Optimizing Your Infrastructure For
If you have looked at other fractional CAIO services and come away thinking "this sounds like an expensive slide deck," that instinct is worth trusting. Most of the market is built on an advisory-only model: the consultant sets strategy, a separate vendor builds it, and you manage the coordination cost and the gap between what was recommended and what actually gets built.
Obsidian Logic was built around a different premise. The people responsible for your AI strategy should also be responsible for whether it works in practice. Two founders, one firm: executive AI leadership and hands-on implementation delivered together.
What is a Fractional Chief AI Officer?
A fractional Chief AI Officer is an executive-level AI leader retained on a part-time basis to own a company's AI strategy. The role covers AI roadmap development, governance, vendor selection, implementation oversight, and team training. It gives growing businesses access to senior AI leadership without the cost or commitment of a full-time executive hire.
The role is known by a few names: fractional CAIO, fractional AI officer, fractional AI executive, outsourced Chief AI Officer, or part-time Chief AI Officer. The title varies by firm and by how the buyer frames the need. The function is the same: someone operating at the executive level, held responsible for building a sound AI program and making sure it produces results.
The role is distinct from an AI strategy consultant. A consultant is typically engaged for a defined project with a defined deliverable. A fractional CAIO is a retained partner who stays involved over months, adapts the strategy as the business changes, and owns both the thinking and the outcomes.
What a Fractional Chief AI Officer Actually Does
The responsibilities of a fractional Chief AI Officer fall into six areas. Every engagement worth its fee covers all of them.
strategy and roadmap
Deciding what gets built, in what order, and why, based on your specific workflows, existing tools, and business goals. Not a template roadmap for companies in your industry. A specific plan for your situation.
governance and risk management
Establishing the policies, oversight structures, and compliance frameworks that let your AI program operate responsibly. This matters more than most companies realize before they run into a problem. For organizations in regulated industries, it matters from day one.
vendor selection
Identifying which AI tools actually fit your stack, your team, and your budget, and which ones are selling you more than they can deliver. Vendor selection done badly is one of the most expensive mistakes a growing company can make. A good AI strategy consultant earns their fee here before a single system gets built.
implementation oversight
Staying involved while systems are being built, not handing off a document to a development team and checking back in six months. This is where the advisory-only model disconnects. A fractional CAIO who is not connected to implementation is giving recommendations into a void.
team training
Making sure your people understand what is being built and how to use it confidently. Most AI implementations fail at this stage, not in the technology.
ongoing governance and reporting
Keeping leadership informed on AI progress, risks, costs, and return on investment across the full term of the engagement.
In a large company, a full-time CAIO runs all of this with a dedicated team and a board mandate. In a fractional model, you get the same executive thinking on a retained, part-time basis, allocated to the priorities that matter most for your business now. You should not need a Fortune 500 budget to run your business like one.
Engagement
Primary deliverable
Implementation
Accountability
Cost
Time horizon
Best for
AI Consultant
Defined project, fixed scope
Strategy document or recommendation
Handed to a separate vendor
Ends at delivery
Project fee
Weeks
One-off questions
Full-Time CAIO
Permanent executive hire
Ongoing leadership
Built by in-house team
Full ownership
Full exec salary, benefits, equity
Permanent
Enterprise companies
Obsidian Logic FCAIO
Retained, part-time executive
Strategy plus working systems
Same firm builds it. No handoff.
Owns strategy and outcomes
A fraction of a full-time hire
Months; adapts as you change
$3M-$50M B2B without internal AI leadership
Engagement
Primary deliverable
Implementation
Accountability
Cost
Time horizon
Best for
AI Consultant
Defined project, fixed scope
Strategy document or recommendation
Handed to a separate vendor
Ends at delivery
Project fee
Weeks
One-off questions
Engagement
Primary deliverable
Implementation
Accountability
Cost
Time horizon
Best for
Full-Time CAIO
Permanent executive hire
Ongoing leadership
Built by in-house team
Full ownership
Full exec salary, benefits, equity
Permanent
Enterprise companies
Engagement
Primary deliverable
Implementation
Accountability
Cost
Time horizon
Best for
Obsidian Logic FCAIO
Retained, part-time executive
Strategy plus working systems
Same firm builds it. No handoff.
