AN ACTIONABLE 10 STEP ROADMAP

Entrepreneurs are looking for your initiative — not your ego.

Susie Eddins

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May 30, 2020 · 16 min read

In our current digital world where information is instantaneously available, the pandemic is further exaggerating how negligible past experience can be. Mindset proves to be the ultimate game-changer to succeeding in the startup industry, especially as many companies find themselves caught in the unexpected. The reality is that many leaders are turning to their team members to generate winning strategies.

Unemployment has soared, but so has individual professional curiosity as people try to decide what is next. From the years 2016 to 2018, the average worker tenure hovered at around 4.2 years, according to a study done by the Bureau of Labor Statistics. For the baby boomer generation, the average number of jobs held in a lifetime leveled out at around 12 according to another survey. These numbers combined with the rapidly evolving landscape of technology and digital media, it should be no surprise that Americans are looking for more changes in their career. Yet simultaneously, millions of Americans are finding themselves paralyzed by the idea of failure and venturing into the unknown.

With all that’s “normal” in the world being shaken upside down, I figured it would be the ideal time to share my roadmap for those craving a career transition into the fast-paced industry of digital marketing. In my recent five years of management roles, I’ve analyzed unconventional resume approaches that have introduced me to brilliant minds.

So, how do you even get accepted into the role to be able to show a new team you can do what they need? Here’s the process I share with others to help build up their professional credibility:

1. Enter the Application Process Educated About the Company (& it’s Competitors)

When you are applying for a job, be aware of what environment you are getting yourself into. Startups and marketing agencies are known for their eccentric cultures, and it is imperative that you research what that means for agencies in your area before you set your sights on one. With a “go with the flow” operation structure, what you see is probably what you get in the startup world.

Start your journey by educating yourself on the following:

• The company websites. Read the content and scope out the teams. What are their missions? What values do they have? Do you recognize their clients?
• Their services. You don’t need to be an expert, but you should be comfortable discussing them. Be familiar with the industry buzzwords, and how standard services impact each other.
• All active social media channels. What personality does that brand have? What is their value add? Do you resonate with their style?
• Recent testimonies or reviews. Know the platforms or people you may need to interact with. How is that agency occupying the space?
• Look for industry partnerships & case studies. A partnership badge usually indicates a high demand or need with that tool or company, or that process is generating the business lots of money. Use case studies as benchmarks for the quality of client work.
• Publications and features. Knowing their current buzz will give you insight as to what image they are potentially working towards. Getting into publications takes time and effort, and they will appreciate you noticing.
• Industry growth and changes. Research what the industry, the company, and potential competitors could be facing. Asking questions about new things that the company could be testing out will show a proactive initiative, which is priceless.

Looking into these areas will display to your employer that you can guide yourself through a basic orientation of the agency. You know their clients, their services, and what they’ve done and you’re still interested. Prepare yourself to avoid obvious questions in the interview such as asking what the agency does or what clients they have.

As you are going through this discovery phase, whether by a handwritten chart or excel sheet, keep a note of what stands out to you for each one to refer back to at a later time.

2. Take Time to Craft a Specialized Resume

Older folks are saying you aren’t trying hard enough — I say that you’re not specialized enough. In times of panic or stress, it is not unusual to want to stretch yourself thin to position yourself as desirable by anyone that crosses your resume. But that’s not necessarily the ideal strategy for 2020.

In a world where remote culture is the new norm and startups are offering the “perfect opportunity”, make sure you’re carving the path that you will want to follow. When you have a hodgepodge of experiences and skillsets, employers may get the impression that you do not actually know what you want and will do anything. It may be difficult to set a new tone for your ambition in the future after you’ve started.

Been a while since you’ve reviewed your own resume? Does it feel outdated beyond repair? Indeed.com offers a few templates here if you are feeling utterly lost. Pick one that fits best to the details you are needing to include for your dream position.

A fellow Medium writer, Richie Crowley, compiled information on the upcoming trend of hype sheets used in lieu of resumes. Given this article is geared towards aspiring digital marketers, I thought it’d be a fun note to end on. I haven’t seen this format utilized yet, but I hope to see a few samples come through in the near future.

