Your team uses AI every day. Your operations still run on people.
Most have AI tools. Few have AI operations.
Built for the organization. Chase sits inside your business one to four days a week, identifies the workflows AI should actually run, builds them, and trains your team to run them after the engagement ends.
AI operations means workflows that run end-to-end, not chat windows your team has to remember to open.
Three tiers, starting at $3,000 CAD per month. Three-month minimum, then six-month renewals. Built to sunset.
Built on the same workspace stack our Solo client base already runs on.
Want to equip people one at a time? Sidekick Solo is the personal AI workspace, built for the individual. Optional alongside Fractional, and discounted if you run both.
See Sidekick SoloA Fractional 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 in your business one to four days a week
- Your team onboarded onto Anthropic's product suite (Claude, Cowork, Claude Code) with workflows configured to your operations
- First workflow in production within 7 to 30 days. Full operating cadence within 90 days.
- Your team trained to operate the system
- Designed to sunset - A bridge to AI-native operations, 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
- An agency contract for project-based deliverables
- A permanent fractional executive seat
Here is what most operators are doing.
Using AI like a search engine. Ask a question. Get an answer. Done.
Running tools, not systems. Automating tasks, not operations.
Hiring for headcount when the constraint is process design.
This is not a tools problem. It is an operations design problem.
Every month you stay here is a month your team does work that should not need a human. The fix is not more software. It is a system designed around what AI can now run end to end.
The morning briefing your team rebuilds by hand every day runs on its own. The pipeline review they skip because it takes too long delivers before the day starts. The follow-ups that pile up after every meeting are drafted in your voice by the time you sit down.
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 youAgent systems
Production autonomous systems at scale. Scoped and overseen by Chase, built outside this engagement by specialist implementation work.
Outside scopeFractional AI Officer
Outside Scope
From six places to check to work already done.
Daily briefs are table stakes. Every AI tool ships one. Executed deliverables are what move revenue, retention, and growth. By the time you sit down, the work is already moving: drafts ready, dashboards built, calendar blocked.
Reads today's red items.
Pulls conflicts and prep gaps.
Surfaces overnight urgent threads.
Flags mentions and escalations.
Surfaces deals needing attention today.
All execution operates within rules you set during onboarding, with a full audit log. Anything outside those rules routes to Ready for your review.
- Routine email replies sent under your established rules
- Direct-report check-ins handled with status posted to team channels
- Calendar conflicts resolved with attendees notified
- Follow-up emails drafted in your voice, awaiting send
- Quarterly review dashboard built from CRM and finance data
- Board prep doc organized with named action items
- Focus blocks added for prep-needed work
- Vendor calls scheduled with prep notes attached
- Deep-work time protected on tomorrow's calendar
The before-after
Manual: spend the morning catching up. With Sidekick: by the time you sit down, the routine work is already done, the deliverables that need your judgment are drafted and waiting, and your focused time is already blocked.
The pattern is already in production across the Sidekick Solo client base. Your Fractional engagement builds the set that fits your operations.
Curious where your business is on this ladder?
Thirty-minute assessment. No deck. No commitment.
What every engagement includes.
AI Operations Strategy
Quarterly review of your AI layer. Bottlenecks named, roadmap tied to revenue and retention, not abstract maturity scores.
Workflow Design and Build
We design the workflow and build the harness inside your stack.
Stack current as of May 2026. We refresh on major Anthropic releases.
Fractional onboards your team onto Anthropic's product suite. Custom multi-agent deployments (Managed Agents architecture, bespoke MCP servers, API-direct integrations) sit outside this engagement; when that work is needed, Sidekick scopes it and routes to an implementation partner. Chase oversees; you own the output.
What we count as a "workflow"
A workflow is a defined operational routine inside Cowork: a trigger, the work it does, a quality check before output ships, a human checkpoint where output reaches a customer, and a named owner on your team. Quality is scored by an AI judge against a reference set you and Chase build together, plus a weekly review by the workflow owner.
