A career built for your life as an educator — and worth what you put in.
I’m Dawnn Hills, Agency Owner and Lead Trainer with National Agents Alliance. I’ve trained teachers, coaches, and former classroom educators across the country who’ve built side incomes that quietly turned into full careers. Whether you want a summer income, evenings-and-weekends income, or eventually a full-time exit plan — I’ll show you the path.
The life insurance industry is one of the largest, most recession-resistant markets in America.
Insurance isn’t a trend or a fad — it’s a $1.5+ trillion industry that’s been around for over a century. The demand for licensed agents has never been higher, and educators are some of the best-positioned people in America to step into it. Here’s the market you’d be working in.
The Need Is Enormous
Over 100 million U.S. adults either have no life insurance or know they don’t have enough. The gap grows every year.
One of the Largest Markets in the World
The U.S. life and annuity insurance market pays out premiums supporting millions of families every single year.
The Senior Market Is Exploding
Every day, more than 10,000 Americans hit retirement age. Final expense, retirement, and legacy planning demand is climbing.
Through Every Economic Cycle
When the economy tightens, families care more about protecting their loved ones — not less. Demand holds steady.
The biggest wealth transfer in history.
76 million Baby Boomers have driven every major industry boom for 75 years. Now they’re entering retirement — and transferring $84 trillion in the next two decades. Educators with the right training are perfectly positioned to help families navigate it.
Follow the Money — A 75-Year Story
Wherever Boomers went, entire industries exploded. Every decade tells the same lesson: the smart money positioned itself in front of them.
From 1946 to 1964, 76 million American babies were born — the largest generation in U.S. history. Companies that positioned themselves in front of this wave built empires almost overnight. Gerber became a household name. Pampers turned disposable diapers into a $4 billion industry. The pattern was set: where the Boomers went, markets followed.
The market followed the babies.
As Boomers became teenagers, they reshaped American spending forever. For the first time, teens — not adults — drove pop culture and dictated what got bought. Barbie became a billion-dollar brand. The Beatles dominated radio. Hot Wheels, rock and roll, and youth fashion turned teen culture into an economic force adults had to reckon with.
Teen spending reshaped America.
Boomers entered adulthood, married, and started families. American suburbs were built around them. Station wagons rolled into every neighborhood. First-time home buying surged nationwide, kicking off a generational real estate boom that still shapes the U.S. housing market today. The American Dream became a mass-market phenomenon — and the industries serving it grew with the generation.
The American Dream scaled with them.
Boomers traded starter homes for bigger ones and station wagons for the freshly-invented minivan. Chrysler sold them by the millions. But the bigger shift happened on Wall Street: the 401(k) went mainstream, and Boomers began funneling billions into the stock market for the first time. The modern retirement-investing era was born — and serious, long-term wealth accumulation began.
Wealth accumulation began in earnest.
These were the Boomers’ highest-earning years. SUV sales skyrocketed. Home values doubled. Stock portfolios surged through the dot-com tech boom, then recovered and climbed again. By the end of this two-decade run, Boomers had become the wealthiest generation in human history — collectively holding more assets than any group of Americans before them.
The richest generation emerged.
This is the moment everything has been building toward. Over the next 20 years, $84 trillion will move from Boomers to their heirs — the largest wealth transfer in human history. 10,000 Americans turn 65 every single day. Most have no estate plan. Most don’t have adequate life insurance. They need licensed professionals — right now.
The opportunity of a lifetime is happening now.
The moment is right now.
Plan Today. Protect Tomorrow. Leave a Legacy.
See How You Fit Into ThisWhy this is one of the best second careers for teachers — right now.
Most teachers have already considered a second income. Tutoring. Summer camps. Curriculum design. Some have tried real estate, found it harder than promised, and shelved it. The old advice — “just do real estate in the summer” — has been quietly broken for over a decade.
