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What did the Startup Say???

This year, Skaled has been working around fifteen different startups, as well as building our own small company. There are certain nuances about startup culture that quickly become evident when you enter the world of entrepreneurs working their asses off to create something innovative and successful. I’ve begun collecting quotes that most every startup seems to utter at some point in the process — including us. Some of them reveal the awesomeness of the startup culture — some, not so much. But I have a feeling all of them will sound familiar…


 "Of course we have whiskey Fridays."

Because we’re startups, and we can. 


"We really need someone to own this project. F*&! it, let’s find some interns." 

Startups rely heavily on interns. Sometimes this is a good idea. Other times it’s a lazy avoidance of the tasks we hate — either way, interns regularly save our asses. 


Startup Interview: 

Candidate: ”I really want to work at a place where my voice can be heard.”

Interviewer: ”Ok, what is that voice and how do you want to use it?”

Candidate: “I’m open to anything and really want to work at a startup, so I’ll do whatever it takes.”

Translation: “I hate my job at “Stuffy Corporation”. Please let me in to magical startup land!”


Every NYC Startup:

"Of course New York is better. Why? Because it’s New York." 

We totally agree with this one, by the way.


Every San Francisco startup:

"New York has startups?? Does foursquare still count?" 



Person 1: “We really need a new salesperson.”

Person 2: “Can’t we just promote the marketing intern? They went to Harvard — I’m sure they can figure it out…Harvard bro.”

No. Not everyone can do sales. Stop pretending they can. 


First time CEO…

"Why is forecasting so hard?!" 

It just is. Get used to it, kids! 


VP of Sales: “We REALLY need this to close. Like, we have to.”

Salesperson: “Don’t we need everything to close…?”



"Have you seen that dude with the Google Glass??"

We all have. And we all secretly want one. 


"We track social media to help you optimize and monetize your campaigns!!!!"

(Speaking of which, follow us on Facebook and Twitter!) 

Do you have one to add? Let’s hear it! 



The Thankful Startup Employee

In honor of the season of giving thanks, I want to take a moment to look back at my past year with Skaled. It was a mix of uplifting triumphs and frustrating fails, but culminated in three major lessons learned that I’m so thankful Skaled has helped me cultivate.

 1. It is very RARELY an emergency. Do not panic.

 Before entering the startup world, I worked in book publishing. My entire work experience was with two massive organizations focused on details, details, details. These tiny pieces of huge puzzles were often made to seem earth shattering. It was not uncommon to see an assistant with a piece of paper clutched in hand, sprinting towards a meeting with something “urgent”. Whether this was merely my perception or the norm amongst working bookworms is up for debate, but this was the mindset I brought with me when I joined Skaled.

This type of panicky energy is devastating to a small office environment.

When I was stressed and antsy, my mood rippled directly to Jake, my CEO.  In those days it was just us – crammed into a client’s office. I quickly learned that my mental calm was essential to keeping our work environment productive. This skill has since translated directly to my sales. Remaining composed under pressure when a prospect objects on a big deal makes or breaks my ability to close. Being able to control my tone and articulate with the right amount of urgency, rather than panic, is crucial.

 2. Know when to hold ‘em.

Kenny Rogers said it best. “You got to know when to hold ‘em, know when to fold ‘em”.  One of the most exciting and terrifying aspects of a startup is that there are often questions without answers. There’s a lot of building the plane as you fly it, and constant iterations and pivots that happen mid flight. Picking your battles becomes very important. You don’t want to be the incessant squeaky wheel, but you also don’t want to allow mistakes to happen without correction.

 By raising your hand the right amount, you can challenge given solutions. That is what makes this ecosystem so much fun to work in. But it’s important to know when this is appropriate, and how to deliver your suggestions. I have come to love the days when I get to say, “No, wait a minute – I disagree.” Productive debate is encouraged in the startup world, and at Skaled, it has helped foster a culture of teamwork and participation.

