Your team might be using AI.
Your operations aren't.
Fractional closes that gap.
Chase embeds in your business one to four days a week, builds the workflows AI should actually run, and trains your team to operate them after the engagement ends.
If your team has tried AI tools without adoption, this is an operations design engagement, not a software rollout. The tools are fine. The system around them is what's missing.
Claude is our default and usually the only new subscription. We are model-agnostic and build on any agent platform your team already runs.
AI pilots fail for a predictable reason.
No one owns it.
Everyone is told to use AI. No one is responsible for making it work operationally. It stays a personal productivity tool instead of an organizational layer.
Wrong tool selection.
Teams land on whatever is easiest to buy, not what fits the stack or the workflows. The result is fragmented tooling that no one trusts and everyone works around.
No transfer plan.
Even when something works, the knowledge lives with one person. They leave. The workflow dies. The team starts over.
The fix is not more tools or more training. It is embedded operations work: someone who builds the system inside your business, with your team, until the team runs it without them.
of enterprise AI pilots return nothing measurable, MIT's NANDA team found. A pilot is not an operating system.
companies actually redesign the workflow around AI, the single strongest predictor of whether it pays off (McKinsey).
You cannot justify a full-time AI hire yet.
A Head of AI at a company your size runs $180,000 to $250,000 per year in base salary alone, before benefits, equity, and recruiting fees. The role makes sense at scale. It does not make sense before the AI layer exists.
Operator-level commitment at a fraction of the cost.
The fractional model gives you embedded expertise at contained cost while the AI layer is being built. When the system is running and your team owns it, the engagement winds down. That is what success looks like.
What every engagement includes.
Quarterly review of your AI layer. Bottlenecks named, roadmap tied to revenue and retention.
We design and build inside your existing stack: your CRM, Slack, and most major tools your team already uses. Anthropic's Claude is our default recommendation, which usually keeps it to one new subscription with no migration; when your team already runs another agent platform, we build on that instead. For tools outside the standard ecosystem, we scope the integration path in discovery. Every workflow runs within rules you set during onboarding, with human-in-the-loop checkpoints and a full audit log; anything outside those rules routes to you for review.
See technical stack
Weekly or biweekly working sessions. Real work on real workflows, not lectures. Until your team can run the system without us.
SOPs, prompts, playbooks, decision trees. The operating layer the AI runs on, not a folder of slides.
Slack or email between sessions. Typically same business day.
Curious whether this fits your business?
Built to transfer, not to depend.
Audit your operations. Pick the highest-leverage AI gaps. Build the first layer of workflows. Your team sees output from week one, not slide decks.
Scale what works. Expand across teams. Coach your leadership and staff inside the system, not next to it.
The engagement winds down as your team takes over. Success means you do not need a Fractional Chief AI Officer anymore. We aim to put ourselves out of a job, on purpose.
At sunset, your team owns operations. Sidekick provides a 30-day handover with a runbook per workflow and a model-version posture for future Anthropic releases.
Where this takes you.
Task-based AI
Using AI to draft, research, and answer questions. The business still runs on people.
Where most startTool adoption
AI tools across apps. Some automation. Individual tasks move faster, but operations are unchanged.
Common todayAI operations
Workflows that run without manual initiation. Infrastructure your team owns, operates, and builds on.
Where we take youCustom AI infrastructure
Purpose-built agent systems on cloud primitives (Bedrock, Vertex, Agent Core). Dedicated engineering team required. Scoped by Chase, specialist-built.
Outside this scopeIn their words.
Sidekick has fundamentally changed how I operate day to day. What they've built is a true personal operating system. When it's set up right, it feels like you suddenly have an admin, an analyst, and a small team working behind the scenes for you.
“I've used it to build decks, CIMs, and pro formas, and it performs at a level that would normally require multiple people. Most people will never be able to recreate this on their own, even if they try to piece things together from blogs.”
I hate written communication. Like I hate it with a passion. I hate sending follow-up emails. I hate drafting communications. I just always have.
Recaps and follow-ups written by hand after a full day of facilitation.
Runs in the tools she already uses. No migration required.
The businesses that execute well are growing roughly 10x faster.
Third-party research cited as adoption benchmarks. Outcomes vary by implementation quality and engagement scope.
Three tiers. One engagement model.
Exit at any month boundary after the initial term with 30 days notice.
Roughly half a day per week.
Workflows in production and your team oriented on Claude. The foundation your AI operations layer is built on.
Capacity reflects a weekly equivalent. Hours flex to what the work requires.
Right for you if you want to prove the model at a contained scope before committing to a broader rollout.
