Tag Archives: hiring

Hiring Startup Executives

I was meeting with a startup founder last week, and he started chatting about some advice he got after his latest round of investment about bringing in a senior management team. He then said he spent the last year doing that. I stopped him right there and asked “Are you batting .500?”. Only about half of those executives were still at the company, and the company promoted from within generally to fill those roles after the executives left. The reason I was able to ask about that batting average is that I have see this happen at many startups before. The new investor asks them to beef up their management team, so the founders recruit talent from bigger companies, and the company experiences, as this founder put it, “organ rejection” way too often.

This advice from investors to scaling companies is very common, but I wish those investors would provide more advice on who actually is a good fit for startup executive roles. Startups are very special animals, and they have different stages. Many founders look for executives at companies they want to emulate someday, but don’t test for if that executive can scale down to their smaller environment. There are many executives that are great for public companies, but terrible for startups, and many executives that are great at one stage of a startup, but terrible for others. What founders need to screen for, I might argue about all else, is adaptability and pragmatism.

Why is adaptability important? Because it will be something that is tested every day starting the first day. The startup will have less process, less infrastructure, and a different way of accomplishing things than the executive is used to. Executives that are poor fits for startup will try to copy and paste the approach from their (usually much bigger) former company without adapting it to stage, talent, or business model. It’s easy for founders to be fooled by this early on because they think “this is why I hired this person – to bring in best practices”. That is wrong. Great startup executives spend all their time starting out learning about how an organization works so they can create new processes and ways of accomplishing things that will enhance what the startup is already doing. When we brought on a VP of Marketing at GrubHub, she spent all her time soaking up what was going on and not making any personnel changes. It turns out she didn’t need to make many to be successful. We were growing faster, had a new brand and better coverage of our marketing initiatives by adding only two people and one consultant in the first year.

Why is pragmatism important? As many startups forgot over the last couple of years, startups are on a timer. The timer is the amount of runway you have, and what the startups needs to do is find a sustainable model before that timer gets to zero. Poor startup executives have their way of doing things, and that is usually correlated with needing to create a very big team. They will want to do this as soon as possible, with accelerates burn, shortening the runway before doing anything that will speed up the ability to find a sustainable model. I remember meeting with a new startup exec, and had her run me through her plan for building a team. She was in maybe her second week, and at the end of our conversation I counted at least 15 hires she needed to make. I thought, “this isn’t going work.” She lasted about six months. A good startup executive learns before hiring, and tries things before committing to them fully. Once they know something works, they try to build scale and infrastructure around it. A good startup executive thinks in terms of costs: opportunity costs, capital costs, and payroll. Good executives will trade on opportunity costs and capital costs before payroll because salaries are generally the most expensive and the hardest to change without serious morale implications (layoffs, salary reductions, et al.).

Startup founders shouldn’t feel like batting .500 is good in executive hiring. Let’s all strive to improve that average by searching for the right people from the start by testing for adaptability and pragmatism. You’ll hire a better team, cause less churn on your team, and be more productive.

Don’t Let Salary Negotiations Leak

If you’re managing people at your company, one thing you will have to do is negotiate compensation packages with people you are bringing onto your team. These negotiations are never anyone’s favorite activity, but they’re necessary and it’s important for someone coming into your team that they feel like they are getting compensated fairly. As a manager, this is frustrating because you generally need someone to start yesterday, and these negotiations push that start date out, if the person accepts, which they haven’t. There is a tendency of hiring managers to vent their frustration of this process with other members of the team. This is a mistake, and I’ll explain why.

If you’re not a hiring manager inside the company, someone negotiating their compensation to join feels like they’re already misaligned with you. You’re inspired by the company’s mission, you’re trying to build something great, and when you hear someone delaying joining you in that because of money, it creates a stigma that they just care about him/herself. What then happens when that person joins is they already have a stigma around them that they won’t be a team player. I have seen this happen multiple times before. What is already interesting is that this is exacerbated when the person negotiating is a woman. Women already naturally negotiate less for fear of backlash, and their co-workers prove them right when they do negotiate.

