3 Secrets on How a 19 Year-Old Got a Tech Sales Job at a Venture Backed Startup

About Author: Jeremy Schifeling is the founder and CEO of Break into Tech, a site that helps anyone launch a tech career, even if you don’t code. He previously served as an Executive at Fidelis Education, and previously worked at Apple and LinkedIn. 

Quick: What’s the biggest factor standing between you and a hot startup sales job?

A weak resume? Boring cover letter? Uninspired LinkedIn profile?

None of these.

So what actually does?

Well, to understand what your hiring manager really cares about, let me give you a glimpse into how I hired sales devs at an edtech startup with $10MM+ in VC funding.


Secret #1: Tech Sales Hiring Process = Sales Process

The first secret for getting a job at a tech startup is to understand the hiring process aligns with the sales process. In other words, everything you do as a job applicant – from introducing yourself via a cold email to closing the deal with a final presentation – directly mirrors what you’d have to do as an actual sales rep.

And so whereas hiring coders is really tricky (i.e., just because someone can write an algorithm on a whiteboard in 10 minutes doesn’t mean they’ll be a workhorse in the crazy 10 weeks before launch), hiring for sales is basically a “What you see is what you get” deal.

Now what that means for you, the applicant, is that you should view every part of the application process as a real-world sales audition.

So instead of spending months perfecting your resume (which is really more of a marketing function when you think about it), spend that time on top-of-the-funnel hustling.

For example, our very first Sales Dev hire was only 19 years-old. And while his resume was both sparse and unpolished, he hounded us for weeks with emails and just flat-out hustle.

Which is exactly the kind of moxie we needed to launch a brand-new product category in an old-school industry like education.

So, don’t be afraid to go hard after startups you’re passionate about.

Because all that hustle isn’t just in pursuit of an interview; it’s actually the first real proof that you can do this crazy tough job.

Secret #2: Know Thy Customer

Stop thinking like a job applicant and start thinking like the ace salesperson you are: What’s the cardinal rule of sales?

Know thy customer.

And so the first secret to startup hiring success is to understand precisely who your customer is for this particular “sale” (i.e., the one with you as the product!).

Let me give you a hint:

It’s not your career counselor, who’s always telling you to make sure all your resume bullets are in the active voice.

It’s not your proofreading buddy, who’s always catching little typos in your cover letters.

And it’s not even all those random people on LinkedIn who keep looking at your profile.

No, your only customer is the hiring manager at that hot startup you’d love to work at. And chances are, she doesn’t really care about your resume, cover letter, or LinkedIn profile.

After all, how many customers do you know who buy 5 or 6-figure products based solely on the sales collateral?


Secret #3: Seeing Is Believing

So you’ve hustled and hustled – and you’ve finally been rewarded with an interview at that awesome startup. Time to start practicing your standard interview answers (“I’d say my biggest weakness is I work too hard…”), right?


Because even though those kinds of answers may be typical fare for big companies, startups don’t have time for that fluff.

They need someone who can come in and hit the ground running. And so, even if they ask some basic questions to get started, know that the only thing that matters is the role play.


Because seeing is believing. Because anyone can learn to recite BS answers to BS questions, but great sales skills can’t be faked.

Either you’re going to stand strong in the face of cold call resistance or you’re going to quiver like the Golden Gate in a windstorm.

So how do you make sure you ace the role play?

Do you have to memorize everything about the startup’s product? Or build a mental rolodex of their entire client list???

While knowledge in all of those areas certainly can’t hurt, I knew it wasn’t fair to judge my interviewees on that kind of insider info. Instead, I focused on three skills that had nothing to do with my specific company or product – but that are hallmarks of sales greatness everywhere:

Do they ask questions?

So many candidates are so nervous in interviews that they practically start their pitch before the interviewer can even lay out the role play scenario. Which of course, is a recipe for failure in a world where sales are based on relationships, not pure speed!

Do they actually listen to the answers?

Slightly savvier candidates will remember to ask questions – but then they’ll robotically go into their pitch two minutes later with no reference to any of the information the interviewer has shared with them. Again, no one wants to buy from a robot, so listening and personalization are key.