Leadership and Team Coaching
Weekly or biweekly working sessions with you and your team leads. Not lectures. Real work on real workflows, until your people can run the system without us.
Team Knowledge Library
A structured operating layer your team uses every day: SOPs, prompts, playbooks, decision trees. The system the AI runs on, not a folder of slides.
Async Support
Slack or email between sessions. Typically same business day. Not a 24/7 helpdesk, not a scheduled call you have to wait for when something breaks.
Three tiers. One engagement model.
First moves into AI. Focused workflows, light coaching, team-ready recipes.
A focused entry-tier engagement: typically one to three light workflows in production, recurring leadership coaching, and a starter set of copy-ready recipes for the team. Cross-team workflows and multi-domain architecture start at Build. Pick this when you want a near-term productivity lift and a starting layer of AI literacy before scaling commitment.
AI built into how teams work. Multi-team workflows plus culture and adoption strategy.
A more comprehensive engagement covering culture and adoption strategy alongside the workflow build. Workflows now span teams and chain into each other. Leadership coaching is continuous, and team training is a deliverable, not a footnote. Pick this when you want a robust productivity lift plus the org-level enablement that makes it stick.
AI as the operating layer. Cross-functional architecture with a shared knowledge layer.
AI is part of how the business runs day to day. Workflows touch multiple functions, share context, and feed each other. Strategy work covers the operating model itself, what roles change, what processes retire, what gets built next. Pick this when AI is the way you intend to run, not a side experiment.
All tiers include
Strategy, workflow design and build, leadership coaching, team knowledge library, and async support (typically same business day).
Operate is the typical fit. Pilot and Build are the entry points.
All prices in Canadian dollars.
A small number of engagements at a time.
Sidekick takes a small number of fractional engagements at a time. The working ceiling is two active engagements at the Build or Operate level. Pilot is short enough to fit alongside without compromising the others. When the calendar is full, new engagements join a queue and start at the next opening.
The reason is simple. Embedded operations work means being in the business every week, learning how it runs, building workflows that hold up under real conditions. Spread that across too many clients and the quality drops. The cost of stretching is borne by the clients who came first. Sidekick will not do that.
If the timing matters, book the discovery call early. The next opening is the next opening; it does not move.
An engagement built to transfer, not to depend.
Month 1 to 3 // Foundation
Audit your operations. Pick the highest-leverage AI gaps. Build the first layer of workflows and infrastructure. Your team sees output from week one, not slide decks.
Month 4 to 12 // Build
Scale what works. Expand across teams. Coach your leadership and staff inside the system, not next to it. Build toward an operating model your team can run without us.
Transition
The engagement winds down as your team takes over. Success means you do not need a Fractional AI Officer anymore. We aim to put ourselves out of a job, on purpose.
During the engagement, maintenance of workflows is part of the retainer. 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.
Engagements wind down when the team is ready to run the system on its own. A few renew when scope keeps expanding. The default direction is always toward independence.
“What Sidekick has 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.
What impressed me most was how much effort is in the backend that I don’t have to think about. Most people will never be able to recreate this on their own, even if they try to piece things together from blogs.
You’re not just buying templates. You’re getting a polished, proprietary operating system that lets you operate at a much higher level with far less friction.”
“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.”
Runs back-to-back full-day facilitations in week 4 of every month. Notes feed into her workspace; session recaps and follow-up emails come back drafted in her voice, ready to send. No new app. Runs inside the tools she already uses.
“I built an interactive dashboard with my company’s branding in two minutes. Commission structures, stages, all of it. Then I built an accounting folder that basically works like a bookkeeper.”
Records training sessions and client calls with Plaud. Files feed into the workspace, which updates Salesforce directly, runs competitive product analysis comparing carrier PDFs against the client’s situation, and drafts follow-up emails in his voice.
Chase founded Sidekick after more than a decade in B2B partnerships and revenue operations at B2B SaaS, marketplace, and healthcare-data companies. Jobber. DoorDash. DrugBank. The work that compounded was the operations work. The AI tooling was the layer that let small teams run like much larger ones.
