Author Archives: Casey Winters

Hiring Startup Executives

February 16th, 2016

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.

Product-Market Fit Requires Arbitrage

January 25th, 2016

One of the most discussed topics for startup is product-market fit. Popularized by Marc Andreessen, product-market fit is defined as:

Product/market fit means being in a good market with a product that can satisfy that market.

Various growth people have attempted to quantify if you have reached product-market fit. Sean Ellis uses a survey model. Brian Balfour uses a cohort model. I prefer Brian’s approach here, but it’s missing an element that’s crucial to growing a business that I want to talk about.

First, let’s talk about what’s key about Brian’s model, a flattened retention curve. This is crucial as it shows a segment of people finding long term value in a product. So, let’s look at what the retention curve shows us. It shows us the usage rates of the aggregation of users during a period of time, say, one month. If you need help building a retention curve, read this. A retention curve that is a candidate for product-market fit looks like this:

The y axis is the percent of users doing the core action of a product. The x axis in this case is months, but it can be any time unit that makes sense for the business. What makes this usage pattern a candidate for product-market fit is that the curve flattens, and does fairly quickly i.e. less than one year. What else do you need to know if you are at product-market fit? Well, how much revenue that curve represents per user, and can I acquire more people at a price less than that revenue.

If you are a revenue generating business, a cohort analysis can determine a lifetime value. If the core action is revenue generating, you can do one cohort for number of people who did at least one action, and another cohort for actions per user during the period, and another cohort for average transaction size for those who did the core action. All of this together signifies a lifetime value (active users x times active x revenue per transaction).

Now, an important decision for every startup is how do you define lifetime. I prefer to simplify this question instead to what is your intended payback period. What that means is how long you are willing to wait for an amount spent on a new user to get paid back to the business via that user’s transactions. Obviously, every founder would like that to be on first purchase if possible, but that rarely is possible. The best way to answer this question is to look with your data how far out you can reasonably predict what users who come in today will do with some accuracy. For startups, this typically is not very far into the future, maybe three months. I typically advise startups to start at three months and increase it to six months over time. Later stage startups typically move to one year. I rarely would advise a company to have a payback period longer than one year as you need to start factoring in the time value of money, and predicting that far into the future is very hard for all but the most stable businesses.

So, if you have your retention curve and your payback period, to truly know if you are at product-market fit, you have to ask: can I acquire more customers at a price where I hit my payback period? If you can, you are at product-market fit, which means it’s time to focus on growth and scaling. If you can’t, you are not, and need to focus on improving your product. You either need to make more money per transaction or increase the amount of times users transact.

Some of you might be asking: what if you don’t have a business model yet? The answer is simple then. Have a retention curve that flattens, and be able to grow customers organically at that same curve. If you can’t do that and need to spend money on advertising to grow, you are not at product-market fit.

Other might also ask: what if you are a marketplace where acquisition can take place on both sides? If you acquire users on both sides at the wrong payback period, you’ll spend more than you’ll ever make. Well, most marketplaces use one side that they pay for to attract another side organically. Another strategy is to treat the supply side as a sunk cost because there are a finite amount of them. The last strategy here is to set very conservative payback periods on both supply and demand sides so that in addition they nowhere near add up to something more than the aggregate lifetime value for the company.

Currently listening to From Joy by Kyle Hall.

My Top Ten Posts of 2015

January 4th, 2016

Since I blogged much more regularly in 2015, my roommate suggested I should do a rundown of my most popular posts. This got me interested to see if there are any trends in the types of posts people want to read from me. Without further ado, here is the list:

1. How To Get A Job At A Technology Company After An MBA
2. A Primer on Startup SEO
3. More On Building Effective Relationships At Work
4. The Three Stages Of Online Marketplaces
5. Scaling Up, The Three Stages of a Startup and Common Scaling Mistakes
6. The Perils and Benefits of AB Testing
7. Loyalty Marketing Part I: Strategies and Segments
8. How To Build a Marketing Team at a Consumer Technology Company
9. First to Product-Market Scale
10. The Startup Marketing Funnel

I sort of expected one type of post to dominate, but the top ten list matches the breadth of the blog pretty well, with tactical (seo, loyalty marketing, ab testing), career advice (mbas getting into tech, relationship building), and company building (marketing teams, product-market scale, scaling up). So, this tells me not to change the breadth of the blog much.

I’d like to thank you all for reading. Onwards to 2016.

