“Looking For My Next Challenge”: How Tech Executives Should Do Itby@YamRe
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1,488 reads

“Looking For My Next Challenge”: How Tech Executives Should Do It

by Yam RegevJune 1st, 2020
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Yaeli Regev is co-Founder, CMO at He shares his advice to help senior executives in any role in the high-tech industry improve their chances of being hired for other desirable positions. His advice is probably best suited for companies seeking to hire their first few executives and the executives competing for those roles. He says the older he gets, the harder it is to hear “NO” and the tougher it's to ask for feedback.
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We try, we fail or we succeed but we always learn.

I’m going to share some feedback now to help my fellow marketing execs who are looking for their next role.

This feedback is based on my experience with the ~130 marketers who reached out to me about a month ago when I posted a message seeking applicants for a senior marketing position.

But there are lessons here for all of us who work and live the startup life and the ever-changing reality of being a modern professional.

My goal in this post is to help senior executives in any role in the high-tech industry improve their chances of being hired for other desirable positions. Usually, senior executives change positions less frequently and it’s not like riding a bicycle — you might not jump right back into the job search and be able to recall exactly what to do and nail it.

For me, the older I get, the harder it is to hear “NO” and the tougher it is to ask for feedback. Can you relate?

First, a HUGE disclaimer: Everything I’m sharing here represents my very personal PoV and experience. I was recruiting for a startup that is in the growth stage and that fact was reflected in the requirements for the role.

Also, I’m not an HR expert. However, I’ve managed hundreds of people over the last 13 years. I’ve interviewed thousands of candidates and built large marketing departments, but recruiting is not my profession.

My advice is probably best suited for companies that are seeking to hire their first few executives and the executives competing for those roles.

Job searching is self-marketing.

It is convincing someone that you are the solution to their problem. So I assessed applicants by sorting their qualifications into the three pillars that make up a marketing strategy:

  1. Brand Marketing, in the case of seeking a new role, becomes self-branding
  2. Product Marketing represents the person’s LinkedIn profile, their CV, the emails that they send, etc.
  3. Lead Generation for executives looking for their next placement is using existing job search efforts to uncover more opportunities

Self Branding

The way you present yourself, directly and indirectly, influences the recruiters’ decisions, how they score your application, and the impression you leave about yourself with the organization.

1. Prepare and practice your own elevator pitch

My most important tip: Build yourself a pitch that is made up of the gold medals that you have accumulated in recent years and that is very relevant (!!!) to the role you are aiming for.

For example, in meetings with investors and clients of zest, I point out that I started my professional career by co-founding a web marketing agency that reached XX employees around the world and generated $XX million in ARR.
don’t say that before the agency experience, Yaeli (my wife) and I operated the biggest mobile smoothies bar for festivals and events in Israel. While it is a gold medal, it adds no value to my fundraising or sales efforts.

2. Never under deliver yourself. NEVER.

Sending the recruiter a message that starts off with: “I may not be a perfect fit for this position because of lack of experience in [field_name]”, weakens your presentation and delivers a negative impression to the recruiter before they have even had the chance to review your LinkedIn profile.

For example, imagine this UVP on a given homepage: “We are Not Sure that this is the Best Product” or “It May Not Be the Product you are Looking For”!

This advice is especially relevant for marketing execs. Candidates who have an issue with messaging or self-branding aren’t what recruiters for marketing roles want to see.

3. Try to burn as fewer bridges as possible

Review the job description (JD) before sending a message. If there are 2–3 elements in JD that disqualify you, move on for these two reasons.

  1. Understanding “fit” is an important skill that any executive should have. If your gut feeling indicates that you are a miss-fit for this or that role, it is perfectly OK and very responsible of you to move on. Fitting or not into a role equals being strategic. Sometimes it’s better to stay on the safe side rather than trying your luck. You might hurt your brand name if the fit-gap is too big
  2. Souring yourself- If you keep applying to jobs for which you aren’t a good fit, you are souring yourself like milk. Your personal brand is taking damage each time you ask friends for introductions or headhunters and HR agencies to help you get hired and overreach. You and your advocates will feel less and less engaged and motivated as time goes by. I know it is not easy to hear. But it is better to make your reaches in reasonable increments.
For example, In the past year or so, I have helped a few dozens of my friends and colleagues who had been looking for new roles and had not had success for various reasons. As time went by and they didn’t find the right job, I was less and less certain that I could help. Was I not pointing them in the right direction? Maybe they didn’t perform well in job interviews? It is very human to feel less motivated when you aren’t able to make a positive impact.
I kept pushing and introducing them to recruiters, but the more times it didn’t work, the more my doubts that I could actually help, increased.

