MCG — VP Medicare Sales Search Notes

★ Quick Snapshot

Client	Medicare Choice Group (MCG)
Search title	Vice President, Medicare Sales
Functional mandate	Head of the Medicare advisor / sales team — not a President title
Reports to	Brendan Miller (CEO)
Location	Remote / national; travel as needed
Target OTE	$275K–$300K target; strong base + performance bonus, room up to $350K for truly exceptional candidates
Search driver	Leadership replacement + scale-readiness ahead of employer and broker demand

Headline: Find a Medicare-native sales leader who can run the advisor team, present credibly to employers, and build scalable execution — without turning the model into a script-heavy call center.

1 The Assignment

MCG needs a senior leader for its Medicare advisor and sales organization. The prior leader is retiring / exiting, and Brendan wants a high-energy operator who can lead the team day to day, professionalize the sales rhythm, and prepare the organization for larger employer-led enrollment volume.

This is not a President, COO, or pure strategy seat. It is the top sales/advisory leadership role: own advisor performance, training, onboarding, capacity planning, employer enrollment execution, and the operating structure needed to scale.

2 Business Context

MCG is growing against broader Medicare-market pressure because the business is heavily weighted toward Medicare Supplement, with continued Medicare Advantage growth.
The core business is group / employer-based — supporting employer populations as people age in, retire, or are already 65-plus.
The model is education-led and consultative, not random individual referral volume and not a rigid call-center script.
MCG is contracted with 50+ carriers and is expanding into ancillary products: life, hospital indemnity, RX, dental, vision, pet insurance, estate planning, and related solutions.
Large employer contracts are in play — including one ~500,000-life employer population — and the team may need capacity before the normal AEP ramp.
Near-term advisor growth may be 2–10 hires, with potential to grow to 10–20+ and materially higher if national broker agreements land.

3 Role Scope

Owns	Builds	Does Not Need To Be
Advisor leadership and accountability	Repeatable onboarding, training, and ramp	A President or broad company operator
Employer enrollment execution	A scalable advisor capacity model	A personal-production role
Presentation quality and live Q&A readiness	Performance standards across productivity, quality, and retention	A script-driven call-center manager
Med Supp, MA, PDP, and ancillary readiness	A sales culture that is consultative but disciplined	A title-heavy executive too far from the floor

4 Candidate Scorecard

Must Have	Strong Preference	Watch-Out
Senior Medicare sales / advisory leadership experience	All-50-states licensure	Needs President / COO scope to engage
Deep Med Supp and Medicare Advantage fluency	20+ years in Medicare or adjacent health insurance	Pure individual-market closer without employer polish
Led licensed advisors, agents, producers, or enrollment teams	Employer / retiree population experience	Script-dependent call-center manager
Can present to employers and handle unscripted Q&A	Broker or national partner-channel exposure	Solo producer who wants personal commissions
High-energy, hands-on, coachable-with-the-CEO style	AEP or large-enrollment surge experience	Benefits leader without Medicare enrollment mechanics

5 Compensation & Close Strategy

Target OTE

$275K–$300K

Stretch ceiling

Up to $350K

Structure

Base + bonus

Position target OTE at $275K–$300K, with room up to $350K for truly exceptional candidates.
Frame compensation as a strong base salary plus performance bonus.
Do not frame the role as enrollment-commissioned. Brendan wants this leader to pass individual enrollments to the advisors who should receive that compensation.
Probe compensation early. Candidates above the target range should only stay in process if they are clearly exceptional on Medicare leadership, employer-facing polish, and scale-readiness.
Sell the package as senior leadership compensation tied to team and company outcomes.

6 Search Map

Best source pockets

Medicare advisory firms with employer / retiree-channel exposure
Medicare brokerage organizations with national or multi-state advisor teams
Medicare Supplement-heavy businesses and benefits advisory firms with Medicare transition teams
Carrier-adjacent distribution leaders with hands-on advisor leadership experience
Senior Medicare sales trainers, regional leaders, and team leads who have managed licensed advisors

7 Candidate Pitch

Report directly to the CEO and own the Medicare advisor / sales organization.
Lead a company growing despite broader Medicare-market pressure.
Build the structure for large employer, broker, and AEP-adjacent enrollment demand.
Coach a consultative, education-led advisor team rather than manage a commodity call center.
Help expand a multi-product platform across Med Supp, MA, PDP, and ancillary benefits.
Earn senior-level OTE without needing to personally produce enrollments.

8 Screening Questions

Walk me through the Medicare advisor teams you have led: team size, products, channels, and results.
How much of your background is Medicare Supplement versus Medicare Advantage?
Have you supported employer-group or retiree-population Medicare enrollment?
What states are you currently licensed in, and have you ever held all-50-states licensure?
How do you train advisors to sell consultatively without relying on scripts?
Tell me about a time you scaled a team quickly ahead of AEP or a large enrollment push.
How comfortable are you presenting to employers, retirees, HR leaders, or broker partners?
How would you handle a 40-minute Medicare education webinar followed by unscripted member questions?
How do you think about advisor compensation, productivity, quality, and retention?
Are you comfortable leading the team and passing enrollments to advisors rather than personally producing?
What OTE range would you need to seriously consider a role like this?

9 Open Items for Brendan

Confirm final candidate-facing title.
Confirm base / bonus split inside the $275K–$300K OTE target.
Decide whether all-50-states licensure is required or strongly preferred.
Confirm travel expectations and whether the leader owns future retention / member-experience roles.
Confirm any systems, CRM, reporting, carrier, or Spanish-language requirements worth adding.

10 Candidate-Facing Posting

Location

Remote / National

Responsibilities

Lead and develop a national team of licensed Medicare advisors.
Coach advisors on consultative, unscripted member conversations.
Support employer-facing education sessions, webinars, presentations, and live Q&A.
Partner with the CEO on advisor hiring, onboarding, capacity planning, and performance expectations.
Build scalable processes for training, sales execution, member experience, and retention.
Maintain operating discipline around licensure, AHIP readiness, carrier appointments, compliance, and advisor performance.

Qualifications

10+ years of Medicare, health insurance, benefits advisory, or related sales leadership experience.
Experience leading licensed Medicare advisors, agents, producers, or enrollment teams.
Deep knowledge of Medicare Supplement, Medicare Advantage, PDP, carrier appointments, AHIP, state licensing, and enrollment workflows.
Active health insurance licensure required; all-50-states licensure strongly preferred.
Strong presentation skills with employers, retirees, members, and broker partners.
High-energy, hands-on leadership style with strong judgment and a consultative sales orientation.

Perks

Earn a strong base salary plus performance bonus, with target OTE of $275K–$300K and room up to $350K for truly exceptional candidates.
Lead a growing Medicare advisory team with meaningful national scale potential.
Work directly with the CEO on sales strategy, hiring, process, and team development.
Help build the next stage of an employer-focused Medicare advisory platform.
Support a multi-product offering across Medicare, prescription drug plans, and ancillary benefits.

We look forward to reviewing your application!