The insurance industry is different. It’s one of the few places where your effort directly determines your income — no committee, no politics, no waiting your turn. And the skills that make a great teacher are the exact skills that make a great agent: you already explain complex ideas, build trust fast, read a room, and serve families who need help.
You don’t need a degree to do this. You don’t need years of grinding. You need a state insurance license (which takes 2–3 weeks, not 2–6 months like real estate), and the willingness to be coached. That’s it. The rest, we teach.
Most teachers who try real estate end up disappointed. Here’s why insurance is the better fit.
Real estate sounds good on paper — flexible, big commissions, prestige. In practice, it’s usually a poor fit for someone with a full-time teaching job and a family. Here’s the side-by-side.
Time to get licensed
60–180 hours of pre-licensing courses depending on state, often spread over 2–6 months of evening classes. Then a tough state + national exam.
20–40 hours of pre-licensing, completed in 2–3 weeks. Single state exam with a higher pass rate.
Demand & schedule fit
Heavy seasonality. Most home sales happen March–August — the same window when you’re wrapping up the school year, doing summer school, or finally getting time off. Showings happen evenings and weekends, when your family is also home.
Year-round demand. Appointments are pre-set with warm leads who already requested information. You pick the times that work for your schedule.
Startup cost
Pre-licensing ($400–$800), exam fees, application fees, MLS dues, brokerage desk fees ($50–$300/mo), Realtor dues, lockbox, marketing costs. Easily $2,000+ before your first commission.
Pre-licensing ($200–$400), exam fee, E&O coverage. Most agents start producing for under $500 total.
Time to your first commission
A transaction can take 30–90+ days from contract to closing. You don’t get paid until close. Most new agents wait 4–9 months for their first real commission.
Most carriers offer advanced commissions — you’re paid within days of issuing the policy, not months later.
How you get business
You’re expected to “build a sphere” — solicit your friends, family, neighbors, fellow teachers, PTA parents. Cold-prospect FSBOs and expired listings. It’s brutal and constant.
You work warm leads from real homeowners and families who already requested information. No cold calling, no pestering your teacher friends or the PTA.
Earning ceiling for part-timers
Part-time agents typically struggle to clear 2–3 transactions per year — often less than $10K–$20K of net income after expenses.
Part-time agents on my team routinely write 1–2 applications per week — $30K–$80K of supplemental annual income while keeping their teaching job.
This was built for educators who are ready for more — without leaving the work that matters.
The teachers and educators who thrive on my team don’t all teach the same subject or grade level. What they share is grit, coachability, and a desire to control more of their income on their own terms.
Classroom Teachers
K-12 teachers who love the work but need more income — without taking on another full job. This fits around your existing schedule.
Coaches & Athletic Directors
You already work evenings, weekends, and through the summer. You know how to motivate, lead, and run a team. The skills transfer directly to building agency.
Special Education Teachers
You’re already an expert at meeting families where they are and explaining complex things in human terms. That’s exactly the skill set this business needs.
Substitute Teachers
You’ve already accepted variable income and a non-traditional schedule. This gives you a much higher ceiling than subbing — and no district can cancel your day on you.
Soon-to-Retire Educators
You’re 3–5 years from retirement and thinking about what comes next. Insurance is the second career that meets you where you are — pension plus real income.
Recently Retired Teachers
You retired with a pension and realized you have decades left. You don’t want to clock back in to a job — you want to build something on your terms. This is that.
Counselors, Admins & Specialists
School counselors, librarians, instructional coaches, principals. You see the work-life pull. Insurance can flex to actually fit your life instead of compete with it.
Spouses of Educators
Married to a teacher. You see how stretched the family income is — and you want to do something about it without taking on another 9-to-5.
Real products that real families need.
You won’t be selling gimmicks. You’ll be helping families lock in protection that pays out exactly when they need it most — homeowners, parents, retirees, and people in your community.
Mortgage Protection
The bread-and-butter of the NAA system. Term life specifically designed to pay off a homeowner’s mortgage if they pass away or become disabled. The leads are homeowners who recently took out a mortgage and have already requested information.
