Grandmasters crestGRANDMASTERS
Now taking applications

Build your agency.
Develop leaders. Leave a legacy.

Bring your team into Grandmasters, a life insurance team within Checkmate Financial Group, with daily training, hands-on mentorship, and real support for you and every rep you lead, in person or fully remote.

Apply to Grandmasters

For leaders of active sales teams · Inbound leads · Remote positions

700+Licensed agents
40+A-rated carriers
50States

Checkmate Financial Group, the agency Grandmasters is part of

Why Grandmasters

Growth Over Grind

We focus on growth and a healthy work-life balance, for you and for every rep you lead. You get the guidance, systems, and support to build an agency that lasts, while still having time for the life you're building it for.

  1. 01

    Daily training for your team

    Daily trainings, both in person and virtual, so your reps keep sharpening without you carrying all of it.

  2. 02

    Structure

    Proven systems, training, and inbound leads, so your team spends its time helping families instead of chasing them.

  3. 03

    Support every step

    Hands-on mentorship and support in recruiting, training, and running your team. You're never building on your own.

  4. 04

    Remote positions

    Your reps can work from our office or fully remote. Our daily trainings are available both in person and virtually.

Apply to Grandmasters

Powered by Checkmate Financial Group

What Your Team Gets

Your reps plug into Checkmate's inbound calls, carriers, tools, and training, so you can focus on leading instead of building infrastructure.

  1. 01

    High-intent inbound calls

    People call in to buy. No cold calls and no bought lists, just high-intent callers and qualified web leads routed to your reps.

  2. 02

    40+ A-rated carriers

    Match every client to the right product instead of forcing one company's fit.

  3. 03

    Live training every day

    Daily live training and real mentorship. Not a static PDF library nobody opens.

  4. 04

    White-glove onboarding

    Contracts, carrier appointments, and portal access handled in the first week, so your reps start selling fast.

Included

AI CRM

Keeps every lead organized and nudges you on follow-ups.

Included

AI Dialer

Smart dialing with call coaching built in.

Included

Agent Portal

CRM, leads, training, and payouts in one place.

Included

Inbound Pipeline

Calls in Spanish and English, callback forms, and quote requests, delivered.

Apply to Grandmasters

Fit

Who This Is For

Apply if

  • You lead an active sales team, in insurance or any other industry.
  • Your reps are capped by someone else's comp plan or culture.
  • You want to build leaders, not just producers.

Don't apply if

Apply to Grandmasters

Getting started

From Application to Your First Team Win

  1. 1

    Apply

    A quick form about you and your team.

  2. 2

    Strategy call

    We learn about your team and map out what bringing them over looks like.

  3. 3

    Onboard your team

    Licensing guidance for reps who need it, then contracts, carrier appointments, and portal access, handled.

  4. 4

    Start building

    Inbound calls in your reps’ queues, daily live training, and support as you grow your agency.

Apply to Grandmasters
Karen Paczkowski, founder of Grandmasters

Meet Your Leader

Karen Paczkowski

Before founding Grandmasters, I was a top producer in health insurance and built experience across property & casualty and Medicare. I learned what it takes to succeed in this industry, and what it feels like to do it without real support.

I joined Checkmate Financial Group to build something of my own: a team where agents and leaders are mentored, developed, and supported every step of the way. If you lead a team and want a culture your people are proud to be part of, let's talk.

— Karen Paczkowski, Founder of Grandmasters

Apply to Grandmasters

FAQ

Questions

Does my team need insurance experience?

No. Work ethic and coachability matter more than background. Your reps get licensed and learn the products with our training and support.

Is there training for my team?

Yes. There is live training every day, both in person and virtual, plus ongoing mentorship and coaching for you and your reps.

Can my team work remotely?

Yes. We offer remote sales positions, and our daily trainings are available both in person and virtually.

How do overrides work?

You earn on the business your team writes, on top of your own production. In general, the difference between your contract level and your reps' is your override. We'll walk through the specifics on your call.

What does Grandmasters provide?

Through Checkmate Financial Group: high-intent inbound calls, 40+ A-rated carriers, an AI CRM, dialer, and agent portal, daily live training, and onboarding handled in the first week. From Grandmasters: mentorship, the rank and recognition program, and a Team Hub for your agents.

What happens after I apply?

We review every application personally. If it looks like a fit, we'll schedule a call to learn about your team and talk through what bringing them over would look like.

Apply to Grandmasters

Manager application

Tell us about you and your team

* Required · Takes about 90 seconds

For example: insurance, solar, roofing, pest control, real estate.

Team selling in the U.S.? *
Licensed in life insurance?

Write N/A if you don't know what this means.

What you sell, how long you've led, and what you're looking for.

By submitting, you agree to be contacted by a Grandmasters representative. Your information is kept private.

Application Received

Thank you for applying. We review every manager application personally and will reach out to schedule a call about your team.

Level Up. Lead. Legacy.

Don't lead a team yet? Use the agent application.