Photo Sherrii Webb Replace with headshot
For more than 25 years, Sherrii Webb partnered with senior leaders to successfully lead enterprise communications, crisis response, and executive advisory work inside Fortune 100 organizations including TIAA, Wells Fargo, Ally Financial, and Bank of America.
What she learned inside those institutions is that communications failures rarely begin with messaging. They begin with unclear decision authority, conflicting executive signals, delayed leadership communication, and overreliance on tactical execution without strategic oversight. By the time the messaging problem is visible, trust has often already eroded, and the cost of recovering it compounds.
Today, Sherrii brings that same senior-level judgment to organizations navigating their most critical moments, without the cost or commitment of a permanent hire. OSA’s depth of experience means the right resources can be deployed for what each situation requires.
The Foundation
Communication as Leadership™
Communication as Leadership™ is OSA's core philosophy and proprietary framework. It holds that communication is not a downstream function of strategy. It is the mechanism by which strategy becomes execution.
When leaders communicate with clarity, teams align. When teams align, initiatives move. When initiatives move, organizations create value. The absence of that chain is where most transformation failures begin.
The Communication as Leadership™ Transition Alignment System guides every OSA engagement. It provides leaders with a disciplined communications execution system that delivers transition control, employee adoption, and measurable business value, while eliminating the costly surprises that derail execution and erode stakeholder confidence.
Let's talk about what you are navigating.
Schedule a Reflective Insights Session to discuss your situation and determine whether OSA is the right fit.
Frequently Asked Questions
Answers to the questions executives ask most.
If your question is not here, reach out. We respond to every inquiry.
About OSA and What We DoWhat exactly does a fractional CCO do?
A fractional Chief Communications Officer provides executive-level communications leadership on a part-time or defined-engagement basis. At OSA, that means taking strategic ownership of communications during a high-stakes transition, advising executives on messaging and stakeholder management, building the internal communication infrastructure that moves change through an organization, and reducing the execution risk that comes from fragmented or reactive communications. This is strategic work at the leadership level, not content creation or media relations.
Is this the same as hiring a communications consultant or agency?
No. An agency provides execution capacity and typically manages campaigns or media. A consultant delivers a report or framework and exits. OSA functions as an embedded executive partner who holds strategic responsibility alongside your leadership team, stays in the work through delivery, and transfers capability before the engagement ends. The authority, judgment, and accountability are at the executive level throughout.
Does OSA do marketing, PR, or brand work?
No. OSA delivers organizational communications strategy, internal communication systems, executive messaging, stakeholder alignment, and change communications. It is the infrastructure that allows your organization to execute strategy, not the external messaging that promotes it. If your need is marketing, public relations, or brand identity, OSA is not the right fit.
Who We Work WithWhat types of organizations do you work with?
OSA primarily serves financial services institutions and PE-backed companies navigating high-stakes transformation. We understand how these organizations work, how their stakeholders think, and what execution risk looks like at the board and sponsor level. High-stakes transitions can cross industry lines, if you are navigating a critical moment, reach out and we will tell you honestly whether OSA is the right fit.
What size organization do you work with?
OSA works with organizations where communications failures create board-level, regulatory, or enterprise-wide risk. That typically means significant stakeholder complexity, not a specific headcount. If you are a PE-backed portfolio company under valuation pressure, a regulated institution navigating a leadership transition, or a financial services firm managing a significant change event, the size of your organization matters less than the stakes of what you are navigating.
We already have an internal communications team. Do we still need OSA?
Often yes. Internal teams are close to the organization, which is valuable, but it creates blind spots and limits the independence needed for direct executive counsel. OSA operates at the strategy and advisory level, working alongside internal teams to provide executive-level oversight, strategic clarity, and the outside perspective that is difficult to sustain from inside the organization during high-stakes moments.
Engagements and ProcessHow do engagements begin?
Every engagement begins with a Reflective Insights Session, a direct conversation with executive leadership about the situation, the stakes, and what execution risk looks like for your organization. From there, OSA conducts an Assessment and delivers an OSA Clarity Report that defines the scope, recommended approach, and engagement structure. Nothing is assumed. Everything is grounded in what the diagnostic reveals.
What are the engagement model options?
OSA offers three engagement models. Fractional CCO is an ongoing monthly retainer for organizations that need sustained executive communications leadership without a permanent hire. Interim CCO is a defined-term, full-scope engagement for organizations in active transition or facing a high-urgency situation. Project-based engagements cover a defined deliverable, a communications audit, M&A integration plan, leadership alignment workshop, or crisis readiness assessment. The right model depends on your situation, timeline, and scope.
How long does a typical engagement last?
It depends on the model. Project-based engagements are scoped to a defined deliverable, typically 30 to 90 days. Fractional CCO retainers are structured monthly and typically run six to twelve months. Interim CCO engagements are typically 90 days with an option to extend or transition. OSA does not position engagements to extend beyond what the organization actually needs.
What does OSA deliver at the end of an engagement?
Every engagement produces the OSA Resolution and OSA Blueprint, documents that capture the strategic decisions made, the communications architecture built, and the roadmap for sustaining communication discipline after the engagement ends. OSA does not hand you a report and leave. The goal is always to transfer capability so your organization sustains what was built without ongoing dependency.
Starting the ConversationHow do we get started?
Schedule a Reflective Insights Session directly through this site. It is a 30-minute conversation with no commitment required. If you are not sure whether OSA is the right fit, that conversation is the right place to find out. You can also take the Communications Readiness Assessment first if you want a clearer picture of where your execution risk is before we talk.
Do you work with organizations outside the United States?
OSA's primary market is U.S.-based organizations. If you are headquartered internationally but have significant U.S. operations or stakeholder complexity, reach out and we will discuss whether the engagement structure makes sense for your situation.
Still have questions?
Use the contact form or schedule a direct conversation. We respond to every inquiry.
Get in Touch
Let's talk about what you are navigating.
Use the form below or schedule directly. We respond to every inquiry within one business day.
Take the Communications Readiness Assessment. About 10 minutes, and it gives you a clearer picture of where your execution risk is before we talk.
Research
The evidence behind the work.
A curated collection of academic research and practitioner studies on the relationship between communication, organizational change, and business outcomes.
Academic Research
Peer-reviewed studies on communication and change.
Reports that internal communications is dominated by change, often driven by transformation, and identifies key challenges in communication quality, leadership trust, and strategic intent vs. execution.
Documents that global engagement dropped to 20% in 2025, with manager engagement falling sharply, and links these declines to change, workload, and leadership stress.
Shows that communication quality is a major execution gap in M&A integration, with leaders and employees often sharply misaligned on whether messaging is effective.
Shows that most acquirers say human capital matters, but far fewer build it into the deal thesis, which contributes to missed synergies and underdelivered value.