Owns strategy and outcomes
A fraction of a full-time hire
Months; adapts as you change
$3M-$50M B2B without internal AI leadership
Where Most Fractional CAIO Engagements Break Down
The fractional executive model has been around long enough that most companies understand the structure. Fractional CFOs, fractional CMOs, fractional CTOs: dedicated hours from a senior person, retained on a part-time basis, for a fraction of the cost of a full-time hire.
The fractional CAIO market is newer. It emerged because companies recognized that AI strategy is a distinct discipline, and that neither their existing technology team nor their general consultants were equipped to own it.
The first wave of fractional CAIO offerings borrowed the advisory-only model directly from management consulting. The deliverable is a strategy document. The implementation is someone else's problem.
For companies with internal engineering resources, that model can work. For companies with 20 to 200 employees and an operations team already at capacity, it does not. The strategy document becomes a well-intentioned artifact. The AI initiative stalls. The engagement ends, and six months later the company is in the same position it was in before, except now with a roadmap that nobody is executing against and a budget line that produced nothing.
The underlying issue is straightforward. Strategy divorced from implementation is expensive advice. And advice that does not move into practice is not worth what it costs, regardless of how sound it is.
The Obsidian Logic Model:
Advise and Build
Keith Mortier and Scott DeSilva co-founded Obsidian Logic in 2025 after watching this failure pattern repeat across decades of combined technology and go-to-market experience.
The firm is built on one structural difference: the people setting your AI strategy are the same organization building your AI systems. When you engage Obsidian Logic as an FCAIO client, you get executive-level AI leadership and direct access to an implementation team that builds what the strategy requires. The handoff problem does not exist because there is no handoff.
This changes how the work operates in ways that matter. A roadmap gets built by people who understand real implementation constraints. Vendor recommendations get tested against what can actually be built and maintained by a team your size. When your priorities shift, the executive leading your strategy adjusts the implementation plan in the same conversation, with the same people.
The work that underpins every FCAIO engagement, the AI Business Strategy Assessment and the operational audits that follow, is a defined diagnostic: deep-dive interviews, workflow mapping across relevant business functions, an audit of the tools already in place, AI feasibility scored area by area, and a written report with a prioritized three-tier roadmap. It has surfaced duplicated reporting work, manual data re-entry running across tools that were never meant to overlap, and handoffs nobody had looked at end to end. This is not preliminary work. It is the deliverable that Strategist and Embedded clients receive as a standard part of month one, before a single implementation project begins. It also reflects what happens when the people doing the diagnosis are the same people who understand how to build the fix.
The model is platform-agnostic. Obsidian Logic does not sell software. The goal is AI that works with what your business already has, layered onto existing systems to remove manual steps and recover time, rather than ripping out infrastructure you have spent years building and training your team on.
IN PRACTICE:
FROM ASSESSMENT TO IMPLEMENTATION.
One Strategist engagement started the way they all do, with the month-one AI Business Strategy Assessment. Over two weeks of workflow mapping and tool audits across the client’s operations and finance functions, we identified manual reporting and data re-entry that three separate tools were quietly duplicating. The roadmap prioritized the two highest-return automations first, and the client approved the build before the readout call ended.
This is the diagnostic work every Strategist and Embedded engagement begins with before a single implementation project starts. The same people conducting the diagnosis are the people who build the fix
"The workflows they built are
repeatable and scalable."
"Obsidian Logic helped Redport modernize and automate key parts of our business development and operational workflows without sacrificing the rigor we need as an information assurance provider. Their team took a structured, methodical approach: mapping our process end-to-end, tightening handoffs, and implementing automation that improved consistency, visibility, and follow-through. The impact was immediate: less manual admin, faster response times, and a clearer view of pipeline activity. Just as important, the workflows they built are repeatable and scalable, supporting the compliance-driven environments we serve while freeing our team to focus on delivering mission-critical security outcomes."
Steve Reinkemeyer
President and CEO, Redport Information Assurance
Three Ways to Engage
Obsidian Logic offers three FCAIO engagement tiers. Pricing is not listed on this page. What matters first is understanding which structure fits your situation. Investment is discussed on the discovery call, after we understand what you need.