Fractional AI Officer is the engagement Chase runs himself. He embeds with a small number of businesses at a time, designs the workflows that should run on AI, builds them, and coaches the team to operate the system once it ships.
The thesis is straightforward. Most owner-operated and mid-market firms cannot justify a full-time Head of AI yet. Most also cannot afford another consulting retainer that ships nothing. 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.
Not a consulting engagement.
Consultants produce recommendations. This engagement produces systems, workflows, and a team that runs them.
Not staffing.
No full-time hire. No benefits, no equity, no recruiting. A fractional lead with operator-level commitment on a contained scope.
Not a retainer for advisory hours.
Hours are scoped to building and coaching, not unbounded availability. The engagement is measured by what ships and what your team can run without help.
Where we say no.
- // no.
Every engagement needs a workflow owner on your team, someone responsible for outputs. If that role is not in place, start at Pilot or hire first.
- // no.
Customer-facing agents that touch PII require a dedicated security review before scope. We will say no until that exists.
- // no.
If month two shows no production usage, the engagement pauses for a re-scope, not a re-up. Months already invoiced are not refunded; future months are credited toward the re-scoped engagement or returned, your call.
Need a custom multi-agent build?
Custom multi-agent deployments (Managed Agents architecture, bespoke MCP servers, API-direct integrations) sit outside the Fractional engagement. Cost is determined by partner and scope, ranging from low 5 to low 6 figures. Sidekick has multiple implementation partners for that work depending on your requirements and base infrastructure. Chase scopes and oversees; you own the output.
Need full-time AI leadership?
Mid-market and enterprise teams that need a dedicated AI Officer, COO-level engagement, or role-replacement-grade leadership sit outside the Fractional engagement. Sidekick is a small shop by choice and focuses on businesses in early-to-mid stage AI adoption. Chase will refer you to a more established fractional-executive firm better suited to operate at that scale.
Running it solo? Sidekick Solo is the personal AI workspace for individual professionals and owner-operators.
See Sidekick SoloWhat buyers ask before signing.
Q
What's the difference between Sidekick Solo and Fractional AI Officer?
The difference is what gets equipped, and from which direction. Sidekick Solo equips an individual: we build one person their own AI workspace, configured around their role, and coach them to run on it. One-time, $1,800 CAD. It works for anyone, an independent professional, a business owner, or a leader inside a large company, and an organization can put its people on Solo one by one. That is adoption from the bottom up. Fractional AI Officer equips the organization itself: Chase embeds in your business, builds AI into how the operation runs, and trains your team to run it without him. From $3,000 CAD per month. That is adoption from the top down. The two work together. Many clients start with Solo and expand into a Fractional engagement, and Fractional engagements can include Solo setups for key people.
Q
Who owns the workflows after the engagement ends?
You. All workflows, prompts, configurations, and documentation are yours to keep. Sidekick retains nothing customer-facing. You own the operating layer Chase builds with you.
Q
What happens if we want to leave mid-engagement?
After the initial three-month minimum, you can end the engagement at any month boundary with 30 days notice. The workflows already in production stay with you.
Q
What tools do we have to switch to?
None. The stack runs in your existing tenants (Claude, your CRM, your file storage, your messaging). Sidekick brings no proprietary tools you have to migrate to or pay separately for.
Q
Is Chase the operator on every engagement, or a junior?
Chase is the operator on every engagement. There is no junior team. That is also why capacity is capped (see above).
Q
What data leaves our tenants?
Operational data stays in your tenants. No training data flows back to Sidekick or to Anthropic for model training. The only data that crosses a boundary is what you authorize through your own tool permissions during workflow build.
See what AI operations would change for your business.
Thirty minutes. We walk through your operations, name the AI work that would matter most, and tell you whether Fractional AI Officer is the right fit. No deck, no commitment.
If it is not the right fit, we will point you to Sidekick Solo or to an implementation partner.