The Crash Guide: How to Start Your Sales Career in 2020 With No Experience

November 2019
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It was only a few hours after my college graduation ceremony had ended. I was standing in a crowded bar with dozens of my peers, celebrating, when I heard someone a few groups over make a claim so bold I’ve never forgotten it: “I didn’t go to college just so I could get a job in sales.”

At the time, I didn’t really know much more about sales than what I’d already experienced firsthand selling ad space door-to-door for a campus newspaper (which was brutal but taught me a ton of really valuable career lessons).

But what little I did know then was exactly why that statement struck such a nerve: sales is not easy.

Pretending that sales is something just anyone can do–and do well–is not just wrong, it’s an obvious admission of a misunderstanding of what sales really is and what it takes to succeed.

Sales can be tough. It’s not for everyone. But it’s not just for extroverts. Nor is it just for people who didn’t go to college. In fact, some of the best salespeople I know are both highly analytical and highly intelligent. Regardless of your background or makeup, a career in sales offers incredible upside–both in personal development and in earning potential.

Sure, the person who can walk into any room and thirty minutes later walk out with 10 new friends has some really-valuable raw material. If that describes you, sales might be a great place to consider starting your career.

But a desire to help other people and a willingness to learn specific behaviors are both far more important than your personality in sales.

If you enjoy interacting with people, connecting solutions to problems, and like hitting goals or have a competitive edge, sales might be a great place to launch your career. But even if none of that describes you, sales still provides a great starting point for anyone who’s interested in learning the fundamentals of business and is serious about working hard.

How to Start Your Sales Career in 2020 With No Experience (Ultimate Guide)

So . . . what is sales, anyway?

Sales tends to get a bad rap. But it shouldn’t–at least, not when done well. The best kind of sales is prescriptive or consultative. Someone in the world has a problem they’re not yet sure how to solve, or one they’re maybe not aware of yet. Great salespeople can identify the people who have a legitimate felt need and build a relationship around filling that need the best way possible.

In its most simple form, sales is about two parties exchanging value for mutual benefit. It’s not about duping people. It’s not persuading people to spend money they don’t have on things they don’t want or need.

Sales done well is about helping other people get closer to what they want.

It’s almost similar to the role of a physician–assessing someone’s issue, diagnosing it properly, then prescribing a remedy.

Sales done well means executing the process of helping people achieve a better life. As a brilliant economist once put it, there are three conditions that stand in the way of us humans taking action:

     1. Unease or dissatisfaction with our present state of affairs
     2. A vision of a better state
     3. A belief we can reach that better state

Sales done right takes people by the hand and guides them through that discovery process so they can achieve whatever is standing in the way of where they are and where they’d like to be.

It doesn’t matter what industry or type of sales you’re in–the basics of it remain the same. And if any of that piques your interest, then a career in sales just might be worth exploring.

What career paths are there in software sales?

If you search a jobs board, you’ll probably find dozens of different titles for sales roles.

It appears under a variety of different names–in tech, titles like Sales Associate, Sales Development Representative, Business Development Representative, or even Inside Sales are all common.

The titles are a bit vague, but basically they indicate where the role fits within an organization and the type of sale. Once you’re familiar with the different titles, you may begin to notice trends.

Most startups or tech companies have an “inside” sales team for their product. As the name suggests, the team works inside the company–usually in the office (though occasionally remote)–but they contact people outside the organization. This usually involves a high-frequency of phone calls and emails.

Contrast that with outside sales and business development. Outside sales usually involves some element of door-to-door sales. No, this doesn’t always literally mean walking door to door, though it can. In many cases, outside sales reps cover a specific territory, and the product they’re selling involves more face-to-face or on-site conversations.

Similarly, business development can involve a lot of face-to-face interaction. Usually business development involves identifying partnership opportunities or larger types of deals that are outside the scope of normal inside sales roles. These deals often have strategic advantages for a company. For example, imagine a payroll company partnering with an accounting software company–both companies could benefit from accessing each others’ customers and offering their services together.

