Keith Cowing

Keith Cowing

Product guy. Entrepreneur.
Career advisor. Read bio

7 Rules for Getting Hired at a Startup

October 3, 2011

Working at a startup is a drastically different experience from working at a large company. Your office space is different, your job is different, your pressures are different, and even your boss is different. So why would you approach getting a job at a startup the same way you approach getting a job at a big company? Many people do and it’s a big mistake. After spending a lot of time reviewing candidates and hiring team members, here are seven of my rules for getting hired at a startup.

1. Engage with the company on social media Every startup is on Facebook and Twitter and they’re fighting for exposure. Use that to your advantage. List your target companies, start conversations with them on Twitter, post insightful thoughts on their Facebook walls, and listen to what they’re saying. Startups are run by small, tight-knit teams, and there are real people behind those accounts. Engage with the company early and learn about them before you ask for a job.

2. Do NOT mail a word doc resume and cover letter I get lots of emails for people seeking jobs at Seamless Receipts. By necessity, I apply a quick set of filters and either flag the person as interesting (to be researched), respond to set up a meeting, or simply delete the message. If you send a Word doc it shows that you didn’t even take the time to PDF it. If you send a resume, send a PDF. What I much prefer is a link to a well-written LinkedIn profile and any relevant websites (such as your blog). LinkedIn should clearly describe your education, your work experience, your successes, and your specific interests as a professional. If there is a powerful message on your resume that doesn’t come across on LinkedIn, then either update your profile or highlight those points in the body of your email. Additionally, Never send a cover letter as an attachment. If you apply to a job at a big company, fine, send a cover letter – they might expect it. But if you’re sending a busy entrepreneur an email, the email is your cover letter! Do not make them open a separate document because they probably won’t. Make the communication short, succinct, and easy to respond to. Making a specific request is better than simply saying you’re interested (ask for a meeting, a brief phone call, etc.).

3. Do your diligence (this is for your sake too) Get to know a startup well. Read about the team, their background, their successes and failures, their investors, their competitors, and get to know their market. When you talk to them in-person it should be an interesting conversation about the battles they’re fighting. You shouldn’t learn anything in an interview that you could have learned with an hour on Google ahead of time. Entrepreneurs want to hire people who are proactive and know what they’re getting into. If you don’t learn the details about the company you want to join before considering a career move (a major, life-changing decision) then why should the entrepreneur think that you will do your homework before pitching a prospective client or making a technology decision? Behavioral patterns are important, so don’t go into an interview and tell someone that you don’t know much about their company except what you read on their website.

4. Start doing your job during the interview process A lot of hires happen through personal networks because referrals provide the best filter for people you can trust. If you are not getting hired through a referral, expect the interview process to be thorough, especially for senior roles. In a small company you will have a tremendous impact on whether or not the business is successful. Just as important, you will have a large impact on the atmosphere in the office. One bad apple truly can ruin the bunch. Taking on an employee is as risky for a startup as it is for you. Entrepreneurs need to know that you excel at a level above your peers and can be immediately productive. The best way to prove this is to take on a project. There is usually a creative way to propose a project that has a small level of commitment, but lets you demonstrate your abilities. Additionally, this gives you a much better sense of how well you work together, which is critical for both sides to know. If it doesn’t make sense for the situation, at least find a way to spend time white boarding technology ideas, sales strategies, or relevant issues for the role. Going through the process of analyzing and solving a problem with the team is a great way to preview your working relationship. Resumes and small talk are nice, but they do not simulate what it will be like to tackle a difficult problem together, in a small office, for hours on end.

5. Make it personal When you join a small business, it’s not just a job. You are joining a team and probably a team full of personalities. A huge part of whether or not you mesh with the company will be based on your personality and how you interact with the team. That is not superficial, that is real. Culture matters, personality matters, and how much you enjoy spending time with your team matters. Joining a startup is like going to battle every day. If you like the people you are in the trenches with, then the battle is fun and exciting. You will enjoy the challenges, the late evenings, and the pressure of working in a high-risk, high-reward role.

6. Show, don’t tell Talk is cheap. When demonstrating your abilities, don’t talk generically about how you’re a diligent, hard-working go-getter (could describe anybody). Show the last site you built. Describe the revenue boost you generated over the last quarter. Showcase a product you delivered and describe the go-to-market strategy you used to get traction. Whatever type of role you are looking for (engineering, sales, marketing, finance, etc.), the company wants to know that their investment in you will immediately start paying off. So prove to them that it will. If you can’t yet – then take on a project that will prove it. Propose an extra project at work, build something on the side, help a friend launch their company. Excuses abound everywhere and ideas are cheap. The true definition of an entrepreneur is somebody who takes the initiative to take those baby steps and move forward. Little by little, every day. Rome wasn’t built in a day and neither was Amazon, Google, or Apple. So start now and build something.

7. Hit the ground sprinting Speed and timing are crucial when launching a new venture. Hastily making progress, building a team, delivering a product, securing partnerships, landing clients (or users), bringing in funding, and iterating before your cash runs out is not easy. It requires hard work and constant execution. If you meander, you may find yourself terribly lost. If you sprint out of the gate you will learn in a short amount of time whether or not your plan holds up. Most products and business models need to be iterated on and fine-tuned over time. Learn quickly, fail fast, adjust and move forward. Startups can’t support this model unless the whole team is in-sync. So be quick to respond, show that you can think on your feet, and make it obvious that you’ll hit the ground sprinting.

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