Start Your New Sales Job Without Skipping a Beat

Whenever Alexine Mudawar starts a new sales job, there are three words she repeats like a mantra whenever she feels overwhelmed: “Back to basics.” 

While she’s established herself as a top-performing account executive and a leader of the sales networking group Women in Sales Club, the first few weeks and months at a new job are never easy — especially in sales. There are new products to learn, new ideal customer profiles and buyer personas to become acquainted with and no track record of success to cushion the blow of early rejections. 

A strategic sales onboarding plan can help, but the fear that she won’t be able to recreate the success she’s had at other companies can be difficult to shake, particularly when an early deal goes south. “Back to basics,” which is written on a sticky note at her desk, is a reminder of what got her there. It’s something she still refers to in the fifth month at her new job as a strategic account executive for B2B gifting platform Alyce.  

“The most immediate fear is: Am I going to be successful? Will I be able to hit my number? How quickly can I do it?” Mudawar said. “And that’s where I get focused on getting back to the fundamentals and remembering I’ve done this multiple times before, I’ve found success multiple times and that there’s a reason the company wanted to hire me for this role.”

Mudawar isn’t alone. It can take several months to feel comfortable in a new sales role. It takes sales development reps about three months to get up to full speed, according to The Bridge Group’s 2021 Sales Development Report. For account executives, it can take a little over four months.  

Those first few weeks and months are a whirlwind of meetings, information sessions and practice pitches — it can be difficult to get your bearings. But the sooner you can get your first win, the better. 

While it may take time to get up to speed, there are some steps you can take those first few weeks to get off to a fast start at your new job.

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Organization and Note Taking Are Key

No matter how well thought out a company’s onboarding plan is, it can be difficult to process all of the information tossed at you during those first few weeks.

There are meetings with HR, strategy meetings, coffee chats, sales tech tutorials and more. You have to be like a sponge those first few weeks, Mudawar said. But even sponges can only absorb so much in one sitting and some key bits of information are bound to leak out.  

That’s why getting organized and taking detailed notes is crucial during those first few weeks. One way Mudawar makes sure she doesn’t miss out on anything is to create a Google Doc listing out each topic on her onboarding checklist from HR introductions to product and services training to prospecting sessions and so on.

From there, she takes detailed notes on all the information she’s given during those meetings. So, if she meets with HR, she’ll have a page listed as “HR Training” with notes on what she learned and important points of contact. If she goes through a prospecting session, she’ll create another page with notes from that session along with any pertinent documents. By the time she finished her onboarding at Alyce, she had more than 70 pages of notes all neatly categorized in the document like her own new company manual.

Rewriting the information makes it easier for her to process everything she’s given, and it also becomes a useful resource guide for her when questions invariably come up later. 

Still, a 70-plus page document isn’t ideal when you start hopping on phone calls with customers. That’s why she also creates a two-page cheat sheet she can refer to during early prospecting calls. The sheet includes details on what her company does, the product’s value proposition, important product integrations to note and more so she can quickly offer that information during calls.

Customer questions are invariably going to come up that stretch the limits on what you can remember from your meetings. Having this document on hand allows you to answer most of those questions quickly, rather than pausing the conversation — and potentially losing momentum — to seek out an answer. 

“Whenever I’m learning at a company and I’m starting to cold call, I want to have something in front of me.”

“Whenever I’m learning at a company and I’m starting to cold call, I want to have something in front of me,” Mudawar said. “That way, if I lose my footing, I at least [have] something I can go back to.”

The last bit of housekeeping Mudawar suggests is to get your sales pipeline and customer relationship management software in order. Create a list of all the tasks you need to complete and make sure the opportunities you’re working are being recorded in the software. That way, as you start to ramp up, you’re checking every box you need to be successful. 

“I find that if I can set the groundwork for that in months one, two and three, it becomes very easy for me to make small tweaks to it for the entirety of my tenure with any company,” Mudawar said.

Get Familiar With Your Product and Pitch

The first few weeks at a new company can feel like an abrupt change in pace for a new salesperson. You go from days loaded with meetings, cold calls and emails at one company to training and onboarding at your new firm.

There’s an itch to get back on the phone and start selling as fast as possible, said Darren McKee, who works as an enterprise account executive at BetterUp, a coaching and training platform. But before you do, it’s important to focus on getting comfortable with your product and new company.

McKee made the switch from working as an account executive at Insperity to his current company a little more than a year ago. When he goes through a career change, he’s found it’s helpful to take the first 120 days to immerse yourself in the company. 

During that time, he’ll try to talk to as many friends, family and neighbors about his new job as a way to hone his pitch. Those conversations describing what he does and what his company does are a great way to piece together what details about the company or product will resonate with buyers and what doesn’t, McKee said.

“I always go back to ‘How do you explain your job to your 6 year old? How do I explain my job to my neighbor who’s a soccer coach?’ He doesn’t understand what I do so I have to break it down,” McKee said. “This really helps when I start prospecting with customers and having conversations. … No one wants to think about what I do, they want to know.” 