I get it–making heads and tails of all these different paths can be a pain. So, to help, here’s an outline of common career paths and first jobs in software sales:
A graphic with columns on entry-level sales positions, common roles for entry-level salespeople (sales development representative [SDR], business development representative [BDR], inbound marketing representative, lead response, outbound sales, inside sales, outside sales, sales agent, sales associate [SA], sales consultant, sales operations), average years of experience for entry-level salespeople (0-3+), average income for entry-level salespeople ($44k), and average commission for entry-level salespeople ($3k-$26k). Also includes mid-level sales common roles (account executive [AE], sales executive [SE], account manager [AM], senior sales representative, sales operations lead, sales engineer, technical sales representative, enterprise sales representative, enterprise account executive) and sales director / manager common roles (sales manager, regional sales manager, sales lead, sales trainer, SDR trainer, director of sales, sales operations manager, director of sales operations), mid-level sales average years of experience (2-5+) and sales director / manager years of experience (3-7+), average income for mid-level salespeople ($53k) and average income for sales managers / directors ($60k), and average commission for mid-level sales people ($3k-$51k) and average commission for sales manager / sales director roles ($5k-$56k) from Payscale. There is a breakdown of sales vice president positions–common roles for sales VPs (VP of Sales, VP of Sales Operations, SVP of Sales, VP of Revenue, head of sales, sales leader), sales vice president average years of experience (10+),  average income for sales vice presidents ($140k), and average commission for sales VPs ($10k-$103k). Also included in the last column is sales c-suite positions–common sales c-suite jobs (Chief Revenue Officer, Chief Operating Officer, Chief Growth Officer, Chief Sales Officer), average years of experience for c-suite sales jobs (10-20+), average income for c-suite sales jobs ($196k), and average commission for c-suite sales roles ($34k-$205k).

How much money do people make in software sales?

Another added benefit of sales is it’s a role that offers a very tangible relationship between results and income.

Because of the nature of the role, there is often a very objective measure for everything–ranging from activity metrics (like how many phone calls per day or week you make) or the average time it takes to get promoted, to the monthly or quarterly revenue quotas attached to a specific role.

As daunting as that might sound, it can make calculating your earning opportunity very black and white.

Most sales roles, especially in software sales, operate on a base salary and on-target earnings (OTE) model. In other words, the role has an income floor and a target to shoot for.

The salary is usually lower than other entry-level roles, but it offers the upside of commission. On-target earnings essentially outlines achievement targets and the commission structure for hitting goals.

Another word on commissions: a lot of organizations also add other features to the compensation mix to drive performance, like accelerators or spiffs. Accelerators are basically increased commission rates for all sales above your quota (think of it like overtime pay on steroids). Spiffs are another feature that can act as a bonus for certain goals–like selling a specific product or achieving a certain percentage above quota, as examples.

Income is often weighted for the first several months a sales rep is starting in a new role. This period is commonly referred to as "ramp time"–which basically means the amount of time it takes for you to learn the role and achieve full productivity. This is a great way to help reps put food on the table while they’re still learning. Usually these decline over a period of the first three to six months in a role.

Wow. Sounds like only upside, right? Well, don’t let anyone fool you into thinking it’s an easy job you’ll for sure get rich doing. Sales takes a lot of work–and the best salespeople I know are masters of executing process. But if you succeed, your earning potential is off the charts.

Here’s a breakdown by experience level of some common income ranges for sales positions, courtesy of Payscale:
A graph of average income for entry, manager, director, VP, and c-suite sales jobs, courtesy of Payscale.
See more details on the Payscale reports for entry, manager, director, vice president, and c-suite sales salaries.

How can I get started in software sales?

Let’s cut right to the chase.

If you’ve read this far, chances are you’re not just looking for more theory. You want to know how the sausage is made–which is exactly what this section is about: how you can set yourself up to land you first sales job, even if you have zero relevant experience today.

First, I think it’s necessary to outline some of the most common activities entry-level sales people spend the vast majority of their time on–so we can talk about specific steps you can take to demonstrate the skills that go along with those activities.