Do they persist in the face of pushback?

Even thoughtful candidates can stumble at the end when, inevitably, the interviewer comes up with some reason to turn down their offer of a demo. And so that’s where a sales superstar can really stand out – by firmly, but respectfully, continuing to push even in the face of adversity.

So as you prep for your interviews, don’t sweat the clichéd questions and answers. Instead, focus on the real thing: Can you do the job that needs to be done? Can you interview prospects, tailor proposals, and persevere when the going gets tough?

Because if you can do all those things, the job is practically yours.

After all, when it comes to sales, seeing is, indeed, believing.


Conclusion: How to Get a Tech Sales Job at a Venture-Backed Startup

So there you go. Startup sales hiring is like no other talent search on earth.

Instead of sweating resumes and cover letters, focus on your customer. Instead of pruning your social media profiles, hustle like you would to generate prospects.

And instead of practicing 100 irrelevant interview questions, focus on the three parts of the interview that actually predict your job performance.

Because when you do so, you’ll make your "customer" very happy. And you’ll close the most important deal of your career!


How the "Neighborhood Technique” Saved a Sure-Thing Deal We Almost Blew

About Author: Scott Britton is the Co-Founder and Head of Growth at Troops, the Sales Acceleration Platform for modern sales teams that use Salesforce & Slack. On the weekends, you can usually find him long-boarding or continuing his quest to make the perfect avocado margarita.

After four follow-up emails, I was still waiting on a response.  I was about to chalk this deal up to the radio silent category.

I landed a meeting with the company through a long shot personalized cold email. They are one of the bigger partners in the space and had recently secured a partnership themselves, which would mean big business for us, or whichever data provider they went with.

Up until now, the deal was going well.

I gave a product demo to each of the key stakeholders on the first call. There was a very obvious fit. We reviewed the deal points verbally on the phone and emailed our boilerplate contract afterwards. It all checked out.

But, here I am, getting the silent treatment. 


The Neighborhood Technique: How to Book In-Person Meetings

The potential partner was located in Northern Europe and embodied a very non-aggressive sales culture...so there was no way the bulldog sales style was going to fly there.

With potential partners of this size, we would typically meet in person early in the deal cycle. But, things seemed to be moving so fast and seamlessly up until this point that it didn’t seem necessary.

But now, after no in-person time with them, we were waiting on a number of unanswered email threads.

My colleague and I strategized on how to revive the conversation. We both agreed that aggression wouldn’t work here. They had all the leverage. And culturally, they wouldn't respond to that.

Instead, we used what we called the “Neighborhood Technique” to see if they would bite.

The neighborhood technique is a low-risk way to propose an in person meeting (face time) with someone you’re trying to close a deal with, by telling them that you’re already going to be in the neighborhood.

The odds of me being in their country were low. I'm based in New York city.

So, I shot them an email to let him know that a month from now, we were going to be in London for business. And since we had a few extra days on our trip, we were considering spending them up north in his city. If he was around, it’d be cool to meet in person and see their office.

No mention of the deal. No mention of the lack of response. Just a casual office tour :)

Two weeks went by, still no response.

I figured I had nothing to lose, so I replied letting him know that we were in fact going to be in his city on Thursday and Friday of that week.

Within minutes, he responded with a few times for Thursday.

I confirmed the meeting time. Then immediately booked a trip to Europe to get the deal done.


So...How Did the Meeting Go?

The meeting couldn’t have gone better.

We talked about each other’s businesses. We nearly glossed over everything we’d spoken about before.

Toward the end of the conversation, he mentioned that he was glad we met in person and felt good about working with us now.

Within a week, the contract was in a redline process and signed by both sides shortly after.


What We Could Have Done Better

We were relieved to have won the deal, but it could have just as easily gone sideways due to my early communication mistake.

In retrospect, it was obvious that we should have met with them in person sooner. Particularly, given things were going so well initially.