Currently listening to Periscope by D’arcangelo. If you’d like to hear my top music of 2015, you can listen here.

Don’t Let Salary Negotiations Leak

November 30th, 2015

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.

What’s Your Mobile Loop?

November 17th, 2015

One thing that is true about internet visitation habits and even more true about mobile visitation habits is the loop. The loop is the sequence of places you visit when you sit down at your computer or pick up your phone. What’s so interesting about the loop is how short it is for most people. With billions of web and millions of apps, most people’s loop only consist of a select few destinations. So, if you’re building an internet business, to be successful, you need to become part of quite a few users’ loops, or find a way to inject your content into the destinations that are in their loops. For example my mobile loop generally looks like this:

Gmail app (only if new content pushed there)
Feedly app
Twitter app
ESPN website
Amazon Kindle app (currently reading Sapiens)

My web loop looks like this:
Gmail
Feedly
Twitter
Quibb
Pinterest
ESPN
some niche sites for music

If you’re capable of becoming a part of people’s loop, you have what I call destination appeal. You are where people want to go to when they are bored. There is another way to have destination appeal, and that is to be very successful at branding, or to have a frequency not at the level of “I’m bored”, but still pretty high e.g. searching. I set the barrier there at monthly. For the former, Airbnb might not be in any of my loops, but it is the first place I go when I need a place to stay. For the latter, I don’t check Google unless I’m searching for something, but I search for things very frequently. See here for more musings on mobile apps and frequency.

If you are not in many people’s mobile loops, even if you can build destination appeal, you probably need to focus a lot of attention on injecting your content into apps that are commonly in people’s loops (Facebook, Instagram, Twitter, Pinterest). For some of these apps, this can be done organically, but much of it comes in the form of arbitrage i.e. paying less to be in front of users on that site than you will make from getting in front of them.

So, examine your loops. Is your company in your loop? If not, are you injecting your company’s content into your loop effectively?

Giving and Receiving Email Feedback at a Startup

November 10th, 2015

If your startup is anything like Pinterest, you receive a lot of email. Sometimes, that email is feedback on the things you’ve worked on. Since email only communicates 7% of what face to face communication does (with 55% of language being body language and 38% being tone of voice), email feedback can sometimes be misread. Email feedback can be given especially directly in a way that can be hurtful to the team it’s given to, making them defensive instead of receptive, because they fill in a tone and body language that isn’t there. I liken some kinds of email feedback I’ve received to someone walking in your house uninvited and starting the conversation like this:

“Man, what’s up with your door? You need to get that fixed. Oh man, those curtains are awful. Why on earth did you pick those? Is that your wife? You could have done better.”

Startups are making tradeoffs all the time. Everything is harsh prioritization with very limited resources. Employees at startups know this because they live and breathe it. But quite often, when startup employees give feedback to other startup employees, they forget that those people have to make the same kind of hard tradeoffs they do, and that might lead to some of the issues they’re emailing feedback on in the first place.

If you’ve gotten in the habit of giving this type of email feedback, a better way to give email feedback is to ask questions:

“Hey, I came across this experience today. Is it on your roadmap to take a look at this? If now, how did you come to that decision? Is there a experiment/document that explains this because I’m happy trouble understanding why this experience is this way? Here were some things I didn’t understand about it.”

If you’re on the receiving end of harsh email feedback, there are generally two things to think about. Firstly, if the email is to you personally, what I tell myself is to divorce the content from the tone, because the tone is in my imagination. A thought out response to the details of the email and why things are the way they are may seem to be annoying, but it’s worth it. What would be even better is if you point the person to a place they can learn about these things in the future.

If the email is sent to other members of your team, long term, you want to train your team on divorcing the tone as well. If you haven’t, you might need to use the email response to defend the team. Otherwise, they think you are not sticking up for them. What I do in this case is send an email defending the decisions as well as explaining them. Then, I will follow up with the email sender in person and tell them “Sorry for the harsh email. You really put my team on the defensive with the perceived tone of the post, and I felt I had to defend them. Next time, can you word your email a bit differently so we can focus on the issues instead of the team feeling like we have to defend ourselves?”

Currently listening to Sold Out by DJ Paypal.

