Darryl T. Agostinelli

Interim Executive & Strategic Technology Advisor

Rapidly aligning technology strategy and building high-performing teams to maximize returns and minimize risk.

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Transformational Technology Leadership

With over 20 years of experience, I provide strategic technology leadership and operational excellence to growth-focused companies and investors. My expertise lies in rapidly assessing technology operations, implementing transformational strategies, and building high-performance teams that deliver measurable results and maximize business value.

Core Services

Strategic technology leadership tailored for high-growth companies

Technical Due Diligence & Risk Assessment

Expert evaluation of technology infrastructure, scalability, and hidden technical risks prior to acquisitions, helping investors make informed investment decisions.

Post-Acquisition Technology Integration

Proven strategies for seamless technical integration that aligns technology with business growth objectives and drives operational efficiency.

Building High-Performance Tech Teams

Practical guidance and coaching to help company leaders build, structure, and retain effective engineering and product teams aligned with business objectives.

Interim or Fractional CTO/CIO Leadership

Immediate and transformational leadership for critical transitional periods, stabilizing operations and advancing technical capabilities.

Strategic Advisory & Roadmap Development

Creation and implementation of strategic technology roadmaps designed explicitly to enhance operational efficiency and support growth objectives.

Exit Readiness & Value Maximization

Strategic preparation of technology organizations to demonstrate maximum valuation to potential acquirers or IPOs, ensuring optimal exit outcomes.

How We Work Together

A transparent and effective process from initial conversation to successful execution

1. Initial Discovery

A no-obligation conversation to explore your challenges, objectives, and how my expertise might align with your needs.

2. Deep-Dive Assessment

Detailed technical discussions, documentation review, and identification of key stakeholders and organizational priorities.

3. Confidentiality & Terms

Exchange of mutual NDA, discussion of engagement structure, reporting relationships, and communication protocols.

4. Scope Definition

Detailed proposal with specific deliverables, success metrics, timelines, and governance structures.

5. Execution

Regular progress updates, hands-on leadership, strategic guidance, and continuous alignment with business objectives.

6. Knowledge Transfer

Documentation of processes, structured knowledge transfer, establishment of sustainable practices and governance.

Types of Engagements

Flexible service models tailored to your specific needs

Interim Executive Leadership

Full-time leadership roles (typically 6-12 months) where I serve as CTO/CIO, providing hands-on leadership during critical transitions, turnarounds, or growth periods. This includes complete ownership of the technology organization and direct reporting to the CEO or board.

Strategic Advisory Services

Regular strategic guidance sessions with leadership teams, typically involving weekly or bi-weekly meetings plus availability for critical decision support. Ideal for companies with existing technical leadership seeking expert guidance and mentorship.

Technical Due Diligence

Comprehensive technical assessments for potential acquisitions or current portfolio companies, identifying risks, opportunities, and action plans. Includes detailed evaluation of architecture, team capabilities, scalability, technical debt, and strategic alignment.

Project-Based Consulting

Focused engagements addressing specific challenges such as technology stack modernization, team restructuring, or product roadmap development. This includes clear deliverables, timelines, and success criteria for targeted organizational improvements.

Industries & Technologies

While my approach is adaptable across sectors, I specialize in:

SaaS & Cloud-Native Applications

Data-Intensive Systems & Analytics

AI/ML Implementation & Strategy

Enterprise Software & Integration

Technology Organizations at Scale

(15-150+ engineers)

Why Work With Me

Delivering tangible results through expertise and leadership

Proven Transformational Leadership

Successfully led major transitions, digital transformations, and integrations for investor-backed and high-growth technology organizations.

Strategic & Tactical Balance

Ability to quickly shift from high-level strategic vision to hands-on, practical execution, ensuring comprehensive solutions.

Decisive Technical Due Diligence

Rapid and thorough assessments, ensuring informed investment decisions and minimizing unforeseen risks.

Coaching and Mentorship

Demonstrated record of mentoring executive teams, building sustainable leadership practices that drive enduring results.

Insights & Thought Leadership

Perspectives on technology leadership and value creation

The Role of Technical Due Diligence in Value Creation

How comprehensive technical assessments can identify hidden risks and growth opportunities in potential acquisitions.

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Building Scalable Tech Organizations in High-Growth Companies

Strategic approaches to constructing technology teams that can support rapid growth and optimize operational efficiency.

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Maximizing Exit Value Through Technology Optimization

How strategic technology investments and operational improvements can significantly increase valuation at exit.

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Ready to Accelerate Your Company's Growth?

Schedule a strategic consultation to discuss how I can help drive technology transformation and maximize value for your business.

Trusted by Industry Leaders

Experience working with companies across diverse sectors

NECC
Microsoft
AECOM
Dell
Wells Fargo
Charles Schwab
QV21
Razorfish
New York Life
Sumo Logic
State of Texas
Banks DIH
Catapult Systems
Valero
Loram
BlueWave Security
last updated: Mon Mar 24, 2025, 23:07:12