This path isn't for everyone. But for the right person, it's the most powerful option in remote sales—because you're not trading time for a salary. You're building something that's entirely yours.
What "1099" actually means:
A 1099 is a tax form — it means you're classified as an independent contractor, not a W-2 employee. You don't get a salary, benefits, or paid time off from the company you sell for. You get a commission on everything you close. That's it.
In exchange? You control your schedule completely. You can represent multiple companies. You set your own hours. You decide how hard you push. And there's no cap on what you earn.
The income ceiling in W-2 sales is your company's pay structure. The income ceiling in 1099 sales is your own ambition.
1099 Independent
You control your schedule
Work when you want. Take time off when you need it. No approval required.
No income ceiling
Your earning potential is based entirely on what you produce—not what a company decided your position is worth.
Can work with multiple companies
Represent more than one product or service. Diversify your income streams.
Tax advantages
Home office, internet, phone, equipment—many business expenses become deductible.
No base salary or benefits
You cover your own health insurance, retirement, taxes. You need to plan for this.
Self-discipline required
No manager checking in. No structure given to you. You build your own.
W-2 Employee (B2B or B2C)
Predictable base salary
Know what's coming in every two weeks regardless of what you close that month.
Benefits included
Health insurance, 401K, PTO, sometimes stock options. These have real dollar value.
Training and structure
The company invests in your development. You have a team and a manager.
Leads provided
Many W-2 roles give you marketing-qualified leads. You're not starting from zero every day.
Income ceiling exists
Your comp plan is set by someone else. You can exceed quota but you can't redesign the ceiling.
Someone else controls your schedule
Core hours, required meetings, manager expectations. Less flexibility than 1099.
"1099 sales" isn't one thing—it's a category that includes very different types of work. Here are the four models you'll encounter most, what they actually look like, and who they're best suited for:
You represent one company's product or service as a contractor. Zero base salary—your entire check is commission on what you close.
How it works:
Where this exists:
Realistic income picture:
Month 1–3 is usually slow while you learn the product and build your pipeline. Months 4–12 can reach $4K–$8K/month as you hit your stride. Year 2+ is where you start seeing $10K–$20K+ months if you're consistent. The upside is real—but so is the dry spell risk at the beginning.
Best fit if: You are self-motivated, can handle income inconsistency while building your pipeline, and believe deeply in what you're selling.
You represent multiple non-competing companies in a specific industry or territory. You're essentially running your own sales business with multiple product lines.
How it works:
Industries where this is common:
Why this model is powerful:
You're earning commissions from multiple companies simultaneously. One customer relationship generates revenue across several product lines. As your network grows, your income compounds—without necessarily working more hours. This is one of the few sales models where you can genuinely build equity in your own business.
Best fit if: You have industry experience or a natural network in a specific sector, you want to build long-term rather than sprint, and you're comfortable running yourself as a business.
One of the fastest-growing 1099 categories right now. You hop on pre-booked sales calls with warm leads and close high-ticket offers—$2,000 to $30,000+ programs—on behalf of a coach or creator.
How a typical day looks:
Why this model is attractive for beginners:
Real example of how the math works:
Conservative start
3 calls/day • 30% close rate • $5K offer at 10%
~$4,500/month
Getting consistent
4 calls/day • 35% close rate • $8K offer at 10%
~$8,960/month
Experienced closer
5 calls/day • 40% close rate • $15K offer at 10%
~$24,000/month
⚠ Important warning about this space:
The online coaching industry has genuinely life-changing programs and also predatory ones. Before you sell for anyone, make sure you believe in the product. Ask for success stories and talk to former clients if possible. Your integrity is worth more than any commission.
Best fit if: You're a fast learner, you're comfortable on video calls, you want flexible hours with warm leads already provided, and you want high income potential without waiting 12+ months to hit your stride.
You work with small businesses or startups who need sales support but can't afford a full-time sales hire. You come in as a contractor, build or run their sales process, and get paid a retainer plus commission.
What you actually do:
Typical compensation:
Why this model is worth understanding:
This is not a starting point—it's a destination. After 2–3 years of W-2 or 1099 sales experience, you can command significant consulting fees because you bring a proven system and documented results. Women who go this route typically have experience in a specific niche (tech sales, healthcare, professional services) and leverage that expertise. It's the model that turns sales skill into a business you own.
Best fit if: You have 2+ years of sales experience, you're entrepreneurial, you want to work with multiple clients, and you want to build something you own rather than work for a company indefinitely.
People romanticize 1099 work without talking about what it actually requires. Here's the honest version:
The non-negotiables:
1. A financial runway.
Most 1099 paths take 60–120 days to generate consistent income. Going in with 2–3 months of expenses saved gives you the space to build without panic-closing bad deals. This is not optional.
2. Genuine self-discipline.
No one tells you to start. No one knows if you skip a day. The difference between thriving and flailing in 1099 work is entirely discipline. If you do better with external accountability, plan for how you'll create it.