Hours per week
Minimum term
Best fit by revenue
Month-1 Assessment
Implementation oversight
Training
Reporting
AI Champions Program
Advisor
~4 hours
6 months
~$3M-$10M
Strategy alignment
None
Quarterly exec briefing
Monthly exec readout
Add-on
Strategist (recommended)
~8 hours
6 months
~$5M-$30M
Included (10-15 page report and readout)
One active project
Quarterly briefing plus 2 workshops per quarter
Monthly exec readout
Add-on
Embedded
~12 hours
12 months
Multi-year AI program
Included
Multiple concurrent projects
Monthly workshops
Monthly board-level and exec
Included
Advisor
Hours:
Approximately 4 hours per week
Minimum term:
6 months
Best for:
Companies between roughly $3M and $10M in revenue that need executive-level AI guidance without active oversight of a build project
What you get:
AI strategy, governance, and vendor selection. Monthly executive readout on AI progress and risks. Quarterly 60-minute executive AI briefing for your leadership team.
Right fit when:
You have some internal capacity to execute and primarily need someone making sure you are building the right things in the right order.
First 90 days:
Month 1: strategy alignment and a prioritized list of where automation and AI tooling would produce the fastest and most defensible returns for your business specifically. Month 2: governance framework and first vendor recommendations based on your stack. Month 3: first executive AI briefing delivered to your leadership team and a clear Q2 action plan.
Strategist (recommended)
Hours:
Approximately 8 hours per week
Minimum term:
6 months
Best for:
Companies between roughly $5M and $30M in revenue that want executive AI leadership combined with active oversight of one implementation project
Month 1:
AI Business Strategy Assessment included as a standard deliverable. Deep-dive interviews with your team, full workflow mapping, AI feasibility scoring, and a prioritized 3-tier implementation roadmap. Written report (10-15 pages) plus 60-minute executive readout.
What you get:
Everything in Advisor, plus: AI roadmap with prioritized initiatives, oversight of one active implementation project, two team training workshops per quarter.
Right fit when:
You want a plan and someone who stays involved while the plan gets executed.
Embedded
Hours:
Approximately 12 hours per week
Minimum term:
12 months
Best for:
Companies treating AI as a multi-year program that want to build lasting internal capability across multiple departments, not just complete one implementation project
What you get:
Everything in Strategist, plus: oversight of multiple concurrent implementation projects, monthly board-level and executive readouts, internal AI program development, and monthly team workshops.
AI Champions Program:
Included in Embedded. Over 3 months, Obsidian Logic trains 4 to 6 of your own employees to become the internal owners of your AI operations. When the engagement ends, your team runs the program. Available as a standalone add-on for Advisor and Strategist clients.
Right fit when:
You are running a multi-year AI program, not a one-time implementation project. You need executive presence across multiple concurrent builds, monthly accountability to your board or leadership team, and a plan for building internal AI capability that outlasts the engagement. The Embedded tier is also the right structure when AI is expected to touch multiple departments simultaneously and you need someone who can coordinate across them at the executive level.
Not sure which tier fits?
That is exactly what the discovery call is for. Tell us where AI fits in your business and we will tell you which structure makes sense, or if none does yet.
Hours per week
Minimum term
Best fit by revenue
Month-1 Assessment
Implementation oversight
Training
Reporting
AI Champions Program
Advisor
~4 hours
6 months
~$3M-$10M
Strategy alignment
None
Quarterly exec briefing
Monthly exec readout
Add-on
Hours per week
Minimum term
Best fit by revenue
Month-1 Assessment
Implementation oversight
Training
Reporting
AI Champions Program
Strategist (recommended)
~8 hours
6 months
~$5M-$30M
Included (10-15 page report and readout)
One active project
Quarterly briefing plus 2 workshops per quarter
Monthly exec readout
Add-on
Hours per week
Minimum term
Best fit by revenue
Month-1 Assessment
Implementation oversight
Training
Reporting
AI Champions Program
Embedded
~12 hours
12 months
Multi-year AI program
Included
Multiple concurrent projects
Monthly workshops
Monthly board-level and exec
Included
Training Is Part of the Work
Every AI implementation Obsidian Logic has observed fail at the team level, not the technology level. The system gets built. The tools work. The team was never given the context, the confidence, or the time to adopt them. Six months later, the system that cost a significant amount of money to build is sitting unused, and the blame lands on AI.