Building Up Respect For a Product Team

November 2nd, 2015

An under-appreciated challenge in a tech company is creating a new product team and building it up from scratch into a valuable, high functioning, and well respected team. Having seen it done well and done poorly, much of what will make a team successful in doing this is pretty counter-intuitive. There is a well established sequence to doing this successfully in a high percentage way. There are two key components to optimize for:

  • team health
  • organizational understanding of the purpose of the team and its progress

Team Health
Team health is about trust between the individuals of the team and confidence of the team. It’s amazing how much of this is solved by having the team collaborate on a few successful projects out of the gate. It is tempting for a team to go after a huge opportunity right out of the gate, but this is typically a mistake as the team isn’t used to working with each other and won’t do its best work on its first project.

The right approach is to find small projects that have a high probability of success to start. This gets the team comfortable with each other, and they build up confidence in each other as well as the mission of the team as they see things ship that impact key metrics. How I like to prioritize projects is to forecast impact, effort, and probability of success. These can be guesses, but ideally a new team has quite a few high probability of success projects with low effort it can start with.

If you’re a team leader or product manager building a roadmap, you should be upfront that you’re prioritizing low effort, high probability of success projects to start for team building purposes. Otherwise, the team will be itching to start on high impact projects they might not be ready for. What happens when you start with one of those types of projects is that is by definition they are less likely to succeed, and with a new team working on it, that increases the project’s probability of not being successful. If the project isn’t successful, the team starts to doubt the mission of the team in general as that was supposed to be one of the highest impact projects for the team.

Organizational Understanding
Once a team is working well together and has some victories under its belt, it is time for the team leader to evangelize the team and its mission. I have seen high performance teams not do this second step as well, and it leads to things like organizational distrust and inability for the team to increase its headcount, which then impact overall team health.

So, how do you optimize for organizational understanding of a team? This depends a lot on the culture of an organization. What’s important to remember is that you need to optimize this understanding both above you and across from you. So, this means you need to increase understanding not just at the senior leadership level, but also to other peer teams of yours. This is not easy. I advise you start with senior leadership and optimize communication for whatever the way that team works. Do they like long strategy documents? Then write one. Do they have status updates? Leverage those.

Once senior leadership has a good understanding of why you exist, you need to address peer teams. For this, you need to understand how information diffuses at your organization. If product managers or engineering managers are hubs, start there. Email them directly with your strategy saying you wanted to give them a heads up as to what is going on with your team. Send them documents. Occasionally ask for feedback even if you don’t need it. Have a notes list? Over-communicate via that. Don’t be afraid to send emails about significant wins the team has had either. You also need to remember new employees and optimize for how they learn about things at the company.

There can be a tendency to just want to move fast with your team if you’re gelling and not invite feedback from other parts of the organization. This is a mistake. Lack of clarity for your team’s role outside your team can kill your progress if you’re not careful. You need to have the entire company on board with what your team is doing, or their lack of awareness could lead to distrust or roadblocks in the future. Addressing both team health and organizational understanding is the only way to have long term progress with a team in a growing organization.

Currently listening to Bizarster by Luke Vibert.

Scaling Up, The Three Stages of a Startup and Common Scaling Mistakes

October 26th, 2015

One of the biggest mistakes I’ve seen management make at startups is mis-managing how their startups scale. There are distinct stages of a startup. Early on, you prioritize speed over precision. Later on, you will trade off speed for understanding exactly what makes the numbers move. Early on, you prioritize self-managers and weed out employees that need a lot of support to be successful. Later on, you have to expand into developing people and training as most employees do not thrive being thrown into the deep end right away. I’ll talk about these stages, the right way to think about how you manage processes, teams, and rigor during these times, and some mistakes to avoid.

The Early Stage
“What are lemons? Okay, I’ll go find some.”

When you are early in a startup, you need to have a bias toward getting stuff done. Strategic thinking doesn’t matter a whole lot. You need to try things and see what works. You do not have a lot of data, so when you try things, you are looking for huge, noticeable gains in aggregate data. You’re not doing any AB testing. Your analytics investment is small, and you pay attention to a small number of metrics. Every investor question requires you to get back to them because you’ve never done that analysis before, or you don’t have enough data yet. You’re also looking to hire entrepreneurial, self-starting jack of all trades. These are people that spot opportunities and just immediately go work on them even if they don’t have much experience. They don’t ask for permission; they just go try to figure it out. Whether it’s manning the phones, pulling data, optimizing an Adwords account, they’ll do it. You use the cheapest tools you can find to achieve your needs. In the early stage, you also want to do as few things as possible, especially from a product perspective. The CEO is deciding many things on a day to day basis and manages almost everyone. The early stage is defined by a few rules:

  • Speed > Precision
  • Jack of all trades > Specialist
  • Done > Perfect
  • Focus > Breadth
  • Execution > Strategy
  • Hungry > Seasoned
  • Cheap > Robust
  • Teamwork > Process
  • Doers > Managers

The Middle Stage
“Let’s make some lemonade.”

