Be a Job Finder not a Job Seeker

September 22, 2020

What does it take to stand out in an incredibly crowded job market right now?

I’m going to share a story a member of my Patreon group shared with me this past week. It’s an incredible story of creativity, determination and results.

“Hey, you mentioned you wanted LinkedIn DM’s about over-the-top applicant stories in the Patreon group. I just landed a job (starting Oct 6th in a mid-market AE role at a SaaS company called “Klue” (competitive intelligence enablement software) that just closed a $15M Series A in Vancouver, Canada) and I’ve been told my cadence was a little off the wall lol.

Here’s what I did:

  1. Reached out to Klue back in March right before COVID hit about a position
  2. Once the crisis hit, stayed un-offendable about not getting an interview and kept my eyes on social media to see when the tide would turn
  3. Stayed connected with the HR consultant. Made an impression and did some digging to get insight into their hiring process and who to connect with. Got feedback from her that timing might be better in July, which I confirmed from seeing their posts on LinkedIn.
  4. In July, reached out to their top enterprise rep for insight into the process. Got her to champion me to the VP HR and new Sales Director.
  5. Connected with both on LinkedIn and hit them with creative emails and video messages (dripping LI posts to the Sales Director along the way to maintain engagement)
  6. Followed up on rounds 1 and 2 with creative video summaries of the interview describing key takeaways and selling the next step **One really practical story of how those video summaries helped me** The VP HR actually rejected me after the HR screening interview because she thought I was a culture fit, but totally lacked the experience they were looking for. I’ve got some B2B experience (~3 years selling small-scale SMB as an AE) but none in SaaS or at their deal complexity, so they told me straight up that they treated me like I had zero experience… She thought I was gritty, personable and smart, etc, but her advice to the new Sales Director was to drop me at that stage of the game because they were looking exclusively for veterans. He took her advice and I was out of the game… But I didn’t know that! (I only discovered this in my second interview when the Sales Director brought it up.) So, I sent a video recap to the Sales Director summarizing what I thought went well and selling the next step and he said “screw it, I don’t care about his experience, I’ve got to meet this guy, put him in a meeting with me” The quick, creative video recap (2-3 minutes max) is a pretty fire tactic that I couldn’t recommend more highly when done properly… it literally resurrected me from the dead in this process…
  7. Interviewed another top AE to get insight into the details of their process and organization to prepare for final interview (who happened to be on the panel in the final round)
  8. Interviewed a bunch of businesses in their ICP (mainly Product Marketing Leaders, also Competitive Intelligence and Sales Leaders) — got 3 leaders to send video testimonials saying they should hire me (one of which was their ICP at G2, including the quote “if you don’t hire this guy, Jacob, call me and I will get you a job here instead”)
  9. Interviewed the VP of Product Marketing at Klue (1st time in Klue’s history that an AE candidate has done that apparently) to get the recommendation of the ICP-equivalent at Klue and get EXTRA prepared for final round. He also gave a testimonial to the CEO and Sales Director — he was also a former client leading Product Marketing at Hootsuite and was an enterprise sales rep before, so they very much value his opinion on these things
  10. Getting additional respected sales mentors to shoot the CEO and the Sales Director testimonials on why they think I’d be a good sales hire (ex: Dave Weiss, Kyle Coleman) The sheer volume of videos propelled some serious “who the hell is this guy?!?!” vibes internally, which is the exactly the buzz I wanted circulating before the last interview.
  11. When the CEO asked one of my referrals if I had “the killer instinct” and “love for the hunt” in an email, I told the referral to respond “Jacob said to check your texts”. I tracked down the CEO’s cell number in an old fundraising press release, called him and texted him a couple voice notes when he didn’t pick up.
  12. Did a bit beyond the standard prep for my mock disco call. Prepped slides that visually aligned with their brand guide, dropping sophisticated insights referencing convos I was having with other industry leaders to validate mock-prospect pain and included some funny moments for extra sauce (ex: got some pretty audible laughter from photoshopping their team’s faces onto a picture of the Avenger’s to talk about how our solution is designed to make them the heroes of the story)
  13. Tapping into my competitive debater roots, I sent a full-scale, formal debate-style debrief analysis (written and video versions) to respond to last key questions they mentioned having about my candidacy in the final interview. **While the written notes were just 3 pages (point form with big font), the last video (and only that video) was literally 14 minutes long… The amount of hype created by the videos throughout the process made them want to watch a 14 minute video from me, affording me a seat in the decision making room I never would have otherwise had… (In fairness, they made the decision to hire me immediately after the interview, so none of that debrief was necessary, but the Sales Director described the last video/notes as “just one more top shelf move after a series of top shelf moves”)