Once you’ve selected the format you think will perform best, here are the baselines of what I look for in a junior applicant’s resume:

• It’s concise and on topic. Make sure you are addressing the job role requirements within the first half page of your resume. While I may be interested in other things you are capable of, I am looking to fill a specific need at that given time.
• Don’t over-promise. In a world where the internet can provide an answer in a second, I’m not looking for you to be a Jack of all trades, master of none. I am seeking a self-starter with situational intelligence and expertise who can live up to the expectations that they outline.
• A relevant skillset. Are you proud to have 18 certifications listed on your resume, but 12 don’t actually apply to the job in question? Congratulations, you’ve played yourself. Keep the focus on the top 5–7 skills you can fully execute on.
• Include trusted certifications. Google, Facebook, SEMRush, Moz, Instagram, and Adobe all offer free courses to educate you on their tools. Don’t discredit sources like Youtube and Skillshare for more in-depth tutorials. You can receive training on most tools for no cost — do not get suckered into thinking you have to sign up for dozens of paid masterclasses.
• A proactive mindset. In startup culture, it is vital that the team is positive to keep the hard work fun. Utilize positive terminology and avoid negative speech as much as you can.
• A likable personality. Do you have a voice? Do you have passion? In moments of high pressure, you may be tempted to vomit your accomplishments on the page. Don’t forget to include inspirations or enriching accomplishments like volunteer work that you are invested in.

If your resume is unable to effectively communicate your true strengths and feels unclear, I will likely pass on you. I will need you to jump right into the projects that correspond to the job listing. Then once you’re settled, is the time to branch out and learn new topics to supplement the team.

Put the finishing touches on it, and then take a few hours away from it.

3. Apply Your Skillset to a Mock Project

Feel like you’re a shoe-in after editing your resume? Put yourself to the start-to-finish test.

I know — your nerves are skyrocketing and stress is nagging you to your core at this stage of the search. Channel that energy into creating a complete package to showcase the upper threshold of your capabilities.

What does the structure of a mock project look like?

• Set the scene. Give background information on the focus client. If you have not had a real client, make one up and give plenty of detail. Be sure to mention your “mock client”, so employers are not confused if they try to research the focus client.
• What are you solving? Outline what the problem is, what resources you are working with, and what the client would ultimately like to see.
• Do work. Make the branding guide. Write the website content. Compile a mock report. Schedule out social media.
• Walkthrough the fix. Expand upon your solution. What was the brand missing? How did you address it? What do you anticipate the results to be?
• Be diligent with edits. Install tools like Grammarly to cover your bases as best you can to avoid grammatical mistakes. Share with friends to catch any misplaced information.

Keep in mind, longevity is crucial in marketing. Can your solution be repeated? Can the process be scaled? Want to go the extra mile? Write a phase two strategy. Elaborate on the next steps you would take with this client based on what you have already completed and what they expressed their problem to be. Are there areas you can foresee things going south? Create a faux plan to buffer these. Ideal services to add on to compliment their marketing foundation? Outline them.

During this portion of the process, see if you can identify where your strengths and weaknesses lie. Make notes of places where pieces do not connect, or simply words you do not know. The employer will likely ask you questions on this work, so you want to ensure you know the details inside and out.

Creating your own project is your work to distribute, and should not be confused with free work. If any agency asks you to do free work for a paying client during your interview process, take your skills elsewhere.

4. Create an Outline of Your Recent Progress

Now for all you recent grads that knew exactly what you wanted to do in college, let’s bulk up your reference docs. In many instances, you have college work to add to your portfolio or resume. I’ve noticed that a lot of candidates leave it all in thinking the more the better.

Review your resume, portfolio, and mock project against each other. Now, analyze whether each piece that you have decided to include is showing progress. While it may feel good to boast yourself, you don’t want the employer to not get to your best work because you included too much of it.

When there are multiple pieces that need to be tied together into a presentation, a PDF file may be too large or potentially compromise the quality of your work. In these instances, there are a few reputable platforms you can use for a seamless user experience to display your work.

I would recommend the following which is cheap with existing subscriptions, or free:

• For Designers: Adobe Portfolio, Behance, Dribbble
• To compile reports: Canva or Google Slides
• For the writer or photographer: Journo Portfolio (This platform offers hosting for up to 10 free articles, and isn’t polluted with cheap branding or ads.)

Add descriptive blurbs highlighting the intention of each submission. Is it a branding project and you changed the color? Explain the psychographic changes behind it. Writing for them? Summarize what keyword opportunities you noticed, audiences you plan on building, and what else you brought to the table. Keep it simple. These blurbs should be between 2–3 sentences.

