Do You Have a Hall Pass?

Growing up, I was a model child. A model daughter, a model student, I did what I was told, obeyed the rules, and always asked permission. Permission to go to the movies, permission to rearrange my bedroom furniture, permission to go to the bathroom at school. I was taught that obedience and deference were positive qualities, that they made me a "good girl." I believe my kindergarten report cards contained some measurement of my ability to "take direction" and "fit in socially," and my entire experience in the public school system was based on steering me towards the path of normalcy via standardized testing and groupthink.

This isn't an uncommon experience. You spend your most formative years in supplication to the world around you, so as an adult it quickly becomes apparent that the skills you've learned have not necessarily prepared you for being a confident and contributing member of society. For your whole life, you have been trained to obey, not to blaze your own path. You've been taught to take direction and follow the leader, skills that are still valued and rewarded by many companies who need drones to stay alive. These companies are large. They are lucrative. They are old. They thrive on hiring the adults who were once recipients of perfect attendance and citizenship awards in primary school.

But they are not doing anything particularly interesting.

As an entrepreneur, you have diverged from the path, probably because you saw a shortcut, or a more scenic route, or maybe you were wearing Nikes so you could run ahead of the pack. Either way, you did something a bit differently, and you're on your right path now; it's time to build out your company with the right people to help take you from inception to sustainability.

Please don't hire the drones.

Creative problem-solver

When people hear the word entrepreneur, they often imagine an individual who starts their own business. Entrepreneurs are intelligent, they are leaders, they enjoy taking risks, and they see the world differently than other people. They can see problems, and they can see ways to solve them. There are many people with these qualities who do not start companies. Hire these people. Develop your employees into being these people.

Anyone who has read The Lean Startup (and you should) or been a part of a failed company knows that founders and executives don't always make the right call. The wrong products are pushed or they don't see the possible consequences of the decisions they've made. When you have one leader and a bunch of followers, the leader only has herself to rely on when it comes to big decisions. That thought can be incredibly appealing, but it's also fairly dangerous. You're as limited as your own knowledge and experience, and your own ability to see potential problems before they become disasters. Surround yourself with knowledgeable, capable, innovative thinkers, and your own limitations can no longer stand in the way of the company's success.

This isn't always easy to do. Most startups and established tech companies profess to nurture such environments through open office spaces, open door policies, and whiteboard paint on the walls, but I have found that the majority of these are surface-level commitments to creativity, transparency, and communication. Just because the physical walls are down does not mean the mental walls have followed. A lot of potential is being wasted because creative, talented employees are too bogged-down in the mire of office politics to speak up when they see a problem or, more importantly, take the reins to develop a solution. More often than not, the culture of permission we have cultivated within our youth ends up backfiring in the workplace. We have all been privy to office gossip, the most damaging of which comes from the "followers."

Followers, after a lifetime of frustration, believe themselves to be martyrs, sacrificing their time working for a company that "just doesn't get it," or managers who "never listen." They complain, breed anger and resentment, and believe themselves to have all the answers. If only someone would see that and give them a management position, all of the company's problems would be solved, right? We've all worked with that guy. Some of us have been that guy. If they really have all of the answers, they should be doing something about it, not just yakking away to their peers about how they wish they could do something about it. It's one thing to spot problems and complain about them, it's another to spot them and solve them. This guy is no better than the office drone who never complains, but also never does anything but wait for the next assignment, either.

As you hire, you will inevitably come across the follower disguised as a leader; sometimes, all it really takes is a little freedom and respect to bring out their full potential. But, just as with any other relationship, once that person regards you or your company with contempt, the situation is unfixable. A loss of respect on either side in the workplace is impossible to correct with anything other than a gentle parting of ways; the longer you wait, the more likely their malice is to spread to their lunch mates. But assuming you're actively weeding out the bad eggs and hiring with leadership qualities in mind, the next step is to create an office culture that can allow leaders to flourish.

It's up to you, the company founder and leader, to dispense with ego and make it part of the culture that no one individual or team is God, and that the voice of dissent needs to be acknowledged. Instill in your company leaders and in yourself the values of trust and respect, and remember you're hiring people who will have a major effect on the success of your company. Give them the room they need to make the best contributions of which they are capable -- it will develop a team of loyal, talented, fulfilled employees. Not every employee can be a leader, but make sure you don't have any LINOS -- Leaders In Name Only.

