Do not waste time hunting for a perfect role. Start with a familiar market, customer, or product category and use that as leverage.
"I didn't look for a sales job. I looked for a company that sold something I already understood."
When I made my switch, I didn't start by searching "remote sales jobs." I started by asking myself: what have I been around? What industries have I worked in? What products have I used, sold, or watched people use? What problems have I seen over and over in the jobs I've had?
Then I looked for companies solving those exact problems. When I got into interviews, I wasn't faking enthusiasm. I genuinely understood the customer. I could speak to the pain. I didn't need to memorize why the product mattered — I'd lived it.
That familiarity, even if it was partial, made me more credible than someone with two years of "official" sales experience who was just moving from industry to industry chasing commissions.
— Katherine
Here's the thing nobody tells you: companies don't just hire salespeople. They hire people who can speak credibly to their customers. And the fastest shortcut to credibility? Having lived in or near the world the customer lives in.
You don't need to be an expert. You need to be relatable. Someone who can say "I've worked in healthcare, so I understand how overwhelming compliance requirements can get" is more compelling to a healthcare software company than someone with zero industry context reciting product specs.
Your background isn't a gap. It's a filter.
Use it to narrow your job search to companies where you already have a head start — not because you've sold before, but because you've lived near the problem they solve.
Worked in healthcare?
Look at companies selling EHR software, medical staffing platforms, healthcare billing tools, patient communication software, or wellness programs to employers.
Worked in education?
Look at EdTech companies, tutoring platforms, professional development tools, learning management systems, or companies that sell to school districts and universities.
Worked in retail or food service?
Look at companies selling POS systems, inventory management tools, HR/scheduling software, loyalty platforms, or payment processing to small and mid-size businesses.
Stay-at-home parent returning?
Look at parenting platforms, family-focused software, childcare tools, or any consumer product you've used and genuinely loved — your lived experience as a buyer is valuable context.
Worked in real estate or insurance?
Look at proptech, mortgage software, CRM tools for agents, or InsurTech companies. You understand the buyer, the process, and the language already.
Worked in admin or operations?
Look at companies selling workflow automation, project management tools, HR software, or productivity platforms to businesses. You've used these tools — or wished they existed.
You don't need to know the product inside and out before your first interview. You need three things — and you already have two of them.
Familiarity — You already have this.
Whatever industry you've worked in, whatever product you've used or been around, whatever type of customer or business you've interacted with — that's familiarity. It doesn't have to be deep. Even surface-level context makes a difference.
✓ Already yours. You're bringing it in the door.
Communication — You already have this.
Every skill from Weeks 1 and 2 — listening, asking questions, building rapport, handling objections, telling stories — that's the actual work of sales. Your communication skills are what close deals. Not encyclopedic product knowledge. Not years of experience. This.
✓ Already yours. This is the skill that does the selling.
Curiosity — This is what you add.
The only thing you're responsible for building is genuine curiosity about the product you're selling and the customers it serves. Read about the industry. Look at the company's website. Talk to customers if you can. Listen in on demos. Ask your manager questions. Curiosity compounds fast — within 60 days at a good company, you'll know more than you think is possible right now.
← This is the only thing you need to develop. And it's not a skill — it's a choice.
Stop searching "remote sales jobs." Start searching from the inside out — from what you know toward what's available.
The 3-Step Search Method
List what you know — industries, tools, problems, types of customers.
Don't overthink this. Write down every industry you've worked in, every type of software or tool you've used, every kind of problem you've seen come up in your jobs, every type of business or customer you've dealt with. Even if it feels basic — write it down.
Search for companies solving problems in those spaces.
Go to LinkedIn, Google, or Crunchbase. Search "[industry] software" or "[problem] solution" or "best tools for [type of business]." Find companies in that space. Look at their careers page. See if they're hiring SDRs, BDRs, or Account Executives. Even if the posting says "experience preferred" — apply anyway. Relevant industry knowledge often matters more than sales history to the right company.
Ask yourself: can I see myself learning more about this?
You don't have to be passionate about dental scheduling software. You just need to be able to say honestly: "I can see myself getting genuinely interested in this space, talking to these kinds of customers, and learning this product well." That's enough. Passion follows knowledge — and knowledge follows curiosity.
Use AI to turn your background into a target company list
Fill in the worksheet below first, then paste your answers into this prompt to get a real list of companies to pursue:
Copy this prompt → paste into ChatGPT or Claude
“Act as a B2B sales career advisor. I am a career changer with a background in [your industry/role]. My goal is to identify specific types of companies I should target for my first remote B2B sales role, based on my existing industry knowledge and the types of customers I already understand. Here is my background: [paste your completed worksheet answers]. Provide me with a list of 8–10 company types or specific company names that sell B2B products or services to the industry I know, explain why each is a good fit, and suggest what role title to search for at each. Ask me any questions you have.”
💡 Copy your worksheet answers directly into the prompt. The more context you give, the more specific and useful the company list will be.
Fill this out now. This is your first job search filter — and it's built entirely from what you already have.
Healthcare, education, food service, real estate, finance, tech, retail, childcare, fitness... anything counts.
Scheduling chaos, staff turnover, billing errors, slow communication, compliance stress, disorganized records, unhappy customers...
Even basic tools count — scheduling apps, point of sale systems, communication platforms, patient management software, anything.
Small business owners, hospital administrators, school principals, restaurant managers, individual clients, corporate HR teams...
Think: who sells to the industry I know? Who sells tools that solve the problems I've seen? Start here.
This map is your starting point.
Take these three company types to LinkedIn Jobs, Indeed, or company career pages. Search for SDR, BDR, Account Executive, or Sales Representative roles at companies in those spaces. You'll recognize the customers. You'll understand the problems they're solving. That's your edge — and it's already yours.
1. When looking for your first B2B sales role, what gives you a head start?
2. Of the three things needed to succeed in B2B sales — familiarity, communication, curiosity — which one do you need to develop?
3. What's the right first question to ask when starting your job search?
Complete the Knowledge Check above to unlock the next lesson.