MICHAEL REGGIO
Omaha,NE
Summary
Senior business leader with extensive experience in sales operations and strategic planning. Demonstrates a strong track record in executing complex business priorities that drive revenue growth and enhance organizational effectiveness through team leadership and strategic decision-making.
Overview
41
41
years of professional experience
Work History
Director, Sales Operations & Enablement
Inspira Financial (formerly PayFlex)
11.2018 - 08.2026
- Lead Sales Enablement team of 4 and develop integrated content, training, and coaching programs designed to increase sales productivity and results.
- Led sales operations RFP/RFP and GTM organization of 10: directed complex proposal strategy, coordinated subject-matter experts, and strengthened response quality through disciplined Salesforce CRM practices.
- Led Strategic Deal Reviews and provide executive/C-level governance for strategic and complex new business and upsell opportunities, improving decision quality, streamlining approvals, and strengthening competitive positioning.
- Partner with Sales leadership to define go-to-market strategy and lead pricing and profitability analysis across Inspiras Consumer Directed Benefits portfolio, supporting disciplined commercial decisions.
- Owned competitive intelligence and territory marketing planning, providing Board-level analysis of product penetration, adoption, market segmentation, and demographics to inform growth strategy.
- Established Inspiras Sales Onboarding program, creating a structured 90-day framework with milestones to accelerate new Sales Executive readiness and effectiveness.
- Directed sales pipeline and revenue target management, managing pipelines up to $60M against annual sales targets of $15M.
- Develop sales compensation plans and conduct Sales Incentive Compensation audits to support alignment, accuracy, and effective sales performance management.
Director, Strategic Planning
PayFlex Systems USA, Inc.
08.2016 - 11.2018
- Facilitated enterprise and business-unit strategic planning across Account Management, Sales, and Sales Operations, translating priorities into actionable business plans that align with organizational goals.
- Led Data Analytics and Strategic Initiatives team, providing recurring analysis of product penetration and customer segmentation by client and geography to support strategic decisions.
- Partnered with Audit, Compliance, Marketing, Product, Finance, and Aetna Service Pricing teams to execute cross-functional strategic initiatives.
- Managed integration of PayFlex product suite into CVS Health's Omnichannel Delivery Strategy, enhancing customer experience and identifying critical customer journey touchpoints.
- Created a Book of Business Profitability Model covering Reimbursement, HSA, COBRA, and Direct Bill product lines to improve visibility into client-level economics.
- Developed business development plans and territory strategies designed to build sales momentum and improve market opportunity execution.
- Managed sales reporting and built a weekly pipeline forecasting tool used to project revenue, membership growth, and retention savings prior to Salesforce.com adoption.
- Partnered with consulting group to develop Account Management Capacity Model, aligning Single Point of Contact by geography and product suite to optimize resource allocation.
Director, Billing & Revenue Assurance
PayFlex Systems USA, Inc.
01.2015 - 07.2016
- Directed monthly client and carrier premium remittance and reconciliation exceeding $10M per month.
- Managed reimbursement, HSA, and COBRA/direct bill client invoicing administration and transfer pricing, ensuring accurate processing for over $125M in annual revenue.
- Developed and implemented a recovery process for custodial cash owed by clients and carriers, addressing negative custodial receivables.
- Directed new business deployment and collaborated with Account Managers on forecasting and feasibility reviews for new and existing opportunities.
- Supervised a team of over 30 employees, ensuring effective workflow and productivity..
Senior Manager, Operations
PayFlex Systems USA, Inc.
02.2010 - 01.2015
- Managed COBRA/Direct Bill client invoicing across multiple platforms, supervising a team of 30+ to maintain service delivery.
- Led conversion of multiple COBRA and Direct Bill administration platforms into a single proprietary platform, enhancing operational consistency and streamlining processes.
- Oversaw reconciliation of premium remittances across multiple systems, ensuring accuracy before monthly remittance to clients and carriers.
New Business Senior Manager
WoodmenLife
01.2007 - 01.2010
- Led intake and output of new business across Life, Health, and Annuity products, coordinating with Field Force, Underwriting, Actuary, and Legal on in-force illustrations to ensure compliance and accuracy.
- Led strategic planning initiatives to align organizational goals with market trends.
- Managed cross-functional teams to enhance collaboration and drive project success.
- Developed training programs to improve staff performance and operational efficiency.
- Chaired Special Investigations Unit, overseeing a staff of 25+ to enhance fraud detection and investigation processes.
Senior Manager, Claims
WoodmenLife
01.1995 - 01.2007
- Led claims operations for health, disability, long-term care, and waiver of premium; co-signed life claims of $250K and above to ensure compliance and accuracy.
- Contributed to long-term care product development; chaired Special Investigations Unit and managed team of 20+ to enhance claims processing and fraud prevention.
- Oversaw compliance with regulatory standards and internal policies across operations.
- Managed budgeting processes and financial planning for multiple business units.
- Led cross-functional teams to develop strategic initiatives for organizational growth.
Senior Underwriter / Manager
WoodmenLife
01.1986 - 01.1995
- Underwrote life and health risks with management approval authority up to $1.5M; trained new hires on risk selection and led a team of 10.
- Developed underwriting guidelines to support consistent decision-making.
- Analyzed risk factors to determine appropriate coverage levels.
- Evaluated insurance applications for accuracy and completeness.
Education
Leadership Development
University of Nebraska At Omaha
Omaha, NE01-2000
B.S. - Business Administration, Economics & Finance
Dana College
Blair, NE01-1986
Skills
- Sales process optimization
- Sales team development
- Compensation modeling
- Revenue forecasting
- Strategic planning
- Market strategy
- Financial reporting
- Budgeting
- Data analysis
- Operational efficiency
- Salesforce CRM
- Excel
- PowerPoint
- Word
- Go-to-market strategy
- Team leadership
- Coaching and mentoring
- Change management
Personal Information
Title: DIRECTOR / VP-LEVEL BUSINESS LEADER
EXECUTIVE LEADERSHIP & CORE COMPETENCIES
- Strategic Planning & Execution
- Go-to-Market Strategy
- Sales Operations & Enablement
- Pricing & Profitability
- Strategic Deal Governance
- RFP / RFI Leadership
- Pipeline & Revenue Management
- Business Development
- Competitive Intelligence
- Data & Analytics
- Revenue Assurance
- Operational Transformation
COMMUNITY LEADERSHIP
- Tournament Director, Battle of Omaha | 06/2010 Present
- Instructor, Ultimate Baseball Academy Nebraska | 09/2014 Present
- Assistant Coach, Varsity Baseball, Westside High School | 06/2025 Present
- Assistant Coach, Varsity Baseball, Bellevue West High School | 09/2014 05/2025
Timeline
Director, Sales Operations & Enablement
Inspira Financial (formerly PayFlex)
11.2018 - 08.2026
Director, Strategic Planning
PayFlex Systems USA, Inc.
08.2016 - 11.2018
Director, Billing & Revenue Assurance
PayFlex Systems USA, Inc.
01.2015 - 07.2016
Senior Manager, Operations
PayFlex Systems USA, Inc.
02.2010 - 01.2015
New Business Senior Manager
WoodmenLife
01.2007 - 01.2010
Senior Manager, Claims
WoodmenLife
01.1995 - 01.2007
Senior Underwriter / Manager
WoodmenLife
01.1986 - 01.1995
Leadership Development
University of Nebraska At Omaha
B.S. - Business Administration, Economics & Finance
Dana College