3.  Saying “no” is just as important as saying “yes”.

I am inherently a people pleaser. While this quality has positive traits, it can also be one of the most deadly, when working in sales. Over promising to close a sale will likely end in a bad deal, rather than creating a strong relationship. To avoid this, I’ve learned to assess my allegiances and prioritize accordingly.

For example, when selling for a client, first and foremost my job is to make sales for that client. This also encompasses walking the tightrope between offering incentives, and still maintaining the integrity of the offer. I am still improving on this skill, but understanding how to navigate this situation has been a really valuable revelation.

Irwin O’Donnell



A Big Tree Has Roots That Spread: Why our best people can slow or hurt growth in small companies


We see this problem frequently with early stage sales departments in startups.

Hire one is a salesperson who works independently and gets the job done.

She’s a go-getter and joined the startup because she wanted more freedom. As the CEO, you’re thrilled because she requires little oversight and helps give product feedback when asked.  It seems like a great fit, and sometimes it can be if your goal is a sales team of five.

But if your goal is to grow in any department, past this small team number, this person can potentially hurt your growth rather than help it. (This can occur in sales, operations, engineering, editorial, etc.)

The problem is often exacerbated by a sense of seniority. These first hires have been with you for a while — they’re doing well, and they’ve likely developed close ties with other first hires at the company.

Here are two potential issues with the superstar first hires:

1. He’s resistant to leadership and those with skillsets that are different than his own, and pushes back on more hires within his department. 

2. She continues to focus on obtaining more accounts instead of working her current book of business.

This can all be avoided with a few difficult conversations early on. You must focus on setting your organization up thoughtfully from the start to avoid dealing with these issues down the line.

Here is what I suggest you do with your first to third hires in any department to short circuit this process.

1. Have a pre-hire conversation about the growth plans for the company. Make it clear that this person will be an important piece, but not the only piece of the puzzle.  They will have a boss and colleagues who will help to grow the organization.

This is a conversation you should have with team members, not only pre-hire, but frequently before and during any expansive growth phase. People need to feel comfortable with change, and opening a dialogue on future growth from the start will enable smoother transitions.

2. Focus on how you distribute accounts early on.

Many companies give their first 1-3 salespeople all of the Fortune 500, or their equivalent of the top 20% of all accounts.

Again, this doesn’t sound like a bad idea when these people are working the top opportunities for the business. However, the potential downside is two-fold as you’re attempting to grow.

First off, this set-up will motivate them to work a wide group of accounts rather than diving deeper on fewer opportunities. A salesperson with 500 accounts will likely give up easier on one than a salesperson with 200. 

Additionally, when you try to scale the organization, these people will have the top opportunities in their name and they’ll likely be reluctant to give them up. This is a sneaky conflict that many companies don’t catch until it’s too late. It may seem like there are still thousands of possible prospects not being worked, enabling you to easily hire 4-6 more people, but you miss the fact that most of the prime real estate is in your first few reps’ names as they’re “still working the accounts.”  

Think of a wide open field. There are only a few trees growing in this field, with plenty of space in between.  From a bird’s eye view, you see plenty of real estate left unclaimed, but below the surface it’s a different story. The trees’ roots have already spread and crowded the room to grow.  They are in everything that is fertile, leaving only less desirable land to the new hires.  

Communicating your goals early on is crucial in minimizing this struggle with growth.  You need a process that encourages reps to stick with prospects and to take accounts out of their name if they are not being worked.  Setting this expectation at the offset eliminates many difficult conversations when the team is expanding down the road.

Set up this structure early on. Ensure that everyone understands the process of scaling, and feels comfortable with their role in that process. This will foster a happy, thriving team that is open to growth. 



Coaching and Autonomy: How do you balance the two?


There is no doubt that many of the hundreds of sales reps I’ve led would say that my style involves regular feedback and coaching.  The same people might also say that once the coaching and feedback is implemented, my style then shifts towards increased autonomy.

