Wendy Fashing — Senior Program Manager | Strategic Delivery & Workforce

01 — Executive Summary

Fifteen-plus years delivering complex programs at scale.

From start-up RPO to one of the world's largest delivery networks, I've spent my career turning ambiguous priorities into structured roadmaps, governance cadences, and the kind of cross-functional execution that holds up under pressure.

I run program management for Amazon's Americas last-mile delivery workforce — a $90M+ operating portfolio supporting 3,700+ delivery businesses, 10,000+ owners, and ~280,000 contracted drivers across the U.S., Canada, and Latin America.

What I do well: scope ambiguous business objectives, build the roadmaps and OKRs, and drive execution across Product, Technology, Operations, HR, and Finance — with the governance, RAID logs, and stakeholder rhythm to keep it all visible to senior leadership.

PMP-trained, fluent across agile and waterfall. I lead with high candor, build successor-ready talent, and have a consistent track record of internal promotion across fast-scaling operations.

$90M+

Budget under management

PMP

Trained, 2025

1.3M

Associates hired (career)

Countries: US, CA, LATAM

02 — Signature Achievements

The work I'm proudest of.

A short selection of the transformations that changed how the business operates — not a comprehensive list.

Field Operations Restructure

Recovered 6,240 annual hours on a 60-day timeline

Redesigned a 70-person field organization into a dual-pillar program model (on-demand support + dedicated hyper-care) — lifting operational efficiency 25% and reclaiming 6,240 annual partner-facing hours.

Enterprise Hiring Program

200K+ annual hires across three U.S. business lines

Delivered 1.3M associates over the program lifecycle — including a record 48,000 hires in a single week — sustaining 95% program performance through COVID-19 disruption via rapid virtual-execution pivot.

Strategic Partnerships

95% participation across a $70M value-added services portfolio

Led strategic alliances with McDonald's, 7-Eleven, and Starbucks to 95% program participation against an 80% target.

HR-Tech Modernization

$21M ATS implementation, end-to-end

Owned vendor selection, contract negotiation (SLAs, audit rights, GDPR-aligned data privacy), implementation, and adoption strategy — hitting 50% voluntary user adoption within 5 months, three months ahead of plan.

AI-Enabled Operating Leverage

13,000 direct report hours saved per year

Pioneered enterprise adoption of 8+ Amazon-built AI tools across the program management function — eliminating manual reporting cycles, accelerating MBR authoring, and reclaiming team capacity for higher-value strategic execution.

International Program Expansion

Scaled field operations into Canada & LATAM

Extended the field-operations program from the U.S. into Canada and Latin America to support 3,700+ delivery businesses — and authored the AMET (Africa / Middle East / Turkey) implementation plan for 2027.

03 — Experience

A career built across enterprise, RPO, and start-up environments.

The throughline: workforce strategy, operational transformation, and the systems that turn hiring into a business advantage.

Amazon

2022 — Present

Sr. Manager, Program Management — Americas Workforce Services

Last-Mile Delivery (DSP Network) · US, Canada, LATAM

Own the 3-year strategic program roadmap for Americas workforce services across five business lines and three VP organizations. Manage a $90M operating plan and $70M value-added services budget. Established the program's first performance-management framework with eight cross-functional KPIs, founded the first agile product team within DSP workforce operations, and delivered 98% enrollment on the enterprise platform migration for 100K+ Amazon drivers.

Amazon

2018 — 2022

Sr. Program Manager, Workforce Staffing Programs

600+ warehouses · ~1.3M hourly associates

Spearheaded the annual Strategic Planning Session for U.S. Workforce Staffing — defining OKRs, milestones, and cross-functional priorities for a 200K+ annual hire program across three business lines. Directed Amazon's first international workforce expansion into Mexico and led the multi-year HR technology replacement of the legacy Salesforce ATS.

Cielo

2014 — 2018

Director, Client Services (Program Delivery)

RPO · Fortune 500 portfolio

Owned a $10M+ enterprise program portfolio for Fortune 500 clients at 86% business margin with a matrixed team of 40+. Transformed an end-to-end driver-recruitment program for a Fortune 500 transportation client — reducing time-to-hire from 14 to 3 days, lifting applicant flow 40%, and improving time-to-fill 25%.