Start with your complex work, and add supplementary cases behind it. Time is of the essence and some employers simply won’t read the whole thing.

Pro tip: Don’t abandon this file. Continue building on this, in the real case that the first gig doesn’t work out. It is substantially easier to recall details at the moment rather than trying to dig them out of a distant memory.

5. Market Yourself as Teachable

What next? Don’t talk about the past, focus on the present. Do not be fixated on how you do not have experience but can “prove it to them”. The sample work you created in the above two steps should do the talking for you.

In your cover letter, explain why you are a fit, and also how you are seeking growth in your role. No brand wants someone that is a creature of habit and isn’t looking to grow. I beg you, do not jump straight to wanting a management role if you’re applying at an entry-level position. Speak to how you are eager to be a part of the company scale. Make comment on our culture, before you ask about if you can come in later because you like morning workouts. Startup life is fun, but work still needs to get done.

Here are two things I look for:

• What are you professionally inspired by? Show me that you are comfortable turning to other insights, in order to keep growing professionally. What end goals are you striving towards?
• What other specialties interest you in the agency? If we get an influx of work in another specialty, will you be eager to hop in?

Again, keep it simple. I am in a management position, and if I switched, I’d say something like this:

“I am inspired by the accountability and empathy that Simon Sinek vocalizes to his audience. His push to get the majority of the general public inspired in what they do has increased my desire to do more and always be learning. In addition to the skills I am hoping to improve my performance in [position in question], I look forward to the opportunity to improve my knowledge of [complimentary position] to possess a better approach to marketing the bigger picture.”

This ambition snippet piques my interest and should do the same for others.

6. Create the Ideal Daily Workflow

Take a deep breath. We’re at the final stretch of the education and preparation stages. You should have 85 percent of your bases covered by completing the previous five steps.

Startups are fast-paced. You will be juggling a few hats. You do not know them all. Give some serious thought to the following:

• Are there tools that you are unfamiliar with that may be vital?
• Are there specific tools that you will utilize to collaborate?
• Are there metrics or terms you that you overlooked?
• What other daily tasks would make sense for you to take on?
• What are irregular items you may be responsible for?
• How comfortable are you being an authority to the rest of the team?
• How often will you need to be client-facing?

Confidence in your ability is key here — both in what you can do, and what you need to improve on. An employer wants to know that if they set you loose on a project, that you are able to fill in the gaps, ask questions when you need help, and are not going to let a poorly executed task slip through the cracks.

Research project management for your particular field to see if other people have talked about their trials and tribulations in the industry. Make a running list to know what you could come in contact with so you can be mentally prepared.

Completely lost on where to source the day to day responsibilities? Salary.com is made to provide transparency about pay but can be useful in giving you an averaged description of job positions to help you out.

Tie a bow on what you’ve accomplished up until this point and take a break. This process is difficult, challenging, and confusing. Recharge your batteries to go into the next phases with a clear mind.

7. Cross Reference Your Workflow & Resume

After you create an ideal workflow, revisit your resume. Are you actively addressing all elements of the job in your resume and cover letter? Do they feel like they will pair together well? Does your resume accurately represent what an employer will find in your portfolio?

If the answer is yes, it is time to call on your college best friend, LinkedIn. This platform will help you speak to real people, with the real experience to give you insight or validation on what you are feeling at this point.

Putting feelers out with people holding your desired job title will help confirm your impressions, and begin to build a relevant network. Request an invite with a unique message. Something along the lines of this usually gets my attention:

“Hi [name], I’m making a career transition into [insert field here] which I see you are currently in. If you have a few moments, I am hoping to connect on a few questions about your day to day responsibilities. Thank you in advance”

Character limits can sometimes be a pain. But in digital marketing, you get a lot of people in your inbox asking about the easy stuff. Make your approach serious but not sales oriented.

The number one thing I tell people is that a job hunt is not personal. Employers have a mission to accomplish, and while they could love your personality, they may just not see you as fit. Continue building your digital platform to reflect the colleagues and brands that you want to surround yourself with to eventually be a part of.

8. Now, Make the First Move

Once you have been able to connect with real people, it’s time to start taking your chances. Obviously, make sure you have corrected anything that seemed off and begin reaching out.

