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Sales for Startups: How to Transition From Self Service to Enterprise Sales

Most early stage business to business (B2B) startups think about which market to target. And it usually boils down to these questions:

“Do we focus on small and medium sized businesses (SMB) or do we go after the enterprise? Or both?”

You on the other hand…

Decided early on to focus on offering smaller, more affordable packages that can be leveraged by organizations of all sizes.

Your pricing options start at “Free” and go up to a few hundred dollars per month. So far, you have several thousand active customers across all pricing options and sizes.

All is going well, and your revenue stream is growing. You have learned a lot about your product from servicing so many smaller customers (who also have been great allies).

Recently, you landed a few enterprise size customers and are beginning to see the impact these larger customers are having on your revenue growth. However, as you expand into the enterprise market, you really don’t understand where to start.

The marketing manager did some sales at her previous job, but this is a completely different experience. Having never focused on enterprise before, you need to begin developing a sales process around this beast!

In today’s post we’re going to create a little recipe you can follow – that will build your enterprise client list in no time. So get on your “sales-aprons” and let’s get cookin’!

I love sales apron

Gather Your Ingredients

To get this recipe to work, we need to gather some ingredients that will help you get off to a great start:


  • Google Spreadsheet
  • CRM System – (recommended)
  • Account (now
  • LinkedIn Account
  • Twitter Account
  • Email
  • Telephone
  • Rapportive
  • Google

Step 1: Create a List of Enterprise Companies

I usually begin with a Google spreadsheet and start to populate it with target and contact data.

Simply categorize columns focused on collecting the most basic (and important) information:

  • First Name
  • Last Name
  • Company
  • Email
  • Title
  • Telephone
  • LinkedIn
  • Twitter
  • Description / Notes

You might want to add geographic location, but this tends to be less important early on.

There are a few ways to find these companies, and, for the most part, it’s pretty obvious.  But what this really amounts to is an important brainstorming session to set your sites in the right place.

The first method is using Google and searching for “Fortune 1000,” “Inc 500,” and/or other company categories that would qualify as an enterprise company to your business.

You also can follow news websites and online trade journals that match up with your target industry, and keep your eye out for opportune moments to engage. Some publications that I recommend are:

  • TechCrunch
  • VentureBeat

Step 2: Find Prospects

Once you have added about 100 companies or targets, you will have to find prospects. Prospects are contacts at a particular company.

A neat trick is to log into your LinkedIn account and use the “advanced search” under “People.” Once you are there, add a particular company name, the title of the prospect that you are going after, and search!

linkedin to find prospects

LinkedIn is the best way to find prospect information that is up to date and easy to consume.

Then you have to find their contact information. This can be a bit tricky, but it is something you must do. You have to try to figure out the conventions (standards) the company uses for its email addresses (and for creating new email addresses for new employees).

For example, is it ( or maybe (

You can use products like, which is now, to find email addresses. Also search the company’s website to look for emails that are listed. Or, you can even use Google to find them by entering a common email convention in the search box (i.e. Jorge. or maybe to see what comes up.

google docs sales process

Step 3: Use a CRM

Now, it’s also important to remember that at some point you are going to have to grow up and buy a CRM system that will help you scale the team and manage your efforts.

Most CRM systems allow for the importing of data via a spreadsheet, which most likely has to be converted into a .csv file pre-upload. Here are some CRMs that I recommend:

  • Gives a clear overview of your sales pipeline
  • Helps you focus on the right contacts, and important deals won’t get dropped

  • “Email for Sales People”
  • Integrated right into Gmail – no tabbing, extra logins or new user interface to learn
  • Integrates with Salesforce and other leading CRM systems, so you spend less time entering CRM data

  • Grab leads from social networks with a single click
  • Excellent mobile syncing

  • Focuses on deals, not contacts
  • Intuitive user experience
  • Unlimited users

  • Some would call the industry standard

Step 4: Reach Out

After you have created your target list, it’s time to reach out and build some relationships.

It’s up to you whether you want to go the “cold calling” route or email.

I suggest trying both and testing to see which method you find more effective.

Email is the new telephone in many ways. In fact, I text and email much more than I pick up the telephone and call people.

This is certainly the case for most of us in business. In my mind, the same rules apply to email outreach.

In the same way that you wouldn’t pick up the telephone and speak 3 paragraphs of content to the other party, you wouldn’t write long cold emails to prospects. If you think about it, the overwhelming majority of us communicate via text messages, which are very short in nature. Also, we nearly all hate getting long emails, especially as a prospect on the other end of a cold sales email.

Think about the last time you received a long email, especially when someone was trying to sell you something. I don’t know about you, but I rarely ever read them.

Almost all of them are clearly sent via an email marketing tool, lack personalization, and feel more like spam.

My cold outreach emails are short and sweet. For example, below is an actual email that I sent to a prospect. Notice the brevity and directness. I also like to have a healthy amount of information in my signature area. This makes me “real.”

linkedin sales prospecting

contact info signature

My entire objective when conducting outbound emailing / cold calling is to engage the person enough to get them on the telephone or get a meeting. That’s it – nothing more, nothing less.

The second image above is the prospect’s response to me. There is now a two way dialogue occurring. Not only have I found out the email convention for her company and/or team, but I have her direct line / phone number if she goes cold or becomes unresponsive via email.

