Here's what to expect—and the mistakes I made so you don't have to.
My First 30 Days at the Company:
Week 1: Overwhelmed. Didn't know what I was doing. I didn't write enough notes, assuming I'd remember or just get used to it. (I didn't. Write everything down.)
Week 2: I tried to do it all alone and held back from asking questions. I thought asking would make me look like I didn't belong. That was a mistake—the people around me wanted to help.
Week 3: Made my first small sale. Felt like a huge win.
Week 4: Realized this was doable. Not easy, but doable.
Week 1: Learning Mode
You'll be absorbing everything. Product training, CRM systems, internal processes. It's normal to feel overwhelmed.
Week 2-3: Pattern Recognition
You'll start seeing patterns in questions, objections, buying signals. Things will start clicking.
Week 4: First Wins
Your first small sale. Your first positive feedback. You'll start believing you can do this.
❌ Mistake 1: Talking too much
I thought I needed to prove I knew what I was talking about. Better: Ask more questions, listen more.
❌ Mistake 2: Taking rejection personally
Every "no" felt like failure. Better: Realize every no gets you closer to yes.
❌ Mistake 3: Not following up consistently
I'd send one email and give up. Better: Have a follow-up system and stick to it.
Remember:
Everyone feels lost in their first 30 days. That's normal. What matters is showing up consistently and being coachable.
What I’d tell myself before day one:
You’re going to feel like you’re behind. Everyone else is going to seem like they have it figured out. They don’t. They’re pretending just like you are—except they’ve been pretending longer.
Ask questions constantly. Write everything down. Don’t try to memorize scripts—understand the intent behind them. Take every call you can get. Review what went wrong without making it mean something about your worth as a person.
The first 30 days are about showing up and learning. Not closing. Not impressing. Showing up and learning. Give yourself permission to be new at this. It won’t last forever.
I'm going to give you what I wish someone had given me: a detailed, honest breakdown of what each week actually looks like. Not the polished version. The real one. What to focus on, what to avoid, and what you'll probably feel at each stage.
What to focus on: Learning your product inside and out. Understanding who your ideal customer is. Getting comfortable with the CRM (the system you'll use to track everything). Learning names, processes, and where to find things. Writing everything down.
What to avoid: Trying to impress everyone. Pretending you understand things when you don't. Comparing yourself to people who've been there for months. Saying yes to every optional thing when you should be focused on core training.
What to expect emotionally: Overwhelm. Excitement mixed with anxiety. You might cry in your car or bathroom at least once. That's normal. You might also feel an unexpected rush of "I can actually do this." Hold onto that feeling.
Daily habits to build now: Start each day by reviewing your notes from the day before. End each day by writing down three things you learned and one question you still have. This tiny habit will accelerate your learning faster than anything else.
What to focus on: Listening to experienced reps on calls. Asking "why did you say it that way?" after you shadow. Starting to practice your own talk tracks, even if they feel awkward. Getting familiar with your territory or lead list. Understanding the difference between a good lead and a bad one.
What to avoid: Going off-script too early. Making your first calls without preparation. Isolating yourself because you feel like you're behind. Skipping 1-on-1 meetings with your manager because you're "too busy learning."
What to expect emotionally: The initial excitement fades and reality sets in. You'll start to feel the weight of "I actually have to do this." Imposter syndrome peaks during this week. You'll hear other reps talking in acronyms you don't understand. That's okay. Write them down and look them up later.
Key mindset shift: Stop thinking "I need to know everything." Start thinking "I need to know enough to ask better questions." Nobody expects you to be an expert yet. They expect you to be curious and coachable.
What to focus on: Making your first outbound calls or emails (if you haven't already). Developing your own rhythm. Starting to recognize patterns in how prospects respond. Getting comfortable with silence on calls. Asking for feedback on your first conversations.
What to avoid: Beating yourself up over bad calls. Avoiding the phone because of fear. Comparing your results to seasoned reps. Getting stuck in "preparation mode" instead of taking action.
What to expect emotionally: A rollercoaster. One hour you'll feel confident, the next you'll question everything. You might have a great conversation followed by three terrible ones. This is the normal rhythm of sales. It never fully goes away, but you learn to ride it.
Small wins to chase: Your first positive prospect interaction. Your first meeting booked. Your first time handling an objection smoothly. Celebrate these. They're proof you're learning.
What to focus on: Refining your approach based on what you've learned. Building a consistent daily routine. Setting weekly targets for activity (calls, emails, meetings). Starting to think about your pipeline strategically, not just reactively.
What to avoid: Thinking you should be "there" by now. Abandoning your process because one thing didn't work. Neglecting to update your CRM (this is how you lose track of opportunities). Forgetting to celebrate your progress.