Here’s a common breakdown of how entry-level sales roles at tech companies (for example, sales development representatives–SDRs for short) might spend their time on any given day:

• Reviewing their calendars and scheduling the day’s activities
• Daily sales standup to discuss deals in their pipeline
• Prospecting and lead-list building
• Researching prospects to personalize outreach
• Cold calling
• Cold emailing
• Following-up with prospects
• Discovery calls
• Scheduling demos with account executives
• Populating a CRM with prospect information
• Responding to inbound phone calls from webforms
• Searching LinkedIn or other platforms to connect with prospects
• Tracking and maintaining records on the day’s activities

This isn’t a perfect list–but it’s a solid starting point for the steps we’re going to talk through about how you can get started. If you read the list closely, hopefully you noticed a theme: most activities make use of a tool or software in addition to a sales rep’s manual effort.

So, in order to prove you’ve got what it takes to land your first sales job, I recommend demonstrating just that: a basic familiarity with tools, in addition to the ability to leverage them to your advantage.

Below, I’ve outlined a number of different specific tactics you might try (and document) in order to prove to a hiring manager you’re worth considering for a sales job–even if you have no experience:

The purpose of the following exercise is to prove you’re capable of identifying the value proposition of a product and who it benefits–which is a useful skill in sales.

First, go visit the website of a company that interests you. Bonus points if it’s a company that’s actually hiring for entry-level sales roles. But it doesn’t matter if they’re not–this is just an exercise to start that you can repeat.

Spend some time reading through their products, pricing, and any customer testimonials. Take notes. Try to hone in on exactly who their customers are–not just what companies, but who might be the person at their customer companies that makes the buying decision. (For example, a company that sells marketing software might be focused on selling a product that makes the lives of marketing associates at startups easier, but the actual decision maker is the VP of marketing. That’s something you’d want to note.)

The purpose of this next exercise is to prove you can perform basic lead and prospect research–which is a big part of an entry-level salesperson’s job:

Okay, so, once you’ve got some basic notes, I’d recommend coming up with some ways you might be able to get in front of that type of customer.

This is where the tools and systems will really come in handy. For instance, if you want to find marketing associates at startups, there are great resources for that–go check out LinkedIn and AngelList and run some searches for titles. Take note of your results and refine your search terms until you get the results you’re after.

The purpose of this third exercise is to demonstrate your ability to transform search results into useable leads–which is how reps at a lot of early-stage companies actually get their lists of people to contact:

In the next step, you’re going to turn your research into a usable set of leads. That basically means figuring out how to extract the contact information from a platform like LinkedIn and getting it into readable format for your CRM software.

To do this, I’d recommend adding a few tools to your belt–like LeadIQ, ZoomInfo’s ReachOut, Hunter.io, WhitePages, and Google Sheets or Excel. Essentially, you want to go from search results on LinkedIn or AngelList (or whatever platform) to a .csv file that has a name, title, company, email address, phone number, and any other valuable information you can extract. Getting all of this information cleanly into a dataset–as a .csv–makes it possible to easily import this to your CRM, then plug it directly into a sales process.

To do this, check out or install one of the tools above (like the browser extension of LeadIQ or ReachOut). Then, as you’re performing searches, use the tool to capture contact information. Most of these tools offer a free trial, so use all of the credits you can. Once you’ve used your credits, go look at the list and download it to a Google Sheet or Excel file. Make sure the data is clean (all the phone numbers are in the same format, etc.).

And that’s it. We’ll use this in a later step.

The next exercise is to show you can think linearly about a sales process for a specific type of potential customer–this is where you can really earn some points:

Using the information you’ve collected so far–like the type of company who might buy the product the company you research is selling and your list of potential customers–draft up a plan for how you’ll reach out to those people, what you’ll say, and how many times you’ll contact them. You don’t have to actually perform these actions right now–this is just an exercise to prove you can think through it.

For example, you might come up with a plan that involves five attempts to contact them by email, phone, and LinkedIn over a ten-day period.

