Category Archives: Sales

So You Want to Build a Sales Team

Every Start-up hits the point where they move from having a couple of sales people to building a sales team.  This might be because sales are taking off or most-likely because you took some funding and were told you had to scale your Demand Generation and Sales.

If only, it was as simple as hiring more sales people. 

Here is some quick and simple advice to help you avoid some common mistakes in building a sales team based on the questions I get most often.

Understand your target customers.  Who is buying your product today and is who is your target customer for the next 18 months?  So much money is wasted because people either hire too senior or too junior of sales people to tackle the challenges of selling to the clients they can close.

Is your sale, transactional and focused on the SMB market or is your solution focused on Enterprise customers?  These are completely different sales and need completely different people. The clearer you are, the less mistakes you will make.

Do you have a sales leader?  You can have 3,4,5 sales people without a true sales leader but if you want to scale a team, you have to hire a professional sales manager.  Alignment, again, is key but they also need to have a sales process they can use to develop the sales people into a team.

They will also help you sniff through a good story and get the right people who can actually do the job.

If you don’t have a sales leader, pay one you know at another company and have them come and help you hire sales people until you find one. 

You will want a simple comp plan….   My Advice…. For One time purchases go with straight percentage and for SAAS, go with 1 to 2X monthly revenue.   Your sales leader will build on accelerators.  Remember, the plan should drive the outcome you want.

You are going to need an CRM.  You can choose to start with Salesforce, Insightly, or Zoho,

Most likely, you will end up on Salesforce eventually but by no means do you have to start there as it can be expensive and not necessary until you start integrating other areas of the business.  You do need a sales funnel and visibility.  Start running your sales team from dashboards as quickly as you can to build that culture from the beginning.

Don’t hire dramatically faster than you can scale Demand Gen.

You want to build in the culture of prospecting from the beginning but you do not want a team where at least 30% of the leads are not uncovered through Marketing. If you have more sales people than leads, you are hiring too fast and need to really focus on scaling Demand Gen to avoid wasting money.

If you have too much Demand Gen, your sales team will get fat and will never prospect.  Sounds funny to have too much Demand Gen, but if your sales people can make their number based on incoming leads, you need to hire more sales people.  Otherwise, this will have cultural ramifications for a long time.  Trust me, if there is a limited number of leads, the sales team will work each one of them like gold

Here is a rule I use…

I want the Sales team to uncover at least 50% of their own opportunities.  With all of the tools out there from LinkedIn Sales Navigator, to ClearBit Connect you do not have to rely on cold-calling but you do need to prospect.

Hope this helps.  We will cover Direct or Channel Sales at a different Time.

Let me know the tools you find most valuable and how I can help.  Let’s build great teams together.







2016 – Give the Gift of Feedback

Throughout the workplace, people are emerging back from vacations, turning their calendars and perhaps wishing they could push the snooze button for one more day…. Just perhaps

The dawn of 2016 also opens the season of annual performance reviews.  This tends to make people want to crawl back under the covers as managers deliver 10-20 of these reports.

Can I challenge you to embrace this season and encourage you to see feedback as a gift that is worth giving; not just once or twice a year?  Let’s make 2016 the year you give people continual and concrete feedback.  Creating a feedback rich environment will cement your culture as a place where “everyone gets better everyday.”

As a leader, it is one of the most significant changes you can make to increase the level of performance, alignment and satisfaction of your employees and co-workers.

Why is this:

  1. Most people are never told, specifically, that they are doing well and where they can improve. You might be the first person to give them effective feedback.
  2. Most people are never shown the outcome of their behavior.
  3. Most people never get supportive feedback that is specific and applicable.
  4. Most people are never told of their blind-spots, until it is too late.
  5. Most people crave it… Certainly the kids of people you want on your team do.

If any of the above is true, why don’t we do it more.

Carole Rubin states it this way..  “But providing feedback to a colleague or a friend can be difficult and scary, especially when it concerns something that is hurting your company or your relationship with that person. That fear, Robin says, is based on a belief that many hold that constructive criticism will harm the relationship…. The reality is that feedback can actually strengthen a relationship, because knowing that another person is going to tell it to you straight creates and builds trust….Taking the risk of providing feedback shows the other person that you are invested in the relationship and willing to take the time to help fix the issue.”