What to expect emotionally: A shift. It's subtle, but around this time something clicks. You start to feel like you belong. Not because you've mastered everything, but because you've survived the hardest part: the beginning. You've proven to yourself that you can do hard things.
What to tell your manager: Schedule a 30-day check-in. Ask: "What am I doing well? What should I focus on improving? Am I on track?" This shows initiative and coachability, which are the two traits managers value most in new hires.
Let me be straight with you about something nobody tells you before you start. The learning curve in a new sales role isn't a smooth upward line. It's messy. And knowing that ahead of time can save you from quitting during the part that feels the worst.
Imposter Syndrome Is Coming. Here's How to Handle It.
At some point during your first 30 days, you're going to think: "I don't belong here. Everyone else knows what they're doing. I made a mistake." I need you to hear me when I say: every single person in that office thought the same thing when they started. Every one.
Imposter syndrome isn't a sign that you're in the wrong place. It's a sign that you're growing. It shows up whenever you step into a new arena where you haven't proven yourself yet. The way through it isn't to wait until it goes away. It's to keep showing up while it's still there.
Practical strategies: Keep a "wins" document on your phone. Every small win goes in there. Every good conversation, every compliment from a manager, every moment where you thought "I handled that well." On your worst days, read that list. It's evidence against the lies imposter syndrome tells you.
Information Overload Is Normal
You'll be learning a new product, new tools, new terminology, new processes, new people, and a new daily routine all at once. Your brain will feel full by 11 AM. Here's how to manage it:
The Emotional Timeline Nobody Talks About
Day 1-3: Excitement and adrenaline. "I'm really doing this!"
Day 4-10: Creeping doubt. "There's so much I don't know."
Day 11-18: The valley. This is where most people silently consider quitting. Don't. This is the hardest stretch. It gets better.
Day 19-25: Small breakthroughs. Things start making sense. You have your first good call. You surprise yourself.
Day 26-30: "I can do this." Not "I've mastered this." But "I can do this." That's enough. That's the foundation everything else is built on.
Working from home sounds dreamy until you realize you need a real setup. Not a perfect one. But a functional one. Here's what you actually need to perform well in a remote sales role, plus the routine that'll keep you productive.
Tech Essentials
Productivity Tools
Building Your Daily Routine
The biggest trap of remote work is losing structure. Without a commute, a dress code, or coworkers around you, it's easy to drift. The women who succeed in remote sales build a routine that creates structure even when nobody's watching.
Sample Daily Routine:
Your Support System
Starting a new career affects everyone around you. If you have a partner, kids, or family at home, they need to understand what's changing. Here's how to have that conversation:
Be specific about what you need: "I need quiet from 9-11:30 every morning. That's when I'm on the phone with clients." Vague requests get vague compliance. Specific asks get real support.
Share why this matters: Help them understand this isn't just a job. It's a career change that affects the whole family. Share your income goals. Let them be part of the vision.
Set boundaries with love: "When my door is closed, I'm working. I'll come out at [time]." Practice this phrase: "I love you, and right now I need to focus. Can we talk about this at lunch?"
Find your people: Join a community of women in sales. Having people who understand your daily reality is not optional; it's essential. You need people who get it.
What you just learned shows up differently depending on which sales path you're exploring. Click your path to see how this applies specifically.
Your first 30 days in B2B sales will be heavily focused on training and absorbing information. Most B2B companies have structured onboarding programs because the products are complex and the sales cycles are long. Expect to spend the first 1-2 weeks in training sessions learning about the product, the market, the competition, and the sales methodology your team uses.
By week 2, you'll start getting set up in the CRM (likely Salesforce or HubSpot). You'll be assigned a territory or a list of accounts. Your manager will probably pair you with a more experienced rep for call shadowing. Lean into this. Take notes on every call you listen to. Write down the exact phrases they use to handle objections. Pay attention to how they open conversations and how they transition to discovery questions.
By week 3-4, you'll start making your own outreach. In B2B, this usually means emails and LinkedIn messages first, then phone calls. Don't expect to book meetings right away. B2B prospects are busy decision-makers who get dozens of outreach messages daily. Your job is to be the one who stands out because you did your research and asked a genuine question.
What to expect from your manager: Regular 1-on-1s (usually weekly). Pipeline reviews. Activity metrics (number of calls, emails, meetings). B2B managers tend to be patient with new reps on results but expect high activity. Show up, do the work, and ask for feedback. That's the formula.
Answer all questions correctly to unlock the next lesson.
1. During Days 11-18 of your first sales role, what is the most common emotional experience?
2. What should you prioritize learning FIRST in a new remote sales role?
3. What is the best way to handle imposter syndrome during your first 30 days?
4. What should you ask your manager at your 30-day check-in?
5. When working remotely, when should you update your CRM?
Complete the Knowledge Check above to unlock the next lesson.