The Ultimate To-Do List For Your First 100 Days in a New Sales Job

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Leslie Ye
Leslie Ye



So you’ve landed a sales job. Congratulations! Your first 100 days at any new company are jam-packed with new information and processes, but the learning curve is especially high in a sales role. Not only do you have to suss out your new company’s culture and dynamics, you also have to learn a new sales process, a new product, and potentially a new industry.

The first 100 days you spend on the phones will set the tone for the rest of your career at your company. And there’s no better time to learn than when you’re ramping up -- once you have a full quota on your head, you simply won’t have as much time.

It can feel overwhelming. But we’re here to help. Experts agree that splitting up a gargantuan task into a few (okay, a lot) of smaller steps makes it far easier to accomplish your goals.

Are you ready? Let’s do it.

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Days 1-33


If this isn’t your first sales job, you already have a handle on the fundamentals of selling. But if you’ve come up through a sales development representative position or have never sold before, browse this blog. We’ve covered sales topics from the beginner to the advanced, and everything in between. (And if you want to subscribe, that wouldnt hurt.) 

Set up email tracking.

Not every prospect you reach out to will respond to every email you send, and that’s normal. But what does their silence mean? Are they not interested? Or did your email get blocked somewhere between your outbox and the buyers inbox?

You can take the guesswork out of the equation entirely by using email tracking tool HubSpot Sales. The free app alerts you as soon as your buyer opens your email, or clicks a link within. A prospect who’s looked at your email seven times without responding (trust me, it happens) should receive a different follow-up than a prospect who never saw your message.

Find industry publications.

To sell effectively, you need to understand your audience. That means putting yourself in your buyer’s shoes. What’s happening in their industry? What do they care about? What are their biggest challenges?

Identify major trade publications, thought leaders, and other relevant news sources. Then, organize your sources. Feedly, a free news aggregator app, is a great way to quickly scan multiple publications. Just plug in the URLs of your chosen news sources and block off 20 minutes a day to scan headlines and choose content to share.

Optimize your LinkedIn and Twitter profiles.

Your social media profiles are your online reputation, and they will be the first things your prospects see when they Google you. Make sure you’re presenting yourself professionally and clearly conveying the value you can provide prospects by rewriting your profiles to attract buyers instead of recruiters.

(Hint: If you don’t already have a LinkedIn or Twitter account, get them! They’re essential tools for social selling and connecting with prospects.)

Share five to 10 pieces of content on social media.

Especially if you’re new to the industry, it’s important to establish yourself as a subject matter expert. After you’ve selected and organized relevant industry publications (see above), get sharing!

Some guidelines for posting content:

  • Don’t just copy and paste a link and leave it at that. Provide some insight or commentary that will appeal to your ideal buyer.
  • Always keep the buyer in mind when posting content. What’s relevant to them? What trends or industry news would they be interested in hearing about? What insight can help solve a particularly difficult problem?
  • Post on both LinkedIn and Twitter (as well as any industry-specific forums) so you’re engaging the widest possible network.
  • Don’t hesitate to use mentions to notify specific prospects you think would find a link particularly helpful, especially if you haven’t previously connected via phone or email.

Set SMART goals with your manager.

As a salesperson, your most important (and easily measured) performance metric is your quota. But a quota is something you either hit or you don’t. In other words, simply referring to that metric won’t tell you much about your overall sales performance. You’ll have to dive deeper and examine each step of your sales process (more on that later) to determine where you’re excelling and where you need to improve.

Sit down with your manager and ask what they’d like to see out of you each month. Maybe they’d like you to boost your activity level, or refine your ability to disqualify. Whatever it is, ensure the goal is SMART for the best results.

SMART goals must be:

  • Specific.
  • Measurable.
  • Attainable.
  • Relevant.
  • Timely.

Pinpoint one or two areas to work on per month, then track your performance diligently.

Learn your company’s sales tools.

If you don’t understand how to log activity, convert opportunities, navigate your CRM, process a sale, or qualify prospects using your company’s sales software, you will fall behind. Spend the first few weeks of your job immersed your company’s sales tools so they become second nature. Find power users and solicit one-on-one help.

Learn your product.

Before you can tell whether a prospect is a good fit, before you can handle objections, and before you can close a deal, you have to understand what you’re selling. So learn everything there is to know about your product. What is it? What problem is it intended to solve? How is it used?

Actively use your product as much as you can if the option is available to you. Dive into common use cases. Know your positioning documents and other marketing collateral by heart. You can’t sell something you don’t understand or believe in, so live and breathe your product until you know it inside and out.

Shadow calls.

Sit in on experienced reps’ calls once or twice a week. Get briefed on the deal beforehand (or read relevant notes in the CRM) so you have context. Then, practice active listening. Write down objections, effective sound bites that resonate with the prospect, and indicators that prospects are good or bad fits. Afterwards, compare notes with the person you’re shadowing afterwards and ask them any questions you have.

