To know what is the enterprise market, we’re going to explore 5 prerequisites that you need for a successful enterprise market expedition.

  • Marketing
  • Companies are now focused on relationships with customers and channels.
  • Hiring
  • Training
  • Sales strategy

1) Marketing: Does your mid market sales appeal to enterprise orgs?

When you are selling to SMB and MM, you can get away with fairly lean marketing. From a collateral perspective, you may only have a core deck, which doubles as a leave-behind for prospects. Your messaging may be focused on only one persona. 6 As you move into selling to the enterprise market that’s going to change. Your marketing needs to be dialed in to your new prospect’s needs, which includes a lot of internal selling that happens after your rep has left the meeting.

Your marketing needs to show that you are a trustworthy person with the best intentions who is ready and willing to help.

If you’re selling to enterprise, be sure that your product marketing is clear and concise.

  • A lot of companies are focused on diversity, especially during the hiring process.
  • The article is about how organizations can help diversify their workforce.
  • It’s important to understand the different types of customers.

2) Selling to Enterprise and Channel Partnerships: Have you found a “lighthouse” customer?

When you’re building out your enterprise functionality, it’s a good idea to find some beta customers who are willing to use the product and go through rough patches for a great deal on the solution.

The companies you choose to work with will have a huge impact on your success. You need to find brands that are seen as leaders in the industry, and others will follow behind.

Now, you know what your company needs to be successful. Now it’s time to get started.

If you want to make the leap into enterprise, it’s smart to partner up with a company that is already successful there. If something changes about your product, they can help.

When Salesforce first started, they made a point to get both financial services companies and their customers on board. They did this by working with the SVP of WW Channels and Alliances at Merrill Lynch, Bobby Napiltonia. This helped them secure Merrill Lynch as their first major client in financial services

Partner Okere was able to help me with the domain expertise and client relationships for this enterprise initiative.

A lot of companies are focused on diversity, especially during the hiring process.

3) Hiring: Do you have the right mid market sales people in place?

Hiring is an area where mistakes are common, especially if you haven’t done it before.

When it comes to the type of salesperson you should hire, there are two approaches. One is to take your high-performing SMBmid-market reps and have them sell into the enterprise market; or hire experienced enterprise reps from other companies.

If you choose a woman candidate, she may have trouble with childcare. If you hire a man, then maybe he’ll need to take care of his elderly parents.

Boosting high-performing mid-market sales representatives

Matt did not know that his top mid-market rep would be unable to replicate success in enterprise.

The rep always did well in the mid-market. He was persistent, gritty and likeable.

We need to make sure that our company has a diverse workforce, but it doesn’t stop there. We also have to consider the ways in which we interact with employees and customers.

The best enterprise reps combine knowledge and reasoning for effective strategic insight.

They are the ones who can turn a product into something that is going to help transform an executive’s agenda. It’s not just about small businesses anymore.

For an account executive in enterprise technology, their day typically starts at 6am and ends around 7pm. They are out meeting with clients or prospects for lunch or dinner meetings to get new business.

Elite enterprise reps have:

I’ve found that people with an MBA or greater finance education are more likely to know ROE and ROA, so I usually hire them.

ESPs stay up to date on the industry by subscribing to journals, maintaining a network of contacts and attending conferences.

When it comes to finding employees, I’m looking for someone who is mentally agile and can process a lot of information.

The truth is, if you sound like someone who cannot make executive decisions or choose the right person for a job position, I will not hire you.

It’s important to understand the internal politics of a company before you start pitching them, and use that knowledge to get what you want.

If a rep doesn’t have the strong project management skills to handle enterprise deals, they won’t be able to succeed.

They want to become a trusted advisor. They try and understand what the executive needs, how they can help them faster or better than anyone else, because this way they know something that an executive NEEDS TO KNOW.

This article is about how to shorten the enterprise sales cycle.

Do you think every company needs enterprise reps?

No. You can promote your current reps if you have a product or service that solves an existing problem with generally accepted principles for solving it.

If you have a vendor-style customer relationship, the sophistication of your reps doesn’t need to be high.

You cannot just engage an Oracle sales rep when selling to an enterprise

Hiring from a company that is already well-known in the enterprise space can be just as risky.

Employees are used to the same level of support they got at their last company, but also expect a product or service that is already well-known.

You can’t just rely on a salesperson who did well at selling the same solution to other companies. You have to look for someone who is skilled in introducing new solutions.

My takeaway is to make sure you write a hiring profile that fits both the company’s needs and the prospect’s. Work with your sales ops department to take some guesses on how productive they will be during ramp, then track their performance.

When hiring an enterprise salesperson, make sure they have the personality and experience to sell a new name into an established market. They need to know how to break into that whole other environment.

Great enterprise reps are expensive for a reason. You need to hire someone who is experienced, but also has the capability and desire to create all of the tools they might need (EG ROI calculators, proposals etc).

4) Training: Do your mid market sales sales reps know what to do?

“A lot of companies think they don’t need to train their sales reps because experience will be enough.”

Misha has heard this before, and yet we still see people who can’t do the most basic skills of a salesperson. For example, they don’t know how to discover what someone needs or connect value with need.

If you want your company to have a culture of learning, it’s important that the enterprise team is also part of this culture. Your training program should be focused on what type deals they’re working and which best practices are in place before hiring them.

One thing I learned is that you can’t just look at a resume and say, “yes this person has the skills we need”. You have to ask them specific questions about their experience and then train them based on what they’re comfortable with.

Related: 12 Expert Tips for Managing a Sales Team.

5) Sales Strategy: Can you face the challenge of selling to enterprise?

Sales teams often don’t know how the enterprise buys before they go in.

Once you start to get into more complex deals, there are new hurdles and risks.

  • The committee selects which stocks to invest in, and the meeting approves when they should be bought.
  • Spending approval limits
  • The chief risk officer
  • Procurement is a business department that deals with how to buy things at the lowest cost and in the best way possible.

When strategic procurement is focused on cost reduction, they can be your worst nightmare. They’ll often work against the champion to prevent any purchase at all.

When you’re trying to get a deal done and it starts feeling like an uphill battle, ask yourself”

We need to see a realistic path before we can agree that this is an opportunity.

You have to know who you are up against, what their buying process is like and how they’re going to respond to your offer.

You need to know the strengths and weaknesses of your competitors before you make a choice on who will be best for your company.

When you are a startup, it is important to have procedures in place for reviewing deals. You need to be able to say no if necessary.


It’s a big decision to go enterprise, and it needs the support of everyone in your company.

A “Best-Middle-Worst” model should be built with a plan to address 5 difficulties before going upmarket, and alignment across the executive team is important.


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Go through a variety of filters to zero in on the leads you want to reach. This is crazy specific, but you could find all the people that match the following: 

  • A company in the Financial Services or Banking industry
  • Who have more than 10 employees
  • That spend money on Adwords
  • Who use Hubspot
  • Who currently have job openings for marketing help
  • With the role of HR Manager
  • That has only been in this role for less than 1 year
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Editors Note:

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Justin McGill
About Author: Justin McGill
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