AI-Augmented Advisory

Technology assessments that measure what matters

Data-driven CTO advisory combining automated metrics collection with expert evaluation. Objective insights in weeks, not months.

7
Assessment Dimensions
28
Scored Subcategories
1-3 wk
Delivery Timeline

Consulting powered by data, not guesswork

Most technology assessments rely on interviews and gut feel. We pull real engineering data before forming any opinions.

Data-First Analysis

We connect to GitHub, GitLab, Jira, and Azure DevOps to pull real metrics — PR cycle times, deploy frequency, sprint velocity, code coverage, and more. No surveys. No guesswork.

AI-Augmented Delivery

Our assessment tools automate what traditional firms do manually. Faster results, lower cost, and higher consistency than any Big 4 engagement.

Actionable Roadmaps

Every finding comes with a scored priority, estimated effort, and clear ownership. You get a 30/60/90/180-day improvement plan — not a slide deck of platitudes.

Four steps to objective insight

Every engagement follows a proven methodology that turns engineering data into strategic decisions.

1

Automated Metrics Collection

Connect to your development tools and pull real engineering data — PR cycle times, deployment frequency, sprint velocity, code coverage, security scan results.

2

Expert Evaluation

Senior technology advisors assess architecture quality, team structure, security posture, AI readiness, and organizational maturity — informed by data.

3

Scored Assessment

Every dimension scored on our Technology Maturity Framework (1-5 scale) with weighted categories, industry benchmarks, and clear gap analysis.

4

Strategic Roadmap

Prioritized 30/60/90/180-day improvement plan with specific initiatives, effort estimates, success metrics, and ownership assignments.

Engineering Practices
Code Review · Testing · Quality
DevOps & Delivery
CI/CD · Deploys · Monitoring
Security Posture
AppSec · IAM · Compliance
Architecture Quality
Design · Scalability · Tech Debt
Overall Maturity
Across 28 subcategories
3.2 /5.0

Strategic technology advisory

From one-time assessments to ongoing CTO advisory, every engagement is backed by data and delivered by senior practitioners.

📊

Technology Assessment

Comprehensive, data-driven evaluation of your technology organization across seven critical dimensions. Automated metrics + expert evaluation + scored framework + actionable roadmap.

1-3 Weeks 7 Dimensions 28 Subcategories
$5,000 – $15,000
Learn more →
🔒

Security Assessment

Deep-dive security evaluation covering 8 domains and 40+ controls, mapped to SOC 2, NIST CSF, ISO 27001, and CIS benchmarks. Prioritized remediation with risk ratings.

8 Domains 40+ Controls Compliance Mapped
$8,000 – $18,000
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🤖

AI Readiness Assessment

Evaluate your organization's readiness to adopt and scale AI across data infrastructure, technology, talent, strategy, governance, and operations. Use case identification and phased investment plan.

6 Dimensions 32 Criteria AI Roadmap
$10,000 – $35,000
Learn more →
🔍

Technical Due Diligence

M&A-focused technology evaluation for PE firms and corporate development teams. Architecture, code quality, team risk, security, data assets, and integration cost estimation.

PE / M&A Risk Rated Deal Impact
$15,000 – $50,000
Learn more →
👥

Fractional CTO Advisory

Ongoing strategic technology leadership. Monthly advisory sessions, quarterly assessment refreshes, architecture review, team coaching, vendor evaluation, and board reporting. All backed by continuous metrics monitoring.

$5,000 – $15,000 / month
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Retainer Includes
Monthly strategic advisory sessions
Quarterly technology assessment refresh
Architecture decision support
Board & investor reporting
Priority access for ad-hoc questions

Built for technology-driven organizations

We work with companies where technology is the business — and the leaders who are accountable for it.

PE-Backed SaaS
FinTech
HealthTech
InsurTech
EdTech
Scaling Startups (Series A-C)
Mid-Market Enterprise
"The data-driven approach changed how our board thinks about technology. For the first time, we had objective metrics instead of opinions — and a clear roadmap to act on."
Operating Partner, Growth-Stage PE Firm
Post-acquisition technology assessment
40%
Avg. improvement in engineering velocity
< 3 wks
Assessment to actionable roadmap
100%
Clients act on recommendations

Transparent assessment packages

Every package includes automated metrics collection, scored assessment framework, and executive-ready deliverables.

