Summary
Overview
Work History
Education
Skills
Education Certifications
Technology Tools
Awards
Hobbies and Interests
Community Service
Skills Expertise
Professional Highlights
Timeline
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Benjamin Sullivan

Buffalo

Summary

Dynamic Senior Sales Director with a proven track record at Activate Solutions, excelling in agent recruitment and sales management. Expert in designing income solutions and driving performance through strategic planning. Adept at building high-performing teams and fostering compliance in Medicare environments, ensuring sustainable growth and exceptional client service.

Overview

12
12
years of professional experience

Work History

Senior Sales Director

Activate Solutions
San Francisco
04.2025 - 10.2025

Lead national growth and agent development initiatives within a high performance Medicare and retirement income platform. Recruit, train, and scale sales leaders and agents while building long term infrastructure for sustainable distribution. Oversee sales management strategy, production performance, and income focused planning solutions for retirees and pre retirees.

Drive expansion through agent recruitment and leadership development
Design scalable sales systems and compensation structures
Support complex retirement income cases and advisor partnerships
Guide teams through compliance driven Medicare and annuity environments
Build enterprise level growth strategies across multiple markets

Senior Director

Exact Medicare
Columbus
04.2023 - 04.2025

Directed sales growth and field leadership for the MAX Division, overseeing agents and team leads nationwide. Built revenue channels through agent recruitment, training, and performance management while supporting families with Medicare and retirement income planning strategies.

Recruited and developed national agent teams
Designed income focused retirement solutions for clients
Provided leadership for Medicare Advantage and supplement distribution
Built operational structure for scale during AEP and OEP
Served as senior resource for complex client and advisor cases

Account Executive

Trusty.care
New York
02.2021 - 04.2023
  • Advance company sales goals through consistent and efficient prospecting and improve platform through effective communication.
  • Exceeded personal sales targets consistently.
  • Helped attract a sizeable user base from ground zero.
  • Generate new business and meet and surpass quotas selling unique Medicare software to individual healthcare businesses and financial planners.
  • Build and manage a sales pipeline from prospect to close to integration through outbound lead generation, selling the value of the product to sign up to agents and agencies to the platform.
  • Deliver software demonstrations to prospects and effectively convey the products benefits as well as address any questions or concerns they may have regarding the software or the company.
  • Qualify inbound and outbound leads and assign them to the correct sales channel.
  • Collaborate with customer service and the technical team to address issues and improve the platform.

Internal Sales Agent

Twin Cities Underwriters, Inc.
Minneapolis
06.2019 - 02.2021
  • Advance company sales goals through attentive, tailored client consultation and tenacious prospecting.
  • Exceeded personal and team sales targets consistently.
  • Commended for development of new sales and lead generation strategies.
  • Collaborate with cross-functional colleagues to fulfill company objectives.
  • Cultivate deep knowledge of products and services and calculate premiums to meet client needs.
  • Develop and deliver engaging workshops for full range of carriers to prospective and current clients.
  • Maintain up-to-date expertise in CMS regulations and plan changes.

Licensed Medicare Sales Agent (Contractor, Medix)

HealthPartners
Bloomington
08.2018 - 02.2019
  • Advanced 705 opportunities for Medicare Advantage, Medicare supplements, and Dental Plans for the 2019 AEP selling season.
  • Presented Medicare Products in formal and informal events generating sales and leads.
  • Processed inbound calls and walk-ins to answer consumer questions about Medicare products.
  • Handled outbound calls to follow up on leads and request for information about Medicare products.

Regional Business Development Representative

TempWorks Software
Eagan
02.2017 - 10.2017
  • Engaged key decision-makers at the C-Level to secure software demonstrations and follow-up appointments for outside sales members.
  • Prospected, qualified, and developed 1-2 sales-ready leads per week through internet and outbound calling for business-to-business sales.
  • Spent 75% of the day outbound prospecting, placing more than 30 calls.
  • Overcame business objections of prospective customers to increase demonstration appointments by 50%.
  • Achieved metrics regarding inside sales activities to generate new business.
  • Accurately logged all activity and leads in the company’s sales customer relationship management system.

