Ahh... the life of having a cushy sales job.
It sounds too good to be true. And yes, like any job, working in sales has its own set of myths, but the truth is that it’s one of the most meaningful career paths you can take—that is, if you get a sales job that’s right for you.
Imagine going in, day after day, and seeing the direct results of the work you put in. Or being the lifeblood that keeps the company’s head above water. Few careers have the sort of meaning and direct correlation between work inputs and rewards received. It’s no wonder so many of us get hooked on the highs of having a sales job.
Every business relies on sales in some way. And the skills and strategies you learn at one company can easily be brought with you when you move up, making sales one of the most in-demand, and transferrable skills in the workforce. If you’re looking to build your career or learn the skills you need to excel as an entrepreneur, there’s no better place to do that than in a fast-paced sales job with a top startup that’s experiencing rapid growth.
So how do you get a sales job at a sought-after company?
This can be a unique challenge, especially if you want to land a sales job at a top startup (or recognizable brand) where you’ll be competing with seasoned inside sales pros.
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Let’s dive into the specifics of how to get a great sales job and then end with some practical sales advice on where to find those elusive sales jobs.
3 key steps to get a sales job at top startups
With how competitive the world of sales is today, you need to pay special attention to how, where, and when you apply for a sales job.
Rather than slap together a resume and start sending out ‘To whom it may concern…’ cover letters, sales managers and startup founders want to see that you can do what you say you can do.
They want you to sell yourself with the same intensity that you’ll sell their product.
That means that the process of finding a great sales job begins before you even start looking for positions. Let’s go through it step-by-step.
Step 1: Create your personal brand
What’s the first thing you would do if someone applied to work for you?
I’d bet good money you’d throw their name into Google and see what shows up.
When you’re out there looking for your dream sales job, this is no different. So before you even start putting yourself on the radar of the companies you want to work for, you need to make sure that what floats to the top when your name gets Googled, is exactly what you want them to see.
Good branding goes beyond just a basic site and a thrown-together logo. You need to use this opportunity to show off who you are. Here’s some tips:
Go beyond LinkedIn and create a personal site or blog
LinkedIn is where business happens. Right?
Sure, having a professional LinkedIn profile (this is a good time to revisit and update your LinkedIn page and profile photo) will help create a good first impression with a potential employer. But these days LinkedIn has become the bare minimum for job hunters, not a differentiator.
Instead, create a personal blog or portfolio site where you can really show off your sales experience, performance, and achievements in your own way. This page will be the backbone of your personal brand and a place to not only show off your personality, but prove that you’ve got what it takes to deliver once you get this sales job.
Now, talking about yourself, skills, experience, and achievements doesn’t always come naturally, but you can think of this site as a stand-in for a meeting with your potential dream employer. What would you say if you were stuck in an elevator with them for 5 minutes?
Start with the basics:
- What’s your speciality? Aka What do you do? However, don’t limit yourself here to what you’ve done. Your portfolio is your chance to shape what you want to be known for. Even if you’re not known for it yet.
- What work have you done in the past? Do you have case studies from past jobs where you can show real results of the actions you took? Even if it’s just from a side project or something unrelated, sales jobs are all about results. And showing you know that and can deliver is a huge selling point.
- What are your relevant skills or education? Do you have experience using specific CRMs or in building out prospect lists? What about workshops or seminars you attended? Show that you put in the time to learn and grow.
- Who have you worked with in the past that’s willing to talk about you? Social proof. Social proof. Social proof. One more time? Nah, you get it. Testimonials and quotes from real people you’ve helped (or worked for at sales jobs in the past) are your silver bullet.
- What makes you stand out from the competition? What is your unfair advantage as a candidate for this sales job? You can even use this as an opportunity to throw in a little personality. People want to hire people they like. Not just the best option on paper. Use your portfolio as a chance to make you a must-hire, not just another name on a long list.
- Where can they reach you? It may seem simple, but so many people miss out on this vital step. Be easily reachable. Add your email, phone number, Twitter handle. Whatever it takes.
Find places to show off your skills as a sales expert
Your personal site and LinkedIn are a start, but to truly get hirers salivating, show off your expertise in outside forums. You want to show your potential employers that you’re considered a sales expert by people you don’t have a connection to. These objective endorsements are what separate the pros from the amateurs.
Let’s look at a few ways you can brand yourself as a sales expert:
On social media: Once you’re on the sales job hunt, know that your social media accounts are fair game for founders and HR reps doing their homework on you. Use your Twitter, Reddit, or other social accounts to share thoughts on sales strategies or add commentary on (relevant) current events. Share relevant articles that show you keep up-to-date with market changes and with the sales industry as a whole.
And the secret sauce? According to serial entrepreneur and social media guru Gary Vaynerchuk: Don’t forget to listen.
