Kelly Gaskin

Senior Principal Managing Partner

Leads executive relationships and escalations for Workday's most complex, high-value accounts.

• Achieved 0% churn and 2% expansion while managing $40M+ in annual contract value.
• Drove $3M+ in organic sales, with customers expanding into three new solutions without considering competitors.
• Retained a $15M Fortune 20 account by surfacing strategic risk in its HR tech migration and reopening negotiations with senior leadership.
• Raised Net Promoter Score by 0.40 through process improvements and engagement programs like "Jam Sessions" and Wellness Plans.
• Named 2024 Managing Partner of the Year (Financial Services); sponsored by Workday as a member of Chief.

Director, Implementation Strategy & Enablement

• Built automated audit tools that cut deployment costs and shortened Financials and HCM implementations by three weeks.
• Curated the Workday Altitude consultant conference, lifting survey ratings from 3.4 to 4.5.
• Rebuilt and stabilized the Field Enablement and Strategy teams, achieving full recovery within four months.

Implementation Strategy Architect, Cross-Platform

Previously Senior Solutions Architect, Global Payroll (2014 – 2016)

• Incubated Workday's first cross-platform advisory role across HCM, Payroll, and Financials.
• Directed go-to-market strategy for new offerings across product, sales, marketing, and services.
• Featured speaker at Workday Rising (2010 – 2016) and Sales Kickoff (2014 – 2016).

Consulting Manager

• Founded and led a national team of 16 consultants in the Payroll, Absence & Time Tracking practice.
• Managed executive-level escalations and influenced product roadmap to meet evolving customer needs.

VP Payroll Operations

Early-stage startup, later acquired by Toast

• Earned a 3% ownership stake and helped acquire the firm's first 2,000+ customers.
• Led a team of 10 serving ~200 clients and 50,000+ employees.

Service Delivery Manager

• Built a metrics tracking system that improved service delivery and protected project profitability.