Overall, it was a fun time! The CEO began the final interview by saying “never in my 25 year career have I had someone do anything like what you just did throughout this interview process. My hat is completely tipped to you.”

I’ve kept all of the content created throughout the process and plan to be posting snippets of the cadence on LinkedIn over the coming months! Actually, I was really hoping to discuss how to build out a content strategy for my new role/myself in general on LinkedIn in our scheduled chat next Thurs Sept 24th (11:45am PST) — excited to learn from you on that! Hope this was an enjoyable read! Looking forward to getting to properly (virtually) meet! Thanks for all you do man :)”

MIND F-ING BLOWN. Who is this person who did this you ask? Jacob Gebrewold – take a bow.

PS: He’ll be starting at Klue pretty quick, so if losing fewer deals to competitors is a hot topic for your team, give him a shout!

It’s almost time for Q4 – what are you doing to ensure a successful finish this year? Stop by Thursday Night Sales this week and let’s talk about it.

Learn how I got promoted from rep to manager in 3 months, how he gets so much done, and why the captain is never the best player. My appearance on The Next Level Sales Leadership Podcast.

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The Pre-Interview Checklist

September 15, 2020

Hiring season is in full swing and there are a lot of people looking for new jobs and the talent pool is deeper than ever. Once you’ve gotten the interview, you obviously want to stand out and put yourself head and shoulders above your competition. Follow this checklist to stand out from the crowd and make it an easy decision for your future employer.


Know coming into the interview that you are not the only person they are interviewing and you need to sell yourself. I always imagine that the person I am competing with has better credentials, more industry experience, and a better suit (you’ll never catch me wearing a suit to an interview). That’s OK. There is a reason you are being chosen to interview and you should come in confident and ready.


Know the product inside and out.

  • Check out the website (all of it).
  • Sign up for their newsletters and other content and read through everything you receive.
  • Check out their product reviews.*
  • Check out their social media pages.

All of these resources will give you insight on their message, their audience and how the product should be sold.


Know the customer profiles, the value the product provides them and how to reach them.

  • Who is buying this and why?
  • What industry are your customers coming from?
  • Are there common demographics or regions for your customers?
  • How are you customers learning about the product?
  • What are the reasons people are not buying your product or canceling your product?

If you know who your customers are and what they care about, it should be easier to understand how to approach them and sell them.

Company & Culture

Know what is important to the company and the kind of characteristics they are looking to hire for.

  • Who are the leaders and what are they about?
    • Check their linkedin posts.
    • Google Search them.
    • Message them, introduce yourself, and ask them what’s important in a new hire.
  • Who will be your peers there?
    • Start a conversation with them and ask them about what it’s like to work there.
  • Talk to people who left the company.
    • You need to know that not everyone works out at a company and some people are bound to have bad experiences. That said, a good litmus test of a company’s character is how they treat people who leave.
  • Check their Glassdoor.*

 Demonstrate Action

If you want to really impress an employer: don’t talk about it, be about it. Some of the best interviews I’ve ever had, the interviewer had called prospects and customers of ours and talked to them about the product, gotten their insights, and talked about their experience. Want to really stand out, come into the interview with a warm lead.

Game over.

Your research should be reflected in your interviews. If something is unclear or needs to be addressed in your research, ask the person you are interviewing with to clarify or explain. As someone who has conducted literally thousands of interviews, I am always impressed when the person comes prepared and turns the interview process around on me. It means they are taking this seriously, they are a critical thinker and they mean business.

Lastly, put on the show. Interviewers are doing tons of interviews and it gets old. Make it fun and show off what you will be like to work with.