No matter where you have been…Here are some places to start….

  1. Feedback Needs to be Constructive:

Feedback is applying how actions contributed or detracted from the team and its overall performance. Random criticism and nit-picking is not the feedback that will get you anywhere.  Might make you feel better but it not worth the cost.

There is an urban legend of IBM founder Thomas Watson….  The legend goes that a top salesman lost $5 million on a project he’d been working on.

Called to see the boss, the salesman prepared to be fired. However, once he was ushered into Watson’s office, he was surprised to find that Watson cheerfully started discussing the next big project they were planning.

Dazed and confused the salesman asked Watson if he was going to fire him for the loss.  “Fire you?” responded Watson. “Why would we want to fire you when we’ve just spent $5 million training you up?”

The Point:  There are times, you will have to fire someone but if you want an open environment where people get better, you have to do it together, and you have to lead this from the top.  Feedback is not shaming, it is an opportunity to get better.

2.  Feedback Needs to be Consistent

If Feedback is saved for a couple times and year and worse yet, tied to the same time of pay increases, people are so geared up for it that they can not really take it in.  There is just too much emotion.  People also need feedback more quickly on behavior so that these changes can be applied and recognized.

People can only absorb 1-2 things at at time.  If changing behavior was easy…  well, then it would be easy.  It is just not.  Until the robots are ready…  Anyway, think about how you like to get feedback and start there.

Too often we put off giving feedback when someone does something that bugs us. We say, “it’s not a big deal.”  Over time, the person does the same thing again, and again. Now we are hacked off at the person.  This is a leadership issue, not a behavioral one.

The Point.  What gets measured, gets done.  When we focus on constant, consistent feedback, we take the emotion out of it and put the focus on constant and consistent improvement.

3.  Feedback Needs to Focused on Person and Progress

In order for someone to receive and apply feedback, there are a couple of vitals.

They Trust You

OK, there is really ONE vital element for feedback to be effective.

How do you build this trust?

  • Tie Feedback to Their Goals.  Example.”  I know you want to lead this team one day….
  • Make the Feedback Behavior Specific.  This behavior caused this reaction. Specific feedback influences specific behavior.  General feedback changes general behavior.
  • Balance Positive and Negative Feedback
  • Be Transparent – Be open to talking about your journey
  • Be Open and Seek Out Feedback about yourself.

Giving effective come more naturally for some then others but there is no excuse. you may have to practice.  So get out there and practice.  Ask for forgiveness if you come on too strong or unintentionally offend someone.  Let’s get better… Everyday.

So, You Want To Sell the Enterprise?

Every Start-up reaches that point where the “Enterprise” segment becomes the next Step… I mean, just look at all that money. They are big, their logos would look so sexy on your web-site and again, look at all that money.

For some, it is not the appropriate next step. More often, businesses get sunk because of the amount of resources it takes to swim in this pond.

It is OK to dip your toe in and determine what it will take for you to sell to the Enterprise.

Before we start, just because you have soled to a couple of larger organizations have bought from you, does not lean you already to proactively sell to the Enterprise. Listen to the early adopters but most in the Enterprise space are not.

You won’t be perfect at it so move forward and keep getting better. Have an answer for what is below. Even if it not perfect, just don’t be surprised. You need to look like you have been there, even if you haven’t

First, Define what Enterprise means to you. … Global 2000. Fortune 1000, Companies over $1B, Companies over 5000 employees, Large Law Firms, etc. If you can’t define it, please don’t try and sell to it. Remember, Aim small, miss small as you get started. Test everything on your way to big.

Next, Is your product/service Ready?   Time to take a long look in the mirror and ask a couple hard questions:

  • Do we provide value to this segment? What changes need to be made?
  • Does the product of service work the way a large organization will use it?
  • Can we actually roll it out? Even SAAS has to scale.

Now, Can you sell it?

