Jessica Pillow

CEO

Miami, Florida, United States20 yrs 2 mos experience
Highly Stable

Key Highlights

  • Expert in global compensation strategies across diverse industries.
  • Certified Compensation Professional and Global Remuneration Professional.
  • Proven track record of leading high-performance teams.
Stackforce AI infers this person is a Global Compensation Expert in the SaaS industry.

Contact

Skills

Core Skills

Global CompensationBudgeting & ForecastingSales CompensationGlobal Compensation StrategyVariable CompensationSales Compensation StrategyData AnalysisCross-functional Partnerships

Other Skills

High Performance TeamsEquity StrategyLeading RemoteHR Department Start-upCross-team CollaborationCompensation PlanningStrategyPerformance ManagementDeferred CompensationHRISHuman ResourcesEmployee BenefitsLeadershipEmployee EngagementManagement

About

I'm not just a curious total rewards leader. I'm a mini-compensation-economist, a forecaster, and a fairness architect. My diverse industry experience is intentional, providing me with a broad perspective that enriches my approach. I excel in global environments, leading with a focus on simplifying processes and achieving sustainable success. I am known for delivering results quickly, always with a positive attitude. Passionate about creating positive change, I look forward to connecting with like-minded professionals and collaboration opportunities. Proud to be a World at Work designated Certified Compensation Professional (CCP) and Global Remuneration Professional (GRP).

Experience

20 yrs 2 mos
Total Experience
2 yrs 7 mos
Average Tenure
1 yr 8 mos
Current Experience

Deel

2 roles

Global Head of Total Rewards

Mar 2025Present · 1 yr 2 mos · Miami, Florida, United States · Remote

  • Oversee compensation, equity, benefits, perks, and mobility for 100+ countries (and counting!).
  • Deel is a global people platform which helps businesses hire and pay anyone, anywhere as independent contractors or full time employees compliantly and in minutes.
  • We are growing! - https://jobs.ashbyhq.com/Deel/

Global Head of Compensation

Sep 2024Mar 2025 · 6 mos · Miami, Florida, United States · Remote

  • Oversee compensation for 100+ countries (and counting!).
  • Deel is a global people platform which helps businesses hire and pay anyone, anywhere as independent contractors or full time employees compliantly and in minutes.
  • We are growing! - https://jobs.ashbyhq.com/Deel/

Hubspot

Director, Global Compensation

Sep 2023Aug 2024 · 11 mos · Miami, Florida, United States · Remote

  • Head of compensation operating across all regions.
Budgeting & ForecastingHigh Performance TeamsCross-functional PartnershipsGlobal CompensationEquity StrategyLeading Remote

Wework

3 roles

Global Head of Compensation

Jun 2022Sep 2023 · 1 yr 3 mos

  • Global head of compensation and variable pay operating in North America, Europe, LATAM, and Asia Pacific. Managing a team of compensation partners that sit in multiple locations.
Budgeting & ForecastingHigh Performance TeamsCross-functional PartnershipsSales CompensationGlobal Compensation

Head of Americas Compensation & Global Variable Pay

Promoted

Mar 2021May 2023 · 2 yrs 2 mos

  • Head of North America and LATAM compensation and global variable pay. Managed a team of compensation partners that sit in multiple locations.
Budgeting & ForecastingHigh Performance TeamsCross-functional PartnershipsGlobal Compensation StrategyLeading Remote

Director, Global Sales & Variable Compensation

Jul 2019Mar 2021 · 1 yr 8 mos

  • Head of global sales and variable compensation operating in 40 countries.
Budgeting & ForecastingCross-functional PartnershipsVariable CompensationSales Compensation StrategyHR Department Start-up

Gartner

Director, Global Sales Compensation

Mar 2018Jun 2019 · 1 yr 3 mos · Greater New York City Area · Hybrid

  • Head of sales compensation CoE that supports 4,000 associates operating in 40 countries.
Cross-functional PartnershipsSales Compensation StrategyData Analysis

Allianz partners

4 roles

Manager, Compensation & Performance

Jan 2017Feb 2018 · 1 yr 1 mo · Hybrid

  • Responsible for formulating and implementing strategies for compensation and performance management programs across North and South America. Identify key trends and recommend effective solutions to ensure that these programs remain aligned with organizational objectives.
Budgeting & ForecastingHigh Performance TeamsCross-functional Partnerships

Rewards & Performance Project Manager

Nov 2015May 2016 · 6 mos · Hybrid

  • Managed the executive compensation and performance management process for 30 countries, presenting future year impacts to the Compensation Committee. Completed a thorough span of control analysis for Allianz Worldwide Partners, contributing to a global transformation effort.
Cross-functional Partnerships

Manager, Total Rewards

Promoted

May 2013Dec 2016 · 3 yrs 7 mos · Hybrid

  • Responsible for strategy and managing various total rewards functions, including compensation, health and wellness, performance management, HR systems, organizational development, and HR analytics.
Budgeting & ForecastingHigh Performance TeamsCross-functional Partnerships

Manager, Compensation

Aug 2009May 2013 · 3 yrs 9 mos · Hybrid

  • Implemented a comprehensive, sustainable compensation function from the ground up. This included the development of a compensation philosophy, formation of the Compensation Committee, salary structure, job benchmarking, internal guidelines and policies, organizational hierarchy, span of control, variable compensation programs (sales, executive, STI, LTI), training at all levels of the organization, annual compensation cycle, and performance management. Served as the liaison between the Americas region and the Global HR Office.
  • Special assignment in 2012: Lead a critical project to configure and deploy an automated executive scorecard via SuccessFactors for 30 countries.
Cross-functional Partnerships

Medicorp health system

Compensation Consultant

Mar 2009Aug 2009 · 5 mos · Fredericksburg, VA · Hybrid

  • In partnership with the healthcare system Board of Management, provided expert advice and recommendations on a broad range of topics, including organizational structure changes, position evaluations, and pay equity concerns. Led the redesign of the profit-sharing program to better align with the organization's strategic goals and objectives, while also ensuring that it was equitable and sustainable over the long term.

Circuit city

Senior Compensation Analyst

Aug 2007Mar 2009 · 1 yr 7 mos · Richmond, Virginia Area · Hybrid

  • Provided guidance on compensation programs for all levels within the organization ranging from executive, corporate functions, call center, and distribution centers. Role encompassed designing and managing a total of 17 variable pay programs, as well as managing stock option grants, outstanding awards, and vesting schedules. Assisted with the company’s bankruptcy hearings and due diligence process.
Cross-functional Partnerships

World kitchen

Compensation & Benefits Analyst

Aug 2005May 2007 · 1 yr 9 mos · Reston, VA · Hybrid

  • Conducted comprehensive external analysis of benefits and compensation programs to identify emerging trends and offer recommendations. Oversaw the management and distribution of stock options while maintaining detailed records for the Board of Directors. Contributed to the design, implementation, and administration of management and sales incentive plans.

Education

George Mason University – Costello College of Business

Management

Jan 2003Jan 2007

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