Moving to Enterprise Sales (Part 2): 5 Go-to-Market Prerequisites You Need to Succeed

Transitioning from mid-market selling to enterprise selling isn’t easy. In our first post we focused on how to be product- and market-ready, but that’s still only part of the solution.

In part two, we are going to look at 5 go-to-market prerequisites that you need to consider if your expedition into enterprise is going to be a success.

  1. Marketing
  2. Customer and channel partnerships
  3. Hiring
  4. Training
  5. Sales strategy

1) Marketing: Does your marketing 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.
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.

There is a tremendous amount of selling that happens behind closed doors, and your marketing has to reflect that buyer questions of “Why Change?” … “Why Now?” … “Why You?

Takeaway: The role of product marketing is more complex/nuanced if you are selling to enterprise. Make sure you have clear messaging that

  • Shows how you are differentiated from the competition
  • Specifically speaks to the needs of the enterprise
  • Uses the language of the different buyer personas

2) Customer and Channel Partnerships: Can you find a “lighthouse” customer?

As you build out your enterprise functionality, it’s a good idea to find some beta customers who support your feature roadmap and are accepting of a lumpy road in return for a great commercial deal on the solution.

Selecting “lighthouse” customers will accelerate your success. Aim to find brands that are seen as leaders in the vertical, who others will follow behind.

Let’s assume that you have all the above sorted out… now what?

Well, you can go it alone and start knocking on enterprise doors, but a proven, low risk, way to make the leap is to work with a partner that is already selling into enterprise. This is particularly critical if you have to make some major product feature changes/additions along the way.

Salesforce did this in their early days as they sought to break into financial services. The SVP of WW Channels and Alliances, Bobby Napiltonia, stewarded this relationship. This allowed Salesforce to secure Merrill Lynch as their first major financial services client, and once they had them on board, many other brands followed.

Partner “Okere” brought the domain expertise and the client relationships to successfully launch this enterprise initiative.

RELATED: From SMB to Enterprise: A 2-Step Strategy to Boost Adoption & Growth

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

Hiring is another area where it’s easy to make mistakes, especially if you haven’t built an enterprise machine in the past.

The two most common approaches when it comes to your team is to either take your high-performing SMB/mid-market reps and have them sell into the enterprise, or hire experienced enterprise reps from other enterprise companies (Oracle, SFDC, SAP, etc.).

Both hiring profiles will run into hurdles.

Promoting high performing mid-market reps

It is true that the typical path is to gradually move up through the segments, but don’t make the mistake that Matt did in the past, assuming his top mid-market rep would replicate his success in enterprise.

The rep was exceptionally good as leveraging his persistence, grit, and likeability to make President’s Club every year in the mid-market.

Unfortunately, those traits are not enough in the enterprise.

The best enterprise reps combine deep domain expertise, financial acumen, comprehension, and critical reasoning for impactful strategic insight.

They are the magicians who can translate an offering into a transformational enabler that connects to the executive agenda. Make no mistake, this is a long way from the SMB sales motion!

RELATED: A Day in the Life of a Sr. Account Executive in Enterprise Technology

Elite enterprise reps have:

An MBA or greater finance education – They know ROE and ROA, whereas standard sales reps wouldn’t know their ROS from their ARR(se)…. Sorry, I couldn’t help myself.

Industry knowledge (Customer, not vendor) – Enterprise sales reps (ESPs) keep themselves up to date by subscribing to industry journals, maintaining an industry network, and attending relevant conferences.

A high IQ – ESPs solve non-obvious problems and create novel solutions. Mental agility and ability to process inputs is a must.

Executive acumen – Hard truth: “I will delegate you down to the person you sound like.”

A sophisticated understanding of internal politics – Enterprise sales often need to understand the internal politics at a prospect company, and how to leverage that information to win the deal.

Strong project management skills – Enterprise deals, by their very nature, have long and complicated sales cycles. If a rep doesn’t have strong project management skills, they won’t be able to handle it.

Voracious curiosity – At their core, the enterprise rep strives to become a trusted advisor. They seek to understand the executive imperatives and how to enable them: faster, better, cheaper. They want to identify an opportunity or issue that a customer can’t see. They gain access because they know something that an executive NEEDS to know.

RELATED: 8 Surefire Ways to Shorten the Enterprise Sales Cycle

Does every organization need enterprise reps?

