Overcoming resume struggles as a startup lover

Departing PatternJam

The time is approaching where PatternJam will likely have to move on without me. While I've really enjoyed my consulting time there, there is a lot of tactical work to get done, and development costs $$. Making sure you're managing the burn rate appropriately is one of the most difficult aspects of a startup, and that sometimes means moving forward with fewer team members. As I update my resume and review my portfolio to consider what's next... I can't help but feel a little anxiety to have to settle on something different but a little excitement to go somewhere new.

I've always been the kind of person who had a lot of interests and passions. I've always craved diversity in my friendships, my activities, my education, and my experiences. My parents never limited my activities or told me I couldn't do something; they were always there to support me. So of course I participated in everything.

I'm not sure what I was born with to give me so many interests in so many things, but it didn't go away in college or once I got a full-time job. But now, as a twenty-something, I'm wondering if it has hurt my career.

The right fit

Although I am incredibly loyal to people and organizations, my interests in business have ranged from customer support to development, from product design to marketing, and from sales to operations. Additionally, I have become incredibly passionate about all kinds of businesses-- B2B SaaS companies, direct to consumer apps, e-commerce stores, market research firms, process consulting firms, etc. Once I have a job with a title, I find myself happiest working with cross-functional teams and collaborating with others on a variety of projects.

In my five years of corporate work experience, I've found two types of companies that suit my interests and passions best: early-stage startups or companies that have a collaborative culture where departments work together to accomplish company-wide goals. The latter is almost impossible to find although many companies love to pretend they work that way. Side note: often times there is an assumption that startups (due to their lower headcount and needing to solve so many business challenges early on) would be more collaborative and open. Not true. Bad assumption. I've made that mistake twice.

Needless to say, I've found the most career promise (for my interests and skills) in early stage startups. So far, it has been a great solution to my jack-of-all-trades character. In startups, everyone wears many hats. For the most part, everyone will do whatever it takes to achieve the next goal/milestone whether or not it's in their job description. Titles are mostly put in place to help give you credibility when dealing with others outside of the company and to justify the extra headcount to investors. Because of this, my titles at said startups likely wouldn't hold true in a large 1000+ employee company due to seniority rules and required years of experience. 

Sounds great, right? I get a great title, I get to do a bunch of things I love and work with a lot of different people with many different talents. It is great! But it's definitely hard, and it definitely has it's downsides.

Why am I concerned? Why the anxiety?

Due to my interest range, I may be the only one in the room who has had any experience in a given area, and then have to lead (more like wing) said project. This has often resulted in helping other departments for special projects or getting moved (more like slowly morphed) into a role outside of my title without a clear understanding of new expectations or how to work with a new boss that I never interviewed with.

This makes it particularly difficult (once I get out of the organization) to draft a resume that doesn't look like I'm a complete lunatic who can't keep a long-term job.

  1. My titles and descriptions don't match the amount of experience or work I completed. In fact, sometimes they are completely unrelated.
  2. My frequent job changes (even moving up within one organization) leave me without a solid amount of time to count toward a specific role or skill set.
  3. You work with so many different people for shorter amounts of time that the list of those you feel comfortable asking for recommendations stays relatively short.
  4. Sometimes startups run out of money and have to cut headcount. There's always a concern that failure of the company is a poor reflection on your ability to get the job done.
  5. I'm young and feel like if I'm going to take risks, now's the time to do it. However, too many risks in a short period of time is visible on a resume and might make it look like I can't make up my mind.
  6. I've maintained contract jobs on the side for a few weeks at a time on and off throughout my full time career. It's not consistent enough to list as employment, but often the contracts give me experience that I feel is relevant. 

Is there a solution?

It's probably no surprise that every job I've gotten since my first corporate job has been based on referrals, networking, or a friendly introduction. It's much easier to sell yourself for the job once you get in the door, and getting in the door is easier when there's someone who invites you in or recruits you without seeing your resume.

However, in the case your only sales pitch is your resume, and you've struggled to maintain long-term positions as a startup lover with a wide range of interests... here are a few tips:

  1. Tell a story in your resume summary.
  2. End your description with a transition to the next job (why you left)
  3. Describe the company and why you were hired originally (instead of a title - then list what you did/accomplished there)
  4. Explain jumps in your cover letter only (no need for explanations on the resume)
  5. Don't focus on what went wrong -- approach it from what you learned
  6. Create multiple resumes based on what job you're going after. It makes it appear like you've been focused in one industry but isn't dishonest. They only need to know the relevant details.
  7. Expand on your Linkedin or personal website. Keep it short on your resume and provide a link (in case they are interested) to the additional details -- it's okay if they don't perfectly match, as long as they don't contradict each other.

Don't burn yourself out

I was talking to my friend the other day who was incredibly frustrated and down. She had applied to over 30 positions in two weeks and had only gotten one call back. The call back was a rejection. Her situation was different than mine because she had to quit her previous job to relocate for her husband's medical school. She's actually a great marketing strategist, but she had become a bit desperate with such a last minute move and the need for a salary. Here she was in tears on the phone feeling like she must be worthless and incredibly overwhelmed by how to approach the next application.

Her situation was a great learning experience. As you're getting ready to find your next position, try to narrow your focus. Identify what you're looking for in a position and write it down in a list. Then review and prioritize the listings you find by what aligns closest with your list. Consider which ones excite you most as well. Take the first 3 from that prioritized list and let yourself focus on those only. Do your research and get to know what you can about that company and craft a cover letter and resume that would resonate with the job description and the company culture. This process may take longer than sending the same cover letter and just changing the addressed HR contact, but it will be more sincere and deliberate. That will set you apart from other candidates. 

If you don't hear back from any of those three, reach out to followup. Take the time to ask for feedback or find out why you weren't a fit. Going the extra mile to learn why will help you with your next round of applications. Do the same, focus on 2-3 more (the next on your prioritized list) with deliberate research and application. Then wait for feedback or seek it out after a reasonable time period. This phased approach will keep you tempered, open, and honest with yourself.