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Good news, I figured out how to get a sales job in 19 days. That means you’re about to learn how too.

3 years ago, I set a personal career goal. I wanted to do sales at a hot tech company. Now, that dream has finally come true.

It’s particularly gratifying given the fact I was abruptly laid off the other day.

So today, I’m going to walk you through exactly how I went from unemployed to working at a hot tech company (only 19 days later).

You asked for the details. This is everything.

Guide on How to Get a Sales Job

For best results, I recommend you do these steps in sequential order.

Read them start to finish. Then go back. Read it again and execute on each step. One at a time.

#1: Get crazy specific

I made one huge mistake during my past job hunts. I defined a job title I wanted first (e.g. investment banker) then looked to see who was hiring.

Now I do the complete opposite. I define the kind of company I want first then identify the position I can add most value.

You Will Achieve More Desirable
Results With a More Targeted Search!

For me personally, I wanted to work at a hot tech company (preferably SaaS) located in San Francisco with 50-200 employees.

What do you want?

#2: Take my list of hot tech companies

Build a list of all the possible companies that you think may be a good fit. You can do this yourself or hire someone on ODesk or eLance to do it for you.

I work with a woman named Rox who lives in the Philippines (she does great work). This is the job description I sent her:

Hey Rox –

I got laid off from my job last week. Ahhhh. I need your help to research available job positions at local tech companies.

See spreadsheet attached please fill in the column details for each company. See first company as an example. You’ll be looking on their website for the job position available for “Sales Development Representative” and “Account Executive”.

– find local address closest to san francisco: on above websites or
– find employee count and capital raised here: first on or then
– find sales role: on their home website under jobs or careers

Can you send this back to me as soon as possible? Like later today?

– Ian


This is what Rox and I created (see below).

BONUS #1: The full list of my 50+ hot tech companies in SF with sales jobs is in the comments section below. I include my interview activity tracking spreadsheet in there too.

The 1st tab is designed to help you track all communication and activity. The 2nd tab is the complete list of all companies with their available job openings.

#3: Copy their sales job descriptions

You won’t find this step anywhere else. From your list of target companies and available sales jobs, pick your top 3.

Then copy and paste the text of their job descriptions into a word cloud generator like WordSift by Stanford University.


This will enable you to immediately uncover popular keywords. Words that are highly desirable to your future employer.

We are then going to use these keywords to update your LinkedIn profile and resume.

#4: Build a pretty LinkedIn profile

LinkedIn is all about telling your story.

Present your story in a way that illustrates how all your past experiences have led up to the very moment you apply for a company. You get the interview when they feel that could be true.

Use the keywords from your word cloud above. This will make your skills and experience more closely aligned with their job descriptions.

Plus, your profile is more likely to appear in recruiter searches.


**Note: if you no longer work at your last company, be honest about it. Indicate the proper dates of employment. It’s not a good idea to start a relationship off being deceptive.

#5: Mirror and match your resume

I encourage you to mirror and match your resume with your LinkedIn profile.

Nowadays, most tech companies see your LinkedIn profile before your resume anyway. So, make sure you tell the same story across both channels.

Layout and design is important too.

Investment Bankers Will Disqualify Job Candidates
Based on This Criteria Alone.

I’m serious. Choose a simple design for your resume. Somethings easy to read and understand. You can find plenty of quality resume templates at Creative Market.

#6: Email blast pretty much everyone

I say “pretty much everyone” because opportunities can be hidden in unlikely places. And you don’t want to leave any stones unturned when you’re hunting for your dream job.

Steps one through five are all preparation step before you begin your outbound campaign.

But now, it’s time to send out a short 3-5 sentence email to your personal network. Explain the type of company you want to join and your desired role. It’s hard for people to help if they don’t know exactly what you want.

Also, email your entire network on LinkedIn. You can easily export their contact info into a csv file (complete how-to instructions here). Then email each contact directly or in bulk.

#7: Make alliances with recruiters

I think recruiters are great. They are your second channel of warm introductions.

They help you prepare for interviews, they make introductions, and even schedule interviews for you.

A good recruiter should feel like a sidekick.

Here in San Francisco, I highly recommend four recruiting firms that specialize in tech sales:

  1. Betts Recruiting
  3. The Lions
  4. GogoHire

Be honest and transparent with your recruiters. They know you will work with other recruiters. And that’s ok.

Just tell them about the other opportunities you are pursuing. That way you avoid any overlap or redundant outreach (sorry Kelley and Caitlin).

#8: Role play interviews over and over

I’m so awkward during interview role plays. I don’t know why.¬† But, there is one thing I can do about it. And so can you.

Practice. Practice. Practice.

Get comfortable telling your own story. Role play phone interviews and in-person interviews with yourself first. Then with recruiters.

Trust me. This exercise will pay off.

#9: Book the phone interview

By now, your network and your recruiters will begin feeding you opportunities.