Once you blow someone’s mind, let me know about it on Linkedin – I love these stories.

*Note that all reviews should be taken with a grain of salt. In my experience, people either leave a 1 start review or a 5 star review. Use them as a source of information and don’t read too much into them unless there are serious red flags.


“He is a misfit of the sales world, just like 90% of the folks that get into the profession and today he tells his story of struggle and triumph.” – Dale Dupree talking bout me, and I am 100% ok with being a misfit.

Wanna hear more? I’m Episode 72 of The Sales Rebellion Podcast

Austin friends: I’m excited to invite you to ISG Partner’s Annual Charity Golf Tournament, Par for the Purpose, benefitting No Kid Hungry. Join Austin’s elite sales professionals on the course to network with a purpose. I’m even sponsoring! Sign up here

Blog Post for Hoopla

Tequila Tuesday 5 Sept 15th 730pm central only on my Patreon

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Set Yourself Apart from the Start

September 08, 2020

So you finally landed the role, congrats!

Whether you’re starting as a VP or a SDR, there are certain actions required to set yourself up from success from day one. Does every role now demand a 30-60-90 day plan?

“What’s the best way for me to prepare for and succeed right away in my new role Scott?”

I’ve been asked this question a lot lately, mostly by nervous [understandably so] sales folks, and I suspect due to the great restart of 2020 (F-U COVID), this question will continue to fill my inbox.

My advice is simple and applicable whether you’re a VP or an SDR:

  • Follow the process. 
    • The process was put in place for a reason, and if done correctly, it works (Shameless plug, this is what I do best. Contact me here). Recently, I was asked by the CEO of a great company, “How much runway should I give my new SDR’s to make the process their own?” I will take a hard stance here that the process was built meticulously and at great costs so you will NOT have to take the risk of having six people working six different ways.
  • Develop your mindset to succeed. 
    • Success boils down to one question: How bad do you want to make it happen?
    • First things first, you have to give a damn. Stop reading here if you genuinely don’t care about your prospect or the problems they struggle with.
    • Read my last few blogs on mindfulness and finding mentors. If you can accomplish those, you’ll set yourself up for success.
    • Join micro-communities, like Thursday Night Sales. I get asked nearly every Thursday, “What can I do to set myself apart from my co-worker?” or “What advice can I give to my counterpart who is struggling?” It is a simple answer. By going out of your way to spend your time learning and networking with your peers and leaders, you’re developing a mindset of success.
  • Know your stuff.
    • New VP’s and SDR’s alike, hear me loud and clear. Prescription without diagnosis is malpractice. Let that sink in.
    • LISTEN and seek to understand before prescribing new ways of doing things. For the sake of everyone’s sanity, do not be the “Well, we always did it this way at my last company” person. You left that company for a reason, right? Give it a rest.
    • VP’s, seek to know and understand your people more than anything else.
    • SDR’s, master your industry. Sounds simple, but it’s not. A few weeks back on my Patreon, we had the pleasure of learning from Jon Selig in a private Patreon-only session. He said something that made me stop and should make you ponder as well: “Most of us sell products we’ve never used to people in jobs we’ve never had in industries we’ve never worked.” Know your stuff.
  • Listen to the prospect.
    • Have you ever noticed how your mind wanders when you’re listening to someone talk? Multiple studies have shown that we can only speak around 130 words per minute, but we listen at around 400 words per minute. When you hear me preach active listening, this is what I am talking about.
    • If you’re going to listen to your prospect, it means being able to shut off that wandering part of your brain. Practice this daily in your regular conversations and again, seek to understand before being understood.
  • Stick to the plan.
    • Quick story. When I worked at OutboundEngine, we sold email and social media marketing services to small businesses. We had a new team member come in, and he had never done this before (let’s call him Bob). Bob was a natural born hustler and we knew he would do well, and he did. Bob did so well that he was eventually gifted with inbound leads, which was rare. All of a sudden, he fell off a cliff. Bob had followed the process with cold calls, but started cutting corners with inbound leads. Bob forgot the process and deviated from the plan. He went from 300% of quota to 20% the next quarter.
    • When you are in the pits, go back to the basics. Re-read Addicted To The Process. Pretend you are back at day one on the job and re-walk the steps you took that made you successful in the first place.