Here’s what that might look like in application:

Day one: a short and sweet cold email that asks what type of software/tool they’re using to solve a specific problem–and if they’re not the right person to answer the question, asking if they’d be willing to introduce you to the right person.

Day three: if there's no response to your email, then a cold call to the contact with the goal to learn what software/tool they’re using and how much they’re paying (bonus points if you can get them to schedule a demo or a more in-depth call)

Day four: if no response, another cold call

Day seven: a response to your first email, reiterating the question

Day ten: a short LinkedIn message

Again, you don’t necessarily have to run this process–this exercise is more about showing you’ve thought through what a successful process might look like. (Bonus points if you actually write out each of the email/LinkedIn messages or a short script for the phone call. Even more bonus points if you actually attempt to sell something while running your process.)

At the end, put together an outline of the process you came up with. We’ll use this in the final step: how to actually apply.

Finally, in this exercise, we’ll outline how to actually go about getting the job.

Assuming you’ve run the above process for a specific company, now it’s time to bring all the steps together. I recommend using two tools to highlight everything you’ve done in this exercise: Google Slides and Loom.

Start by creating a new slide deck. Add the company’s logo and colors to the cover slide with your name and the role you’re interested in. Example: “Hey Acme Corp., I’m Mitchell, and this is why I’ll crush it as an SDR.”

Bonus points: to take this to the next level, go use LinkedIn to try to figure out who the hiring manager for the company might be (even if it’s just your best guess). Then address the presentation to that individual. It makes it feel even more personal.

Then, in a few slides, outline what you like about the company, why what they do matters to you, and how the skills they ask for translate well with your existing skills (even if you don’t have a ton of experience). Then, spend two to three slides outlining the results of the exercise you put together. Don’t go too into the weeds here–you’ll cover this in the Loom video. Then, on a final slide, add how they can get in touch with you.

Once you have your deck finished, hop on Loom, and record yourself on-camera talking through the slides. Explain the content, and go into a little more detail about what you learned through the exercise and how you can apply that to be successful in the role.

Then, last step–this is critical: after you send in your application, go back to LinkedIn, find the person you think might be the hiring manager, message them and share your video, slides, and the lead list you created. While you’re at it, go ahead and send an email as well (“I want to make sure you saw this”). Then, if you don’t hear anything back, follow up every 24-72 hours until you hear something.

This is sales–so you’re trying to get a response (even if it’s a "no"). If you can prove you’re capable of persevering through rejection until you hear something, then it’s a good signal. Sure, use your judgement, and try not to be annoying. But remember, if you don’t have any experience, leveraging your effort and willingness to work hard can both be secret weapons.

So I know that’s a lot of information. But I promise you, running that exercise until you get results will do more than just land you a job–it will provide you a solid base of learning about the fundamentals of sales that will translate directly into the job once you land it.

Sales is about a mutual exchange of pleasure. The first keyword is mutual, and the second pleasure. When a transaction between a seller and buyer takes place, it isn’t because the seller is greedy and the buyer is stupid. Buyers are not stupid; they know exactly what they’re doing. And what they’re doing is giving you something you want (money) in exchange for something they want (what you sell).

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What skills do you need for a career in sales?

Contrary to popular belief, sales is not all about talking. Sure, the ability to hold a conversation and pick up the phone to call a total stranger is valuable. But listening and understanding a potential customer’s needs are equally, if not more, important to being effective in sales.

Awareness is also a great soft skill in sales. How do people perceive you? Can you read a room or social cues well? This is also a valuable tool in your sales kit.

Other useful skill sets include the ability to present, articulate communication, time and task management, the ability to create or manage workflows, a level of comfort on phone or video calls, written and verbal communication, and a high level of emotional intelligence.