"Twitter is a cocktail party,” Vaynerchuk shares. “How do you become really good at a cocktail party? You show up, you go into a circle, you start talking. If you are a listener and you actually add something to the conversation, we become friends."
And sometimes you can make more than friends with the people you meet on social channels. According to a recent Glassdoor survey, 49% of sales professionals found work or landed a sales job through social media.
On Medium and other publications: If you’ve got the gift of being able to write, tons of household name publications like Inc., Entrepreneur, Forbes, and Huffington Post accept guest columns—if you nail your pitch. If you can’t land an article on one of those major sites, try starting with writing on Medium, an open platform for writers and publishers used by millions of people every month.
Marketing yourself is any activity that puts you in front of your audience, explains startup mentor Jon Westenberg, who used Medium to grow an audience of over 110,000 readers and launch his own consultancy.
“It's actually about understanding where you have or can have a touch point with your audience, your key customers, and then refining that touch point,” he shares.
Westenberg’s advice brings up one more great place to get noticed for a potential sales job: blog comments. It’s more than likely the people you want to get in front of read the same blogs as you do (or have a sales blog for their company). Show your value by commenting on posts and asking insightful questions. The more touch points you create, the better.
At meetups or other in-person events: Sure it’s easier to hide behind your screen, but meetups and hosted events can be a great way to break out of that safety zone and show off your skills in the real world. Look for local meetups or check for events hosted by local companies and startups. In that same Glassdoor survey I mentioned earlier, they found that hosted meetups were the 2nd most popular places to find sales jobs.
But remember, at meetup events you can’t be too sales-y about selling yourself. Meetups are about creating lasting, personal connections, not just spamming your CV to any senior level employee who’s hanging out.
Step 2: Find your dream sales job
Now that you know a recruiter is going to find the best possible content when they search your name, it’s time to start putting the wheels in motion.
Getting a sales job, especially one at a high-growth startup that’s growing in popularity, takes a level of strategy and more than a little bit of luck.
First, create a list of companies you want to work for (and why)
You’re on the hunt, so why act like you can pick and choose where you want to find a sales job?
The truth is that without having some sort of deeper connection to the place you want to work, you’re going to end up losing motivation, fast. As CreativeLive founder Chase Jarvis explains, “when things get hard, if you’re chasing just the dollars, you’re not going to be able to have the fortitude, the passion, to stay with it.”
Your sales job hunt starts with a spreadsheet of companies you passionately feel you’d be a good fit with. Here’s a spreadsheet template you can use for your sales job outreach.
Make a copy of the spreadsheet, save it to your own Google Drive and you’re ready to get to work on finding a kick-ass sales job.
Choose only places where you think you can actually picture yourself at. Look at similar interests, shared values, company culture videos or even just companies (or leaders) you’re inspired by. Have a clear reason when they inevitably ask, “why do you want to work here?”
List all these sales job opportunities in a spreadsheet (we’ll be using this to track contacts and follow ups later). And remember, while most companies have a jobs section of their website where they list open opportunities, you don’t need permission to apply.
In fact, reaching out when they aren’t actively looking for someone can give you the advantage of not fighting against hundreds of other hungry applicants.
Then, use smart networking to get your name out there
With your list in hand, it’s time to start reaching out and getting in front of the right people who can be decision-makers on your sales job prospects. But put those stale cover letters and resumes aside. The key to really selling yourself well isn’t going through cold outreach, but in finding a warm lead.
“Just because you have it in your Outlook, just because you have your Facebook friends or your LinkedIn friends, that’s not truly a network. A network is, if I send out an email, and I need something, how many people respond? That is a network.”
To build that kind of network—the kind that can help you land a sales job, especially in the startup space—you need to focus on a few specific methods:
1. Tap into your existing connections on LinkedIn
Search through your contacts and see if anyone is connected to one of the companies on your list. Once you’ve found them, add their name (and ideally email address or phone number) to your tracking spreadsheet and keep going. Finding your dream sales job is a numbers game.
Once you’ve got a few prospects, it’s time to reconnect. Regardless of the exact role your connection has within the company they’re at, if that company is on your list, that's a great opportunity to chase down—they’ll know the decision-maker.
Pick up the phone to catch up, grab coffee and ask if they'd be willing to introduce you to the right person within their organization for chatting about a sales position. At the very least, walk away from these conversations with the name for who you should be reaching out to.
2. Check out relevant startup events and meetups
Just like these are great places to show off your skills and build your clout as a sales pro, in-person events and meetups are fantastic places to make connections that could lead to a sales job. It should go without saying that you should be following any companies you’re interested in working for on social media or by email so you can be notified when they’re throwing events or speaking at conferences.
But remember, it’s especially easy to fall into ‘spammy’ territory when you meet someone in-person. Founders and hiring managers can smell desperation, and that’s the last thing you want to put off. Instead, attend the meetup or event just to be there and to get to know a few people. The same way as you would with going through your contacts on LinkedIn, any person you know at a company can be your in.