The real cause is simpler: training was treated as an afterthought, scheduled for the end of the project when everyone was already moving on to the next thing.
Obsidian Logic treats training as a core deliverable from day one, not a line item that gets cut when the engagement runs over schedule.
Every tier includes executive AI briefings: 60-minute sessions with your leadership team covering AI strategy, relevant developments in the market, and what your business should be preparing for. These run quarterly at the Strategist tier and monthly at the Embedded tier. They are not vendor pitches. They are working sessions designed to keep your executives informed and capable of making sound AI decisions.
Every Strategist and Embedded engagement includes team workshops: 90-minute hands-on sessions run by department or by use case. Your team works through specific applications relevant to their role, using your tools, on your actual problems. Not a general overview of what AI can do, but a practical session with takeaways your team can use the next day.
The AI Champions Program, included in Embedded and available as an add-on for other tiers, takes this further. Over three months, Obsidian Logic trains four to six of your employees to become the internal day-to-day owners of your AI operations. The goal is a business that does not need an outside partner to keep its AI running.
Additional training components available across all tiers: an Executive AI Literacy Workshop for boards and senior leadership teams; a Department Head AI Series for functional leaders in Sales, Operations, Finance, and HR; a Practitioner Bootcamp for the employees who will use AI tools daily; and a recurring Lunch and Learn series for ongoing organization-wide AI literacy. All are scoped per engagement.
Not ready for a retained engagement?
Start with the AI Business Strategy Assessment: a standalone, fixed-scope diagnostic that delivers the same month-one report and prioritized roadmap that Strategist and Embedded clients receive. Act on it yourself, or use it as the foundation for a future retained engagement.
Who This Engagement Is For
The fractional CAIO model fits a specific type of company in a specific situation.
You are a CEO, COO, or founder at a $3M to $50M B2B company. You know your business needs to do something with AI. You may have tested a few tools already, with results that ranged from genuinely useful to disappointing. You do not have the internal bandwidth or expertise to build a coherent AI program on your own, and you are not ready to hire a full-time executive for it.
You have systems you are not going to replace. Your CRM, your finance tools, your project management stack: you have spent years building with them and training your team on them. You want AI that works with what you already have, not a pitch for wholesale infrastructure replacement.
You have been approached by AI vendors and consultants before. Some of them were credible. Most left you with a sense that you were being sold something rather than shown something. You want someone who can tell you specifically what to build, explain why that order makes sense for your business, and then stay in the work while it gets built.
You want a partner with accountability, not a vendor who delivers a document and marks the engagement complete.
Who this is not right for
If your business is under $3M in revenue and what you need is a small set of automation scripts, the economics of a retained fractional executive engagement will not work in your favor. There are better structures for that stage.
If you are an enterprise company running a formal procurement process and comparing Obsidian Logic to the large consulting firms, we are the wrong choice. Obsidian Logic takes a limited number of concurrent clients by design. We do not compete on volume.
If you want a strategy document to present internally and nothing beyond that, a standalone AI Business Strategy Assessment will serve you better than a retained engagement. Details are on the Assessment page.
The Founders
Every FCAIO engagement is delivered by Keith Mortier and Scott DeSilva. One founder is the named engagement lead. The other serves as the supporting principal. Every major decision gets input from both. Read more about the firm and how Obsidian Logic came together on our about page.
Keith Mortier
Keith Mortier spent more than two decades building, running, and securing enterprise technology systems, with a career anchored in the cybersecurity and information assurance space.
For nearly thirteen years, he served as President of Lunarline, a cybersecurity and information assurance firm serving both public-sector and private-sector clients. He built the company from the ground up, grew it through a range of federal and commercial engagements, and sold it in 2017. That is a full cycle: build, run, scale, exit. It is a credential that a significant majority of people who call themselves fractional executives do not have.
