Ryan Woolam
Kansas City,MO
Summary
National sales leader who builds qualified pipelines, guides C-level sales conversations, and develops tailored solutions for complex funding and risk transfer needs. Brings strengths in sales strategy, CRM use, team training, competitive analysis, and contract support, with a record of opening new markets and improving conversion.
Overview
16
16
years of professional experience
Work History
National Sales Director
True Captive Insurance
Overland Park, Kansas
2025.06 - 2026.09
- Prepared tailored captive solutions for employer prospects and referral partners.
- Cultivated broker and consultant partnerships to enhance market penetration in captive insurance.
- Built sales pipelines for self-funded benefits and risk transfer opportunities.
- Identified potential customers and new market opportunities to drive sustained revenue growth.
- Facilitated prospect discussions on funding models and underwriting to tailor solutions that meet client needs.
- Collaborated with marketing and operations on lead generation and client outreach.
- Trained sales teams on True Captive Insurance messaging and market positioning.
- Assisted with proposals, renewals, and plan reviews alongside internal teams.
- Prepared monthly, quarterly and annual sales forecasts to plan sales strategies.
Senior National Account Executive
Medcor Group, Inc.
2022.01 - 2025.05
- Developed new business opportunities with C-level executives, providing financial assessments for healthcare organizations and securing 3-5-year contracts in 10 new states.
- Conducted in-person and web-based sales presentations for C-level executives and board members, educating prospects on health care market trends and government training.
- Managed full sales cycle using HubSpot CRM, achieving a 30%-40% increase in new lead-to-customer conversion rate.
- Organized national trade shows and events, generating $10M-$15M in new sales opportunities annually.
- Partnered with revenue cycle analysts and healthcare executives to cultivate vendor relationships, enhancing reimbursement processes and delivering premium health care services.
Senior Revenue Cycle Management Sales Executive (Team Lead)
eSolutions, Inc/Waystar, LLC
2015.09 - 2022.01
- Facilitated achievement of monthly and annual software sales and margin goals using Salesforce & HubSpot CRM.
- Prospected 60-100 new client calls per day across the Federally Qualified Health Center, Hospital/Acute, Skilled Nursing & Durable Medical Equipment Markets Nationwide.
- Led team of 6-8 account reps, coordinating efforts to enhance sales effectiveness.
- Oversaw product sales lifecycle from closing through delivery and technical support to ensure client satisfaction.
- Develop and conduct online webinars to demonstrate software capabilities.
Account Executive/Outside Sales
Steel City Media
2014.08 - 2015.06
- Maximized sales opportunities and enhanced portfolio exposure through targeted outreach and relationship management.
- Achieved display targets and maximized revenue by scheduling appointments with agencies and clients and preparing tailored sales materials.
- Negotiated price adhering to established budgeted yields. Monitored and analyzed competitive media for business leads.
- Responded to client inquiries promptly, ensuring high satisfaction and retention.
Inside Sales Representative
Med4Home/Lincare Pharmacy
2012.05 - 2014.07
- Made 100-125 calls daily to physicians, patients, and external companies to sustain high activity levels for the sales team.
- Interacted with patients and physicians to manage multiple patient accounts, achieving monthly sales quotas.
- Processed current and new patients in multiple databases, ensuring compliance with Medicare and HIPAA guidelines.
Business Development Representative
Pro Athlete Inc.
2011.01 - 2012.04
- Handled high volume of daily calls to effectively engage clients and support retention.
- Identified client needs and established future opportunities to strengthen relationships.
- Managed and maintained multiple athletic accounts and ensured customer satisfaction
- Enhanced online shopping experience for customers, contributing to revenue growth.
Education
B.A. - Criminal Justice/Pre-Law
Park University
Parkville, Missouri2010-01
Skills
- Sales strategy development
- Sales pipeline development
- Sales forecasting models
- Revenue generation
- CRM utilization
- Proposal creation
- Contract management
- Pipeline oversight
- Competitive analysis
- Team management
- Consultative selling
Accomplishments
- Scholarship athlete for Park University Baseball team for 4 years.
- Completed P1 Learning Sales Systems Training
- Top Oxygen Sales Consultant at Med4home:
- October November 2013: Top Sales rep in the dept.
- 2013 4th Quarter: Top sales rep in the region
- Apr. 2014: Top Sales rep in the dept.
- Top Account Executive at eSolutions/Waystar:
- 2017 Q1/Q2 Top Sales Leader
- 2017 Q4 Highest MRR Account Executive
- 2018 #1 in ARR on Sales Team/
- 2019 Q2/Q3/Q4 Top Account ExecutiveMRR New Business
- 2020 Q1/Q2 Top Account ExecutiveMRR New Business
Timeline
National Sales Director
True Captive Insurance
2025.06 - 2026.09
Senior National Account Executive
Medcor Group, Inc.
2022.01 - 2025.05
Senior Revenue Cycle Management Sales Executive (Team Lead)
eSolutions, Inc/Waystar, LLC
2015.09 - 2022.01
Account Executive/Outside Sales
Steel City Media
2014.08 - 2015.06
Inside Sales Representative
Med4Home/Lincare Pharmacy
2012.05 - 2014.07
Business Development Representative
Pro Athlete Inc.
2011.01 - 2012.04
B.A. - Criminal Justice/Pre-Law
Park University