Senior Broker Support Representative

UnitedHealthCare
Minnetonka
06.2015 - 11.2016
  • Delivered quick response resolution for field market organization partners and superior sales support to the highest-producing agents in a fast-paced call center environment.
  • Focused on additional sales support to hundreds of local agent managers and field sales agents.
  • Assisted agents with Medicare Advantage, prescription drug, and Medicare supplement plans.
  • Built rapport with agents and members to ensure a superior service experience.

Project Manager / Insurance Claim Specialist

Interstate Roofing
Edina
06.2013 - 05.2015
  • Marketed business to people in the metropolitan area and across the country while establishing a client base.
  • Contacted 40 potential clients per day door to door to increase customer leads by 10-40%.
  • Spoke with homeowners to assist with inspection of their roof and provided an overview of any issues.
  • Managed and oversaw projects, following up with project to ensure completion to code.

Education

Bachelor of Science - Business Administration

Bethel University
St. Paul, Minnesota

Skills

  • Consultative sales and market analysis
  • Agent recruitment
  • Sales management
  • Medicare compliance
  • Sales strategy
  • Customer relationship management
  • Team leadership
  • Performance analysis
  • Data-driven decision making
  • Income solutions design
  • Effective communication
  • Training development
  • Sales presentations
  • Negotiation expertise
  • Competitive analysis
  • Team building and project coordination
  • Strategic planning and forecasting
  • Brand development and advertising
  • Effective communication and presentations

Education Certifications

  • Bachelor of Science (Candidate), Business Administration, List if over 3.3, Bethel University, St. Paul, MN
  • Certified in UnitedHealthcare Medicare Products and Ethics and Compliance, Fraud, Waste and Abuse, Compliance and HIPAA regulations

Technology Tools

  • Salesforce
  • Jira
  • Microsoft (Word, Excel, PowerPoint, Outlook)
  • Slack
  • Avaya
  • MARx
  • SharePoint
  • GPS/ATS/CRM/Linkedin Sales Navigation

Awards

  • Top Sales Associate – UnitedHealthcare Agent Recruitment Campaign
  • Highest Customer Satisfaction Ratings – UnitedHealthcare

Hobbies and Interests

  • Sports
  • Hiking and outdoor activities
  • Travel

Community Service

  • Goodwill
  • Red Cross
  • Raptor & Wildlife Nature Center
  • Water Treatment Center St. Cloud

Skills Expertise

  • Consultative Sales
  • Team Building
  • Strategic Market Planning
  • New Business Forecasting
  • Market Analysis
  • Market Penetration
  • Brand Development
  • Advertising
  • Communications
  • B2B/B2C Project Coordination
  • Presentations
  • Consulting

Professional Highlights

  • Earned a reputation for cross-collaboration to develop winning sales strategies.
  • Frequently called upon to engage key C-Level decision-makers.
  • Secured 705 opportunities for Medicare Advantage, Medicare supplements, and Dental Plans for 2019 AEP.
  • Awarded 'Top Sales Associate' and 'Highest Customer Satisfaction Ratings' at United Healthcare.
  • Cultivated strong Medicare and Retirement knowledge and background from time at UnitedHealthcare and HealthPartners.

Timeline

Senior Sales Director

Activate Solutions
04.2025 - 10.2025

Senior Director

Exact Medicare
04.2023 - 04.2025

Account Executive

Trusty.care
02.2021 - 04.2023

Internal Sales Agent

Twin Cities Underwriters, Inc.
06.2019 - 02.2021

Licensed Medicare Sales Agent (Contractor, Medix)

HealthPartners
08.2018 - 02.2019

Regional Business Development Representative

TempWorks Software
02.2017 - 10.2017

Senior Broker Support Representative

UnitedHealthCare
06.2015 - 11.2016

Project Manager / Insurance Claim Specialist

Interstate Roofing
06.2013 - 05.2015

Bachelor of Science - Business Administration

Bethel University
Benjamin Sullivan