Here’s a list of useful sales skill sets (though not all are required out of the gates):

• Written and verbal communication
• Ability to handle rejection
• Phone skills
• Calendar management
• Proficiency with calendar and calendar management software
• Familiarity with CRM (Customer Relationship Management) software
• Familiarity with Sales Enablement software
• Prospecting
• Ability to perform basic lead- or company-related research
• Active listening
• Ability to speak to complete stranger
• Basic proficiency with email and office suite tools
• Copywriting
• Time management
• Task management
• Natural curiosity
• Product knowledge (or the ability to learn quickly)
• Industry knowledge (or the ability to perform basic market research)
• A desire to improve your performance
• Coachability
• Ability to follow processes (and know when to deviate)
• Good judgement
• A general understanding of businesses work (including the one you want to work at and the type of companies you might be selling to)

What are the most common softwares and tools salespeople use?

Beyond soft skills, a broad range of proficiency in different sales tools and software–added with the ability to quickly learn–will also serve you well. To dive deeper into what that looks like in tangible terms, we’ve highlighted some of the most popular softwares and tools sales teams at startups use to manage their deal flow on a day-to-day basis.

Click on the categories to see more!
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What are the best resources for learning more about what a career in sales is like?

We could create a ton of other helpful content around sales, but I don’t think that’s the most useful approach for you. What’s better, in my opinion, is showcasing all of the resources from the people who do it best–so you can pursue your learning on your own terms. Of course, we’re here to help in any way we can. But we’re not the hero in your career story–you are.

So, to help you take the next step toward starting a career in sales, we’ve put together a list of some of the best resources already available to you for free on the world wide web–from podcasts and books, to thought leaders and companies. Enjoy.

P.S. Want to accelerate your career? Learn software sales in under twelve weeks through PreHired's Science-Based Sales program. Learn more here.

P.P.S. Here’s a great resource from MockQuestions, where they’ve highlighted a collection of, well, mock questions, for sales-related job interviews.

The Best Sales Podcasts to Start Your Career

Good news for you, sales is a really popular topic people of every level talk about a lot. Which means there are a ton of great learning resources readily available for you to add to your favorite podcasting app so you can learn on the go.

Here’s a short list of some of our favorite sales- and startup-related podcasts:
The Official Saastr Podcast, Harry Stebbings
Masters of Scale, Reid Hoffman
a16z Podcast, Andreeson Horowitz
The Prospecting Podcast, LeadiQ
The Enterprise Sales Podcast, Noah Goldman
Sales Chats, SalesPop!
Sales Hacker Podcast, Sales Hacker
Sales Dev Squad Podcast, Mateo Elvira

The Best Sales Books to Start Your Career

There’s no shortage of great books in the world–especially as it relates to building or growing a business. But even beyond your typical business books, you can find a ton of inspiration on how to better understand people, how they make decisions, and ultimately, how to sell better through a wide variety of books. To give you a rundown, we’ve put together a list of some of our favorites to nudge you in the right direction.

So, without further ado, here’s The Essential Reading List for Every Aspiring Young Salesperson in 2020.

Here it is:

The Sandler Rules, David Mattson
The Sandler Success Principles, Bruce Seidman and David Mattson
Spin Selling, Neil Rackham
How To Win Friends & Influence People, Dale Carnegie
Selling 101, Zig Ziglar
Delivering Happiness, Tony Hsiegh
Made in America, Sam Walton
The E-Myth Revisited, Michael Gerber
Winning with Data, Tomasz Tunguz and Frank Bien
Predictable Revenue, Aaron Ross
From Impossible to Inevitable, Aaron Ross and Jason Lemkin
80/20 Sales and Marketing, Perry Marshall
Made To Stick, Chip Heath and Dan Heath
The One Minute Manager, Ken H. Blanchard and Spencer Johnson
Start With Why, Simon Sinek
Outbound Sales, No Fluff, Rex Biberston and Ryan Reisert
The Sales Development Playbook, Trish Bertuzzi
The Challenger Sale, Brent Adamson and Matthew Dixon
Triangle Selling, Hilmon Sorey and Cory Bray
Ogilvy on Advertising, David Ogilvy
Scientific Advertising, Claude Hopkins
The Boron Letters, Gary Halbert
The Psychology of Influence and Persuasion, Robert Cialdini
Zero to One, Peter Thiel

P.S. If you like this list, you may also enjoy this robust reading list from our friends over at SalesHacker–it includes sixty of their favorite sales books, complete with short summaries. Check it out here.