1. Set yourself up with Google Drive, if you haven’t already. Upload all of your assets into your drive if you are utilizing PDF format. Compile your go to links.
2. Send a test email to a friend. It seems silly, but they can see glaringly typos, potentially receive errors, or point out that you uploaded the wrong file.
3. Revise errors.
4. Find employer contacts and take the chance!

If you reach out to the employer with proof of your expertise, by the time they get to your resume they are excited to see what else you have to say.

• Keep the body short and sweet. I mean 3–6 sentences about why you’re invested in the company, how you've prepared for the job, and what your attachments showcase.
• Keep the file sizes and platforms easily accessible. It is not uncommon for these to be viewed on the go.

A template for you to get your brain gears turning:

“Hello [employer],

I came across your [job position] listing on [website source]. Your brand [pick a relevant piece of work or brand attribute] resonates with my skillsets and I would . I look forward to growing your brand by contributing my [design] skills.

I have attached to this email examples of my work. What additional materials can I provide to discuss how I can be a fit within your company?

Any feedback you have on how I could be better suited for this position would be appreciated. Thank you in advance for your time,”

In a world where instant gratification and automation is prevalent, effort shines through. Your employer has the advantage. They have the job offering and you need to stand out. Making it convenient for them to see what you are capable of is key.

Make sure you are researching for the hiring manager or the correct department. And please, if the listing says to not reach out outside of the listing, do not apply this step.

9. Have Invested Questions at the Ready

When I am starting to favor a candidate and I bring them in for an interview, I am searching for the final “wow” factor. Once you are in front of the employer, even if digitally, you want to show them why you are more than just a good fit, but you are the right investment for them to make.

Show the employer that you are invested in the position by asking questions that people would normally hold back until they are offered the job. In this introductory phase, do not prematurely celebrate. Avoid asking about pay, time off policies, or the perks.

Questions like this can include:

• Are there materials I can provide for you for the next steps of this process?
• What is the largest misconception about this job role that I should be ready to tackle?
• What additional responsibilities can I expect that are outside of this job description?
• What do you enjoy most about your job or the industry?
• What supplementary traits do you envision the ideal candidate to have to compliment the team?
• What is the next milestone that the company is aiming to achieve?

Time is of the essence when you realize that the ball is in your court. Having a list of advanced questions will reduce stress if the employer requests an interview in a short amount of time. You are able to brush up on your resume and be ready to have personal conversations afterward.

10. Monetize the Follow Up

The end of the interview cycle is without a doubt mentally challenging. You have spent hours and hours preparing for a position. The reality is, in our current world and in a highly competitive world like marketing, you are going to face rejection. Here is how to optimize the end of an interview opportunity.

Craft an intentional email to tie up all loose ends with each employer that granted you an interview. Include points such as the three below:

• A thank you. A sincere thank you in your follow up will go a long way in a society of instant gratification and truthfully, entitlement. You do not owe them anything, but voicing your gratitude shows your awareness that their time benefited you.
• Qualification improvements. Ask what qualifications could make you better prepared for the role, or if there were specifics to that the agency prefers.
• General constructive criticism. Were you lofty in your responses? Too aggressive on your past experiences? A little too confident to the point that you didn’t answer their questions? Was your portfolio not clear to them?

Gaining this feedback won’t cost you a dime and this teachable mindset can leave an impression on your employer that you will be adaptable and are comfortable with putting your ego aside.

Turn the negative into a positive by creating a “Career Roadmap” from feedback to know exactly what real-time offers are looking for. While you may not have the job, you will have clarity. And you will have gained insight into more skillsets that will lead you towards being more qualified for the next job.

With materials at the ready, you should now be confident to approach other agencies if the first doesn’t work out. The idea behind this process is not that you are guaranteed any job that you apply for. Each agency will have its own specifications, and sometimes you may not be a fit. These steps are made to build you up and give clarity when tackling a monumentally terrifying task such as entering a completely foreign market.

I have passed on candidates and hired them at a later time. Not because they were “overqualified”, but because I knew that the compensation that I had allotted for that given job role was not respectable for their skillset. They were not a fit, but made a lasting impression, often by doing the things above. Some have come back after improving their skillsets. And a few have gone through the interview process, faked their way, and turned down the offer out of fear.

These 10 steps will work to build up your knowledge of the industry, the ever-changing responsibilities of your sought after position, and most importantly boost your confidence to show that you can do it. The learning process can be frustrating and demotivating, but simultaneously it can be exhilarating and freely. Chin up, and best of luck.