After the Lunarline exit, Keith served as CEO of Philemon Security, where he led the company's Zero Trust architecture practice and worked with enterprise clients on securing application and data access. He also served as CISO of Redport Information Assurance, delivering risk-based, federal-grade cybersecurity programs to government and commercial clients where the cost of failure is measured in regulatory exposure and operational disruption, not just dollars.
Keith leads FCAIO engagements where technical depth, governance, and cybersecurity are the primary concerns. His lens throughout his career has been consistent: not what looks good in a presentation, but what holds up when it is running in production inside a real organization.
He holds a B.S. in Computer and Information Sciences from Strayer University.
Scott DeSilva
Scott DeSilva spent more than 15 years building go-to-market organizations for technology companies, with a career that spans cybersecurity sales, channel development, AI automation, and enterprise operations.
His most significant early role was VP of Sales Americas at Cryptzone, a publicly traded Swedish company and the developer of AppGate SDP: the first Software-Defined Perimeter built on Zero Trust principles. Scott built the North and South American sales, marketing, sales engineering, and customer success organizations from scratch, reporting directly to the CEO and leading a team of eleven focused on enterprise accounts above $750M in revenue. He helped drive the company's multi-million dollar cross-border sale and recapitalization by Medina Capital in 2014. He then defined and executed the channel go-to-market strategy for Cyxtera Technologies' security business unit through the spin-off of AppGate as a standalone company in 2020.
After Cyxtera, Scott served as Service Partner Director at Sumo Logic during the company's early build stage, launching its Service Provider Program and driving new revenue across MSSPs, MDR providers, and global systems integrators. He has served as VP of Sales and Operations at Philemon Security, Executive Advisor at Indigo9 Cyber, and currently as a consultant on AI Executive Services at Redport Information Assurance.
Scott leads FCAIO engagements where revenue operations, lead generation, and go-to-market AI are the primary priorities. He approaches AI from the standpoint of what actually moves pipeline, removes friction for customer-facing teams, and produces results that a sales or operations leader can point to.
He holds a B.B.A. in Marketing from Florida Atlantic University.
What the First 90 Days Look Like
The most common reason companies hesitate on a retained engagement is that they cannot picture what the first few months actually involve. Here is a practical picture by tier.
Advisor
Month one covers strategy alignment: an initial deep-dive into your business, your current AI situation, and your goals, followed by a prioritized list of where automation and AI tooling would produce the fastest and most defensible returns for your business specifically.
Month two moves into governance and vendor evaluation: a basic governance framework suited to your risk profile, and the first round of vendor recommendations based on your existing stack and what you are trying to build.
Month three delivers your first executive AI briefing, where we present both the strategy and the evidence behind it to your leadership team, and a clear action plan for the next quarter.
If that sequence sounds like what your business needs, the next step is a short conversation about where AI fits and which tier makes sense.
Strategist and Embedded
Month one is the AI Business Strategy Assessment. Over 10 to 14 business days, we conduct deep-dive interviews with key members of your team, map your workflows across relevant business functions, audit your existing tools, and score AI feasibility across each area. The output is a written report of 10 to 15 pages with a prioritized three-tier implementation roadmap: what to build now, what to build in the next 90 days, and what the longer-term opportunities are.
The 60-minute executive readout at the end of month one is where most clients describe the clearest moment of the engagement. We are presenting a specific plan for your workflows, your tools, and your team's actual constraints. The report is actionable from the day it is delivered.
Month two begins oversight of the first implementation project from your roadmap. Common starting points include report automation, sales process automation, CRM integration, and inbound triage and response. For Embedded clients, multiple projects may be running in parallel from month two onward.
By month three, your first working system is in final testing or live. Your team has completed at least one training workshop. Your leadership team has had its first executive AI briefing. You have a clear picture of what the next quarter looks like.
Those are not hypothetical timelines. Month one follows the same diagnostic sequence every time, and the roadmap it produces is specific enough that clients have approved the first build before the readout call ended. That pace comes from arriving in month one with a diagnostic methodology that is already proven, then building real systems against what it finds.
Common Questions
Hire a Fractional CAIO.
Tell us about your business and where AI fits. If the FCAIO model is the right structure for what you need, we will tell you which tier makes sense and what the first 90 days look like. If it is not the right fit, we will tell you that too and point you in the right direction.