Pre-AI
Seed round · August 2026
The AI MSP
built like a
software company.
Chiri turns company-specific problems into governed software and remains accountable for what happens next.
$5MSeed
$50MPost-money
$1M+ARR
AI for judgment.
Software for proof.
Software for proof.
01 / WHY NOW
Generation is abundant.
Accountability is scarce.
Post-AI
One living context plane lets a smaller team govern expanding work.
Intelligence can handle expanding routine work, software can preserve context and proof, and people can focus on the exceptions that require judgment.
02 / THE MID-MARKET GAP
Every important AI project becomes a company-specific systems problem.
Mid-sized operators have enough complexity to need a tailored system, with too little spare platform capacity to design, govern, and run one alone.
Context
What does this company mean?
Connectivity
Where does the work happen?
Control
Who may see, decide, and act?
Verification
How do we know it worked?
Ownership
Who is accountable on Monday?
03 / THE ANSWER
Get the AI system and the expert team accountable for running it.
A new operating categoryAI Managed Service Provider
04 / ONE ACCOUNTABLE MOTION
From company problem to managed production.
One partner remains accountable across the entire lifecycle.
01
Outcome model
Design
Define the outcome, workflow, authority, and evidence before a line of product code becomes the answer.
System stateIntent mapped
02
Working system
Deploy
Build and connect the company-specific software box inside the systems where the work already happens.
System stateSystem live
03
Proof layer
Verify
Test code, behavior, permissions, structure, and controls. Use deterministic software wherever judgment is not required.
System stateProof attached
04
Managed responsibility
Operate
Monitor the system, resolve exceptions, support users, and remain accountable after the launch moment.
System stateControl active
05
Reusable leverage
Improve
Capture exceptions, reuse mechanisms, and expand into adjacent workflows as the relationship compounds.
System stateLeverage retained
05 / THE SYSTEM BEHIND THE SERVICE
One context plane. Every system. Always current.
Chiri Waypoint is the accountability layer for a post-AI way of operating. Select a layer to inspect the system and its current maturity.
Chiri Waypoint / 01
Accountability
Chiri Waypoint is being built to collapse fragmented systems into a single plane of unified context that never goes stale, so monitoring, exceptions, support, and improvement share the same operating truth.
Maturing
06 / DOCUMENTED CLIENT PROOF
Already solving high-value, company-specific work.
Private intelligence
Private markets platform
14,000+transaction records analyzedMarketplace ingestion, scoring, alerts, and reporting in a private operating dashboard.
Reuse in action
Marine services operator
N → N+1generalized template to scaffoldA client application scaffolded from the reusable platform pattern derived from prior work.
Brownfield healthcare
Diagnostics provider
SOW →architecture, workflows, roadmapDocumented integration work designed around HIPAA/PHI-sensitive requirements.
07 / THE COMPOUNDING MECHANISM
Every engagement should leave behind software.
Private markets platform
Reference stack
Generalized
Client template
Marine services operator
Application scaffold
Next
More capability on day one
IntegrationsWorkflowsValidatorsAccess patternsEngineering mechanisms
Delivery creates the asset. The asset increases the leverage of future delivery.
08 / BUSINESS MODEL
Land with a build.
Compound through managed responsibility.
One-time
Initial build
Outcome-defined deployment
Recurring
Managed operations
Recurring accountability + platform
Recurring + expanding
Expansion
Adjacent workflows, usage, and applications
The margin thesis
Managed scope and recurring revenue expand faster than delivery headcount.
Chiri Waypoint, the accountability layer introduced in section 05, automates routine coordination and directs people only to the exceptions that require judgment.
09 / MID-MARKET FIRST
Mid-market first
Big enough to have the problem.
Too lean to build the answer alone.
Complexity
Multiple systems, fragmented data, and tribal operating knowledge.
Urgency
A measurable workflow constrains growth, quality, or control.
Ownership gap
No internal team can design, deploy, verify, and run it end to end.
Enterprise expansion is upside, not the assumption required to win.
10 / GO-TO-MARKET
Already in motion
Proof is already moving through a partner-powered distribution engine.
Chiri wins and learns directly, then works with channel partners already contributing qualified introductions, referrals, and distribution.
Founder + client network
High-trust problems, direct learning, and customer referrals.
In market nowDelivery creates the playbook.
Every engagement leaves behind reusable software, operating knowledge, and evidence.
Chiri SummitContent + GTM OS
Turns delivery proof into reusable content, GTM workflows, and partner enablement.
Channel partners
AdvisorsMSPs + MSSPsPortfolio partners
Qualified introductions, referrals, and scaled distribution.
In market nowMore proof→More partner trust→More qualified demand→Compounding distribution
11 / COMPETITIVE POSITION
Most providers make you choose.
Chiri compounds both.
Accountability without software leverage becomes another headcount curve. Software without accountability becomes another tool the customer must operate.
Internal team
Owns the outcome.
Capability scales with headcount.Chiri AI MSP
Builds, verifies, and operates production.
Outcome ownershipSoftware leverageCompounding IP
Every engagement strengthens the system.Consultancy
Delivers the project.
Knowledge and accountability leave.Point AI / SaaS
Scales the tool.
Customer integrates, verifies, and operates.12 / FOUNDER-MARKET FIT
Built by operators who understand work, systems, and scale.
Co-founder, CEOMathew Caldwell
Founded RocketPower and was Instacart's first HR executive. Scaled hiring infrastructure for Instacart, Mozilla, and DEEM. He has lived the problem of scaling human operations.
Co-founder, CTOMatthew Wimberly
AI systems architect who has built engineering teams and enterprise systems across healthcare, government, and finance. Deep experience with knowledge graphs, regulated infrastructure, and platform architecture.
Co-founder, CPONick Cote
More than a decade at the frontier of emerging technology, from regulated digital-asset infrastructure to embedding AI in companies. Architects, builds, and ships with AI daily.
Co-founder, CSODustin Haugland
RocketPower co-founder with multiple exits. Combines operating strategy, positioning, partnerships, and client growth. He knows how to scale a services business into a platform.
Co-founder, COOJeff Baumgarten
RocketPower co-founder who led operations through scale. Brings enterprise rigor from Accenture to startups across finance, legal, operations, and corporate administration.
13 / THE ROUND
$5M turns capability into repeatable managed revenue.
$50MPost-money$45M pre · 10% simple implied ownership
Go-to-market
$2.50M
Chiri Platform
$1.00M
Forward Deployed Delivery
$1.00M
Internal operations
$0.50M
14 / THE SEED PROOF
Five numbers will decide this company.
Delivery leverage
Accounts per FDE · workflow capture · human exception load
Software mix
≥40% platform mix on new logos · path to 60%+ blended GM
Recurring quality
Standard contracts · retention · ≥110% NRR target
Repeatability
Three vertical blueprints · activated partner channels
Trust
Security/compliance progress · evidence-ready operations
Building the operating layer between commoditizing intelligence and accountable work, so companies can turn abundant AI into trusted, repeatable business outcomes.
Continue the conversation
The system and the team accountable for running it.
Review the materials, inspect the evidence boundaries, and meet the operators building the new AI MSP.