See full scope
- →Light workflows built to production within capacity
- →Shared knowledge repository scoped and seeded
- →Prompt library and workflow recipes for the team
- →Leadership coaching and AI strategy orientation, two sessions per month
- →Async support, typically same business day
- →Monthly progress review
Exit at any month boundary after the initial term with 30 days notice.
Roughly one dedicated day per week.
Depth across multi-step workflows, formal change management, and individual coaching.
Capacity reflects a weekly equivalent. Hours flex to what the work requires.
Right for you if you have a leadership team to bring along and want comprehensive workflow coverage across your operations.
See full scope
- →Multi-step workflows chaining skills and capabilities
- →Employee rollout plan and change management strategy
- →One-on-one coaching with executives and team leads
- →Knowledge library scoped, seeded, and maintained
- →Async support, typically same business day
- →Monthly KPI review against the adoption plan
Exit at any month boundary after the initial term with 30 days notice.
Roughly two to three days per week.
Full organizational depth across functions, executive strategy, and employee enablement.
Capacity reflects a weekly equivalent. Hours flex to what the work requires.
Right for you if AI operations is a strategic priority and you need full depth across the whole organization.
See full scope
- →Comprehensive workflow architecture across functions
- →Executive strategy workshops and operating-model design
- →Employee enablement workshops and training programs
- →Shared knowledge layer wired into how teams work
- →Weekly priority and roadmap working session
- →Async support, typically same business day
“You suddenly have an admin, an analyst, and a small team working behind the scenes for you.”
Sidekick takes a small number of engagements at a time, with a working ceiling of two active Build or Operate engagements. If the timing matters, book the discovery call early. The next opening is the next opening; it does not move.
All prices in Canadian dollars.
Chase founded Sidekick after more than a decade in B2B partnerships and revenue operations at SaaS, marketplace, and healthcare-data companies. Jobber. DoorDash. DrugBank.
The thesis is straightforward. Most owner-operated and mid-market firms cannot justify a full-time Head of AI yet. The fractional model is the bridge. Built right, it sunsets once the team is running the system without him.
Based in Metro Vancouver, BC. Selectively taking new engagements.
Know what you are buying.
A Fractional Chief AI Officer brings the work of a Head of AI at the intensity your business needs, for a business that is not ready to hire one. Not a consultant handing you a deck. Not an agency billing hourly. An embedded operator who sits inside your business one to four days a week, picks the workflows AI should actually run, builds them, and trains your team to keep them running after the engagement ends.
What this is
- ✓An operator embedded one to four days a week
- ✓Your team onboarded onto Claude Cowork, with workflows configured around how your business actually runs
- ✓First workflow in production within 7 to 30 days
- ✓Your team trained to operate the system
- ✓Designed to sunset. A bridge, not a permanent cost line.
What this is not
- ×A custom multi-agent build with bespoke MCP servers or API plumbing
- ×A weekly strategy call without execution
- ×A retainer for unbounded advisory hours
- ×A SaaS subscription with templates and a Slack channel
- ×A permanent fractional executive seat
- noEvery engagement needs a workflow owner on your team. If that role is not in place, start at Pilot or hire first.
- noCustomer-facing agents that touch PII require a dedicated security review before scope. We will say no until that exists.
- noIf month two shows no production usage, the engagement pauses for a re-scope, not a re-up.
Need a custom multi-agent build?
Custom deployments (Managed Agents, bespoke MCP servers, API-direct integrations) sit outside this engagement. Chase scopes and oversees; implementation partners build. Low 5 to low 6 figures depending on scope.
Need full-time AI leadership?
COO-level or role-replacement-grade leadership sits outside Fractional. Sidekick focuses on businesses in early-to-mid stage AI adoption. Chase will refer you to a more established firm better suited for that scale.
Running it solo? Sidekick Solo is the personal AI workspace for individual professionals and owner-operators.
See Sidekick Solo →What buyers ask before signing.
Who owns the workflows after the engagement ends?
What happens if we want to leave mid-engagement?
What tools do we have to switch to?
Is Chase the operator on every engagement?
What data leaves our tenants?
Advising the client is your job. Building is ours.
If you advise businesses for a living, the AI question is landing on you whether you invited it or not. You do not need to become the AI expert to answer it. Sidekick is the implementation bench fractional executives and coaches pull into client engagements: you work with the founder to find the areas worth pursuing, we map the workflows and build to fit them. Your client gets installed systems. You stay the strategist they hired.
Start with the six questions your clients are already asking: what to tell clients about AI, answered for fractional executives. When a specific client is on your mind, bring the workflow and we will tell you what we would and would not touch.
Looking for a personal AI workspace instead? Sidekick Solo is built for individual professionals. →