What sales enablement changes do we need to make as we shift focus from selling to SMB and mid-market to selling to enterprise?

It’s exciting that your company is making the shift up-market! The first question to ask is whether you have the right people in place to sell into enterprises. Promoting the best people on the mid-market team is highly risky, although that decision is usually outside the purview of product marketing. Having a seasoned enterprise sales rep or two is essential to success because they can guide the broader organization in transforming in the way that it needs to.

For enablement specifically, it’s likely that you’ll need an entirely new set of content.

• Pitch / narrative: the same story that resonates with companies fresh out of Y-Combinator won’t land in the Fortune 500. The differences can be as simple as terminology (Innovation vs. Digital Transformation), but often it’s more than that. For example, enterprises will care more about things like the size of your customer base, ability to scale, and validation from Gartner, because they have a lot more to lose in taking a risk with an up-and-coming company.
  
• Sales process: Deal cycles can be significantly longer, which means your approach will need to change. For example, at a past company SMB deals would close in 30-60 days while enterprise deals averaged 6 months from start to finish. This is fairly common and means the standard questions, like “who has the budget?” and “who needs to sign off?” are much more difficult to answer. The most fun changes are related to heavier involvement from Legal, Security, and Procurement, which make forecasting much more challenging. Mapping this all out is a great exercise.
  
• Content: This one is fairly intuitive but applies across the board, to all your materials. For example, add logos of Fortune 500 customers to your enterprise two-pagers and decks. You’ll also likely need enterprise-specific content like RFP / RFI templates (Request for Proposal). You may also need to re-think your buyer personas if new types of people are involved in the purchase process.
  

The right changes to make will be specific to your company, and it’s worth pulling together all the people with enterprise experience to provide input into the plan.

This is a tough question to answer because this problem isn't all a PMM problem. This problem is also a sales organization problem. An SMB/Mid Market rep isn't an enterprise rep. A sales leader who only has managed SMB/Mid-market isn't an enterprise sales leader. However, you inherit what you inherit, so here are my recommendations. First, you will need to spend money to get a sales trainer who can train the sales team to sell to the enterprise. Second, make sure you as a PMM clearly define what is enterprise versus mid-market. The definitions are different from company-to-company. Third, the enterprise segment requires solutions and use cases, so outlining clear use cases with personas are ready.

While there are some common themes regardless fo the segment, there are some unique things down market:

- Volume is much higher - reps have a 1000s of accounts versus handfuls so productivity is harder

- Value selling is different - most buyers in those segments, especially SMB, won't have time for a full value pitch, so you need different types of quick hit ROI calculators/value messaging for down market 

- Typically, in mature companies - your enterprise sellers also tend to be more tenured and your SMB - less so, so you have a higher skill ramp (which goes with the shorter sales cycles in SMB).

On the plus side, the sales are shorter, simpler, and faster. Your buyers tend to be single threaded (versus the complex enterprise buyers) with simpler processes. 

Some of the big differences you will see include:

• Longer sales cycle
• A bigger group of buyers and influencers
• More focus on security, certifications, and customer proof

The main change is to incorporate additional personas in the sales cycle which will include new messaging and positioning. When you go from having to convince 1 or 2 people to buy your product to 5 or 7, more work is needed.

In the Enterprise market you will also be asked more questions about security, certifications, global support, etc. so enabling the team to handle these questions will help.

Finally, the sales cycle will likely be longer and thus training for the sales team on how to handle the longer sales cycle, how to accelerate deals, how to build rapport with different stakeholders will be important. Many companies when expanding to Enterprise also want to review their sales methodology and approach.

As you re-think enablement programs to address the enterprise market, work with the enablement team on these key differences and adjust training and enablement sessions as needed. 

Great question! Core things to keep in mind: 

1. You will be selling to a committee, versus one person/one core contact

2. Due to that, you'll want to really understand the composite of that committee: what are their roles, what are their pain points and objections. Moving upmarket means coming face-to-face with buyers that might be outside your core sweet spot of understanding. 

3. Once you get that understanding, you need to understand what they value and how: what content do they need and what delivery method makes the most sense. 

4. You will likely have short-term things you can address and long-term things (like analyst reports, which is a longer-term effort). This is important for stakeholder management to understand what can move now versus down the line. 

As you go upmarket, third-party influencers become crucial in the sales process—specifically, analysts such as Gartner and Forrester. Enterprises are lower tolerance for risk, and they can lean heavily on the magic quadrant or the Wave placement while making buying decisions. Your enterprise sales rep will care a lot about this topic. Sales enablement has to factor this motion at some point in the company's journey.

The influencers and blocker persona become more relevant in the enterprise motion. For example, the security team may influence the buying motion even though your product is targeted to the engineering/development team. So, making sure that persona care-abouts are well covered and have materials for objection handling will be relevant.

Enterprise customers also have complex needs. So, a platform approach or a product that can customize to both legacy and modern stacks can be critical.

I am assuming here that you have already created stories/collateral that will be required to sell into the enterprise. FWIW, here is a framework I use to develop stories - https://www.linkedin.com/pulse/20141028002202-1469522-product-marketing-in-three-words-part-i/, but happy to drill down with you here or offline if that helps.

Selling to the Enterprise is likely to be very different from selling to SMBs and mid-market. Some key differences to note:

• The sales cycles are longer
• The decision making process is more rigorously defined (or laborious depending on how you see it)
• You will need to deal with at least three key constituencies in the sales cycle - evaluators, influencers, and decision makers - and possibly a fourth (exec sponsor)
• You likely have a committee of influencers and in the worst case, a committee of decision makers
• You may need to go through a POC or trial before the customer will make a decision.

As a product marketer, this translates into two key questions:

• Do you know the personas that constitute the evaluators, influencers, and decision makers?
• Do you have story elements that will address the pain points of the most common use cases for each persona?

Depending on your product, you may need to create a map of the personas and the assets that will support your team across the various phases of the sales cycle. (Unicast me and I can share an example of a grid that I use)

Also, you need to know how the Sales team is evolving. Is a new team being hired? Or, is the existing team being refocused to sell to the Enterprise? Your content and enablement strategy needs to keep this under consideration. For example, if the current team is being refocused, then you need to support them as they adapt to the longer sales cycles. In this case, you will likely need to create new content, but you may not need to radically change the cadence of your sales enablement programs. If it is a net-new team, then you will likely need to create content as well as training programs for the team. But this is a deeper question in and of itself.