Lately, I’ve been struggling with this paradigm —wanting to give more room for autonomy and letting people fail more often early on. I want to let them adapt, instead of hopping in with feedback along the way. Perhaps this is due to a shift in workforce dynamics and what people want from a job, but I’m still negotiating the balance of what works best in the long run.

What I do know is this: too much coaching early on nurtures dependence, and not enough structure early on leads to misaligned expectations and unnecessary turnover.

This is highly dependent on the individual, but I believe there are two best practices that have stood the test of time.  

            1. Growth is mandatory after a certain point. 

2. You must be open to people doing things differently early on as they may disrupt your process for the better.

Professional growth and a desire to improve are major areas that I screen for in the interview process. People that I hire need to have a strong desire to grow as a professional and as a person. This has multiple benefits as typically these people fit my style and tend to make progress faster.

At times, coaching doesn’t work — even with people that say they want feedback in order to improve.  There have been many times in the past when I’ve labeled such people as uncoachable.

As it turns out, however, some of them simply need more autonomy to try things out on their own — even if it means failing at first — before they are ready to utilize feedback.

I had a potential superstar sales rep in 2008 that gave me a dose of my own medicine when he coached me on leaving him the F$&! alone.  This rep was eventually promoted off my team and then twice more in the next three years.  He was extremely coachable but just needed a little more autonomy at first, to open him up to the coaching process.

Autonomy may lead to more mistakes early on, but with the right level of patience, it can produce equally effective outcomes in the long term. We all need a different mix of both coaching and autonomy at various points in our career. The key as a leader is to discover the right mix for you, your leaders, and your team.

What are your thoughts on the topic?  How do you balance the two?

Jake Dunlap, CEO



How do you interview for sales people? How to get it right…most of the time

Hiring salespeople is hard.  Even after years of experience and hundreds of hires, if I bat 80-90%, I am happy.  It is easy to spot the ones that would never work in a sales role, and rock stars can be few and far between. Finding the talent that’s stuck somewhere in the middle is where hiring gets tricky. The A+’s and F’s are obvious, but how do you find your B and C players? 

Many people look at sales as a role they could not be good at because they aren’t outgoing enough. On the flip side, many people go into sales because their friends/family say their personality makes them a great fit. This creates a group of overenthusiastic junior and mid-level sales people who show the characteristics that non-sales leaders attribute to sales success. How do you get past this and to the real details that separate the middle from the top and bottom? How do you identify the high potentials from the mediocre masses?

Remove emotion from the process

This can be tough while interviewing for sales. Most candidates think their personality makes them a fit, so they really turn it on in the interview, and become very likable.  They can also show a level of healthy aggression and interest in really wanting the job. This is easy to mistake as a sample of their ability to ask for the business and close.

The only way to remove emotion from the process is to have a regimented system that scores candidates similarly.  We teach a method called the four quadrants which forces you to pick four key skills for the role, develop 5-15 questions for each quadrant, and then assign quadrants to specific people involved in the interview process.

The quadrants that we find most effective more mid-level sales hires are:

Past experience - Is their experience relevant? Were they successful? What would their previous boss say needs improvement? Other non-sales experience that may add to their ability to do the job.

Passion/charisma - Removing emotion from evaluating does not mean it’s not important and you shouldn’t test for this skill. How would people describe your sales style? What are you passionate about in life? The key here is to listen how they talk about these things as opposed to just the content. 

Intelligence and critical thinking - This is one of the most important characteristics that many processes do not address. Intelligent people not only learn quicker, but can adjust and implement feedback – two skills critical for success within sales.

Integrity/Leadership – The competitive nature of sales opens can sometimes open the door for less than stellar behaviors. You need to know if getting ahead is more important to your candidate than doing the right thing. When have they had to make a tough call they knew would hurt their numbers? How would their peers describe them? 

