Grandmasters crestGRANDMASTERS
Now taking applications

Build a career in life insurance
with a team that has your back

Grow a lasting career in life insurance with daily training, hands-on mentorship, and real structure, in person or fully remote.

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Licensed or not · Training provided · 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 agent growth and a healthy work-life balance. You get the guidance, systems, and support to build a business that lasts, while still having time for the life you're building it for.

  1. 01

    Daily training

    Daily trainings, both in person and virtual. Learn directly from leaders who have done it, with real coaching, real feedback, and someone in your corner from day one.

  2. 02

    Structure

    Proven systems, training, and inbound leads, so you spend your time helping families instead of guessing what to do next.

  3. 03

    Support every step

    You're never on your own. Ask questions, share wins, and lean on a team that genuinely wants to see you succeed.

  4. 04

    Remote positions

    Work from our office or fully remote. Our daily trainings are available both in person and virtually.

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Powered by Checkmate Financial Group

What You Get

Grandmasters is a team inside Checkmate Financial Group, so you get Checkmate's leads, carriers, tools, and training, with our team's mentorship and culture on top.

  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 you.

  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 you 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.

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Fit

Who This Is For

Apply if

  • You're coachable, and you stay a student of the game no matter how good you get.
  • You're hungry to grow, personally and professionally.
  • You want to lead a team one day.

Don't apply if

  • You want a capped, fixed salary.
  • You aren't willing to learn and put in the work.
  • You already lead a sales team. Apply as a manager instead.
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Getting started

From Application to First Commission

  1. 1

    Apply

    A quick form. Tell us where you are and what you’re looking for.

  2. 2

    Meet the team

    A call to talk through your goals, the right fit, and next steps.

  3. 3

    Get onboarded

    Licensing guidance if you need it, then contracts, carrier appointments, and portal access, handled for you.

  4. 4

    First commission

    Inbound calls in your queue and a coach in your corner from day one.

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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 are mentored, developed, and supported every step of the way. My goal is simple. Help you grow, and help you build a legacy.

— Karen Paczkowski, Founder of Grandmasters

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FAQ

Questions

Do I need a license or sales experience?

No. If you aren't licensed yet, we'll guide you through getting your life insurance license before you start selling. Coachability and work ethic matter more than background.

Is there training?

Yes. There is live training every day, plus ongoing mentorship and coaching from our team. You'll learn the products, the process, and how to serve clients well.

Are leads provided?

Yes. Through Checkmate Financial Group, people call in to buy. High-intent inbound calls and qualified web leads are routed to you, so there are no cold calls and no lists to buy.

Can I work remotely?

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

Can I start part time?

You can start while you transition out of your current job. The agents who grow fastest treat this like a real career, and we'll help you build a plan that works for your life.

What happens after I apply?

We review every application personally. If it looks like a fit, we'll reach out to schedule a conversation so you can ask questions and we can get to know you.

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Agent application

Tell us who you are

* Required · Takes about 60 seconds

Currently licensed in life insurance? *

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

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 application personally and will be in touch soon.

Level Up. Lead. Legacy.

Lead a sales team already? Use the manager application.