It certainly helps to supplement this activity with some direct outreach of your own. Especially to any high priority companies where you don’t have a warm intro.

As the opportunities flow in, start to schedule those phone interviews. Typically, I will schedule no more than 3 interviews per day.

You can use to easily propose times.

#10: Research with a cheat sheet

Do your research before any interview. Hot tech companies want to know you are hot for them. So do your research.

With so many interviews everyday, I struggled to remember all the important facts and questions. So, I just created a one-page cheat sheet that I could reference on every phone interview and also bring with me for in-person interviews.


Bonus #2: CLICK HERE to download my sales interview cheat sheet in pdf format. Bring it with you to every interview. Without it, I rambled aimlessly. With it, I felt confident and prepared every time.

Remember at the end, it’s the questions you ask them that will become the deciding factor.

Take a moment to really think through what you want to know about each company (you may be working with them soon).

Don’t you want to know what the company’s goals are? And whether they are aligned with yours?

Pretend like all the companies on your list gave you a job offer. What information would you need to know from each of them, in order to make the best decision?

#11: Convert the phone interview to an in-person

Remember to tell a story. Here’s the basic story framework:

  1. Setting
  2. Complication
  3. Turning Point
  4. Resolution

When they ask you questions, think through all your own personal experiences. Then choose one experience each time to best represent the full range of your skills and abilities.

These stories should come more naturally once you complete steps one through ten here.

At the end, always ask for next steps. I wouldn’t get too caught up in “closing” people.

Just let them know you’re fired up about the opportunity and want to take next steps with them. And next steps are to meet in-person for an interview.

#12: Buy the essentials for every interview

I had no idea how powerful this stuff is until I tried it myself.

I can think of three specific items that significantly influenced the outcome of all my interviews.

Here they are:

No joke. Pull these items together for yourself. It’s like David Copperfield. Magic.

#13: Show up to the in-person interview

Always wear a suit and tie.

That’s what you you’ve been told, right?

Well, I don’t recommend it for hot tech companies. A jacket is a nice touch, but nothing more is needed.

Remember, most people in tech love flannels and tee shirts. I advise you to dress slightly above your audience, but still look like you are part of the team.

When you sit down, pull out two copies of your resume and one copy of your cheat sheet. Casually, place them on top of the binder resting in front of you.

Engage with them, tell them your story and always ask for next steps.

#14: Receive and negotiate the best offer

You want to love where you work. And they want you to love it too!

So, gather as many job offers as you can. Until, you find the right one. Then negotiate that one offer to close.

Traditionally, there isn’t too much negotiating for junior roles. But as I understand it, the more valuable you become to an organization the more leverage you will have.


This takes work. I went non-stop for three weeks straight. I was booking 2-3 interviews per day.

In 19 days, I interviewed at 14 companies.

Today, I am tremendously grateful to say I joined the Yesware team.

And I’m confident, if you follow these steps above, you will find your dream sales job at a hot tech company too.

I hope that helps.

– Ian

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28 Comments How to Get a Sales Job at a Hot Tech Company in 19 Days

  1. Jan says:

    Well written and well done Ian!

    Good luck at Yesware!

  2. Cait says:

    Thanks for sharing Ian! I love Yesware. We use it every day. Congratulations!

  3. Alicia says:

    Hey thanks for the great content. I wanted to download your list of companies as well as your cheat sheet to see how you organize yourself. Unfortunately optinmonster is not responding. Is it possible someone can shoot those my way? Thanks

  4. Brian Groth says:

    Great tips, many of which I’ve used too. Anyone looking for a new job would be crazy to ignore this advice.

  5. Kira says:

    Great tips for any job seeker! I really enjoyed reading. Well-written, concise, and actionable!

  6. Vincent Lim says:

    Awesome stuff Ian! i’ll give it a try and best of luck in Yesware team!

  7. Kelley McCarthy says:

    Great article Ian!! Thank you for sharing. Hope all is going well at Yesware!

  8. Tim says:

    Hi Ian,

    Loved your story and great background,

    I live here in the San Fran Bay Area and am always looking to associate with likeminded Salespeople/Entrepreneurs. Please let me know when your next Senator Club Event is. Would love to attend.

    Tim Hansen
    Sales/Business Dev/Staffing

  9. Amol says:


  10. Teesta says:


    Great article! As someone who is considering a transition from financial sales to tech sales, this advice is invaluable.

    I would love to attend your next meetup session. Could you send me more info on that?


  11. VP says:

    How do I get part-time tech sales positions? I have a long tech background, lots of experience with enterprise customers and a people friendly personality combined with sharp analytical skills, but I’d like to only work part year so I can travel abroad for family and nonprofit work – any suggestions regarding part time bay area enterprise sales would be great.
    Thanks so much for your time

  12. Veronica Jin says:

    You always come up with an article filled with insights. Thanks a lot for writing this article and how is your new company?;)

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