Role-play is non-negotiable

Before buying a car, you always take it for a test drive. You need to see your candidate’s skills in action to get a good idea of how successful they will be. In order to get this right, I like to make sure of a few key pieces.

Be sure everyone role-plays the same scenario. We send candidates a case study followed by a 15 min coaching session before the interview. The coaching session is important because it details what you expect.  Some companies want candidates to just “figure it out”, but I have found a little coaching ahead of time goes a long way in improving the quality of the role-play. Often times, we will do a second role-play within a day of the first, to see if they can implement additional feedback.

Another important rule: no more than 3-4 people in the room or on the role play call. This creates a “too many cooks in the kitchen.” Too many opinions often make the feedback effective internally.

Drive group think out of the process

 Group think can be a problem when reviewing candidates in any environment, but this is especially true in startups. The company is usually made up of junior people with little to no formal training in how to interview. Their opinions on candidates are based off who they “like” or who they “think they would be good” instead of the skills described in the four quadrants.

Additionally, discussing the candidates as a team can muddy the waters of what each candidate actually thinks; the loudest or highest ranking person will typically win out. The hiring manager or person in charge of the interview process should talk to each person individually after they meet with the candidate. This will expose true opinions and make for a more accurate assessment. Force your people to interview and form opinions based on skill. You must try to keep your people focused on specific skills and ensure they do not taint their co-workers to eliminate group think.

 Interviewing for salespeople is not a hard science but the more scientific you can make it, the better off you will be.  Every time I go back to the unsuccessful hires I have made, I can typically attribute the misstep to one of these factors.  An organization that makes metrics driven decisions for accessing skills and then evaluates culture as a part of that hiring will make fewer missteps than their less structured counterparts.

Jake Dunlap, CEO




When an enterprise level prospect asks for a trial extension. 

This. Is. Everything.


When an enterprise level prospect asks for a trial extension. 

This. Is. Everything.



Building a Culture While Growing Your Company

There are obvious necessities that people think about when they are building a company. The endless conversations about resrouces the company needs to grow financially, how the product is developing and the forecasting of where the company will be in six months to a year. But one of the most important aspects of building a company that can often be overlooked is what your culture will look like. It can be difficult to try to establish this in the early stages, but building a foundation of culture can serve as a guideline for how the rest of the company will form. Here are a few tips on how to start building a successful culture:

Hire People You Like

This may seem a bit obvious, but a fantastic resume can often overshadow the person behind it. In most cases, especially start up world, more time is spent with your colleagues than anyone else. They are the people who will not only influence your day-to-day attitudes and activities, but could potentially be someone you will be partnered with for years to come.  When going through the hiring process, ask yourself if this is someone you would enjoy spending time with even if you didn’t work together. If you genuinely like your colleagues, work will be a much more enjoyable place to be.

 Build Relationships 

One of the first things people will tell you about personal relationships is that they are hard work; the same goes for professional relationships. They need to be developed and nurtured, or they will not progress. The easiest way to develop these relationships is spending time getting to know each other outside of the office. Learn about the interests of your colleagues and start participating! Someone is a hockey fan? Hit up the Rangers game as an office! Someone else is into ghosts? Go on a ghost tour together! These types of events will not only help you get to know each other but are also help to build the entire team into tight knit unit.

Communicate the Culture

You always want to make sure that everyone on the team is bought in to the culture you would like to build. The only way to do that is to have a clear idea of what is important to you and communicate it to your team. Each individual will have their own set of values and standards so it’s important to be on the same page. If you don’t have a basic set of guidelines (the image you want to give the clients, office dress code, what time you will start/end the day), you open the door for discrepancies. You are then building an office based on assumptions. It is almost guaranteed that all the business logistics of the company will be planned far in advance, so it is important to be transparent when planning expectations for culture as well.

The idea at any startup is for the organization to grow. There is sure to be long nights, successes and failures. Building a strong culture can prove to be the glue that holds everything together as you navigate the world of entrepreneurship.