Next Steps

Once you find a process that works, you should just keep doing it until the job is done and there is nothing left for you to do and nowhere left to grow.

To keep growing, you have to keep moving. Sometimes, that means moving away from something easy and familiar. Recognize when you’ve hit the ceiling in a certain role or particular organization. When you decide to push yourself towards that new challenge, you are saying you won’t settle for mediocrity.

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How to Find a Mentor

August 31, 2020

What are some good ways to find a sales mentor? What should I look for in a sales mentor? Red flags?

What are some good ways to find a sales mentor?

  • Internally
    • More accessibility
  • Externally
    • Fresh perspective

What should I look for in a sales mentor?

  • Define what you want out of a mentor
    • Difference between a coach and a mentor
    • Mentors should extend beyond the teachings of a manager
      • Managers (micro), Mentors (macro)
      • Mentors come in when you need exponential growth
  • Someone who has done it and is still doing it
  • Someone who is still learning and teaching it

How to respect your mentor?

  • Be respectful
    • Time management
    • Come prepared
    • Demonstrate how you are using their advice
  • Be honest/don’t hold back – surface level conversations are not going to help you grow
  • Leave your ego at the door

Red Flags?

  • High energy, low substance
  • Distracted, hurried, rushed
  • Self interested

Behind almost every great sales professional is a mentor that provides guidance, support, and – in my case – a much needed shot of tequila here and there. If you’re going to excel in any profession, you have the option to figure it out yourself when the people around you don’t have a solution or you can bypass a lot of tedious trial and error and find someone who has been there before (a few times) and ask them how they did it.

Finding the right mentor is not always an easy thing to do though. You need to find a person who is willing and able to provide sage advice beyond your current management and coaching. They also need to be willing to take on the responsibility of giving you their time to guide you to the next level. Here’s a simple guide on where to find the right person, how you should approach them for guidance, and how you can get the most out of the relationship so that it is meaningful and beneficial for both of you.

Start with you

To start, you need to be very specific when defining what you want to get out of this relationship. You should have a vision and goals of what you want to do in your career before you approach a mentor or else you are going to be disappointed by very short conversations. If you are too vague, you’re pointing too much of the burden onto your mentor. Make it easier for them. Don’t say: “I want to know how to sell” or “How do I get to your level?” Please, don’t do that. Instead, say: “What are 3 tips you can give me to try and get more of my demos to show up?” Please, do it this way.

Define for yourself:

  • Do you want to go into management or be an individual contributor?
  • What industries interest you most and why?
  • Where are your current coaching and guidance resources limiting your growth?

If you know what you want to achieve, you just have to plug that into your criteria for a candidate. For example, if you want to go into management, find someone you admire as a manager that is in the industry you want to focus on. Approach them with areas you’re limited and the challenges you’re having. Lay out the specific scenario, what you have tried and the results and then ask them for advice on specific situations. There is no substitute for somebody as a mentor that has done the role you are trying to get or succeed in.

People are much more likely to engage with you if they know that you have thoughtfully attacked a problem, but are struggling with a resolution. You need to put in the due diligence to find the right mentor and approach them the right way.

What to look for

After you have defined what you want to learn, now you can start your search. An easy place to help you narrow down your search is by asking yourself, ”who do I admire and why?”. Chances are if you admire them, they’re successful, you like their style, and would like to emulate what they have done.

Make a list of people and don’t be afraid to put somebody on the list. They can be people inside the company you work for or outsiders. They can be well-known or unheard of. Also, remember that everyone on that list was at one time trying to figure it out just like you are right now, so don’t think there are people who are ‘untouchable’. Worst case scenario, they tell you “no” or don’t respond. We’re in sales…we deal with rejection. Shoot your shot anyway.

When you approach the people on the list, you want to make sure you stand out. They are likely busy people and only have so much bandwidth, so you need to sell them on why they should offer you advice and agree to mentor you. Lay out what you’d specifically like advice on, why you think they would be a good fit, and a plan of action.