If the company has call recording software, McKee also suggests spending a few hours each week listening to the company’s bank of recorded conversations. (If your company doesn’t have call recording software, ask to sit in on sales calls with your peers). He usually tries to listen to two or three calls a week — sometimes in his car, other times during work when onboarding is slow — that touch on different parts of the sales cycle from discovery to proposals to deal strategies.

“I want to know why people are buying from us and why people might not be [buying from us],” McKee said. “I want to know how we address [different] situations, and how we address pushback.”  

Still, it can be overwhelming to figure out which calls to listen to in a library that may contain hundreds or thousands of hours of conversation. To help navigate the system, he may search via the keywords he’s trying to learn about — whether that’s a particular type of objection or stage of the sales cycle. McKee will also listen for sales reps who most match his style and a few that are opposite from him, and then seek out their calls.  

Every salesperson has a different style, which means it’s not always the best idea to emulate the top performing rep, McKee said. Some spend more time on slides, while others connect with stories. If the top performer doesn’t match your style, it could lead you to perform in a way that isn’t natural to you. 

When you find reps who match your style and a couple who have a different sales process, it’s easier to think through your own approach and add new ideas.

“I’m trying to understand in those first few days, ‘Where’s my sweet spot?’ And you’re able to pull from key talent that we’ve had over the years to really help,” McKee said. 

Once you start making calls at your new company, it’ll feel like you’ve been doing them all along, he added.    

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Start Building Internal Relationships Right Away

No matter how much preparation you do before your first calls, relationships with other members on your team and on other teams will be critical to your success.

When a customer has a timely question about product integration or security, it can help to know who to seek out and what information they need to help you in a timely fashion. Fortunately, there’s no better time to build relationships at a company than the first month on a job when introductions are more natural, Mudawar said. 

“With new companies, there’s almost like a one-month timer where you can get access to anyone in the company you could possibly want,” Mudawar said. “If you want to connect with a C-level at the company or to talk to someone on another team, it’s a very easy ask.”

“There’s almost like a one-month timer where you can get access to anyone in the company you could possibly want.”

Mudawar tries to do brief meet-and-greet sessions with each team leader and then arranges longer, deeper dive sessions with her peer-level counterparts on other teams. During those conversations, she’ll ask about their role, what situations they typically work with salespeople and what information they need to help. 

Mudawar then creates an organizational chart with notes on who to reach out to when. It’s a handy document that pays dividends down the line when she’s working with customers.  If a customer asks for an integration feature that may not exist in the current offering, for example, she knows what information she needs to collect from the buyer first and then who to go to for help.

“I don’t want to waste any of my customer's time. … If I already know what to ask, then I can grab that information right off the bat and our next conversation can be pushing the needle forward,” Mudawar said. “The more pieces of insight you can gather internally, the easier it is to work with customers and the more knowledgeable you seem down the road.”

McKee also spends those early days building relationships with other team members. He’ll often ask them to describe how they like to work with account executives. Since sales often relies on help from other teams like customer success, IT and product to work and close deals, he’s able to use their feedback to foster a better relationship with them.

Relationship building doesn’t stop after the first month, either, McKee said. It needs to be an ongoing process as new people join the company. But it helps to lay a foundation at the onset. 

“Last thing I want to do is to be in the final minute of a huge deal and have to talk to our security team, and I don’t know who works in our security department,” McKee said. “I want to make sure they understand how I operate and how they do so when that time comes, we’re a couple steps ahead.” 

Take Time to Enjoy the Small Wins

Listening to calls, taking notes and building relationships are all well and good, but it often takes closing that first deal to feel like you’ve truly settled in at your new company.

Depending on the sales cycle, however, it can take weeks to months to earn your first sale. In between, there are countless false starts and cold calling rejections to wade through, all while other reps are bringing in deals. As a result, the pressure to close that first deal can easily get out of control, Mudawar said. And even after you close that deal, there’s the pressure of making your first quota.

To help maintain perspective throughout those early stages at a new company, Mudawar relies heavily on her sales network outside the company. Whenever she gets stuck on a deal, she’ll turn to one of those peers to get a read on the situation and make sure she’s taking the right steps. If she’s feeling down after a rejection, she has other friends she can talk to for a pep talk.

“The community piece is important because we’re all working for different companies and have different goals, but at the same time, we’re all facing similar challenges,” Mudawar said. “You need people like that who can remind you of who you are and politely yell at you when you need it.”

It’s also important to remember that those early rejections aren’t an indictment on your sales skills but rather an opportunity to learn, Mudawar said. If a customer says something you don’t understand but should, take the opportunity to ask. Or if a deal goes sideways, you can review what happened and learn from it. 

Still, the best way to build toward that first deal without too much pressure is to celebrate the small wins. 

Take the time to appreciate when the first customer gets back to one of your emails or when you asked a good question or got an agreeable response from the prospect. Those are the moments that show the process is clicking, and eventually, that first deal will come.

“Be patient and understand that you’re in a brand new environment, and you’re going to be learning a lot at once and it can feel overwhelming,” Mudawar said. “Just remember that people expect you to ask questions. Ask as many questions as you need to, ask for resources if you need them and get yourself organized. Then you’ll be off in no time.”