Strategy & Execution Specialist
DeWinter Group, San Francisco, CA, United States
Title: Strategy & Execution Specialist
Job Type: Contract (W2 Only)
Contract Length: 3 months (Potential for extension)
Pay Range: $95 - $105/hr
Start Date: ASAP
Location: Remote (PST Business Hours)
About the Opportunity
Our client, a leader in Data & AI Platforms, is looking for a skilled Strategy & Execution Specialist to join their team for a 3‑month engagement. This project involves leading day‑to‑day execution of key workstreams on strategic cross‑functional programs intended to drive business priorities such as Migrations, Go‑to‑Market (GTM) optimization, and Agentic transformation. This is a high‑impact role that requires a self‑motivated professional who can hit the ground running and deliver results quickly.
Key Responsibilities & Deliverables
Facilitate working group sessions with cross‑functional stakeholders: set agendas, drive decisions, track actions, and close loops.
Build and iterate on agentic AI workflows to automate recurring program tasks (e.g., status aggregation, data pulls, stakeholder communications, competitive benchmarking).
Own and ensure successful delivery of key initiatives and deliverables for specific workstreams, including design and implementation of new GTM system capabilities.
Define scaled execution plans to operationalize successful initiatives across the company and drive effective change management.
Collaborate with the program SMEs to prepare and present executive‑ready materials (e.g., monthly Business Owner Review decks and quarterly GTM Leader Review materials).
Required Skills & Experience
8+ years of professional experience in program management, management consulting, or strategy & operations at a technology company.
Deep expertise and a track record managing large‑scale cross‑functional programs with executive stakeholders (VP and SVP level). This isn't a learning role—you need to be a subject matter expert.
Demonstrated ability to build agentic AI workflows—not theoretical; show what you have shipped.
Strong analytical orientation with hands‑on SQL and dashboard skills.
Formal design‑thinking or process re‑engineering experience (IDEO, Stanford d.school, Lean Six Sigma, or equivalent applied methodology).
Excellent written and verbal communication; able to produce executive‑ready decks and status updates with minimal direction.
Demonstrated ability to work autonomously and manage your own time effectively to meet project goals.
W2 only (No C2C or 1099 contractors)
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Key Responsibilities & Deliverables
Facilitate working group sessions with cross‑functional stakeholders: set agendas, drive decisions, track actions, and close loops.
Build and iterate on agentic AI workflows to automate recurring program tasks (e.g., status aggregation, data pulls, stakeholder communications, competitive benchmarking).
Own and ensure successful delivery of key initiatives and deliverables for specific workstreams, including design and implementation of new GTM system capabilities.
Define scaled execution plans to operationalize successful initiatives across the company and drive effective change management.
Collaborate with the program SMEs to prepare and present executive‑ready materials (e.g., monthly Business Owner Review decks and quarterly GTM Leader Review materials).
Required Skills & Experience
8+ years of professional experience in program management, management consulting, or strategy & operations at a technology company.
Deep expertise and a track record managing large‑scale cross‑functional programs with executive stakeholders (VP and SVP level). This isn't a learning role—you need to be a subject matter expert.
Demonstrated ability to build agentic AI workflows—not theoretical; show what you have shipped.
Strong analytical orientation with hands‑on SQL and dashboard skills.
Formal design‑thinking or process re‑engineering experience (IDEO, Stanford d.school, Lean Six Sigma, or equivalent applied methodology).
Excellent written and verbal communication; able to produce executive‑ready decks and status updates with minimal direction.
Demonstrated ability to work autonomously and manage your own time effectively to meet project goals.
W2 only (No C2C or 1099 contractors)
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