So, what do you do as a hiring manager? Do not divulge any details about the negotiation process to other people on the team. If someone asks if the person is joining, just say that you are still working on it. If that same person asks what is taking so long, say that hiring is a process, and it’s better for both sides not to rush.

How to Get a Job at a Technology Company After an MBA

Having been working in technology and startups for a decade and completing an MBA in the process, a frequent question I receive is how can an MBA graduate transfer into the technology industry post-graduation, and many times specifically, into a startup. This question has broken my rule of four: once a question has been asked of me four times, I write a blog post answering it for the masses. This post outlines my advice to those people.

Let’s Say the Hard Thing First: Most Startups Don’t Want You
The thing you have to understand about startups is that they are about belief. A (usually first time) founder with (usually) not much of an understanding of an industry decides s/he can take it on and make it better. If someones has that type of belief in him/herself, that person also believes they can learn all of the skills necessary to execute on their vision, but they don’t have any of those skills when they start. If things happen to go well, the founder/s quickly realize they do have some skills they can’t or don’t have the time to learn that are necessary to scale the business. So, what they look for in people they bring onto their teams is someone with a skill set that can fill a weakness of theirs or their teams. This usually means previous experience in startups as the challenges are so unique.

Most MBAs do not have any startup experience, and founders won’t be impressed if you won your business plan competition during school. They probably never wrote one anyway. If you don’t have a skill they need right now, they feel like they are wasting their time talking to you. In fact, the more likely a startup founder is to talk to you, the less likely it is going to be a successful startup.

Most startups also pay below market values, and MBAs tend to have salary requirements to help them pay down their debt. I remember interviewing MBAs for a position that would report to me. Almost all of them asked for more money in salary than I was making. Essentially, what happens is they don’t want your salary, and they don’t yet need your strategic skills. They need executional skills you probably don’t have.

The Baby Step: Start at an Established Tech Company
Most MBA are deep in debt, and they want to go head on in a new direction. Some times, that may work. But my advice for people wanting to get into startups is to take a baby step. Instead of targeting companies with 15-50 people, target established tech companies. The main reason for this is to build up the set of skills startups needs. Where can you learn those skills? From people that previously worked in startups. Many of those people are still working for what was a startup and is now a successful tech company. The bonus of this situation is that since these companies are bigger, they are more likely to value MBA skills and more likely to have training programs to help you learn the skills startups need. So, if you work at a, say, LinkedIn, for two years, you probably learn a thing or two that scales down to a startup. The other great thing about established tech companies is they are likely to offer internships for MBAs, which are critically important during the summer time off.

What to Do at an Established Tech Company
The next question becomes what to work on at an established tech company. This is a trade off between how much of your skills translate to what they need, and what you want to learn. Let’s say you were in finance before your MBA, and you want to get into marketing. Perhaps an FP&A position that focuses on marketing spend would be an ideal option as it gives you exposure into all the marketing data and probably a lot of the marketers you want to learn from. Perhaps there is a marketing position available that they can train you in at the start. That is ideal. If not, you may be able to transfer later as you learn the lingo.

The Bottom Line
Changing industries is a long term play. You can’t expect to just hop into a new industry with no expertise and get your ideal role at your ideal company. If that role is a role at a startup, play the long game by building skills at a larger company first and working with the right people to make sure that can translate a few years down the line.

Why You Are Your Title at Your Current Job, and Why You Want to Be

The Start-up of You
I just finished reading Reid Hoffman and Ben Casnocha’s The Start-up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career. It’s a great read about operating your career like a startup. I generally think that Reid Hoffman’s is one of the smartest entrepreneurs out there, and I’m supremely impressed with what LinkedIn has done, and how they’ve done it. I do take issue with one suggestion of the book, which, while good-natured, can have the opposite effect of what it suggests.

Reid suggests that individuals create their own story highlighting their competitive advantage as business professionals, which I agree with. One way he suggests to do that though is to basically create your own title. So, instead of making your LinkedIn headline “Online & Interactive Marketing Director at GrubHub”, he suggests it read more like “Experienced Marketing Manager in Online Marketing and Product Strategy”. I disagree with this suggestion entirely. My reasons coalesce nicely with my Personal Branding’s Not About You post, so I’ll reiterate a couple of those points.