No. If your product or service is solving a known problem, and if there is a generally accepted set of principles for solving it, then you can likely just promote your current reps.

The same is true if you have a vendor-style relationship with your customers You don’t need a high level of sophistication from your reps.

You can’t just hire an enterprise rep from Oracle if you are a startup

It can be just as risky to hire people from companies that are already well known in the enterprise space.

Not only are they going to expect the same level of support that they got at their last job, but they are also used to selling a known entity.

Your enterprise rep may have been very good at selling a solution that everyone has heard of, but will they be able to break into companies selling a solution that’s completely unknown to the prospect?

Takeaway: Write a hiring profile that fits both your prospect’s needs and your stage of company. Work with your sales ops to take some guesses on productivity during ramp, and track performance to see if you need to tweak your hiring profile.

When hiring an enterprise rep, make sure they have the personality, experience, and drive to sell a new name into the market. It’s not enough that they know how to sell into enterprise. They need to know how to break into a whole new market.

Great enterprise reps are expensive for a reason. They aren’t just experienced mid-market reps. They come with an extraordinary ability to generate value. You need to hire someone who is a utility player with early-stage experience, who has the capability and desire to create all the tools/assets that they need (EG ROI calculators, proposals etc).

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

We hire for experience, so we don’t need to train our reps.

Misha has heard things like this a lot, and yet, we are seeing an increase in “experienced” enterprise reps who are unable to do extremely basic sales skills, such as discovery or connecting value to need.

If you talk about your company having a culture of learning, it’s vital that your enterprise team is also a part of this culture. Your enterprise training program should be focused on the types of deals that your enterprise reps are working, AND it should confirm that they have the best practices in place that you believe they had before you hired them.

Takeaway: Even if you hire for experience, training can confirm that your reps actually have the skills that you believe that they did during the interview process.

RELATED: How To Manage A Sales Team: 12 Expert Tips For Success

5) Sales Strategy: Can you handle the challenges of enterprise?

Do you know how the enterprise buys? This sounds basic, but you’ll be surprised (or horrified) by how many sales teams don’t know this before they go into the enterprise.

When deals get big, you run into a new set of hurdles:

  • Buying committees and scheduled investment approval meetings
  • Spending approval limits
  • The chief risk officer
  • Procurement (AKA sales prevention office)

Strategic procurement is a highly valuable function, but if their remit is cost reduction, they can be your worst nightmare. At times, they will be working against your champion in order to prevent ANY purchase at all, let alone driving your price into the ground.

To combat these challenges, you need to view enterprise deals with a different mindset. Ask yourself…

Is this really an opportunity? Until we can see a realistic path to contracting, it’s not.

Do we have the relationships we need to win? You need an understanding of the politics, powerbases, and buying roles in the target company.

Do we have the strongest solution fit relative to the alternatives? You need to have done your due diligence and know your competitors inside and out.

Do we want to win? You never asked that in SMB did you? The size of enterprise deals can consume a start-up, and you need to have a process for deal reviews that ensure that you don’t make commitments you can’t/don’t want to keep.


The decision to go enterprise must be supported by a sequence of prerequisites and investment commitments from the board down.

A “Best – Middle – Worst” case model should be built, and alignment should be gained across the executive team before you head up-market. Keep these 5 difficulties in mind, and make sure you have a plan to address each of them.

Matt Cameron is the Managing Partner at SaaSy Sales Management, Silicon Valley’s SaaS go to market leadership development community. A regular speaker and columnist on the topic of SaaS sales leadership, Matt partners with venture firms to build world-class B2B sales leadership within portfolios. Formerly as the WW Head of Corporate Sales at Yammer and a RVP A/NZ Enterprise Sales for, he enjoyed building sales engines for high growth companies, which continues to be his passion. Misha McPherson has 20 years in the tech industry and is the sales enablement program director at SaaSy Sales Management. The first ten years of her career was in sales. The last ten years of her career has been in SaaS Sales Training and Enablement. Misha built programs at Yahoo! HotJobs,, Yammer (acquired by Microsoft), Responsys (acquired by Oracle), Spredfast, and Mixpanel before breaking off on her own to focus on companies that are building sales enablement for the first time. Misha is passionate about Sales Enablement as a way to make revenue scalable and predictable, and loves helping sales enablement leaders build transformational programs.

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