You also should begin conversations with prospects on Twitter. Even if you have established contact with them, it’s always a nice gesture to retweet something they have posted or say hello.

Now you have a foundation for your initial outreach. I can assure you that if you repeat the steps above over and over, you will generate prospects, which will become deals. Remember, focus on the fundamentals: appointment setting, calls, demos, meetings, etc.

Step 5: Identify their Needs and Pains

When you transition into enterprise sales, you need to be more deliberate about understanding the job titles that you should be targeting. It’s important to make sure you come to a consensus regarding:

  • What are the needs and pains of the company?
  • How do they make these types of buying decisions as a company?

When you target the SMB market, you tend to find yourself in a volume situation where your goal is to onboard as many people as possible. You do not see the type of complex issues that you run up against in speaking with enterprise businesses.

This results in some restructuring of your prospecting strategy and your conversations to accommodate multiple players / titles within the same sales opportunity.

Step 6: Closing

Now, assuming you have followed the process above, some of your outreach will convert into dialogues or conversations. Some of these conversations will last longer than others.

The conversations that are meaningful to you are the ones that reach a point where both parties’ interests are aligned and a financial transaction occurs.

In the enterprise sales world, this often means a proposal was submitted and a legally binding contract is required for the parties to do business.

This is what closing is all about. It’s merely the next step to take, based on the conversations you have been having with the prospect and other stakeholders on their team.

It turns out that a lot of “noobs” in enterprise sales are afraid to pull the trigger and ask for the business. They wait to see if their potential clients will ask first. Please do not be afraid or forget to ask for the business! You must get comfortable with being direct.

Step 7: Be Patient and Keep on Trucking

If you follow the outline for the processes and ideas that I have listed above, I promise that you will start developing a pipeline of sales and begin to close enterprise businesses.

You must understand that these sales cycles are much longer than those with small customers. This is not easy, and you will be frustrated and doubt your ability to engage prospects. Please do not become discouraged. Stick to the process. The law of averages will work in your favor!

Don’t Forget To Show Off Your Victory Flags

I know it seems sort of corny, but this is important. As you continue to close enterprise level customers, ask them if you can add their logo to your website, and then do it!

Needless to say, it adds credibility and is attractive to other enterprise prospects. Not to mention the effect it has on other customers that now feel great about being able to afford a product used by much larger companies.

About the Author: Jorge Soto is the co-founder of Sales4StartUps – a San Francisco based company focused on: a) educating, training, and consulting web technology startups on all things sales, with a strong emphasis on inside sales; and b) building easy-to-use, lightweight web and mobile apps for sales people at startups all the way up to the established enterprise.

  1. Interesting to see a step by step for this process. Being at a startup myself, our approach has been similar right down to the tools we are using. We have a few other ideas and strategies up our sleeves that we are planning on implementing this quarter.

    • Hi Ken – Great to hear that you are using the same tactics. One of the many challenges we face as startup entrepreneurs launching a sales process is that we dont have any trends or data to refer back to. We have assumptions around what will work based on fundamental truths in sales — i.e we have calls, call backs, prospects/leads, deals/opportunities, best practices, etc, etc. I think its incredibly important to stay focused, patient, and agile. Tactics and strategies will change and we need to be ready to collect data/feedback, implement, and scale across our teams.

      At the end of the day all we can do is control our effort, commitment, and attitude. Everything else will surely follow.


  2. Simply brilliant! Love the run down and advice that you’ve given.

    Another pointer I’d make is that with the LinkedIn (social media) outreach you could use it as another angle – creating a champion.

    Champions are great, especially for the software B2B industry as once you have someone within the company you ‘hunting’ you’ve already got a fighting chance. Sometimes (most of the time?) you get the ‘Not interested’ email and this is when most people leave it – simply hedge the contact with a free offer, a trial or anything you need to ensure that even though they may not be interest they still have something of value in front of them.

    Again brilliant article!

  3. Sanket Nadhani Jan 10, 2013 at 9:47 pm

    One of the very few articles on the KISSmetrics blog that I didn’t learn anything from.

    • Agreed. I was excited when I saw the title of the post but it really fell short. Learning how to find people to cold-email (read: spam) is not the essence of enterprise sales and that’s what the article mainly focused on.

  4. The post is interesting and is currently right in the middle of what our company is doing.

    On thing about “getting” the email address and using linkedIn. Once you found a right contact, i’ll advice to try to smartly Connect with them. There’s 2 advantages:
    – once they accept the request, you’ll access their email and sometimes their phone number
    – you can mention about it in your first email, which is always a plus / nice way to get close to your prospects

    Antoine @Datafieldapp

  5. Agreed with the other posters here, title led me to higher expectations… unfortunately, if you don’t haven’t already mastered the content in this post, your chances of success in enterprise sales is fairly low.


  6. I am having great experience while I am reading your blog post.
    It was very interesting and useful content.

  7. Jenifer Taylor Jan 20, 2013 at 3:27 am


    Thankyou for sharing this great article with us.This article will help a lot.

    Jenifer Taylor

  8. Wow! I thought I knew of all the helpful software tools out there. I will definitely be using the base one.


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