At the time, a trip to Europe for what seemed like a fast tracked deal appeared to be unnecessary.

But, with opportunities of certain sizes, the initial pace and geometric proximity shouldn’t dictate how high touch you approach the opportunity.



The major takeaway here is that momentum of a deal shouldn’t push you to deviate from your process. For us, this meant getting face time early and often with partners of a certain size.  

You never know what’s going to happen. So, you must control the controllables. Adherence to a proven process will give you the best chance to succeed.

Win or lose, you can rest assured that you gave yourself the best chance to succeed given the information you had at the time.

Have you tried this before?


Why I Lost a Fortune 500 Customer that Accounted for 30% of Our Revenue

About Author: David Aldridge is a Business Development Lead at Lohika, partnering high growth companies with elite engineering teams. In his off time, he climbs rocks, plays board games and watches movies far too seriously.

“We decided to go with your competitor.” - Words every sales person fears, dreads, loses sleep over.

I was dumbstruck. Jeri and I had been talking for several months. Like any enterprise deal, it had been an exercise in patience and hope.

I first met Jeri during our initial product demonstration. If we closed her organization, a Fortune 500 medical device company, it would be the biggest contract deal our scrappy little start-up by a factor of ten. So of course I went the extra mile.

We gave her an extended trial account for her to champion our product to her superiors. We then further extended that trial so that other audiences in the company could see it in action.

And then she went dark on me. Which, in hindsight, I should have seen as a sign.

But then without warning, I received a notification that her organization purchased our enterprise monthly package. We were jubilant. We’d just increased our annual revenue by 50% with one client.

After a week, I checked in with Jeri to make sure everything was copasetic on their end. It wasn’t. They’d discovered a bug, found new must-haves that our product didn’t have at the time, and generally had buyer’s remorse.


Short-Term Risk for Long-Term Gains

We offered to fully refund them their purchase, but still allow them access, and fix the bugs. A magnanimous gesture like that would have to help make them happy. That was the thinking, at any rate.

However, when I personally delivered the good news, Jeri did not react as I expected. She requested additional features and asked how soon we could deliver on those. Keep in mind, we’re an early stage start-up with a single-digit headcount. Moving quickly on features outside of our product roadmap would be challenging to say the least.

But the features she mentioned were features other clients had put on their wishlist as well, so we prioritized her needs.

A few weeks later, after the latest release was pushed, tested and approved, I reached back out to Jeri to schedule a demonstration of our new and improved product.

The demonstration went great, and Jeri indicated that her organization was ready to look at a monthly deal again.

Shortly thereafter, though, I heard the fateful words at the start of our story. Yep, the competitor ones.


What Happened to Our Fortune 500 Customer?

In our final conversation, Jeri confessed to me that her organization had originally purchased our product because of a feature that only came up briefly in our conversation. To be honest, it was a feature we hadn’t really invested that much in because our current customers didn’t use it often. Or at all. And in my defense, Jeri hadn’t emphasized its importance.

As a result, their organization chose the leader in our market segment. They were better funded, had a more mature product, and while it didn’t have that same feature, Jeri’s company felt it was a better match for their needs.



As salespeople, we’re taught to uncover all the layers of the onion. But sometimes, even if you think you’ve figured it out, you’re still looking for unknown unknowns.

Keep digging.

Or you too might receive those same words.

Bad Rapport Building on Intro Call Cost Me $50,000 Opportunity

About the author: Ian Adams is a Mid-Market Account Executive at Yesware. Certain details have been anonymized out of respect for all parties involved.

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Every week, I have about 15 buyer conversations. That breaks down to 2­ - 4 calls/meetings per day where rapport building comes into play. Some of those meetings are booked by me, others are intro calls booked by the Sales Development Representatives (SDR) I work with. 

On Wednesday morning, an SDR sent me an invite for an intro call later that afternoon. It was with the Sales Operations Manager of an 800+ employee company with a 90 person sales team. They offer accounting and compliance software and have raised over $100 million from investors.