Free them up to experiment, to make mistakes, to find unconventional solutions to problems, to take risks, and reward them when they do. As an entrepreneur, you know the road to success is often paved with small failures and the skeletons of incomplete ideas. Surround yourself with individuals who will ultimately make your company stronger, not simply toe the line. Your investors are willing to bet on you, that your idea, talent, and work ethic will make for a successful company. They don't want to have to step in and run it themselves, they trust you to do that. You, in turn, need to be treating your employees like investments -- give them the freedom and the support, and you will see a great ROI.

Let me know how it goes.

Jen

P.S. I'll be reading the suddenly wildly popular Holacracy this month and I'll be back to report on it. I'm pretty sure I'll love it.

Invest In Your IRA and Your Ad Ops Team

Everyone spends time wondering about their financial future. To be human is to daydream about being wealthy, or be fearful of being poor.

Start up founders are looking to their financial future on a daily basis. Which product will be the most lucrative? How can we monetize this feature? What will my investors say when I report last quarter's financials? What do our revenue projections need to look like to keep my employees happy and excited? What's my runway and how can I extend it? They're constantly thinking of the bottom line and of ways to increase it.

Especially during a funding round. 

Why then, isn't every start up investing in their advertising operations team?

Let's be honest. The collective wet dream of tech-savvy millennials everywhere is to have a sticky product with a subscription-model business plan. Netflix, Birchbox, the toilet paper industry, they all have it made in the shade. But not every content site can rely on users to regularly pay for access. The truth is that quite a few subscription-based services also have free, ad-supported services, and for a lot of sites, ad revenue is key to survival. 

When you begin your ad revenue-supported company you are going to invest in two very key components: great content and a platform on which to share it. For a long time, this will be your focus. Once you've gained enough traction to get a good number of viewers on your content, your next natural step will be to focus on monetization. So you go out, and find yourself an ad operations hire, and the money starts growing.

Great! Wonderful! You have a surplus, and your development and content teams have been running on Red Bull and promises for so long. They need new hires! Better tools! It's only natural that the surplus goes to growing those teams and filling other needs. And in six months, your content team has tripled in size and you're producing quality, interesting content at a 500% faster pace, and your development team has made the site responsive and decreased load times. With your increased visitor counts you are starting to attract some serious advertiser attention, and RFPs come pouring in. But after months of growth, your revenue suddenly plateaus, or even drops. What happened?

The one ad ops hire you brought on six, nine, twelve months ago is struggling. They're trying to handle all of this new work on their own, and their only tools are a free ad server and Google Docs.

For a year at Grooveshark, I was the only media planner, account coordinator, and trafficker for direct-sold campaigns. As our popularity exploded, I found myself handling fifteen RFPs a week, coordinating and trafficking thousands of dollars' worth of inventory each day, and working to maintain our relationships with agencies and representatives. I was working 12 hour days, ate lunch at my desk, and was barely keeping up. I was tired, and starting to make mistakes - mistakes that cost money - but there wasn't a budget for hiring in ad ops. I was ready to quit and take a nice, long winter's nap.

Behold the symptoms of ad ops burnout

Eventually the budget came along and I got to sleep more. But Grooveshark almost lost a loyal, hard-working, trained employee. In a startup environment, we all have to pitch in and work with what we've got to an extent, but don't make the mistake of rewarding other teams with hires and tools while thinking that since ad ops is newer, they can bootstrap for longer. You're just putting limitations on your revenue.

Let's approach this logically. If you've done your job well and hired the right ad ops professional for your company, they're going to naturally want to optimize for their job. And optimization equals less expenditure, more income. They're already in the mindset to get you more bang for your buck, so when they come to you and say "I need to hire," or "I need this tool," it means they need it to be able to get you more money. If they're spending all of their time and energy maintaining revenue, they don't have anything left with which to brainstorm and experiment on new revenue streams, or ways to cut costs. So by denying them help, you're denying revenue potential.

And that's just dumb.