In the middle stage, the things that were easy for jacks of all trades to cover with a few thousand visits or a few customers become impossible to maintain with more customers and more visits. So, you start to hire more specialized people, but still relatively hungry and more junior, and people are still doing multiple jobs. You bring in a few or promote some people to managers so the CEO doesn’t have tons of direct reports. The CEO isn’t aware of all the decisions being made, but keeps the company still very focused. The manager’s job is mainly to clear roadblocks for the executors, and they generally still do individual contributor work themselves. The managers handle some of the what is now cross-functional communication gaps, and put in some lightweight process to organize what’s going on. Focus is still extremely important, but you start to think about some expansion opportunities. You typically have over a year’s worth of data at this stage, so you expend some effort understanding seasonality, maybe making some projections. You have more metrics and formalize things like LTV, CPA, runway, and can generally answer investor questions when they are asked. You still mostly rely on SQL and Excel for detailed analysis instead of full dashboards or analytics suites. You do start to invest in some better tools since you have scaled beyond some of your initial choices. The new rules:

  • Speed with some precision
  • Specialist = Jack of all trades
  • Doers with some doer-managers
  • Focus > Breadth
  • Execution > Strategy
  • Hungry > Seasoned
  • Cheap and robust are more closely traded off
  • Some process
  • Done > Perfect

The Late Stage
“Screw your lemons. We ain’t going anywhere until I get 5 apples, ten oranges, and some kiwi”.

In the late stage, you have a large team, and you need full-time managers and a senior leadership team that can filter communication up and down. The CEO is approving large, strategic decisions made below him rather than driving every decision. Every individual contributor has a specialized role, is much more seasoned than before, and you’re appropriately staffed for every job you’ve prioritized to get done. You create a good amount of process to streamline work between teams. Shipping changes in product and marketing are hard to measure for effectiveness, and could have significant negative effects, so you rely on experiments to measure impact of your work and prevent catastrophe. You invest in analytics tools to easily understand the high level and detailed metrics without having to do custom work. You start to work on expansion opportunities as you max out your initial product and market’s value. You invest in sophisticated forecasts so you can understand if you’re off track and what causes are for fluctuations. You buy or build enterprise level tools to help specialists do their jobs better, whether that’s advanced analytics packages, marketing software, sales CRM systems, etc. You also start to codify specific strategies before executing instead of just trying different things and seeing what works. This is valuable to make sure you’re going in the right direction, and to build organizational confidence in different teams who don’t work so closely together anymore. The new, new rules:

  • Precision > Speed
  • Specialist > Jack of All Trades
  • Managers + Specialists
  • Breadth traded off with focus
  • Strategy just as important as execution
  • Seasoned > Hungry
  • Robust > Cheap
  • Process first
  • Perfect vs. done more clearly traded off

The Common Mistakes: Not Scaling and Scaling Too Early
The biggest mistake I see startups make is staying in the early stage longer than they should, or adapting the policies of the late stage too early. The former is typically led by the CEO. In this case, the CEO loves being hands-on and can’t let go to help the company scale. What this actually does is keep the company in the early stage and prevent it from growing. I’ve seen it happen. The best way to help the CEO realize he is entering a new stage is to have a board shepherd that process or former CEOs as mentors who have gone through this transition. It isn’t easy.

Conversely, many CEOs see what the best companies do and assume their company should do that, not recognizing the difference in stage between them. These companies invest in robust analytics and testing solutions before they have enough data to use them, hire full-time people managers too early who need to justify their existence by hiring big teams, invest in too much process that inhibits growth, and have a team of too many strategists and too few doers. Their burn rates are high, and their growth rates are low, and they typically need to raise huge rounds to continue operating. The best way to prevent companies from doing this is to have them recognize the stage they’re in and hire people appropriate for that stage. A too late stage of hire in an early company will cause massive distraction, culture shock, and an increased burn rate. These CEOs need to let the problems of their business guide them to scale up in stage, not emulate other companies at later stages. It isn’t about where you want to be, but where you are today that should judge how you run the company.

Currently listening to Hallucinogen by Kelela.