Make sure to shadow a variety of calls -- connect calls, discovery calls, demos, negotiations, and closing calls. Each conversation requires a different skillset and is designed to accomplish a different goal. Furthermore, different reps will approach the same calls differently, so vary the people you shadow to expose yourself to the widest possible range of styles and strategies.

Make calls and send emails.

This one sounds obvious -- after all, isn’t this your job?

Yes, but in your first few months your approach will be and should be a bit different. As you gain experience, you’ll develop a sense of what types of prospects are worth reaching out to. But during your ramp-up period, you’ll need to reach a certain volume of calls and emails so you can start honing that sense.

With your manager, determine an appropriate activity level per day or week, and hit it. The more comfortable you are on the phones and the more prospects you speak with, the better you’ll be able to distinguish good fit opportunities from bad.

Run calls with your manager.

Once a week, sit down in a conference room with your manager and have her act as a silent partner on your calls. Ask her to provide real-time feedback as you speak with prospects -- tips for handling objections, suggestions of phrases to use, and so on. In this way, you can incorporate coaching into your calls on the spot for more successful outcomes.

Write down every objection you hear.

Whether they’re from your own calls or the ones you’re listening in on, keeping track of all the objections you hear is crucial to your professional development.

Trends will start to emerge. Maybe your product is expensive and price objections are common, so you need to get good at selling value. Maybe your product isn’t highly differentiated, so your colleagues know competing vendors’ products inside and out. Pay special attention to objections that come up again and again -- those are the ones you need to drill yourself on.

Take other reps on your team out to lunch.

There’s no better place to seek advice than from reps in the trenches. Ask your manager to identify top performers, and take them out to lunch. Find out how they set themselves up for success, and adapt the practices you think will work best for you.

Days 34-67

Record calls and review them with your manager.

During your first month, you ran calls with your manager. You should now be more comfortable doing calls by yourself, but you’ll still want to collect feedback.

Each week, pick your best and worst calls, and review them with your manager. What went well? Why did you get tripped up on your less-than-excellent calls? By diving deep into good and bad calls, you’ll come away with actionable feedback for future conversations.

Participate in a group call review.

A spin on the manager call review, sitting down with your peers to review your (or their) calls as a group will also provide you valuable insight. Your manager probably hasn’t been on the frontline of sales in a while, so getting feedback from colleagues who do the same thing you do every day can give you a fresh perspective. You never know -- maybe one of them faced the same issue you’re currently struggling with just yesterday.

Learn to handle common objections.

During your first month, you wrote down every objection you encountered. By the second month, you should be well on your way to handling them effectively. Crowdsource responses to the most frequently heard objections, and soon you’ll have an arsenal to reference during calls.

You shouldn’t expect to be able to overcome every single objection you hear by the end of the month, but you should start to familiarize yourself with the most common and understand the best way to counter them. Make sure to consistently refine your approach as you gain experience.

Learn your company’s value proposition and how to customize it.

This is something you probably covered in new hire training, but it won’t truly hit home until you start speaking with real prospects. Your company’s value proposition goes beyond what your product is and how it works. Thoroughly understanding how and why your product helps buyers is as good as gold. Stop saying, “We make/build/sell X,” and replace it with, “We help X do Y better/easier/faster.” The second statement will be more persuasive, every time.

Learn your company’s sales process.

As you make more calls and send more emails, your outreach approach will become increasingly targeted because you’ll get better at recognizing good fit prospects. And if you had a solid first month on the phones, you might have a crop of prospects you’ll need to advance in the sales process.

To focus your prospecting, learn how your company defines a qualified lead. Understand the difference between a discovery call and creating a sales plan, and learn how to implement a plan. Tune into the signs that indicate a prospect needs help selling your offering internally, is ready for a demo, or will sign today if pitched the right way.

Study up on your competitors.

Learn everything there is to know about competing products. Whether it’s how other companies price their offerings or the features that differentiate your service from theirs, you will eventually be called on to stack your product up against a competitor’s.

Eventually, you’ll find yourself in a competitive situation. By understanding your rival companies’ products inside and out, you’ll be able to position your product in a unique way from the beginning, automatically setting it apart in your prospects’ minds.

Study your ideal buyer.

You should already be familiar with your buyer’s industry, but that doesn’t mean every single prospect in the space will be a good fit opportunity. Dig into what a perfect fit customer for your company looks like. Read up on your company’s buyer personas, study your most successful customers, and learn why closed-won customers bought your product, either by asking the rep who sold them, or by reading notes in the CRM.

Review organizational sales benchmarks.

Once you’re familiar with the sales process, sit down with your manager and identify top-level metrics you can use to benchmark your own performance. What’s the typical conversion rate from opportunities created to qualified prospects? How many prospects who go through a product demo end up buying?

Here are some benchmarks to get started:

  • Daily activity level (calls made, emails sent, voicemails left)
  • Average deal velocity (how long it takes a deal to close)
  • Average deal size
  • Conversion rate from discovery calls to product demonstrations
  • Average number of touchpoints before a successful connection with a prospect
  • Lead to close ratio
  • Percentage of opportunities won by lead source
  • Percentage of opportunities lost to a competitor

Eventually, you’ll have worked enough deals that you can use your own benchmarks instead of your company’s, but until then, don’t sell in the dark.