Nicole Hipp, Skaled



What You Need to Know About Lead Generation - Keep it Interesting and Cut Ties Quickly

The day to day of sourcing companies and prospects to find the right contact can be difficult. Add in essentially stalking them to find the right email/call can become a grind for most people.  There is the constant frustration of spending 25 minutes to find the right person. Then there is the guessing of their correct email, which usually leads to having it bounce, followed by the five variations of the email address bouncing as well…So maybe you try your luck with a phone call, and get shut down there, too.

Repeating this process day in and day out can be both frustrating and mind numbing. How do we shift this paradigm? How do you turn this laborious process into an amazing job while keeping your department and individuals motivated? Also, how can you identify when it’s not going to work?

Look at the Statistics

Lead generation without a focus on optimization is extremely wasteful and demoralizing.  Adding the right tracking tools so your team and individuals can monitor and adjust best practices is critical to building a successful organization and keeping up spirits. The key metrics you must track are:

Open rate:This indicates how strong your subject line is

Clicks: this shows how compelling content is – do prospects want to know more?

Replies:  This will tell us how our messaging is received. Whether its “I want to set up a meeting,” “I have no interest,” or “I’m not the right person,” we can learn and adjust accordingly our segments or messaging.

Success:  We booked the meeting!

Having an organization that is set up to measure and focus on these numbers incentivizes everyone to focus on each step of the process and creates a feedback loop for your team.  They are now focused on success metrics and the complete cycle instead of just the frustration of sourcing and rejection. There are fantastic companies that allow you to track these measures, including industry leader ToutApp.

Clearly define success

Many times people in lead generation roles get focused on using daily activities as benchmarks for success as opposed to working towards a clear desired outcome. The focus turns to hitting 100 calls a day rather than booking 2-3 meetings from those calls. This can be a dangerous trap. Reps think they are successfully doing their job but they are missing the bigger picture.

To avoid this, continue to focus on rewarding the outcome.  If they are doing the activity but not setting meetings, look to analyze the output and coach on best practices. Unfortunately, many lead generation people will never get over this mindset, so know when you have to cut them loose.  If their continued focus is on activity versus outcome, it may be time to find a new hire.

Typically we look at the world of lead generation as a necessary stepping-stone to sales. It helps junior professionals become more comfortable with the sales process.  If you can consider these two points, you can not only motivate your top people, but also help to know when you need to cut ties as well.



Sales Forecasting in a startup. Why is it so hard?

Forecasting is one of the more difficult processes in a sales role, even at large, established organizations. With the chaos and uncertainty that surrounds early stage businesses, this process becomes much more arduous and ambiguous. Why is this? 

There are many obvious reasons why forecasting for startups isn’t easy. There are usually a low number of sales at the onset of a business, which means you don’t have reliable data or processes in place. Couple this with a lack of experience and the results will be inaccurate at best. However, if you know where most of the mistakes are made, successfully avoiding these roadblocks can greatly improve your forecasting ability.

1. Initial Sales Team is Usually Inexperienced in Forecasting

The first sales hires at a startup are typically more junior and have little experience as executive leaders. There is a high probability they have never been trained how to forecast accurately. Perhaps they can add a close date or know how to use opportunity stages but the criteria behind how they come to these conclusions is usually where the inexperience comes in.

So how can you get the most from your data with your green sales team? To start, make sure that all your opportunities are action based: a specific action that happened with the budget process, decision maker details, and timeline for each deal clearly noted. These are the three most critical pieces of information you need to make an accurate forecast. With this information in place, your reps can form an action based plan to move opportunities through the funnel and allow you to forecast close date much more accurately.

2. Your Sales Process is Still New

There are numerous different factors that can affect the life cycle of a sales process. With startups, the sales process is still new and usually a work in progress. This makes it tough to identify where the kinks are and how to improve. Are deals are running long because of product issues or is the sales process sloppy? This alone will cause a large variance in setting up reliable forecasting because we don’t know yet the difference between the two.