Quick Assessment
Fast diagnostic to identify your top technology risks and opportunities.
$5,000
1-week engagement
  • Automated metrics collection
  • Technology maturity scorecard
  • Executive summary report
  • Top-5 prioritized recommendations
  • 60-minute findings review
Get Started
Comprehensive
Full assessment with all modules, workshops, and ongoing support.
$15,000
3-week engagement
  • Everything in Standard, plus:
  • Security + AI Readiness modules
  • Technical strategy workshop
  • Board-ready findings presentation
  • 30-day follow-up advisory
Get Started

Security assessments, AI readiness, due diligence, and retainer advisory priced separately. Contact us for custom scoping.

Guides for technology leaders & investors

Practical, no-fluff guidance on the decisions that shape technology organizations — from fractional leadership to M&A diligence.

Fractional Leadership

What Is a Fractional CTO? When to Hire One & What It Costs

How part-time technology leadership works, the signals that you need it, and how to tell a fractional CTO apart from a consultant or contractor.

Read the guide →
M&A / Private Equity

The Technology Due Diligence Checklist for PE Firms

The architecture, security, team, and AI-readiness questions that separate a clean deal from a costly post-close surprise.

Read the guide →
AI Strategy

AI Readiness Assessment: A Practical Guide

The six dimensions that determine whether your organization can actually adopt and scale AI — and how to close the gaps.

Read the guide →
Fractional Leadership

Fractional CTO vs. Full-Time CTO: How to Decide

Cost, commitment, and fit compared — plus a simple framework for choosing which your company actually needs.

Read the guide →
Pricing

How Much Does a Technology Assessment Cost?

Typical price ranges, what drives the number, and what a credible assessment should deliver for the money.

Read the guide →
Engineering Operations

DevOps Maturity Model: The 5 Levels Explained

The five levels from manual to optimized, the metrics that define each, and how to deliberately move up.

Read the guide →
Security & Compliance

SOC 2 Readiness Checklist for SaaS Companies

The five Trust Services Criteria, what auditors look for, Type I vs Type II, timeline, and cost.

Read the guide →
AI Strategy

AI Governance Framework: A Starter Template

The policies, roles, risk tiers, and controls you need to adopt AI responsibly without slowing down.

Read the guide →
Engineering Operations

Engineering Metrics That Actually Predict Delivery Risk

The DORA four plus a few flow metrics that predict delivery risk — and the vanity metrics to ignore.

Read the guide →

Browse all insights →

Common questions

Quick answers on fractional CTO services, assessment pricing, and how data-driven advisory works.

A fractional CTO is a senior technology executive who provides strategic engineering and product leadership on a part-time or retainer basis. You get C-level guidance on architecture, security, AI strategy, and team scaling without the $300K–$400K cost of a full-time hire. Jimmlr's fractional CTO advisory runs $5,000–$15,000 per month.

Jimmlr technology assessments range from $5,000 for a one-week diagnostic to $15,000 for a comprehensive three-week engagement with security and AI-readiness modules. Specialized security assessments, AI readiness, and technical due diligence are scoped separately.

Most assessments are delivered in one to three weeks. Automated metrics collection from tools like GitHub, Jira, and Azure DevOps lets us move far faster than traditional consulting firms that rely on manual interviews.

Technical due diligence evaluates a target company's architecture, code quality, engineering team and key-person risk, security posture, data assets, AI readiness, and post-acquisition integration cost. Every finding is risk-rated and tied directly to deal impact and the investment thesis.

Traditional assessments rely on interviews and judgment. We connect to your engineering tools first and pull real metrics — PR cycle times, deploy frequency, sprint velocity, code coverage — then layer expert evaluation on top. The result is objective scoring instead of opinion.

Ready to measure what matters?

Tell us a little about your situation and we’ll be in touch within one business day to set up a free 30-minute discovery call.