The Best Sales Leaders to Follow as You Start Your Career

Sure, books and podcasts are great–but maybe you’re like me and also like to learn from real people. Well, don’t sweat it, because below we’ve put together a short list of some of our favorite sales leaders and companies who are worth a follow. Enjoy.

Sam Nelson
Aaron Ross
Brian Burns
Jason Lemkin
Ali Mirza
Kevin Dorsey
Josh Jordan
Jeremy Donovan
Kyle Porter
Mark Cranney
Marko Savic
Max Altschuler
Ryan O’Hara
Will Fratini
Zach Barney
Corporate Bro
Funnel Cake
Gong
Insight Squared
Outreach
Sales Hacker
Sales Loft
Mattermark
Up-and-Coming
Plus, you may also enjoy connecting with these up-and-coming sales professionals.

Mateo Elvira
Bradley Metz
Max Sakiewicz
Luke Ruffing
Reid Anderson
Jackson Lieu

P.S. Know someone we missed? Tweet their name and why you like ‘em @CareerCrash and we just might add them.

The Best Sales Companies to Work Full-Time in Sales

It’s not enough to just read about sales and understand it in theory. It’s also helpful to be on the receiving end of a great sales process. So we wanted to highlight a few companies who we think do it really well–so you can experience great sales firsthand (on- and offline).
Companies and Why We Like 'Em
Apple – You can hardly step foot into a store without being greeted by someone. They let you play with their products. Plus, any time you need help, there’s always someone only a few steps away.

Drift – Whether you drop by their site or are on the receiving end of their emails, you get a sense they’re actually interested in helping you do business better. It’s very conversational and authentic.

The Hustle (Signals) – If you’ve ever received one of Sam Parr’s emails, then you know what I’m talking about when I say The Hustle knows how to sell the sizzle, not the steak. Their free, daily newsletter covers a range of hot topics–and their premium version, Signals, is something just reading success stories and conversations from their community makes you want to have.

Nordstrom – Going into Nordstrom is a truly worthwhile and model sales experience–it doesn’t feel like you’re being sold to. It’s an experience.

Outreach – If you want a case study in consistency, look no further than Outreach. Their sales team consistently delivers a great experience–reps are knowledgeable, helpful, and cut right to the chase. Truly a model company in B2B SaaS sales.

RealThread – RealThread sells apparel online–competitive market, right? But their friendly, warm, and personal touch any time you interact with the team is one that makes this process easy and almost feel frictionless.

What are some of the best sales career success stories you've ever heard?

If all of the above information is still not enough to convince you a career in sales might be worth considering, then check out some of the stories below from people in the real world who’ve launched their careers in sales–with and without experience.


Luke Ruffing

In this podcast episode, Luke covers what it was like to move across the country to join the sales team at a fast-growing starting, how he got started, and how he leaned on his background in sports to help him find success.


Kevin Cherrick

Kevin was on the hunt for a new job in sales–and he didn’t want to wait for anyone to pick him. This is his story about how he turned three rejections into two job offers by taking control of his job hunt process.


Robert Cohen

"Make it personal." That's the mantra Robert stuck to on his job hunt–and it got him more than thirty interviews, multiple offers, and a remote sales job. Here's his story and the tips he has for other job hunters.

Bradey Metz

On the hunt for a sales job, Bradley went heads-down on a six-step email and sales sequence–and ended up getting four to five interviews a week. This is his story on how he did it, as well as some templates and tips for running a sales job hunt like a sales process.

Justin Murphy

For a guy who studied history in school, Justin didn't see a career in sales operations coming his way. But his love for strategy and a few handy connections led the way to two sales roles. Here's what he shares about how to break into the sales game with no experience.

The Job Hunt is Sales: A Collection of Stories and Job-Hunting Tips from Salespeople

This post is all about salespeople and their tips for winning great sales jobs–even without experience. Check it out to hear from a few awesome people who've won roles at Toggl, PandaDoc, preHIRED, and more.

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