Final Expense
Whole life policies designed to cover funeral, burial, and end-of-life expenses for seniors typically aged 50–85. With 10,000 Americans turning 65 every day, this is one of the fastest-growing product lines in the industry.
Term Life Insurance
Affordable level-term policies that protect young families during their working years — usually 10, 20, or 30-year terms. The simplest sale in the industry. Most families know they need it; they just need someone to explain it and write it.
Indexed Universal Life (IUL)
Permanent life insurance with cash-value accumulation tied to a market index, with downside protection. Sold to families who want both protection and a tax-advantaged savings vehicle. Larger premiums, larger commissions, longer relationships.
Annuities & Retirement Solutions
Fixed and indexed annuities for clients approaching or in retirement — helping them protect their nest egg, generate guaranteed income, and avoid running out of money. This is where experienced agents on my team build serious six-figure books.
Disability & Critical Illness Riders
Living-benefit riders attached to base policies that pay out for disability, critical illness, or chronic illness — often called “the insurance you can use while you’re alive.” Sold alongside life policies, these meaningfully boost average premium per case.
Real opportunity. Real support. Real results.
National Agents Alliance has helped thousands of agents build six-figure careers in mortgage protection, final expense, and life insurance. This isn’t a side hustle — it’s a business model with leadership behind every step.
Proven Lead System
Work warm, qualified leads from real homeowners and families who’ve requested information. No cold calling. No begging friends and family. You sit in front of people who already raised their hand.
Build Your Own Agency
This isn’t a job — it’s a business. Promote through the contract levels, build a team, earn overrides, and create income that scales beyond what your hands can produce alone.
Coaching That Closes
I personally train every agent on my team. From your first ride-along to your first six-figure year — phone scripts, presentations, objections, closes. You will not be left to figure it out alone.
How warm leads actually work in this business.
Most “sales jobs” hand you a phone book and tell you to dial. NAA’s model is the opposite: families come to us first, then we follow up. Here’s the full pipeline.
The Family Requests Info
Through direct mail, online inquiries, or response cards, a homeowner or family member voluntarily fills out a request asking for information about mortgage protection or life insurance.
The Lead Reaches You
That request becomes a qualified lead with the family’s name, address, age, mortgage info, and what they asked about. You receive it in your CRM — fresh, exclusive to you, never resold.
You Set the Appointment
Using a proven phone script, you call to introduce yourself and book a 30–45 minute appointment. Most lead-to-appointment conversion happens in 2–3 attempts on warm leads.
Run the Presentation
In-home or virtual, you walk the family through their situation, present options, and write the application. We give you the exact presentation that’s been refined over years of in-field results.
Underwrite & Get Paid
Most policies issue within 1–14 days. Once issued, you’re paid your commission directly by the carrier — advanced commissions are available, meaning you don’t wait months to collect.
Start at 55%. Earn your way up.
NAA’s contract structure rewards production with promotions. Every agent on my team has a clear, written path to higher commission levels — and I’ll show you exactly what it takes to get there.
Trainee
Senior Agent
Field Trainer
Director
Agency Owner
Promotions earned through production milestones. Override income on top of personal production starts at the Field Trainer level and compounds at every leadership tier above.
What the math actually looks like at each commitment level.
Four scenarios — from summer-only to full-time transition. These are at the 55% starting contract, based on average premium and typical close rates on warm leads. Your actual results depend on your activity, training, and consistency.
| Activity Level | Apps / Week | Avg Premium | Weekly Comm. | Annualized* |
|---|---|---|---|---|
| Summer-Only Hustle | 4 apps | $1,200 AP | ~$2,640 | ~$32,000 |
| Evenings & Weekends | 2 apps | $1,200 AP | ~$1,320 | ~$48,000 |
| Year-Round Part-Time | 2-3 apps | $1,300 AP | ~$1,820 | ~$90,000 |
| Full-Time Transition | 4-5 apps | $1,400 AP | ~$3,300 | $165K+ |
*Summer-only assumes 12 producing weeks. Evenings & Weekends assumes 36 school-year weeks. Year-Round and Full-Time assume 50 producing weeks. AP = Annualized Premium. Earnings depend entirely on individual production and are not guaranteed. Most committed teachers on my team see $30K–$80K of supplemental income their first year, with full-time transition agents commonly reaching six figures within 12–18 months.
