Hello! I'm James
Values-driven sales executive with 17 years of progressive leadership experience at Workday, joining as employee #280 when the company generated $3 million in ARR and contributing to its growth journey to nearly $10 billion in ARR. Advanced through six positions from Business Development Representative to Regional Vice President, currently overseeing nationwide enterprise sales operations for the US Diversified Industries business unit while managing four regional directors and 24 account executives.
My leadership approach, rooted in family values of hard work and sacrifice, has provided the resilience to navigate multiple economic cycles including the dot-com bust, financial crises, COVID-19, and market volatility. This foundation enables me to build scalable systems that drive sustainable go-to-market success while hiring exceptional people who enable continuous learning, precise forecasting, and sustained competitive advantage through unwavering commitment to innovation in sales methodologies and market expansion.
Currently driving to win with 120%+ year-over-year growth in net new enterprise logos, with a proven track record of launching new business units and scaling high-performing teams from 5 to 42+ account executives. Previously achieved 11 consecutive quarters of over-attainment and "Region of the Year" recognition through deep expertise in matrix leadership across solution consulting, value engineering, and revenue operations. Success stems from solving complex challenges alongside great people committed to winning while maintaining relentless focus on customers, helping enterprise clients realize measurable outcomes in global expansion, compliance, workforce planning, and AI adoption through Conversational AI and AI driven CLM.
James Yack
SALES LEADER
415-545-8213
Email: jryack@gmail.com
Address: 258 Paraiso Dr. Danville CA 94526
EXPERIENCE
February 2023 - Present
Workday
Regional Vice President US Diversified Industries
Second-line enterprise SaaS sales leader overseeing nationwide net new customer acquisition and expansion strategy across diversified industries. Directly manage 4 Regional Sales Directors and 30+ AEs, with cross-functional leadership over solution consulting, value engineering, industry strategy, marketing, and revenue ops. Partner with C-level stakeholders (CIO, CFO, CHRO) to drive digital transformation in workforce planning, global expansion, and AI adoption.
Key Highlights
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Built a new GTM team from the ground up: Hired 4 front-line sales leaders and 33 AEs to create an enterprise-focused sales org.
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Consistent Overachievement:
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FY25 – 120% YoY growth
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FY26 – Tracking to 126% YoY growth
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Market Coverage & Pipeline Penetration
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Enterprise TAM coverage: 55%
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Enterprise active pipeline: 10.3%
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Sales Focus Areas: Application consolidation, workforce optimization, AI adoption, compliance, and global expansion.
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Selling Into: C-level decision makers across CHRO, CFO, and CIO organizations.
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Sales Motion: Land-and-expand, net new logo acquisition, value-based enterprise selling.
February 2020- January 2023
Regional Vice President Sales, West
Workday
Led a medium enterprise SaaS sales organization spanning the Western U.S., with 4 front-line managers and 42 AEs. Responsible for full GTM strategy and execution, including forecasting, pipeline creation, coaching, talent development, and cross-functional execution with pre-sales, sales development, marketing, and revops.
Key Achievements
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11 consecutive quarters of over-attainment
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Grew team size from 20 to 42 AEs
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FY21 – Presidents Club 101% of COVID-adjusted plan
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FY22 – Presidents Club 121% of annual plan (Region of the Year)
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FY23 – Presidents Club 112% of annual plan
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Best 8-quarter performance across 22 business units:
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271 Closed/Won deals
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$107M ACV
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$398K average sales price
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201-day avg sales cycle
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October 2018 - January 2020
Regional Sales Director
WORKDAY
Front-line sales leader managing 5 AEs in a matrixed SaaS environment. Drove full-cycle sales execution across pipeline generation, opportunity management, and deal closure in medium enterprise.
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FY18 – Presidents Club 142% of annual plan (Top Sub-Region in Medium Enterprise)
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Focused on operational forecasting, deal coaching, and pipeline quality
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Led value-based selling initiatives in partnership with solution consultants and industry experts
January 2012 - September 2018
Account Executive
Workday
Hybrid AE role combining strategic expansion of existing accounts with net new logo acquisition. Excelled in consultative, value-based selling to enterprise buyers.
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FY13 – Presidents Club 140% of annual plan
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FY14 – Presidents Club 145% of annual plan
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FY15 – Presidents Club 200% of annual plan (#1 Top Performer, Medium Enterprise)
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FY16 – Presidents Club 153% of annual plan (Top AE, Bay Area)
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FY17 – Presidents Club 158% of annual plan
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Built multi-threaded relationships with CHRO, CFO, and VP-level stakeholders
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Managed complex sales cycles and cross-functional buying groups
October 2010- December 2011
Renewal Specialist
Workday
Focused on first-renewal lifecycle management of enterprise accounts. Proactively retained and expanded customer relationships, identifying upsell and cross-sell opportunities.
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Strengthened first-renewal success and minimized churn risk
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Collaborated with Customer Success and AE teams to maximize customer lifetime value
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Led renewal strategy sessions for high-value clients
June 2008 - September 2010
Sales Development Rep (Employee #280)
WORKDAY
Prospected and qualified enterprise accounts, driving early pipeline growth for the field sales team.