Sales Cycles tend to be much longer as the deals get bigger. Weeks will become months and it will be weeks even after you hear, “yes.”  Here are some of the top things you will have to prepare for:

  1. Security – Whether it is specific regulations like HIPPA, GLBA, or ISO27001, every Enterprise customer has a least one Security Expert whose job it seems like it just to say, “Will this work with our security?”
  2. Liability – You may not have had to deal with this before but get ready and make sure your contracts are tight and your contract team has experience.
  3. Professional Procurement – Welcome to working with people where buying things is their full-time job. They are judged by their ability to get a good deal for their company. .. Not yours. They get things done but also make sure it follows a process. This will not speed up your deal.
  4. Pricing – Don’t, Don’t, Don’t fall into the trap of giving pricing early. You will feel this pricing pressure throughout the sales process. This is a negotiation… from Beginning to End. Too often the eager beaver is stuck eating a toothpick because he gave away the tree.
  5. RFP – These three letters (or the just as nefarious RIP and RFQ) have been written on more tombstones of start-ups who had an innovative solution. You job at this level is to get to the next step. Don’t provide more resources than are necessary but make sure you nail it.
  6. Contracts – The negotiation, the process and the contracts will all of a sudden get longer and
  7. Size – People have to believe your company will be around. People will not risk their job for even a better technology if they think there is a chance. Your bigger competition will drop landmines all over this one.
  8. Cost of Sales – Sales people become more expensive, Cost of sales go up with travel. Make sure you test your way into this as well. Make sure there is substance in your sales team and leaders, not just flash.
  9. Cost of Support – Welcome to Quarterly Business Review, metrics, etc. These customers are going to want a dedicated person or team. They will stand in line for resolution.

Many SAAS and Platform Start-Up companies today are making a killing in the SMB and Mid-Market. Fewer of them have made a significant impact in enterprise. Eventually, you will need to navigate this jump into the ocean of Enterprise Selling like Salesforce, LinkedIn, etc.

We did not touch on using a Reseller Network, VAR and Partners to sell. We will touch on that one later.

You may decide to not play, yet. Continue to let the early adopters teach you as you go. Enterprise Selling will change how your organization Goes-to-Market, so go in with Eyes Wide Open.

What Did I Miss? Would love your thoughts.

No Mirage, No Silver Bullet… Now Get to Work

In movies, we often see people lost in the desert and the inevitably come upon a mirage, an optical illusion of water. This is caused by the heat reflection on the sand or the road.

Reason gives way to this false hope and people are driven toward their ultimate doom.

Building a company, a team, an organization or a church can often feel like a long walk in the desert and on this journey we can be tempted to fix our gaze on things way out in the distance.

This can be helpful if it is a mile marker that marks that you are on the right path. If it looks like it’s your solution, it is probably a mirage.

If you are not careful, this will become a fixation.

Here is what it sounds like…

“If we can Only Get…

  • The Next Round of Funding
  • That Executive
  • A New Building
  • That Next Client
  • That Merger

then we will be all set.”

The Truth is a Mirage, no matter how tempting, is just another pile of sand. There is no silver bullet for building an impactful company.

Success looks like waking up every morning, putting the right people in the right places, focusing on your top priorities, working your butt off, honestly assessing, getting smarter and then waking up the next day and doing it al over again.

The quick fix is sexy but the quick fix is a mirage, so stop focusing there and don’t let others do it either.

Focus on your Vision, your Fundamentals, the Value you provide and your processes that will get you there.

Impactful companies and team are built by providing value. They attract and focus on hiring and developing great people and building great products. They do it day in a day out.

Keep your focus on the things that really matter, make tough decisions, keep your good people with you and stay out of the desert.

Always Be Qualifying

Wait!!! We didn’t win the deal. Wait!!! You decided to go with another Vendor!!! I thought we had agreed that we were doing this. I thought we had this locked up. What do you mean you went with someone else?

Ever had one of those meetings? Whether you are sales person talking to a “Sure” prospect that went south, hearing an acquisition target that sold their company to someone else or an executive talking to a “surprised” sales-person who is shocked the deal went south, it is perhaps the most frustrating meeting you will ever had. The deal went south all you are left with is frustration and the cost of going after that deal.

