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KAREN BAILEY
United States
Summary
Dynamic enterprise software executive with extensive leadership experience in Financial Services. Successfully drove revenue growth across Fortune 1000 and Global 2000 accounts, cultivating executive relationships and executing go-to-market strategies that enhance digital transformation and client engagement.
Overview
25
25
years of professional experience
Work History
Senior Vice President, North America Enterprise & Strategic Sales
Emburse
01.2025 - Current
- Lead enterprise and strategic sales organization responsible for growth across Fortune 1000 and Global 2000 accounts.
- Owned customer acquisition and expansion strategy, overseeing pipeline generation, enterprise sales strategy, executive deal governance, forecasting, pipeline management, and territory planning.
- Recruit, develop, and coach enterprise sales leadership and talent while establishing scalable operating processes in a hybrid vertical and geographic model
- Partnered with Product, Marketing, Solution Engineering, Customer Success, and executive leadership to accelerate revenue growth.
- Drove executive engagement on AI-enabled spend management and financial operations modernization to support business transformation.
Founder & CEO
BAIX
01.2012 - Current
- Achieved over 20 percent year-over-year growth in consulting revenue.
- Advised prominent clients, including Bank of America and Allstate, on strategic initiatives.
- Delivered tailored solutions to enhance operational capabilities for diverse organizations.
- Established advisory firm focused on digital transformation and revenue growth strategies.
Vice President, Solution Consulting
Vertafore
01.2024 - 01.2025
- Led strategic customer engagement and solution consulting teams supporting insurance industry growth.
- Partnered with sales leadership on enterprise pursuits, competitive positioning, and business value development.
- Cultivated executive relationships with carriers, brokerages, and agency leadership teams to enhance collaboration and drive strategic initiatives.
- Facilitated revenue growth across Vertafore’s insurance technology portfolio by aligning solutions with client needs and market trends.
Senior Vice President, Global Head of Industry & Ecosystem
Kofax
01.2022 - 01.2023
- Created and executed global industry strategy resulting in 140% growth in targeted market engagement.
- Developed ecosystem and revenue-sharing model that expanded pipeline generation significantly.
- Aligned industry, partner, product, and sales organizations to drive strategic growth initiatives.
Global Head, Financial Services Ecosystem Strategy
Microsoft
01.2019 - 01.2022
- Led Microsoft's Financial Services ecosystem strategy spanning Banking, Insurance, Capital Markets, and Wealth Management.
- Cultivated executive relationships with leading financial institutions, technology providers, and strategic partners to enhance collaboration and drive strategic initiatives.
- Facilitated growth initiatives for cloud, data, AI, and business applications within a $24B market opportunity, contributing to overall business expansion.
- Honored with Microsoft Platinum Club recognition for outstanding contributions to business performance and strategic goals.
EVP & General Manager, Americas
VeriPark
01.2018 - 01.2019
- Led go-to-market strategy and expanded market presence for Financial Services software solutions (built on Dynamics 365), driving customer acquisition and revenue growth.
- Built a $12M first-year pipeline and secured strategic OEM relationships.
- Supported digital transformation initiatives for banking, wealth management, and insurance across the Americas, enhancing client engagement and operational efficiency.
Business Applications Executive
Microsoft
01.2017 - 01.2018
- Received Microsoft Net New Customer Add Award recognizing contributions to business applications (Dynamics 365) growth.
- Led strategic sales initiatives for enterprise customers to drive successful business transformations.
- Led cross-functional teams to develop innovative software solutions.
- Coordinated strategic planning sessions to align company objectives.
- Mentored junior executives in effective leadership practices.
CIO, Retail Division & Corporate CTO
Brown & Brown Insurance
01.2015 - 01.2017
- Directed modernization programs that improved service delivery for over 9,000 employees.
- Negotiated enterprise contracts exceeding $50M and transformed operating models to streamline processes.
- Led enterprise transformation initiatives that enhanced operational capabilities for one of North America’s largest insurance brokerages.
Client Executive
Cisco Systems
01.2014 - 01.2015
- Led executive customer relationships and multidisciplinary teams selling to transformational healthcare customers.
- Delivered strategic growth and large-scale technology modernization programs.
- Over 400% growth in YoY revenue
- Grew from the bottom of the leaderboard to number 9 in the geographic area
Leadership Roles
Bank of America, Wachovia, Asurion
01.2001 - 01.2012
- Held senior executive leadership roles across technology, operations, risk management, enterprise transformation, customer-facing strategy, driving organizational alignment and strategic initiatives.
- Led large-scale organizational transformation programs impacting hundreds of thousands of users and contributing billions in enterprise value.
Education
MBA -
Auburn University
BS - Management Information Systems
Strayer University
Skills
- Enterprise & Strategic Sales Leadership
- Financial services expertise
- Insurance industry expertise
- Large Enterprise Negotiations
- Customer acquisition
- Forecasting, Pipeline & Operating Cadence
- Strategic Partnerships & Ecosystems
- Value-based selling
- Leadership development
- Strategic partnerships
- Enterprise negotiations
- Executive communications
Industry Expertise
- Financial Services
- Banking
- Capital Markets
- Wealth & Asset Management
- Insurance
- Brokerage
- Enterprise Technology
- SaaS
- AI
Selected Executive Qualifications
- Enterprise & Strategic Sales Leadership
- Financial Services, Banking, Wealth & Asset Management
- Insurance & Brokerage Industry Expertise
- Enterprise SaaS, Cloud & AI Solutions
- Customer Acquisition & Revenue Growth
- Forecasting, Pipeline & Operating Cadence
- Executive Relationship Management
- Value-Based & Outcome-Based Selling
- Leader of Leaders Development
- Strategic Partnerships & Ecosystems
- Large Enterprise Negotiations
- Board & Executive Communications
Professional Highlights
- Extensive experience leading large multi-layered organizations
- Led enterprise growth initiatives across Fortune 500 and Global 2000 organizations throughout Banking, Insurance, Healthcare, Manufacturing, Retail, and Public Sector markets.
- Microsoft Platinum Club recipient, awarded to the top 1% of employees globally.
- Supported Financial Services growth strategies spanning a $24B addressable market.
- Built and scaled high-performing sales, industry, and ecosystem organizations across global markets.
- Negotiated and influenced enterprise agreements exceeding $50M in value.
- Deep executive relationships across banking, insurance, brokerage, wealth management, and technology sectors.
Timeline
Senior Vice President, North America Enterprise & Strategic Sales
Emburse
01.2025 - Current
Vice President, Solution Consulting
Vertafore
01.2024 - 01.2025
Senior Vice President, Global Head of Industry & Ecosystem
Kofax
01.2022 - 01.2023
Global Head, Financial Services Ecosystem Strategy
Microsoft
01.2019 - 01.2022
EVP & General Manager, Americas
VeriPark
01.2018 - 01.2019
Business Applications Executive
Microsoft
01.2017 - 01.2018
CIO, Retail Division & Corporate CTO
Brown & Brown Insurance
01.2015 - 01.2017
Client Executive
Cisco Systems
01.2014 - 01.2015
Founder & CEO
BAIX
01.2012 - Current
Leadership Roles
Bank of America, Wachovia, Asurion
01.2001 - 01.2012
MBA -
Auburn University
BS - Management Information Systems
Strayer University