Before each intro call, I thoroughly research the company and individual I'll be speaking with. I once heard a saying that, "the length of your call warrants at least that amount of time in preparation." So, if you have a 30 minute call scheduled, it warrants at least 30 minutes of preparation.

During my research, I'd discovered that the Sales Operations Manager I was speaking with also happened to manage an herbal remedy health website. She had run this site for the past 7 years, and I'd imagined one who offered such products would be in touch with their earthly, spiritual side.

I'd also noticed that the company was headquartered on an island off the coast Oregon. That would be a valuable piece of information to break the ice, at least I thought it would be.


Rapport Building at Beginning of the Intro Call

Well, I dialed into the conference line at 4pm pacific time. She dialed in 1 minute later.

"Hello Stephanie?" I asked.

"Yes, hi Ian. It's nice to meet you." She replied.

"It's nice to meet you as well. I noticed you are located on Stronghorn Island. Based on the photos I found online, it looks beautiful out there." I said.

With a short tone, she said, "Our company moved to Seattle last fall. We are not located there anymore. Listen, I don't have very much time, can we get to the point?"

I could feel my face becoming flush. You know that feeling of warmth and rapid reddening in the cheeks. That was me. Fortunately, I could hide behind the phone and only hope my voice didn't reflect how I was truly feeling.


What Really Went Wrong?

Who knows what went wrong. Maybe she was having a bad day. Maybe I misread the situation.

My pre­-call research led me to believe that she would have an "Amiable" personality. They are dependable, loyal and easygoing. They like things that are non­threatening and friendly. They hate dealing with impersonal details and cold hard facts.

That however, was not the case in this situation.


Listing Off Features Doesn't Solve Problems

She proceeded to interrogate me about one feature after another. It was a barrage of "tell me what features you offer?" Then before I could explain further, it was followed by, "we can already do that, what else have you got?"

It felt like Yosemite Sam (her) forcing Bugs Bunny (me) to dance by shooting at his feet. I was doing the feature dance.

Traditionally, my intro calls last no longer than 15 to ­30 minutes. This was on target to wrap up at the 15 minute mark.

Surprisingly, I still booked next steps with her because the company is qualified. But not surprisingly, she no ­showed and has gone completely dark on me. Isn’t that the best.



On an intro call, rapport building is less important than business value. Maybe you've experienced a similar situation on an intro call. It was an unpleasant experience for me, and unproductive for both of us.

These days, I skip the chit­chat. The small talk. The weather. I leave it out (unless they lead with it, then I go along for a brief moment).

Instead, I focus on asking questions that have a purpose. Leading with information that brings them closer to achieving their personal or business goals. The focus is on the value. If you get their buy­ in on the value first, there will be plenty of opportunity to build rapport later. 

Because ultimately, the amount of value you bring to their business will determine the success of your relationship.

Would you share a few ideas on how you structure your intro calls? 


How a Great Discovery Call Earned Me the Biggest Deal in My Startup's History

About the author: Dan Smith is a Growth Specialist at Winning By Design, consulting for high-growth B2B technology sales teams. 

The new era of sales comes down to a great discovery call. You need to find out the real issues your customer is trying to solve. If you lose deals due to price, competition or the frustrating black-hole of “gone dark” - it’s most likely because of a poor discovery call.

If I had to choose one thing that helped me win the biggest deal - it would come down to this: I asked one unusual, but simple question at the beginning of our discovery call.

After that, we had a great conversation without distraction on either side. I was able to pick up more things from her answers and quickly adjust the pace of the conversation when I realized something resonated or was not important.


Get to Know the Customer on the Discovery Call

6 months into being a the 4th AE at a fast growing startup in the midst of raising our Series B, I landed a call with the Director of Sales at a $2B valued public company.  Jill (not her real name) was leading a team a team of about 30. After a short previous qualification with her direct manager the week before, this call was scheduled for 30 minutes on a Thursday afternoon late October. Everything about this call was normal until I asked:

“May we turn this phone call into a video call?”

Instead of doing an audio only with a presentation, I asked Jill to speak with me face to face, business person to business person.