3. A belief in what you're selling.
In 1099 work, you are choosing what you sell and who you represent. Selling something you don't believe in—or for a company whose ethics you question—will destroy your performance and your integrity. Both matter.
4. Basic business setup.
LLC (optional but smart), separate business bank account, quarterly tax payments. These aren't complex—but ignoring them costs you money and creates stress later.
The tools you'll want in place:
CRM (free options exist)
HubSpot Free, Notion, or even a Google Sheet. You need to track every lead, every conversation, every follow-up.
Calendar booking link
Calendly (free tier is enough). Looks professional, saves time, reduces friction for people scheduling with you.
LinkedIn profile
This is your professional presence. Week 4 covers exactly how to optimize it.
Video call setup
Clean background, decent lighting, reliable audio. This is your office. Make it look like one.
Quarterly tax savings habit
Set aside 25–30% of every commission check. Before you spend any of it. Non-negotiable.
A simple contract template
When you're working with multiple companies, document your agreements in writing. Protects you both ways.
My honest take on the 1099 path:
I chose W-2 sales—and I'm still in it, still at my company, still closing. That was the right choice for where I was: one month postpartum, needing stability, needing a salary I could count on while I figured out what I was doing. I wasn't in a position to wing it.
But I want to be real with you: some of the highest-earning women I know in sales are 1099. They didn't start there—they built their skills in a W-2 role first, then took that knowledge and made it work for themselves on their own terms. The path isn't "1099 from day one." For most people it's "W-2 until you have proof of concept, then 1099 once you know what you're doing."
The closer model is the one exception. It genuinely is accessible earlier—if you find the right company with the right product and get real training before you start taking calls. It moves faster than most paths because the leads come to you.
1099 might be your path if:
You have strong self-discipline and don't need external structure to perform
You want maximum schedule flexibility—true flexibility, not "we allow WFH"
The income ceiling in traditional roles genuinely frustrates you
You have (or can build) a financial cushion of 2–3 months of expenses
You want to eventually own a business, not just have a job
Consider W-2 first if:
You need a reliable income now—bills, kids, mortgage, no cushion
You're brand new to sales and need training wheels before riding without a team
You want benefits (health insurance, especially) included in your compensation
You thrive with a manager, a team, and an environment to learn from
⚠ How to Spot a Bad 1099 Opportunity
The 1099 sales world has incredible opportunities—and also a lot of predatory ones designed to extract your labor without compensating you fairly. Before signing anything, check for these red flags:
You have to pay to get started.
Legitimate 1099 sales arrangements don't charge you to sell their product. If someone wants you to buy inventory, buy a kit, or pay for "training" before you've earned anything—walk away. (MLMs operate this way.)
The product is vague or the company is evasive about it.
If you can't easily explain what you'd be selling and why someone would want it, don't sign a contract to sell it. You can't close deals you don't believe in, and believing requires understanding.
Income claims are emphasized over substance.
If the pitch is heavy on "$20K months" screenshots and light on product details, sales process, lead generation, and support structure—be skeptical. Good companies lead with their product and their process.
No written contract or unclear commission terms.
Always have a written agreement that specifies: commission percentage, what triggers a commission, when you get paid, and what happens to your commissions if you stop working with them.
They want you to recruit, not sell.
If the money is primarily in recruiting other salespeople rather than selling to end customers—that's an MLM, not a sales job. Leave.
The 1099 path is freedom—but freedom you have to earn.
No one gives you structure. No one sets your schedule. No one hands you leads unless you've earned the right relationships to get them.
But if you're willing to build it—and you have the patience to let the pipeline fill before the income follows—this is the path where women in sales build actual wealth, not just a career.
The 1099 path looks different for every person who walks it. Here are real profiles of the kinds of women who made independent sales work—each from a different starting point, each building something that fits their life.
Profile 1: The Corporate Escapee Who Became a Fractional Sales Leader
After five years as an Account Executive at a mid-size tech company, she was burned out from corporate politics and wanted control of her time. She reached out to three early-stage startups that needed sales but couldn't afford a full-time VP of Sales. She offered to build their sales process, run their outreach, and close their first customers—as a contractor. Within six months, she had three retainer clients at $4K/month each, plus commission on everything she closed. She works 30 hours a week and earns more than her corporate salary.
Why this worked: She had a proven track record and specific industry expertise. She didn't start 1099 on day one—she built the skills in W-2 roles first, then leveraged them into independence.
Profile 2: The Mom Who Found High-Ticket Closing
No sales background at all. She was a former teacher who took a high-ticket closer training program during her maternity leave. She started taking calls for a business coach who sold a $12K program. Her first month she closed 2 deals (earning $2,400). By month four, she was closing 5-7 deals per month ($6,000-$8,400). She works during nap times and after bedtime—about 4 hours a day, 5 days a week.
Why this worked: High-ticket closing is one of the few 1099 models where you can start without existing sales experience. The leads are warm, the calls are pre-booked, and the framework is learnable. Her teaching background gave her the patience, structure, and communication skills the role requires.