From day one to your first commission check — built around your school year.
Here’s the exact path the teachers on my team follow — from licensing during evenings or summer, through first appointments, to first commissions hitting your bank account.
Intro Call & Onboarding
We get on a call. I assess fit, you ask every question you have. If we’re aligned, we get you enrolled in pre-licensing and set up your CRM, lead account, and carrier appointments.
License During Evenings or Summer
Most teachers complete pre-licensing in 2–3 weeks of evening study, or a long weekend during summer. I help you choose your state’s right course and walk you through exam prep.
Field Ride-Alongs
You shadow me or a senior trainer on real appointments — in-home or virtual. You watch the presentation closed multiple times before you ever run one yourself. This is where it clicks.
Your First Solo Appointments
You order your first batch of warm leads, book your first appointments around your school schedule, and run them solo. We debrief every one — what worked, what to fix.
First Commission Checks Hit
Policies you wrote in weeks 6–7 begin issuing. Your first carrier commission deposits land. The math becomes real — supplemental income hitting your bank account every week.
First Promotion in Sight
Most committed part-time agents on my team are within range of their first contract promotion (55% → 65%) by the 90-day mark — a permanent raise on every policy you write going forward.
You’ll never have to figure this out alone.
The biggest reason agents fail in this industry isn’t talent — it’s lack of support. On my team, you get a system, a schedule, and a mentor who’s actually invested in whether you make it.
Weekly Live Training Calls
Sales scripts, presentations, product training, and field debriefs — every single week, live and recorded.
In-Person & Virtual Ride-Alongs
Watch real appointments closed in real time before you run your own. The fastest way to learn is to see it done right.
Direct One-on-One Coaching
My personal cell, text, and Zoom — available to every agent on my team. Not a corporate help desk. Me.
Licensing Support Start to Finish
Not licensed yet? We walk you through the pre-licensing course, exam prep, application, and carrier appointments — step by step.
Annual Conferences & Conventions
National events with top producers and leadership. The relationships you build at these events change careers.
CRM, Tools & Tech Stack
Lead management, e-app submission, virtual presentation tools, and back-office support — all included.
I’ve trained teachers, coaches, and former educators across the country — and the agents on my team who came out of classrooms are some of the highest performers I’ve worked with. The skills already transfer. What I bring is the system. What you bring is the work ethic. That’s the partnership.
How this actually fits a teacher's week.
A typical week during the school year, plus what the summer months look like when you flip to full-time. The schedule is yours — this is just the rhythm that works for the educators on my team.
Quick Confirms
School year: 15–20 minutes at lunch or after dismissal to confirm the week’s booked appointments by text.
First Appointments
7–9pm: two pre-booked appointments at family kitchen tables or on Zoom. Applications submitted same night.
Lead Order
Order next week’s leads during your prep period or after-school window. 30 minutes, done.
Follow-Ups & One More
Lead follow-up calls plus one more pre-booked appointment. Home by 8:30pm. Submit any pending business.
The Big Window
9–11am: one or two in-home presentations with families who couldn’t meet on weekdays. Highest-quality appointments of the week.
Flip to Full-Time
June–August: 3–5 appointments per day, big income spike, set the table for next school year. Most teachers earn more in 12 summer weeks than in 36 school-year weeks.
What teachers worry about — and the actual reality.
Every teacher I talk to has the same 5 or 6 hesitations. They're all reasonable. They're also all wrong. Here's what's actually true.
“I don’t have time to do this during the school year.”
Most teachers on my team run 2–3 appointments per week — total time commitment 4–6 hours, all evenings or Saturday morning. It fits, and it doesn’t bleed into your classroom.
