PE – Growing ARR Via Enterprise Sales (vs MM Sales)

I wanted to share the differences as well as similarities between the more complex and longer-cycle Enterprise Deals vs. Mid-Market deals where as the first type requires more Field Sales (and project-managing the complexity) while the second has more of an Inside Sales motion.

It’s obvious that Mid-Market Deals have less complexity and a shorter sales cycles (sometimes they are referred to as “high-velocity” but typically they are 45-60 days so they’re actually not “as high velocity” but certainly have a shorter cycle than the larger and more complex deals).

The key takeaway is that anyone who sells mid-market deals can learn to sell standard SaaS Enterprise deals.  It’s not rocket science and there are a couple of things that need to be done differently.  Additionally, the sales rep needs to be more relationship-focused and more polished approach with an executive presence.  Many other things can be learned if your sales professional is intelligent (which is one of the 3 key criteria you should be hiring for anyway so let’s presume all your reps are A-level and intelligent).

Here are the key big picture differences:

1. Enterprise is a true “Team Sport”
   • Enterprise sales is a team sport.  In fact, it’s a “Company Sport” as Erica Schultz, a former CRO at New Relic calls it.  You will have more pre-sales teams like “sales engineers” and others.
   • You will want and likely need to involve your internal executives and senior leadership – the bigger the deal then the more senior you will have to go internally to get help and leverage.
2. Longer Pipeline Cycles & Sales Cycles
   • When you sell into Mid-Market, a lot of the Opportunities created in the cycle will be won in that cycle but not so with larger Enterprise deals which can take 9-12 months (in some cases even longer). With Enterprise deals, pipeline generated in one quarter will end up getting closed several quarters later.
3. A shift in Marketing Strategy
   • With Mid-Market sales, marketing creates a lot of momentum and lead generation for the sales team. But this dynamic will change in Enterprise Sales.  The Enterprise Sales team (typically referred to as “field reps” or “outside reps” although many large $ACV deals can be sold without getting on the road) will be spearheading the process with much more relationship building than you have in MM sales.
   • With MM, marketing may not have as much to do on creating pitch decks and other materials because the “free trial” allows the product to be selling itself. But with Enterprise selling, the Enterprise Reps will need a lot more to begin and build the relationships.
   • You will have much more Field Marketing effort than you ever did with MM sales process.
4. A shift in Product Strategy
   • With Enterprise Sales you have to incorporate a lot more of the custom requirements and customer feedback into the product and this will really shift the Product team’s strategy and perspective.  In MM sales motions, the product team drives its own strategy and is typically not going to customize anything for any single customer but this will change considerably with Enterprise sales.
5. Talent Shift (Enterprise Reps)
   • Enterprise Reps must be far more strategic and agile than your typical inside sales reps focusing on the Mid-Market.
   • An Enterprise Rep must also be very good at project management – there is a lot to do behind the scenes both internally and at the customer to drive the deal forward.

• Field – a lot more of “On-site” and in-person visits which require a more of an “executive presence” and polished approach to communicating
• Longer sales cycle – 9 to 12 months (but can sometimes be 12-18 months for larger and more complex deals)
• It’s not an “activities game” but it’s truly an “impact game” on the entire enterprise/company, not just on a business unit
• It’s about building into your sale & positioning to the buyer the high value (of a large, enterprise deal)
• It’s about getting the meetings with senior executives (getting to power right away)
  • Read: How to Get a Meeting with Anyone by Stu Heinecke
• It’s about leveraging your own executives to help you – this is key in enterprise deals
  • Need to find more leverage and use your own execs to win big enterprise deals – you coach your execs more on the deal, you create a lot of asset value and ROI for the buyer
• When you start the year, you won’t be able to clearly see the numbers behind how you will hit your quota – that is a big difference from driving the funnel for high velocity or even Mid-Market sales motions
• With Enterprise Sales, you will have the business unit drive (unless you sell very technical products) and will see involvement from IT, finance, security, compliance, and procurement – each of them has their own challenges, priorities, requirements and agenda
• It’s not about delivering incremental improvements to the buyer but about delivering significant impact
• Typically an RFP is involved
• Bigger deal size but ideally “Enterprise Deal” should be > $1 Million in SaaS and even $750k deals are not *that* big and can be sold via Zoom online meetings (not necessarily needing to meet buyers in-person)
  • There is a sales pro at Oracle named Jamal Reimer on the Brian Burns podcast (March 2019) who sells $50M – $100M deals (8 digit to 9 digit deals) and that’s truly a “big deal size” but far bigger than $1M or even $2M deals done by most software companies
• More complex because there are more influencers, decision making authorities and detractors too
  • Multiple stakeholders and stakeholder groups contribute to every complex sale.
  • Need “Account Maps” that is > transactional sale (but it is still similar)
  • In fact, what is even more complex, is that you will need to know who are the tacit and unobvious “outside influencers” like big consulting firms such as McKinsey, Deloitte or others who will  “de-risk” the project for your buyer (e.g. read about this example from an expert on “Mega Deals”)
• More relationship-driven deal (i.e. you need to build strong professional and “personalized” relationships over the longer time frame)
• Land & Expand plays a big part in larger deals
• “Fishing vs Whale Hunting” – different equipment, different boat, different approach – you don’t throw a fishing rod into the sea, instead use big spears
• Need to have executive presence, polish, executive communication skills, complex C-Level negotiation skills, intelligence and broad interests so that you can take prospective customers out for dinner and for wine (i.e. and know the difference between a cheap Merlot and an Italian Barolo)
• Enterprise customers are very Risk-Averse
• You will not use Sandler selling but rely more on selling methods and insights from like Miller Heiman – Strategic Selling, Mastering the Complex Sale by Jeff Thull, The New Solution Selling by Keith Eades, Selling to Big Companies by Jill Konrath, Selling to the C-Suite by Nicholas Read, SPIN Selling by Neil Rachkham and his Major Account Sales Strategy, etc.
• Summary of winning complex Enterprise deals
  •  High risk
  •  Many stakeholders
  •  A long sales cycle (6-12 months)
  • High investment
  • Complex
• Also, in such cases the Sales Manager has a “low span of control” and may have fewer reps under them to manage

• You provide and create value in both scenarios
• Customer focus comes first
• Prove the ROI
• Buyers at all sizes of companies want to avoid something bad from happening
  • reduce fraud
  • reduce risk
  • reduce costs
• Buyers at all sizes of companies want something good to happen
  • increase revenue
  • increase margins
  • expand market share
  • improve internal productivity