Profile 3: The Insurance Rep Who Built a Book of Business
She started as a W-2 insurance agent, learned the products, built client relationships, and got her licenses. After two years, she went independent—representing multiple carriers instead of just one. This meant she could shop the market for her clients and offer them better rates, which dramatically improved her close rate. She now manages a book of 400+ clients who come back every year for renewals, plus she earns commission on every new policy. Her renewal income alone covers her monthly expenses.
Why this worked: She built the foundation in a structured environment first. By the time she went independent, she already had clients, skills, and credibility. Her W-2 years were the investment; her 1099 years are the payoff.
This is the section that separates 1099 dreamers from 1099 earners. The freedom is real. But the financial reality requires planning that most people skip. Here's the honest version.
Taxes: The 25-30% Rule
As a 1099 contractor, nobody withholds taxes from your checks. That means every dollar you earn feels like more than it is. If you earn $5,000 in commission, you need to immediately set aside $1,250-$1,500 for taxes. Not next month. Not when tax season comes. The moment the money hits your account, transfer the tax portion to a separate savings account you do not touch.
Set up quarterly estimated tax payments (Form 1040-ES). If you don't, you'll face penalties at tax time on top of the tax bill itself. This catches more new 1099 workers than anything else.
The Irregular Income Buffer
Your income will not be steady. You might earn $8,000 one month and $2,000 the next. The way to handle this: calculate your minimum monthly expenses (rent, food, utilities, insurance, essentials only). Save 3 months of that number before going 1099, and keep replenishing it. Pay yourself a consistent "salary" from your business account each month, and let the excess build your buffer.
This approach turns unpredictable income into predictable spending. It removes the panic from slow months and keeps you focused on selling instead of worrying.
Benefits You Need to Cover Yourself
Health insurance: Check your state marketplace, your spouse's employer plan, or COBRA from a previous job. Retirement: Open a SEP IRA or Solo 401(k)—you can contribute as both employer and employee, which means potentially larger tax-advantaged savings than a W-2 worker. Disability/life insurance: Consider a policy, especially if you're the primary earner.
The total cost of covering your own benefits typically adds $500-$1,500/month depending on your situation. Factor this into your earnings requirement before going 1099.
Whether you're closing for online coaches, repping products as an independent agent, or consulting for small businesses—you need clients. Here's how women on the 1099 path actually find them.
Networking That Actually Works
Join industry-specific Facebook groups, LinkedIn communities, and local business meetups. But don't sell in these spaces—contribute. Answer questions. Share insights. Help people for free. When someone needs what you offer, you'll be the person they think of because you've already demonstrated value.
Rule of thumb: Give value 10 times before you ask for anything once.
Referrals: Your #1 Growth Engine
Every happy client is a potential referral source. After you deliver a great result, ask directly: "Is there anyone else in your network who might benefit from this?" Most people will say yes if you've done good work. Referred leads close at 2-3x the rate of cold leads, and they cost you nothing.
Build a referral ask into your process, not as an afterthought but as a standard step.
Your Online Presence
Your LinkedIn profile should clearly communicate what you do, who you help, and what results you deliver. Post regularly about your area of expertise. You don't need to be an influencer—you need to be findable and credible when someone Googles you after a referral.
Week 4 covers LinkedIn optimization in detail. Start thinking about your profile now.
Strategic Cold Outreach (Done Right)
Cold outreach as a 1099 is different from spam. Research the person, reference something specific about their business, and explain exactly how you can help. Three sentences, not three paragraphs. One clear ask: "Would a 15-minute call make sense?" Personalization is the difference between being ignored and getting a reply.
Expect a 5-10% response rate on truly personalized outreach. That's normal and enough to build a pipeline.
You're exploring the 1099 path right now—but seeing how the other paths compare will sharpen your understanding of what you're choosing and what you're trading off. Click each path below.
B2B W-2 roles give you what 1099 doesn't: a guaranteed base salary, health insurance, a team, a manager, and structured training. If you're deciding between B2B and 1099, the honest question is: can you afford the ramp-up period without a safety net? B2B gives you that net. 1099 gives you freedom but no floor.
Many of the most successful 1099 women I know started in B2B. They learned pipeline management, CRM discipline, and consultative selling on someone else's dime—then took those skills independent. If you're brand new to sales, consider B2B as your training ground before going 1099. You'll be a stronger independent rep for it.
The B2B-to-1099 pipeline: 2-3 years as a W-2 rep, build industry expertise and a network, then transition to fractional consulting or independent sales. It's the lowest-risk path to high 1099 earnings.
Before you move on, let's make sure the key concepts really clicked. Answer all questions correctly to unlock the next lesson.
1. What does "1099" refer to in the context of sales work?
2. How much of every commission check should a 1099 worker set aside for taxes?
3. Which of these is a major red flag when evaluating a 1099 sales opportunity?
4. What is the most common recommendation for people who want to pursue the 1099 path but have no sales experience?
5. What is the key advantage of the 1099 path compared to W-2 sales roles?
Complete the Knowledge Check above to unlock the next lesson.