In short, do not “spray and pray” but rather, “aim and nail it.” Make sure your qualifications fit the JD and, more importantly, develop more relationships. Try new channels and recommendations instead of using the same connections every time.

4. LinkedIn Vs. CVs #1

It is easier to click on a link than to open a file.

It is easier to quickly scan a LinkedIn profile than to look for quick anchors like job titles, name of companies, and years of employment when skimming through hundreds of PDF files.

5. Chats and DMs Vs. Emails

Chats and DMs are better than emails. They are more human, more conversational, shorter, faster, and increase your chances to engage. Try to be accurate and focused when you message a recruiter. Stay human and understand that they might be dealing with gazillions of messages.

6. Think twice before calling

Be careful with the phone. Do not immediately call the recruiter.

On the receiving end, I can tell you it is kinda weird and exhausting to get calls about a JD you published. If you really want to call, go the permission marketing route and send a text message to get consent before doing so.

7. Use the correct lingo

Following my post about the marketing role, I received 17 messages and emails that opened with words like “I saw the ad you posted.”

But, I didn’t post an ad. I published a post. Knowing the industry lingo and using it correctly is important. Your chosen first words can help or hurt your efforts.

Product Marketing

You, your email address, your LinkedIn profile, and your CVs. They all must be neat, tidy and aligned.

1. Keep your Linkedin profile picture sharp

Make sure you smile in your image and that it is clear and uncluttered. Use a recent image so that recruiters aren’t surprised in the interview :) (Yes, many of us used to look different a decade ago.)

Also, try to make sure that the picture is close enough to see your facial features. You want to be recognizable and memorable

2. Don’t use buzzwords in your LinkedIn profile and CVs

Going crazy with buzzwords is not likely to impress recruiters who are themselves senior marketing people and it can hurt you.

Keep it real and use numbers to fill out your profile rather than fluffy words.

For example, look at these two sentences I could add to my profile based on what I’m doing at Zest:

“I conceptualized and executed a bootstrapped marketing strategy from scratch”


“I brought 120,000 users and 40,000 monthly active users to the platform”

Which of the above do you think recruiters prefer?

Data tells your story. The second statement makes it clear that I can generate traction demonstrating that I know how to develop and execute a strategy. Also, it’s more clear, straightforward and authentic than the first one, IMHO.

3. Make sure that your LinkedIn profile is aligned with your CVs

Even if you send only a PDF with your CV, every recruiter who receives it is going to check your LinkedIn profile. So make sure they match.

It is an absolute m-u-s-t to make sure that the years/roles/titles/company names are aligned on both your CV and LinkedIn. A mismatch lowers your credibility and professionalism, especially when it comes to senior marketing professionals.

4. Be honest with yourself about Applicant-Job Fit

Understanding “fit” fits in here as well: Just like in product-market fit, you should feel a high degree of confidence between your experience (Product) and the job (Market).

For example, if the JD states that you must have 6 years of experience in an executive role and you were self-employed for 6-year as a freelancer, you have no fit.
But it goes beyond what is explicitly stated in the JD. Be realistic about whether your experience in one role or industry is transferable to another.
If the company that opened the position is a product-based company (e.g. a startup) and all your experience is with agencies, chances are you aren’t going to have a high applicant-job fit.
Marketers with experience in a product-based company and marketers with experience in an agency are different types of animals, in my opinion.
I was fortunate enough to work in both types of companies . In addition, I have recruited for both types.
Crossing from agency to startup or the reverse isn’t necessarily a deal-breaker, but the roles are very different, especially when it’s about senior marketers. It may be worth trying it out and applying, but understand that your chances might be lower.

5. Your email address should be generic or branded, but not weird

Keep your email address simple.

Use a Gmail email address or one from another commonly used service. You can also use a branded email, just keep these following rules in mind:

  1. Personally I find it a bit odd to receive an email from a email address. Not even sure why
  2. Don’t try to be funny or too disruptive. For example, applying as [email protected] is a nope

6. Keep your emails short and use bullet points to break things up

If you decide to send an email to a recruiter, keep it concise. 2–3 prominent bullet points to highlight your core message should be enough.