“I’d have to leave teaching to make real money.”
You don’t. Many of my highest-earning team members are still in the classroom. You build at your pace and decide on your terms — insurance funds the life teaching alone can’t.
“It’s basically real estate with a different product.”
It’s not even close. Faster license, lower startup, year-round demand, warm leads, no listings, no open houses, no cold-calling FSBOs. Completely different game (see the comparison section above).
“I’d have to sell to coworkers and PTA parents.”
You won’t. You work qualified leads from strangers who’ve already requested information. Your school relationships stay completely separate from your work.
“I’m a teacher, not a salesperson.”
Good. You don’t need to be a salesperson — you need to be a teacher. Explain things clearly, build trust, meet people where they are. That’s exactly what this business actually is.
“What if it doesn’t work out?”
You’re 1099. Your contract follows you. The worst case is you spent a few weeks getting licensed in a useful field. There’s nothing to “fail at” except not trying.
Meet Dawnn Hills
Agency Owner · Lead Trainer · National Agents Alliance
I built my career in this industry the same way I’m asking you to build yours — with the right system, real mentorship, and the discipline to show up. Today I lead a team of agents that includes teachers, coaches, former classroom educators, and second-career professionals from every background.
My approach is simple: I teach what works. Not theory. Not motivation. Real conversations with real families about protecting what matters most. If you’re willing to learn, willing to work, and willing to be coached — there is room for you on my team.
If you’re an educator weighing whether this fits for you — whether you’re looking for a summer income, a side income year-round, or eventually a way out of the classroom — let’s talk. The first conversation is free, honest, and pressure-free. I’ll tell you straight if it’s a fit, and if it’s not, I’ll tell you that too.
What teachers actually ask.
Yes. Most teachers on my team work 4–7 hours per week during the school year — typically 2–3 evening appointments and one Saturday morning. Many never miss a school commitment, kid’s game, or family dinner.
Faster license (2–3 weeks vs 2–6 months). Lower startup cost ($300 vs $2,000+). Year-round demand vs seasonal. Warm leads vs cold prospecting. No brokerage desk fees, no MLS dues, no sphere-of-influence pressure. Different game entirely — see the comparison section above.
No. Most teachers on my team keep teaching and earn $30K–$80K of supplemental income per year. Some build to the point where they choose to leave teaching. Some teach forever and just want the extra income. It’s your call — no pressure either way.
Almost no district prohibits independent 1099 contractor work outside school hours, and selling insurance is the same legal category as any other side business or summer job. That said, check your district’s policy. I’ve never had a teacher run into an issue with their administration.
No. Your teaching pension and benefits are tied to your teaching job and aren’t affected by outside 1099 income. Many teachers actually use insurance income to maximize their 403(b) and 457 contributions while still teaching.
That’s up to you. Summer is the highest-leverage time to scale this business — three months of full-time activity can be transformative for your annual income. But many teachers keep summer slower and use it to reset. Either way works.
You’ll complete 20–40 hours of pre-licensing depending on state, pass a single state exam, get appointed with carriers, and apply for non-resident licenses in other states as you grow. Total time: typically 2–3 weeks. Total cost: $200–$400. Compared to a real estate license, this is dramatically simpler.
No. You can build a personal-production-only career and earn well into the six figures without ever recruiting a single agent. Recruiting is optional — it’s how you scale into agency leadership and override income, but it’s never required.
Then it’s not, and we both move on with no hard feelings. The intro call is genuinely two-way — I’m looking for the right fit just as much as you are. I’d rather you say no than join and quit in 90 days.
Your next chapter starts with a conversation.
Let’s get on a 20-minute intro call. I’ll walk you through how this works for educators specifically — what the first 90 days look like for your schedule, what’s realistic, and whether this is the right fit. No pressure. No pitch. Just real answers from someone who’s trained teachers into producing agents.
Or call directly: (510) 754-3165