Let me say it point blank: if you're an ad revenue-supported service, your ad revenue has to be your top priority. This is your income, the way you pay your employees, the thing that allows you to innovate, and what attracts investment and buyouts.

Think of investing in your ad ops team like you would invest in your own personal financial future. Short-term gain in the form of additional developers for flashy new features or a social media guru for Pinterest exposure both sound really awesome. But you have to do the necessary. You can't retire on short term gains. You retire by investing in something that gives you compounding interest with growth over time. And that's the ad ops team.

Make good choices,

Jen

One Fish, Two Fish

Quite possibly the most frustrating thing about working in ad operations occurs when it comes time to build out a team.

Unless you live in New York or San Francisco, you're going to find that there's a serious lack of experienced ad ops professionals. Most folks don't even know what ad operations is, let alone how to operate an ad server.

Can I list Microsoft Word as a skill?

As a small business owner, your time is much too precious for you to be spending hours in DFP each day trying to determine why your campaign progress is so low. For you, the days are too short, you can never get enough done. You don't want to waste weeks searching for an ad ops professional you can't afford, nor do you want to end up hiring a noob who doesn't know what an impression is.

Living and working at a large publisher in a college town for five years, I frequently found that I didn't have a choice. Nobody from NY or SF wanted to move to my town, so by default I was looking to hire people who had no ad ops experience and likely no relevant work experience at all. During the time I was there, I had to build out an ad ops team from scratch roughly three separate times, and I'm here to tell you it can be done.

Let's assume you're building a team from scratch, as well. After setting a budget, the very first thing you need to do is determine what kind of person you want working for you. What values are important to your company? What's the culture like? Who will best fit in? If you hire someone smart and resourceful but their personality is such that they won't get along with the rest of your team, they might work out for a little while but the odds are they will ultimately feel like an outsider and leave for another job. Don't fall into this trap and hire the wrong fit for your company culture - how your employees feel about each other is one thing you simply can't control, but you want to try to set them up for success.

The next thing to consider is what kind of skills they need to have. Obviously ad operations experience is a major plus, but you may not get so lucky. What work experience and interests would likely make for a great ad ops hire, you ask?

COMFORTABLE WITH NUMBERS

They will be working with numbers all day, every day. Manipulating them, experimenting with them, recording them, reporting on them. If they aren't comfortable with algebra-level mathematics, you're gonna have a bad time.

DETAIL-ORIENTED, WITH LOGIC AND PROBLEM-SOLVING SKILLS

Keeping campaigns on track means looking at them every. Single. Day. Spotting the little inconsistencies. Remembering to insert pixels where they need to be inserted. They will perform the same tasks hundreds of times and if they don't pay attention to the little things, you can bet something will go wrong. And no matter how diligent they are, the day will come when something's broken. When your revenue chain has a broken link, it's of the utmost importance that it gets repaired. They have to be able to track a problem down to the source and then resolve it quickly.

SELF-STARTERS

The ad space is always changing. Every day, new buzzwords are invented for things advertisers decide they suddenly care desperately about. Your ad ops team will be the primary knowledge resource for your sales team, your advertising partners, and you. They need to know what's going on in the industry, and they need to get your company in the best position for attracting business.

That's it! If you can suss out their skills in an interview and they have all of these personality traits, you've got a real winner on your hands. Bonus points if they have a background in statistics, data analysis, or marketing. And since you've hired someone with little to no experience, you'll be able to pay them a lower starting salary. Likely they will also feel very grateful for the opportunity, and if you play your management cards right, you will have the loyalty of this individual for a long time. Don't underestimate the power that believing in someone can have on their love for you and your company. It will go a long, long way.

But what's next? As self-starter-y as they may be, you can't just give them a desk and expect them to make you money right away. Though there are many pluses of hiring a future rockstar, it does come with one pretty major pain point: you have to take the time to train them. Like any good manager, you understand that by taking the time out now, you will create a self-sufficient team that will consistently take your revenue to the next level.

If you don't have the time, or don't have the knowledge, consider hiring an ad ops professional to train them for you. Even the most basic knowledge can go a long way, and since you've hired cheaply, you can afford a one-time investment, right?

May your resumes be ever plentiful,

Jen