Propose a plan that is reasonable and not overly intrusive. For example, “I’d like to meet over the phone or in person once a month for 30-45 minutes and bring some specific challenges that I would like your advice on.” Be aware that successful people are not looking for a sidekick or someone who is going to need constant guidance on their day-to-day.

Day-to-day advice should come from your manager. A mentor’s advice should come in where your manager’s advice ends. Think about it this way, there are a ton of baseball coaches out there, but if you want to learn how to throw a major league level slider, your best bet is to find someone who has done it before (and preferably with the same hand).

Finding that person

There are over 1,500 dating apps and websites. All of them have people looking for the same thing in principle but very different things in practice. Just like in the dating world, there is no formula for finding that perfect mentor, but there are some easy places to start.

Internal mentors are great for a number of reasons: they are close and it’s easier to form a deeper rapport with them, they are keenly aware of the challenges of the company you’re with and products you’re selling, and you can closely observe how they operate on a day-to-day basis and visa versa. If you can find a mentor internally, that’s great, but realize that there is only a limited pool of people that you work with. There may be more capable mentors elsewhere, but that does not mean you should not lean on internal mentors and learn from them.

Outside mentors are easier to find these days with LinkedIn and networking groups, but they are going to be less available simply because they don’t work in the same business as you. The upside here is that you can find people who are posting useful content that will help you better vet them as a professional before you put them on your list. They can also bring a fresh outsider’s perspective to your situation that may be exactly what you need to see a problem through a different lens.

The “close” for an outside mentor is going to be a longer cycle and it is very likely that you will get less attention than someone working internally, but the long term relationship can also be more fulfilling. As you form a relationship with an outside mentor, there may be opportunities to work with them and close that gap.

The real key to searching for a mentor is diversifying where you’re looking to get the best pool of candidates and advice.

Red Flags

If you follow the selection process above, you should be able to avoid a lot of people that will not be good fits for what you are trying to do career-wise. However, you still need to keep your eyes open throughout the mentor process.

If finding a mentor was as simple as you walking up to someone you admire and saying, “Will you be my mentor?” …. Well the world would be a weird place. Aside from the world being weirder, it would be far less productive for everyone involved. Remember that this is a relationship and both parties are getting something out of it.

There are some people that on the surface level seem like they would be a great mentor, but – in reality – are not reliable, not as skilled as you initially thought, or not present when offering advice and guidance. If you are not getting much out of the relationship and it’s more work than it’s worth, it’s ok to remove yourself. Obviously, I would recommend stepping away graciously, but sometimes it just doesn’t work out and that’s ok – you can find someone who will be a better fit for what you need.

Also, every mentor has a different reason for being a mentor and I would like to believe most of the people who mentor are doing it for good reasons, but the fact is that is not always the case. Do not do something that you feel would compromise your character. If a mentor (or anyone for that matter) asks you to do something that puts your morality in question, get out of there and fast. This may seem obvious, but when someone you once admire asks you to do something it’s not always easy to say ‘no’.

Clearly, I hope you never encounter a situation like this, but just like Drake said, “being humble don’t work as well as being aware.”

Give back

Good mentors will give you guidance, perspective, support and so much more. They selflessly give their time to help someone else grow and succeed. They can be pivotal to your development if you choose someone who is capable and caring, but to do that you also have to do your part too. Show up, be prepared and attentive, implement the advice and report back on how it’s impacting you and your career.

This relationship – like most relationships – does not happen overnight. They need to be developed, nurtured and maintained properly to get the most out of them. During the relationship, if you have the opportunity to help your mentor, take it. This is not a purely one way road. The spirit of mentorship is helping, so do your part too.

Finally, whatever level you are at, there are other people who can gain from your knowledge as well. There are few better ways to test your knowledge than to teach it. Just because you have a lot of room to grow in your career, does not mean that you are not qualified to help other people. Start your journey as a coach and a mentor early, test your knowledge, and help other people develop.

“A mentor is someone who sees more talent and ability within you, than you see in yourself, and helps you bring it out of you.” -Bob Proctor

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