3. Connect with a startup recruiter
Yes, I know. Recruiters aren’t my favorite way to find sales jobs either. But the truth is that some are excellent gatekeepers to the startup world if you don’t have other connections.
Search LinkedIn for recruiters specializing in recruiting for sales jobs the industry you’re interested in, or ask around at the meetups you attend. These recruiters are typically well-known in the community and easy to find. As insiders, they’ll know who’s raising money and looking to expand their team with new sales jobs in the coming months, and who you should be talking to.
Reach out and see if you can help them in any way, or if they’re interested in meeting up to talk over your options. It’s in their best (financial) interest to get you a high-paying sales job, so befriending one of these recruiters can be a fantastic advantage.
Lastly, find and reach out to the right decision maker
You’ve got your list. Your name’s floating around the office. It’s time to go in for the kill.
You don't want to spend time convincing a gatekeeper on the company's HR or recruiting team that you’re the best bet for this sales job. Instead, you want to go straight to the person who's going to be in control of the hiring decision. You want your first real ‘touch’ to be with someone who speaks your language.
For any sales job, your ideal point of contact is likely someone with one of these titles:
- Director of Sales
- Sales Manager
- VP of Sales
- Head of Growth
You want someone in a fairly senior position who can make the call or push you through to the interview scheduling process with a thumbs up. What's important here is that you skip the application, and go for connecting directly with real people.
Next, open up a new tab and head back to LinkedIn.
In the main search bar, type in the title of the position you want to connect with—choose to display results for people with that job title or skill.
Then, you can filter those results by people only with that job or skill at the company you're targeting, by typing in that company's name within the current company field (as seen above). Now, your results will be hyper-specific.
The right people. The right title. The right company.
Add those names and titles to your spreadsheet. Now it’s time to find their email.
Start by installing the free Rapportive Chrome extension for Gmail.
Rapportive adds a sidebar to your Gmail account that shows information pulled from LinkedIn when you enter someone’s email address they have connected to their LinkedIn.
Now, when you type in a suspected email address for someone you want to reach out to, and hover your mouse over it, the Rapportive sidebar will populate a bunch of information about the person right in your inbox—if this email address is at all connected to their LinkedIn account.
If the sidebar appears and pulls in what looks to be the right person's photo and description, you've got the right email address.
Cycle through testing the most popular email formats and verifying with Rapportive.
Nine times out of ten, you’ll get their email address in less than a minute of this and it'll be in one of the above formats.
Using our example from above with finding a sales director from Oracle, the first email address format I guessed and tested for Abe Seraj, the person in the top search result here was correct.
Remember to stick with the smart networking technique and provide real value first, don’t just ask for a recommendation for the sales job you want.
If you’re not able to verify their email address with this method, find them on Twitter to see if they have contact information (or chase a link to their personal blog that might have their contact info).
The final step, is your actual outreach email. This shouldn’t be too hard as:
- You know you’re passionate about helping the company
- You know you’re talking to the right person
- You’ve got their email address
Show genuine interest in them, make it clear that you’re thinking about how you can improve their business already. Help them imagine you as a part of their team. If you need some more help, here are a few more email templates I’ve used to land multiple jobs for myself.
Step 3: Nail the interview
If all of this has gone according to plan, the next step will be landing an actual interview for the sales job you want.
If we’ve found one common theme throughout this entire post already, it’s that hunting for a sales job involves as much strategy and planning as it does action. This section is no different.
Do your homework
Because you picked the company you’re interviewing with, you should already have a good idea of what they do, where their strengths are, and where you can help them grow their sales. However, now that you have access to the inner circle it’s time to go deeper.
Start by reading their blog and Twitter. What do they write about? Look for company updates on LinkedIn or the CEO’s personal account. What issues can you tap into and show that you understand their market?
The more you do now, the easier the rest of the interview process will be.
Prep for interview questions
Every interview will be different, but the fundamental questions are the same. They want to know that you weren’t lying on your resume, that you are personable and friendly, and that you can talk objectively about your strengths and weaknesses.
Here are 10 typical sales interview questions you should be able to knock out of the park before you step foot in their office:
- Why sales?
- Why do you want to sell this product?
- What do you know about our customers?
- What do you know about our competitors?
- When was the last time you were really stressed out and how did you deal with it?
- When was the last time you took a really big risk and it didn’t pan out?
- When was the last time you lost a deal?
- When was the last time you won a deal?
- What was the last sales tactic you learned?
- How do you think this interview is going so far?
You should also prepare to show what you’ve got.
As Close.io CEO Steli Efti likes to say, “How can you find out if someone is a great basketball player? Do you: Interview him and ask a lot of well-thought out questions, or watch him play? Watching him perform is a much more reliable indicator of skill and talent.”