Get comfortable disqualifying prospects.

Your most valuable asset as a salesperson is your time. As you book more meetings and connect with more prospects, you’ll have to be more discerning about who you spend your time with.

It’s difficult to get in the mindset that spending a lot of time with a small handful of prospects is better than courting two or three times as many. After all, more prospects would seem to suggest more potential sales. But some prospects will never buy from you, and it’s better to weed those out as soon as possible. This way, you can focus on the prospects likely to become your best customers.

Share 15 to 20 pieces of content on social media.

Continue posting to your social networks. Pay special attention to the types of content that have been performing well, and then double down on similar posts.

This month, aim to post more targeted content. At this stage of your development, you’ll be able to better define what type of content appeals to specific types of buyers. Post content that will resonate with the buyers you’re most interested in selling to.

Strive to achieve a higher connect rate.

In your first month, making calls and writing emails is largely intended to build up your “muscle memory;” that is, you’re repeating the process until it becomes second nature. In your second month, keep up the pace set by your manager, but start being a bit more deliberate about who you reach out to.

Check your gut instincts against results. Are the prospects you deem likely to agree to a discovery call actually agreeing? Follow them through the sales process and track how many convert at each step and eventually close.

Days 68-100

Learn to conduct a demo.

Sales demonstrations are a crucial part of the sales process. If your product is complex enough to warrant a walkthrough, demos won’t be easy to master. Start by shadowing sales engineers, technical experts, or tenured reps on their demos to see how they position the product for a prospect’s specific needs.

Then, learn how to set up a successful demo or presentation. Find out what your prospect wants to see, and practice playing up how specific features address specific needs.

Finally, present to a real prospect. Some companies employ sales engineers for extremely technical calls, but for the most part you’ll be tasked with running your own demos. Practice presentations with your manager or mentors and ask for feedback. Then do it again and again.

Develop a trusty arsenal of outreach templates.

Don’t waste time writing variations on the same email over, and over, and over again. Of course, you should be personalizing cold emails and follow-ups depending on your prospect, but there’s no need to reinvent the wheel every single time.

Take advantage of canned email templates from your colleagues or sales blogs. The latter option enables you to track open and clickthrough rates for all of your templates, and easily personalize fields depending on the recipient.

Share 25 to 30 pieces of content.

If you’ve been posting consistently, you should have now developed a good sense of what kind of content drives engagement. Going forward, exclusively post this type of content.

In addition, start sharing industry news and announcements. While this type of content won’t necessarily drive discussion of the problems your product addresses, it establishes you (and your company) as having your finger on the pulse of your target buyer’s industry.

Engage with five to 10 new people on social media.

Social selling isn’t just about sharing content -- it’s also about starting conversations that establish you as a trusted advisor well before you ask for a meeting.

At this point, you should be familiar enough with your target industry that you can thoughtfully engage with others in the same space. Look for prospects on social media who have either interacted with your content or have a lot to say on relevant topics. Respond to their posts or share content specifically with them through a mention or private message.

Review your 90-day pipeline with your manager.

By your third month, you should ideally have opportunities at every stage of the sales process. Review all deals in progress with your manager to determine whether you have enough pipeline to meet your quota, and adjust your activity if necessary.

Put together a business case.

A business case won’t be necessary for every prospect or even every product, but on occasion you may be called upon to provide numbers demonstrating ROI. You can either prepare a custom business case using your prospect’s data, or put together a case based on a current customer’s results (with their permission).

Keep the cases as short as possible -- your prospect isn’t going to want to read an eight-page book report. Instead, stick to the essentials: What quantifiable improvements did your customer see? What goals did they achieve thanks to your product?

Include a few short testimonial sentences where appropriate. Statements like “Customer service rep X made setup incredibly easy,” or “We’re so happy we chose Vendor Y,” are great for boosting credibility.

Run closing calls yourself.

You’ll likely have closed a few deals by the time you hit your third month, although your manager or a peer may have been running these calls with you. This month, start closing deals yourself -- first with your manager in the room as a silent partner if you’re feeling shaky, then without any outside help at all.

Review your performance with your manager.

Now that you’ve been selling for three months, you’ll have a fairly large body of activity to reference. Look over your average deal velocity, call/email/voicemail/meeting activity, and any other relevant metrics with your manager to determine whether you’re at the place you need to be.

Dig deeper to determine your weak areas. For example, if you run a lot of discovery calls but see many of your prospects go quiet afterwards, it’s possible you’re struggling to instill a sense of urgency. Your manager will be adept at spotting qualitative areas for improvement by looking at your metrics, so go through the data together with a fine-toothed comb.

Day 101

You made it! Your first three months are officially over. Now what?

By this time, you’ll be equipped with an arsenal of sales tactics and strategies. You should have a better sense of your sales style, what techniques work best for you, and where you need to improve. Keep honing your skills and working on your weak areas, and in no time at all you’ll be crushing it on your sales team.


Topics: Sales Training

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