The recruiter might think that you aren’t able to convey your thoughts succinctly if you send them an email filled with lengthy paragraphs. Also, sometimes they don’t have the time/patience to read a long email.

7. Get feedback: Ask for rejection reasons #1

If you don’t get invited for an interview or you do but aren’t hired, of course, you want to know why. (You actually deserve to know why!).

Feel free to ask the recruiter the reason for your rejection, where you fell short, and how can you improve. Just like product managers seek their users’ feedback, then iterate to make their product better.

8.Demonstrate professionalism

Demonstrating professionalism is not about showing off what a great marketer you are, but what a great human being you are. Here are the minimums to show that you understand the behavior an executive role requires (I demand the same things from myself as an interviewer):

  1. Arrive 10 minutes before the meeting starts
  2. Do not call to ask questions such as where to park a few minutes before the interview starts. This is something you should find out yourself before the interview date
  3. Do not interrupt another interview by knocking on the door to announce your arrival or make a request
  4. During the interview, sit upright but relaxed in your chair
  5. Understand the dress code of the company and choose your interview attire. accordingly. If you are meeting with a growing startup, showing up in a suit and tie might be awkward

Demand Generation

Maximize your effort by using each point in your job search to generate more job opportunities

1. Get introduced

When entrepreneurs raise a fundraising round, they know that getting the right introductions to investors can make all the difference. It’s the same for job seekers. If you have an indirect relationship with the recruiters or someone in the company, ask for an introduction and do not contact them directly.

A recommender can also point you toward a company you didn’t know was looking. Keep yourself in their minds as they can be a great tool to “generate leads” for you.

2. Push for an interview

You didn’t make the cut through the first or second screening? So what! Give it a shot and ask the recruiter to invite you for an interview. Be crystal clear about why you think you deserve it. If you get the interview, you will be able to create a relationship with the recruiter or someone else from the company. They may refer you to other positions within the company or in other companies.

3. Ask for rejection reasons #2

I mentioned before that you deserve it.

A 10-minute phone call with the recruiter will help you sharpen yourself and also make personal contact with the recruiter. This will increase the likelihood that the next time a similar job opens or the recruiter hears about something, they will think of you and you’ll be prepared for the opportunity.

4. Spread the word that you are on the hunt, but be wise about it

Increase your number of “leads” by making sure your friends and colleagues are aware that you are looking for your next gig. Update your LinkedIn profile if it’s already public.

But, be careful not to post too much about your search on social media. You don’t want to appear desperate. One post on each social media network should do. If it doesn’t, try other channels.

5. LinkedIn Vs. CVs #2

Making connections lasts longer than just sending a CV via email.

If you are applying to a company why not send a LinkedIn message so you can connect there?

Engaging with someone on LinkedIn produces a long-term connection that may pay off in the future. You never know what might happen if you connect to key people in the company, including the recruiter. If you send an email application be sure to add a link to your LinkedIn profile.

In the image below you can see the parameters I used to score candidates during my recent recruiting effort. This scoring system was a guide for choosing who would progress to each next level. But, recruiting isn’t pure math. You can’t make a cold decision based on hard skills and experience only.

I used this scoring system to help me keep track of each candidate. Because, when asking myself why a given candidate fit or not, I needed a clear answer and did not want to let my memory fool me.

So for each of the parameters you see, I used a binary metric to help- either 1 or zero for each parameter, summing them up at the end.

These are the parameters I used to score candidates during my recent executive recruiting effort

Finally, a word for the recruiters amongst you

Keep your candidates informed. Communicate with them and update them in the same way your company communicates with your users. You are representing your brand.

Remember that they are real humans and humans need to be informed and updated.

I tried to do my best to keep everyone informed and updated. I sent them feedback, had phone calls with whoever asked and I also tried to introduce most of the candidates who didn’t make it to my own network.

Any kind of help is SO needed in this situation and I know that if my time comes to ask for help, these good people will be happy to give me a hand.

Below is a Thank You email reply I received from one of the candidates I sent a rejection email to

Previously published at my account on LinkedIn Pulse on March 10, 2020