Tyler Durden

First, I’ll tackle the entrepreneur case. If you are currently running your own business, it should be your goal to get that brand in front of as many people as possible. That means your optimal title would not be “Entrepreneur & Blogger” but “Founder, MyAwesomeStartup.com”, just so people see that URL. Second, if you’re not an entrepreneur, one of the key competitive advantages an employee or potential employee can have is showing other potential employers that they can be dedicated to the company they work for. So, if I know someone works for a certain startup, and has a title on LinkedIn that doesn’t mention it but only mentions things about them specifically, I know their heart’s not in that startup. That makes me question whether their heart can be in any company, or are they just all about themselves.

Part of what you are selling if you are looking for a job is that you can become part of a whole, and the best way to demonstrate that is by showing you’ve done that before. Optimizing your LinkedIn to be less company specific shows the opposite, and raises some flags. Employers want to know that you can work well with a team and develop a passion for their brand and not just your own personal brand or your side projects. These days, with personal branding being all the rage, many people can’t do that, which makes it precisely one of the competitive advantages Reid suggests you harvest in your career.

Is This an Interview or a Test?

I’ll split this post up into two parts, related to hiring for a position and interviewing for a position.


When hiring new people for your team, it’s as important that you choose a candidate based on what he or she can bring to the table as it is that a candidate choose your company based on how well the role suits them and their goals. At GrubHub.com, we strive to design interview processes that don’t just test if candidates will be successful or not in the role, but also display what the day-to-day role will be like to the candidate, so that they know this is a job they want to take. The end result is that you should know pretty damn well whether the candidate will be successful in the role, and the candidate will know pretty damn well if this is something they want to do, or a company they want to work for.

How do you design such a process? I suggest that at every step of the process, you design tests that simultaneously test whether a candidate is competent and also display what you’re looking for the candidate to do. For a data entry position, this might be a typing test. For an analyst position, it may be a case study done in Excel. If candidates don’t like to type or use Excel, it will be pretty clear they don’t want the job. If you’re having trouble thinking of a test, perhaps the job requires more definition. It is also important to test this for culture. This can be more difficult, but smart questions around how they like to work can get you most of the way there.

Pretty much every job interview I’ve had, all companies have done is talked to me. They’ve never tested me on what they want me to do in the role. Thinking smart about how you can test candidates instead of just talk to them helps both the employer and the candidate make a more informed decision.


If you are a candidate for a position and you don’t know if there will be a test of some sort or not, refer back to the first half of this post and think of tests you would prepare for the role you’re about to interview for if you were hiring for it. Are you ready for those tests? If not, maybe you should prepare for them. If you are a candidate for a position and feel there may not be an actual test of your skills, there are some ways for you to create your own test and pass it to make the company know you can do the role. In some cases, bringing a portfolio of past work and presenting it is a smart play. For a sales position, asking at the end what are the qualities they are looking for in a salesperson and then proceeding to pitch yourself as having those qualities is smart.

As a candidate for an job opening, you should go into an interview with the goal of getting across a few points about yourself that should make you desired for that position. These points aren’t necessarily the bullet points of the job spec, though that is a good place to start. For example, maybe the position is a senior position you don’t quite have the number of years experience to justify, but you’re confident you have some other qualities those that would have that level of experience don’t have. Your goal is to convince the interviewer that that these qualities you do have are more valuable than the experience of others. Maybe it’s your intelligence or your creativity.

Someone who interviews you for a position should be able to come away from your interview with at least a couple points that clearly define you as a candidate, and you should define those pre-interview instead of hoping they find two that show you in a positive light toward others. It amazes me how few people do this. Think about this. If you are a CEO about to go on the Today Show to talk about your business, would you have a couple things prepared to make sure you get across to that audience? Of course you would, so you should do that for a job interview as well. If you don’t know what the points you’re trying to communicate as a candidate are before an interview, you should postpone the interview until you do.