How to find your second startup job

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There's been a ton of great advice on how to get your first job in startups (see: Tim's post (opens in a new tab)), but after a successful first run how do you find your next great gig? It’s daunting and there are even more choices available. Worse - you are still responsible for high performance in your current gig. After an incredible run at LiveIntent (opens in a new tab)(what a first job!) I was ready for something new and recently went through this process. Here’s what I learned along the way.

Determine what’s important

Be scientific in your approach and use frameworks to plot out what is most important to you (ex: a certain industry or skillset you want to learn, problem you want to solve, company size, salary, velocity/stability, work/life balance, etc.). Choose a couple things that are most important to you and go from there.1It’s likely that you may not have a full picture of what it is you want. For instance I straddled the line between wanting to be the first product hire at a startup to learning within a well-oiled product org at an established “startup”. By talking to people and companies you will refine what’s important to you. Start with what you know and dive into those ambiguous items. It may take longer than you think to sort them out but this is part of the process.

Off hours

The hardest part of your job search is making time for it while performing at your current job. Since well-run companies have thorough hiring processes and can take around 30 days to close (or more) you need to make sure you are not just getting by in your current job but thriving. The worst outcome is to burn through cycles exploring opportunities that don’t close (or end up not being good fits) to find yourself underperforming in your current job. Make time outside of work hours to focus specifically on your search. Not just the work parts: research, outreach or exercises but the actual conversations, meetings and interviews. Hiring managers will help accommodate you here, even if you have to have calls or meetings at 4pm or after - definitely beats mid-day. They will understand that you have a job and responsibilities that you won’t shirk for something more attractive. If you have pressure here, it may be a sign that the company is more concerned with closing out their process than finding or nurturing talent.

Something will have to give here. By specifically working in off-hours, you will have less time for your social life, exercise or other hobbies. Understand this and make the necessary tradeoffs. You don’t have to give up all of those things, but you need to be aware of your priorities and putting some things on hold. For instance, I was learning android development and beginning work on some side projects at the beginning of my search and ultimately determined that these things could be resumed after my search ended. They would add to my resume and talking points, but ultimately weren’t going to get me hired for the roles I was looking for.

Prospecting adds up

It’s important to make measurable progress from the beginning. You probably have a few good connections and leads or are super passionate about one particular company. Don’t let this distract you from gathering robust research and maintaining a good flow of outreach!2 Think like a salesperson. Organize your outreach and gather a list of open roles. Include the top companies you want to work for regardless of whether there are positions available at the moment. Make time to maintain this list 2-3 times a week.

You'll find that setting up time to research and record takes the onus off of constantly evaluating and overanalyzing each and every gig that pops up. Jot down anything that is remotely interesting at first glance (along with basic info and a link to the opening). I used a Trello board (opens in a new tab) to record opportunities and then prioritize and track them. When you revisit these (later in the day, or according to a schedule) the interesting things will pop out at you. Then you can hone in on researching, crafting your approach and getting in touch with the company. If you jump right to this step without the first one, you can end up wasting time on opportunities you’re not truly passionate about. This process will help you filter these.Additionally, a calculated approach will help you feel like you are making constant progress instead of riding the ups and downs of here and there opportunities.

Ride ups and downs

Using a calculated, marketing and data driven approach will prevent you from hitting too many highs and lows, but won’t eliminate them. Some weeks there will be an exciting development at your current company other times you will get rejected in an interview - don’t let extremes take away your focus from your mission. The hardest part is feeling like you are restarting your mission after returning from one of these lull periods. Yes - in some cases this means taking new meetings and screens even while you are in closing stages. You can be far more selective here and should always be honest about your status with potential employers. Keep hitting the pavement.

Make time

This may seem obvious, but a job search is going to take up a significant amount of your time. Career decisions are among the most significant you will make, and you want to be thoughtful and intentional. Make a rough time line of when you expect to land your new role and start early. Be patient and understand that the time between first connection and an offer can take up to 30 days. Put in the time, and don’t expect to rush to the conclusion.

In addition to giving yourself a reasonable time to complete the process, give yourself the time you need each day/week to make progress. Set processes and short term goals around each step of the funnel: prospecting, getting introductions, screens/meetings, interviews. By setting a single focus per day or work session you can increase your productivity and continue to add more to your funnel.

Machines are eating your job search

Set up angelist, VentureLoop, and any others job listings. Rather than spending hours poring over job openings, let them come to you at daily or weekly intervals. Set different filters to make sure that you are getting a wider breadth of opportunities. Some of my filters were:

This type of alert could be set up by email (most services provide this), RSS or some kind of IFFT or Zapier hack that scrapes opportunities to a spreadsheet or database. Get creative. This can make for a good story when asked “how did you find us?".

DON’T rely on technology...

There are a ton of services focused on placing people at startups. I set up accounts, consisting of a profile, resume and some settings, for a few of these and didn’t get much back. The best connections tend to be personal or something you really chase after. Unless you have an overly accomplished resume (and don’t require the services) don’t expect a lot to come through here. I used these as a way to force myself to think about how I position myself and refine my story and profile. If something comes from these avenues, great! But don’t rely on them.

DO rely on people

Leverage your network. You may have been afraid during your first job to reach out to accomplished people in your network, and hopefully you spoke to them anyway. By now, you should be confident enough in what you've done, your knowledge of your industry and the startup ecosystem for those concerns to be nonexistent. If they persist or you are on the introverted side, you need a refresher in how simple this is and how willing most people are to give you advice or help you make connections. Make a commitment to reach out to X number of people per week. These can be totally casual and frank. Ask people in industries you are interested in or have experience in a similar role for what you’re looking at for help.

Make intros easy

When you do have an opportunity that you want to pursue, make the ask for an intro. When you make your outreach for each of the prospects you deem worth, search for common connections or a way in. Relationships are massive in this world and as we all know, an intro beats the best cover letter (or 10). Give your connections ammo to pass along to their colleagues, friends, bosses or investors. Use a self-contained, forwardable email (opens in a new tab)that can be passed on directly. Put time into these and don’t burn your connections by not following up properly or selling yourself for something that’s not really a fit.

Job searches can be exhausting and challenging but can be incredible transition periods for you. You have the opportunity to reflect over and over again about your experience and iterate on your personal narrative. There is a concrete goal at the end, but don’t forget to appreciate the process and your growth throughout it. Good luck!

  1. If you are solely interested in mega-growth companies, check out the resources on https://breakoutlist.com/ (opens in a new tab)

  2. You should absolutely go for broke on something that you are passionate about! These should be top priority, but not the only priority.

  3. Early stage companies may not have fully defined and specialized positions yet, which may or may not be what you're looking for.