Jill and I had a valuable first conversation. We built a relationship around sharing best practices in sales, and she shared with me the strategic initiatives for the company, and the impact it could have for her personally.

We randomly met 1.5 years later on the streets of San Francisco during Dreamforce, she still remembered our first meeting.


A Qualification Problem is a Big Problem

The top 3 mistakes salespeople make on first calls are 1) not listening to the customer and being curious about their business, 2) pitching the same features to everyone - regardless of what the customer is actually interested in and 3) not setting appropriate next steps.

Most new sales professionals offer feature based solutions way too early into the convo. This was especially bad for me - I loved getting into the in’s and out’s of the product so I could answer any customer question.

When I was speaking with Jill - I could see if I started going down the wrong path based on her level of engagement.  I immediately got out of the weeds by asking a question, and ultimately learned about what was most important to the potential solution we could provide.

Don’t worry if you make this mistake at first - it’s easy to understand why: you work for a company you are excited about, with paying customers who love you.  Every prospect is a potential customer, right? As soon as you become aware of this common selling mistake, change your approach in favor of being curious about your customer by asking a question, or clarifying your understanding of their desired solution.

Too many sales people don’t realize that customers want to be qualified. I learned later, Jill usually checks emails, or texts during “vendor” sales calls - but because we were on video, not only were we both fully engaged, we were able to end the call early.


Learn the Anatomy of a Discovery Call

Preparation: Do some research about who you’ll be speaking with. If your company has already had conversations with the person you’ll be meeting with, find out what the customer mentioned they care about.  Check LinkedIn for uncommon-commonalities (Did they attend the same school? Marathon runner? Volunteer experience?).  Show that you care.

Strong opener to set the tone of all successful meetings.

The best start accomplishes three things - the expectations of what will be discussed, the time and the format.  Discovery calls need to be conversations, and not 1-way sales pitches. The customer needs to know they have control, and their concerns will be addressed.

Try this on your next call and let me know how it works: AxNOT

  • Appreciate you taking the time for today’s call.
  • x = time →  “We have 30 minutes scheduled to speak today - does that still work for you? {Remember to listen to their response, and adjust your call if necessary)
  • Naturally, you will have questions for me about my company….
  • Obviously, I have questions for you about your team, goals to understand if we could help.
  • Typically, this call will end with us determining next steps in evaluation, or if at any point you realize this is not going to be a good fit - will you please interupt me to let me know?  I have thick skin…. :)

Once you complete this opener (about 45 seconds) - confirm the agenda you sent over before the meeting - is there anything else your customer wants to cover? Then ask everyone on the call what they are looking to get out of the call. Write down their names, and make sure you address their top priorities before the end.


Diagnose After Discovery

Ask them close ended questions first - then lead into open-ended.  Question Based Selling and SPIN are the two best frameworks to have a customer centric conversation.

Start off with situational questions that show you have done some research, but also help you qualify the customer on basic minimal requirements.  If you’re selling a collaboration tool, instead of asking “How many offices do you have?” Ask “I noticed you are hiring in at least 3 of your global offices in Boston, Dublin and Shanghai, how many people are you looking to expand to?

When you begin asking problem questions - don’t just ask the generic and over-used “what keeps you up at night?” Instead ask more thoughtful “When speaking to other Directors of Sales, they mention challenge 1, 2 and 3 are on their top priorities to solve. To what extent is [customer challenge #1] important to you?”

Outline of a Discovery Call

Once I properly diagnosed Jill, we customized her “prescription” of how to evaluate our solution that was based on her timeline that would solve her challenges.  

Jill mentioned their Fiscal Year ends in December - so we agreed to a mutual plan for a pilot to line up with their holiday schedule, procurement process, training requirements to ultimately make sure her team would hit the ground running in Q1.



Because of the trust we had built starting with our first call, Jill went to bat for our mutually agreed upon solution even when the pilot didn’t go perfectly. We were able to address her team’s concerns, and expand the opportunity throughout the entire company and found the price that was fair for both parties.

What are the most important questions you ask on your discovery calls?