What if you could build a process that much more predictable? What if you could identify earlier in the process who was a good target and who wasn’t? What if you could align your time, talent, focus and resources on the deals that actually have a chance?

The good news is that you can. The key is not to be a better negotiator, even though that helps. The key is to become a world class Qualifier.

While, we can’t make people buy, we need to develop real rigor to tell a good prospect earlier on and then continue to qualify them throughout the process.

The truth is that only 5-50% of all potential people who walk into your store, call -in or respond to a marketing campaign will buy your solution.

This means, depending on your business, that up to 95% of potential people are actually a waste of time when it comes to closing business. It is with that backdrop that highlights the importance of qualifying deals and buyers. Optimism is an incredible attribute that keeps us motivated.

Optimism, however, is not the basis of a good strategy as it will cause you not only believe deals will close when they won’t but it will also be the root of wasting a ton of time, focus and money on deals and prospects that really have not chance. Talk about a double whammy. You are setting yourself for a tom of frustration.

Years, ago in the movie Glengarry Glen Ross, Alec Baldwin popularized the Acronym ABC:

  • Always
  • Be
  • Closing

Since that day, thousands of sales managers have repeated that phrase in sales meetings around the globe. Buying has changed a lot and we need to close the door on this and embrace the future of selling.

Good Qualifying kicks “Good Closing’s” butt everyday of the week and twice on the last day of the month.

A much more effective Statement would be:

  • Always
  • Be
  • Qualifying

I grant you, it is not as catchy. But this is much more effective as you will make you’re your time, effort, focus are all focused on people who will actually make a decision.

So how do you Qualify?

(While I am framing this around the sales process, this process is applicable and adaptable to everything from finding employers and employees to sales to dating. Dating is the ultimate qualifying process and I think we would all agree that the effort of qualifying in that area should not be compromised any less than at our companies.)

Let’s get to it…

I will tie these to actual sales stages in a post later this week. For this post, think of your sales stages in 3 large stages. Depending on your selling process, this process can take anywhere from 5 minutes for selling apples on the side of the road to 2 years for selling an airplane.

There are essential elements in each stage and then there are other “Nice to have Elements” in qualifying a deal. For this post, let’s just deal with the essentials.

Early Qualification – Before you propose

  • Pain – Is there an actual company or personal pain with their current solution?
  • Money – Is there money to solve the problem? What are they currently spending?
  • Engagement – Are they actually willing to be part of this process? If they are just looking for price or they are not responsive to you at all, they are not likely interested and your chance of closing this are right next to ZERO. I told you it wasn’t that different than dating. This is the most important one.
  • Need – Is there an actual reason they are contacting you?
  • Technical requirements – You will gather these over time but vital to understand if there is a show-stopper that you can’t do.
  • Current solution – What are the barriers to making a change.? Change is the hardest thing people will do. IT is not easy and should not be minimized.

* Many processes will include Authority in this area. It is good to ask, but most prospects will “stretch the truth” here you will believe you are talking to a decision maker when you are not. If you always assume that you are not dealing with the decision maker until the proposal Stage, you will be a good position.

Proposal – Actually Presenting the Deal

As advice, qualify the crud out of the contacts before you present pricing or your recommended solution.

For large or significant deals, always try and deliver this proposal verbally, over web-ex, in person, before you ever give it in writing. Once you have given a prospect a written proposal, they do not need you for anything and you will notice most will stop calling after they get it.

Here is what you need to understand before you present pricing or your final recommendation:

  • Buying process – Who else will see this? Are you presenting to decision makers or do you have to sell through one of their people?
  • Reaffirm Budget
  • Criteria for decision-making – What is most important?
  • Competition
  • Timeline for making a Decision

Once presented get feedback so you can make all necessary edits before you send it. Remember, once you send a written proposal or pricing, they don’t need you for anything else and will assume they have your best deal. Even if you are just delivering budget pricing, you do it in writing, you have given away your leverage.

Get Direct and Specific Feedback

Stack-rank against completion

What else do they want to see?