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FY10 – Presidents Club
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Played a key role in early revenue growth from $3M to $200M ARR by qualifying and generating pipeline for enterprise sales.
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Partnered with field AEs to book high-value discovery meetings with C-level prospects
EDUCATION
B.A.Kinesiology, Minor Business Administration
Western Colorado University
A public university in Gunnison, Colorado, situated at 7,700 feet known for its mountain setting and focus on immersive, real-world educational experiences in a variety of liberal arts and specialized fields, including unique programs like High Altitude Exercise Physiology.
COMPANIES I'VE HELPED
MY IMPACT
LAURA HINCKLEY, SALES ENABLEMENT
James I wanted to formally thank you for your willingness to work with me on so many big picture items this past year! It's been an incredible opportunity for me to develop new skills, grow as an individual, and learn from your perspective in the West. I so appreciate your support of my feedback and your encouragement in continuing to provide it. Your trust in me to lead important initiatives for your team has been a huge confidence booster, and I can't thank you enough for the continuous support! Thank you!
MIKE QUIGLEY, GVP SALES
There’s never been a moment in our years working together where your effort hasn’t been 110%. Thank you for all you do.
JOHN MILLARD, ACCOUNT EXECUTIVE
James is one of the most influential leaders in my career. For 4 years it was incredible to see him truly build a culture and process across the ME org. He clearly worked tirelessly and passionately. He's the Dan Campbell (Detroit Lions Head Coach) of ENT
sales, he cares about his people, his company and his customer. There wasn't a situation James didn't have a top notch strategy for, and regardless of good or bad he keeps the course in a positive and uplifting way. He makes everyone around him better. I'm fortunate to have learned so much from him and truly enjoyed our pursuits together.
STEPHEN FRITSCH, SALES LEADER
James, I wanted to take a moment and congratulate you on your incredible 14 years at Workday. I have thought of this many times, but there are probably 3 or 4 leaders in my 18 years in software that have had the biggest impact on my career—and you are one of them. Your leadership and your ability to lift people up has not just changed my life, but has had an incredible effect on so many Workmates. I can see it. And I often think: this is the leader I aspire to be.
Thank you for all that you do for us. And I’m excited to help build the business with you. Stephen
JOHN MORTON, PRE-SALES LEADER
James, reflecting on the year, one of the greatest accomplishments witnessed is the culture you built within your organization. Watching the team celebrate you on your anniversary milestone was one of those moments that demonstrated the unique camaraderie, and bonds built as workmates. And I’ve seen it played out since. You’ve inspired the team to embrace FY25 as a build opportunity, and true growth is realized through adversity. I believe the team will agree that your leadership has created impact that will last beyond just this year. It’s a pleasure to serve with you.
DAYTON KEANE, SALES LEADER
Having worked alongside and observed numerous leaders throughout my career, I can confidently say that your skills stand out. Your strategic thinking, discipline, transparency, authenticity, and ability to foster camaraderie demonstrate exceptional
leadership. It's evident that you possess all the key elements needed to successfully lead a sales organization. Your achievements and the position you've earned are truly commendable, and you should take great pride in your accomplishments.
MY APPROACH
Leading a Strategic Pivot from Tech & Media Dependence to Diversified Industries
The Challenge:
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Tech & Media dropped from $7.4M (FY23) to $1.7M (mid-FY24)
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Forecasting showed continued decline
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Over-dependence on single industry created risk
The Decision:
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Diversified across multiple industry verticals
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Reallocated resources from traditional stronghold
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Preserved existing relationships while building new markets
The Execution:
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Aligned cross-functional teams on new strategy
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Retrained account executives on industry dynamics
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Created sector-specific messaging and tracking systems
The Results:
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Built resilient revenue foundation
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Eliminated single points of failure
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Established repeatable expansion frameworks
Sales Storytelling Framework: From Vendor to Trusted Advisor
The Framework:
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Acknowledge their desires
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Explore the problem
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Tease the promise land
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Reveal the hidden enemy
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Show your recipe for success
Core Stories to Develop:
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Personal transformation story
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Customer success example
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Differentiation narrative
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Prospect's future vision
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Closing confidence builder
The Results:
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Build trust through insight revelation
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Transform vendor meetings into advisor conversations
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Create emotional connections that drive decisions
Sales Forecasting Framework: From Gut Feel to Data-Driven Decisions
The Challenge:
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Gut-feel forecasting creates inconsistent results
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Incomplete information leads to missed opportunities
The Framework:
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Pain/ROI: Understand challenges and validate business case
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Economic Buyer/Signer: Engage funding and contract decision makers
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Connections: Map executive sponsors and influencers
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Process/Competition: Understand buying process and competitive position
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Timeline/Event: Validate compelling events driving urgency
Requirements:
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Create targeted plans for weak areas (Red/Orange)
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Focus on strategic questioning to gather missing information
The Results:
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Evidence-based forecasting improves accuracy
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Early risk identification drives proactive behaviors