Accolo

2007 — 2014

Director, Client Management

RPO Start-Up · Chicago

Managed enterprise program portfolio across Midwest/East region, building C-suite relationships that drove above-benchmark retention and expansion revenue. Designed customized program delivery models, KPI dashboards, and governance frameworks across diverse industries.

CareerBuilder

2006 — 2007

Vertical Market Manager

Retail, Hospitality, Restaurant verticals

Designed and executed go-to-market programs across retail, hospitality, and restaurant verticals — enabling 200+ professionals through structured rollouts. Built a scalable training curriculum that reduced new-hire ramp time by 60% and lifted solution adoption by 45%.

04 — Leadership Philosophy

How I lead.

Three things I've come to believe after fifteen years of leading through change.

Candor is a kindness.

People can't course-correct on feedback they don't get. I name what I see early, with respect — and I expect the same back. It's how trust gets built and how teams move faster under ambiguity.

ii.

Build the bench, not the hero.

The job isn't to be indispensable — it's to make the team unstoppable without you. I coach for successor-readiness, promote internally, and treat development as an operating priority, not a side project.

iii.

Strategy without operating muscle is decoration.

A great deck is the easy part. I focus on the executable layer: who owns what, how it's measured, and what the system looks like six months after launch when the energy fades.

05 — Currently

What I'm reading and listening to.

The inputs that are shaping how I think about leadership, transformation, and the future of work right now.

On the bookshelf

Reading

Multipliers

Liz Wiseman · on leaders who amplify the intelligence of others
An Everyone Culture

Kegan & Lahey · on building deliberately developmental organizations
The Advice Trap

Michael Bungay Stanier · on leading with curiosity over expertise
Co-Intelligence

Ethan Mollick · on living and working alongside AI

In my ears

Podcasts

Projectified

PMI · strategic conversations on leading complex programs at enterprise scale
Manage This

Andy Crowe & Bill Yates · the craft of project management, deeply and practically
SmartLess

My guilty pleasure — because not everything has to be a learning moment

Thinking about

On my mind

Where AI redraws the line

Which workforce roles fundamentally change in the next 24 months
Speed without burnout

How fast-scaling teams hold pace without losing their best people
The new operating model

What workforce strategy looks like when hiring is no longer the bottleneck

06 — AI in Practice

How I'm using AI in my own life.

I don't just lead AI adoption at work. Here's how I've folded these tools into how I run a household, plan, learn, and think.

i.

The household co-pilot

Weekly meal planning, grocery lists tied to what's actually in the fridge, family calendar triage, and travel itineraries that flex around real constraints — not just tourist defaults.
ii.

Budgeting & financial planning with Copilot

Copilot has become my personal CFO — tracking spend against goals, surfacing the patterns I'd otherwise miss, and turning long-term financial planning into a conversation rather than a spreadsheet I dread opening.
iii.

Supporting a family business launch

I used Claude to help my husband stand up his latest venture, Water Warriors Mokena — building the website end-to-end with embedded registration and waiver forms, plus Calendly integration so scheduling runs itself. AI turned what would've been a months-long project into a week.
iv.

A second brain for big decisions

I use AI to pressure-test thinking before high-stakes conversations — mapping the steel-man case for the other side, surfacing assumptions I'm carrying, and rehearsing tough feedback before I deliver it.
v.

Learning faster, on my own terms

Whether it's a deeper understanding of a new domain, parsing a dense article in 10 minutes I don't have, or building an executive-summary version of a book I haven't finished yet — AI shrinks the cost of curiosity.
vi.

Personal writing & reflection

From sharpening a recommendation letter for a former direct report to drafting a tough family email, AI is the editor I always wanted — one that pushes for clarity without rewriting my voice.

"The leaders who'll matter in the next decade won't be the ones who know the most about AI — they'll be the ones who've lived with it long enough to know exactly where it helps, where it gets in the way, and how to redesign work around it." — A working principle

Turning ambiguous business problems into programs that actually ship.