Did this meet their needs?

Are we wining?

Negotiation – Between Proposing and Closing the Deal.

Congrats, they have verbally told you they are moving forward. Most people rest on this and forget to keep qualifying. It is Amazing how many done deals get blown up at this stage. This is preventable. Let’s look at how to keep qualifying and minimize the amount of surprises.

Engagement – We qualify this in the beginning. Define the process, timeline and milestones. Make sure you assign you and them tasks. Are people hitting their timelines?

Competition – Do they have a current vendor? Does their current vendor get a chance to keep the business? Are they moving down this road with multiple vendors?

What are the big issues to be ironed out in legal, roll-out, customization, etc.

Transition to implementation – Are they willing to start to take ownership of the roll-out?

A rigorous qualifying program is not easy and sometimes as we all want to believe the best about every deal, every prospect and that everyone is being completely up-front with us all the time.

The evidence would point out that they are not. While a good, disciplined and rigorous qualifying process is not a magic wand or a silver bullet, it is the best think you can do to make sure your time, talent, resources , money and attention are focused on the deals that actually have the best chance to close and that is why you are in business in the first place.

You want to get the deal closed…




Letter From Sales… Get the Most Out of Your Sales Team

Dear Boss (VP Sales, CEO, President, Owner, Manager, GM, VP, etc.)

Hi, I am your best sales person. There is a lot being written about me lately and the affect I may or may not be having on the growth of your business.

I wanted to tell you little about myself and how you can make sure you are getting the most out of me and the rest of my team. I realize, I flipped the pro-noun there but I like the way it sounds better.

So, First a little about me.

  • I love to talk about me, I love it when I talk about me. I love it even more when you and your boss talk about me. I don’t put my head-down and not want to be noticed. I go after big elephants in hopes to bring home a trophy that you will hang on your wall. Even if I sell to the SMB. I am looking for the biggest one or the biggest number. I am special and I want you to notice.

I know most people think I am completely money motivated. Actually, while I appreciate the compensation as a motivator. As long as you pay me enough, recognition, rewards, competition and opportunity for advancement will be what gets you my extra effort.

  • I will buy into your vision more than anyone else in our company. I don’t like to admit it, but I am easy to sell as I am a bit emotional. If I buy into the vision, there will not be a wall I wont run through.
  • I am a strategic thinker but even more so, I am optimistic and enthusiastic. I am always inclined to see the growth opportunity in any situation. We can always make it, there is always enough time and I will find a way to hit a five run home run. You need my optimism and my energy. If I understand where we are going, my enthusiasm is contagious and I will infect the rest of the team.
  • I can’t stand complex answers to simple questions.

Example: How much will I make on this deal?

Complex Answer: It depends… (Actually, All I hear after this is Blah, Blah, Blah, and I now assume I am getting hosed.)

Desired Answer: You will make X. If you are above 100%, you will make more. ( I really like that answer)

Example 2: Are we better than the competition?

Complex Answer: We are better in some areas while they are better in others…. (Here are going to get into some technical explanation, I can feel it coming)

Desired Answer: Yes, We dominate them today and more importantly, here is our plan to continue to dominate them.

  • No one can get you closer to the customer than I can. You and your teams need to understand what our customers are saying, how they are reacting to our messaging and how they really think about us. I need you to be engaged and it means the world to me when you spend time with me talking to customers. It helps me get better to hear how you think and I will aplly that learning to get better and sell more for you. If you have my back, you will win my loyalty.

Lastly, a little more about me

  • Let’s talk about reporting. I know, you know and we all know I am not great at entering my data into our CRM (, etc) You need to help me see value out of it and you will barely even have to remind me to put the data in. Use the data for competition, use it for rewards but most importantly, use the data to coach me and make me better. If you do that, it will mean more than just money ever will. I may not tell you that, but you will get my discretionary time, effort and ideas.

I hope this little letter helps you as you think about how to manage and build the sales team. You can get much more out of us than you ever thought. I see myself as a leader in sales even if I do not want to manage anyone. If you can ever use me as an example to the rest of the team, I am happy to volunteer and will never turn down that opportunity. If you need me to teach newbies the ropes, I will do it all day long. That is my love language.

