David Kaplan · Cultivar Tech Advisory

Fractional / Interim CTO

Transformation · Maturity · Impact

Build a technology organization that moves with speed, quality, and confidence.

Build a technology organization that moves with speed, quality, and confidence.

Build a technology organization that moves with speed, quality, and confidence.

I partner directly with founders, CEOs, CTOs, and investors to help venture-backed companies scale, mature, and optimize their product and engineering organizations.

I partner directly with founders, CEOs, CTOs, and investors to help venture-backed companies scale, mature, and optimize their product and engineering organizations.

Schedule a consultation

Email David

Operating Brief

15+ years leading Software Engineering, Data, InfoSec, and IT organizations through scale, transition, and measurable operational change.

18 → 140+
team scale

4
functions led

3

acquisitions

About David

From scrappy growth teams to generative enterprise engines.

I help leadership teams turn engineering into a strategic advantage—building durable operating rhythm, sharper technical decision-making, and organizations that can execute through growth, profitability, and M&A.

Proven track record

Alma — modernized a 110-person tech organization through transition to sustainable profitability.

Policygenius — scaled technology from 18 engineers to a 110-person enterprise function.

Yodle & Bloomberg — led acquisition integration, agile transformation, and architecture modernization.

Advisory Services

Executive leverage for the moments that define your company.

Executive leverage for the moments that define your company.

Fractional & Interim CTO Leadership

Executive leadership for growth milestones, leadership gaps, architecture decisions, and organizational transitions.

Fractional & Interim CTO Leadership

Executive leadership for growth milestones, leadership gaps, architecture decisions, and organizational transitions.

Transformational Projects

AI-first delivery, operating maturity, role design, DevOps transformation, and leadership workshops.

Transformational Projects

AI-first delivery, operating maturity, role design, DevOps transformation, and leadership workshops.

Leadership Coaching

Structured coaching for CTOs, VPs, Directors, Engineering Managers, and Staff Engineers becoming strategic leaders.

Leadership Coaching

Structured coaching for CTOs, VPs, Directors, Engineering Managers, and Staff Engineers becoming strategic leaders.

Strategy & M&A Assessments

Data-driven technology maturity and due-diligence evaluations that surface risks, capability, and a practical path forward.

Strategy & M&A Assessments

Data-driven technology maturity and due-diligence evaluations that surface risks, capability, and a practical path forward.

How we can work together

How we can work together

Fractional CTO Retainer

10–30 hrs/week · 3–12+ months

Fractional CTO Retainer

10–30 hrs/week · 3–12+ months

Interim CTO

Full immersion · 3–6 months

Interim CTO

Full immersion · 3–6 months

Project Scope / Sprint

Fixed engagements · 1–6 months

Project Scope / Sprint

Fixed engagements · 1–6 months

Coaching Cadence

3–6 month recurring cycles

Coaching Cadence

3–6 month recurring cycles

Start with the hard conversation

Get the clarity and operating momentum your next stage demands.

Get the clarity and operating momentum your next stage demands.

Get the clarity and operating momentum your next stage demands.

dave@cultivartechadvisory.com · NY / NJ Area / Remote

dave@cultivartechadvisory.com · NY / NJ Area / Remote

linkedin.com/in/davebkaplan