Interviewing for a sales job could just as easily mean picking up the phone and cold calling a prospect. It’s at this point where all the research you’ve done comes in handy.
Follow up and show you’ve got what it takes
You’ve done the deed, now all you do is sit back and wait for the offers to come rolling in, right?
Not a chance. This is sales, where no answer is as good as a flatout ‘no’. Head back to your spreadsheet and track when you had your interview and when you last heard from the company. Set a schedule of follow up messages to check in and see how they’re coming along with the decision.
And if you want to really go for it, a personalized thank you note is a great way to send a reminder and stand out from the crowd.
Where to find your dream sales job
We’ve talked a lot about how to get a sales job, but let’s take a step back for a second and look at where to find them.
First off, if you’re looking for an exciting, high-growth startup sales job, forget about the likes of the major hiring sites like Monster, Indeed, or SimplyHired.
Most companies you want to work for won’t be posting their sales jobs here in the first place, and if they do, you know they’ll be inundated with applications—meaning your shot at getting an in is close to zip. Instead, the best places to find startup sales jobs are more targeted or niche communities.
Let’s look at a few:
With nearly 25,000 startup jobs currently listed from companies like Facebook, Yelp, Medium, and even Tinder, AngelList is your first stop for startup sales jobs. Once you’ve created an account you can apply privately to companies (so your boss won’t know you’re looking), see salaries upfront, and get access to key decision makers, not recruiters.
They’ve even put together a tool where you can search jobs by salary. I mean, if it’s all about the Benjamins, this feature is for you.
ZipRecruiter is the #1 rated job search platform on iOS and Android, and for good reason. Not only do they have 8 million active job postings on their platform, but they send you notifications when your application has been viewed or you’ve been contacted by someone at the company you applied to. While the listings are less ‘startup’ focused overall, the sheer number of sales jobs and quality of the search experience makes this site a great option.
If you want a sales job at a promising startup, following the venture money is a safe bet. That’s the idea behind VentureLoop, a site that helps venture-backed companies and startups find the best talent out there. They count some of the best VC firms in the business as their clients, including Accel Partners, Andreessen Horowitz, Sequoia Capital, and over 80 more. There’s no fee to browse up to 50% of listed jobs, with a $14.95/month membership required for full access.
If you’re looking for a local sales job, VentureFizz is a localized job board stacked with startup jobs in Boston, Seattle, San Francisco, London, and more. The location angle makes this site perfect for people who are using their local network to find jobs or who don’t want to have to relocate for a role.
5. The Muse
If you’re looking for all around career advancement, The Muse pairs an awesome job board with company directories, expert advice, career coaching and courses, and personalized advice. While the search functionality isn’t as robust as some of the more focused job boards, the quality of sales jobs listed on the site and the added value of career advice and content are well worth scrolling through a few additional pages.
If you’re sick of the standard ‘send in resume, never hear back’ format of sales job hunting, HireArt is for you. HireArt lets you upload videos, work samples, and more that are screened by humans (not robots), promising that you’ll be judged on merit—not where you went to college. Currently, their job list isn’t as in-depth as some of the other options here, but the process means it’s worth checking in from time to time.
7-10. Lever.co, Jobscore, Greenhouse.io, Breezy.hr and other applicant tracking tools
Some of the best startup sales jobs aren’t listed on job boards, but live only on the company’s website. However, you can still find these jobs without searching for the ‘careers’ tab hidden on a startup website’s footer. Today, most companies use applicant tracking and recruitment software to take care of the mess of dealing with thousands of applications. Sites like Lever, Jobscore, Greenhouse, and Breezy all handle this in their own unique way.
So how does this help you as a job hunter? Using a simple Google hack, you can search these sites for all jobs listed with the keywords you want (like ‘sales manager’ and “inside sales’).
Simply head over to Google and enter “site:[Name of the site you want to search] “[search term]”. So, to look for sales jobs on Greenhouse, I’d Google site:greenhouse.io “sales” and get a list of all jobs listed on the site with ‘sales’ in the title.
11. Individual VC firm websites
Venture Capital firms (the people throwing millions of dollars at startups with big dreams) have a vested interest in stacking their portfolio companies with the best talent, and will often list open positions—including sales jobs—on their own sites.
Start by making a list of VCs that specialize in the kinds of companies you want to work for (you can search this VC Directory or this Wikipedia article to find all of the big players). Then, use that same Google hack to search each page and see if anything comes up.
Over to you
There are few careers more rewarding, both in compensation and meaning, than sales.
While this process may seem like a lot, all you’re really doing is ensuring that you have a job where you wake up every single day excited to get out there and get results.
“If you get a job you love, you’ll never work a day in your life,” may sound like a cheesy motivational line, but talk to me after you land your dream startup sales job and we’ll see if you still feel the same.
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