Invest in me and we will crush this thing.

All My Best,

Your Best Sales Person.

Why? Why? Why? – Never Stop Asking

Yesterday, my 8-year-old son, Nolan, asked me a question about World War II. As I was explaining certain battles and what happened, he cut me off. “Dad, I know what happened, I want to know WHY they did it.” He had many questions and all of them dealt with why generals and leaders made the choice they did. That opened up a discussion about how to make hard choices and what he would do if he faced a hard decision.

He left with a “Thanks dad. That makes sense now.” And with that, he was off to explore Legos.

I have been in hundreds, maybe thousands of meetings where teams get together and discuss what is happening and what we are going to do about what is happening. Reviewed the numbers and the data, what the team was doing, or not doing, what the numbers were, what they should be and what we were going to do about it.

Sometimes, we even tried to determine whose fault it was that numbers were what they were.

I have been involved in meetings where we discussed what kind of culture we wanted to create, what we stood for and what we going to do to get our culture and mission statement into the hearts of our employees.

Most of these meetings were not very effective.

This is because we are asking the wrong question. We need to start asking “Why” instead of “What.”

Why builds ownership, not more programs. Why will change your team. It is the question that changes the world.

As a leader, you need to be as relentless as a 3 year old asking “Why, Why, Why.

Why is your most powerful tool. If people understand the “WHY”, they can create the “WHAT.” If they don’t, the best you can hope for is enthusiastic compliance where the momentum only lasts as long as you keep them pumped up. Why allows you to know if they understand the vision, and how to build alignment

Here are a couple of examples:

  • If the team understands that you are cutting a project to put resources into a much faster growing division, a negative event all of a sudden looks like a growth opportunity.
  • If a leader understands you are moving her to a “lower-profile” position because only she can build this vital division correctly, it takes on a whole new significance. No one will outwork her.
  • If you don’t understand what is going on. Asking why allows you to hear people’s thought progress, their passion and how they got where they are. This involves listening more, talking less.

Culture is created through answering “Why”, not What. What we do is the visible of proof of how we answer why. Spending time on why we make the choices is harder, more time-consuming and can be more abstract to measure. By the way, answering the “WHY” is REAL the job of a leader. No one else is measured on why.

I think that is why many people and organization spend so much time on the what.

  1. It is easier to move the deck chairs around than ask why we have a deck in the first place.
  2. Measuring the “What” is easier than the Why. We are a bit data obsessed. It harder, not impossible, but harder to measure the impact of Why we do what we do in the first place.
  3. We never seem to have enough time to deal with Why. It is easier to put a couple more programs together or measure data than it is to measure impact and progress.
  4. People’s comp plans are usually ties to outputs of what.

The result is that we only deal with why at the beginning, when we change leaders and when the wheels are coming off the bus.

In truth, Why establishes the targets you are aiming at. Without it, programs all become self-serving where campaigns exist only to reach a certain return rate, not are we actually reaching the people we intend to reach.

What measures metrics. Why measures Impact and progress. We have to make more time for this. Otherwise, work and busy work begin to look the same.

I would recommend:

  1. Lay out your vision and why your organization even exists. Then your people can buy in, take ownership of this and begin to drive their teams and programs toward this vision.
  2. Spend time to make sure people understand the why behind the decisions you are making. This will help make sure all of your activity is aimed at the same target. This is vital as you are asking people to change behavior.
  3. Allow people to question which activities actually have greatest impact to moving you to the goals.
  4. Be willing to sacrifice programs if they don’t align to why. That builds culture more than 100 ping-pong tables ever will.
  5. Eliminate the meetings where you simply discuss data and outputs. Most of this information can be sent via e-mail. Use this data to drive your “Why” meetings. A bunch of meetings can go away right there.

Momentum is a group of people moving in a direction. Why is like turning on the lights and making sure everyone is running at the same target. They will feel more secure. No one runs fast in the dark.

The paradox is that the quality and efficiency of the “what” will actually improve tremendously the more clarity your team or family has concerning the “Why.”