These complications are usually tough to mitigate. You can start by standardizing your sales process with the understanding that it will adapt and change over time.  It is critical to have a baseline process so you are able to create some initial benchmark that creates some form of a typical sales cycle.  Even if there are issues with the product, you can remove some of the variables of forecasting by keeping your process static.

3. Leader May Be Inexperienced Themselves

Finally, many startup leaders also do not have sales forecasting experience and rely on financial based models to project their results.

Financial models and round table meetings discussing what they “think” or “feel” will close this week never check for the key variables mentioned above: budget, timeline, and decision makers. Leaders not familiar with the sales process won’t know where to look for accurate forecasting and will become consistently frustrated and confused with why their sales people consistently miss targets and close dates.  

To avoid this, make sure you have mandatory fields for these variables so you can actually see how far along a deal has progressed. Don’t accept the “they really like it” as a main reason for buying; look at the facts of the case. This will also allow your sales reps to understand what you’re looking for during weekly meetings and will help them build a replicable sales process and forecasting system. Adding this criteria to each account conversation is crucial, especially if you and/or your sales team have a limited background in forecasting.

The key to a great sales forecast is to make sure you are clear on the criteria you need to know, you have a process in place to benchmark from, and you are coaching your team in how to gather the right information that is necessary to actually get a deal done. Forecasting can always be tricky, but starting with these steps above will provide a great foundation for building out your process.



Coaching up. Making Your Boss Better and Your Life Easier


Over the course of my career, I have been fortunate to have great leaders who have shown me how to manage up at the middle and executive levels of a company. 

However, there is a difference between politics and managing up. Doing the right thing to make your boss look good is not always “sucking up”. Below are three key learnings that you can implement tomorrow which will make your boss’ life, and therefore your life, much easier.

Show Me the Data!

Most of the time, your boss doesn’t enjoy being on your tail. But without data and a plan, it is tough to grant high autonomy in high-pressure situations.  If you have a plan, write it out and be prepared to back it up. If you have an idea, lay out the pros and cons, detail the data, and then present it. The beautiful part about this plan of attack is not only will you be doing your boss a favor, you will also be more organized with your own thoughts and ideas.

Caveat: Bring the right data.  Be sure your data is accurate and tells a complete story. Don’t be tempted to omit facts just to make your case look stronger.

Manage Expectations

Many people, myself included early on in my career, think that doing a good job equals success.  However, the phrase “good job” can be subjective, so be aware that your boss may have a different idea of what equals a “good job.”

When I was 26, I went to my director of sales and told him that I wanted to be a leader in his group based on the fact that I was consistently crushing my quota. He looked at me and said that my perspective was flawed. For him, he chose leaders based on top performance in daily activities and those who spent time helping other team members.

With eyes now open to what equaled success in his eyes, I had an accurate roadmap to achieve my goal.

A few months after our conversation, a leadership role opened up. I was up against a woman who had relocated to that specific market, had been with the company for nearly 3 years, and had higher sales numbers than I did. But because I understood my director’s expectations, I had worked on daily productivity and teamwork, and I was chosen for the position.

No Surprises with Mistakes

Missing a deadline is bound to happen from time to time. However, not raising your hand and asking for help in time to effect the outcome is a different story.  Your project is a small piece of your boss’ responsibilities. Surprising the boss with a mistake close to the deadline means they have little time and resources to correct it, and they are the one with egg on their face. If you get off track, take action and alert your boss of the situation. Own your mistakes and learn from them. Missteps and oversights will happen, but nothing is worse than excuses about how the dog ate your homework.  

By giving your boss the tools they need to make great decisions, you make your boss the hero. Have a clear plan, understand their expectations, and make sure surprises don’t come up. This will not only be appreciated by your higher-ups, but will cement you as a valuable member of their team.