Sales Management: Complex Enterprise Sales vs. Mid-Market Sales

I was recently meeting with a startup CEO and sharing my views on the differences as well as similarities between the more complex and longer-cycle Enterprise Deals vs. Mid-Market Deals which 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).

Enterprise Sales of $100k – $1M in $ACV
  • On-site and in-person visits which require a more of an “executive presence” and polished approach to communicating
  • Longer sales cycle – 9-12+ months
  • Typicall an RFP is involved
  • Bigger deal size
    • But, not THAT big
    • 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)
  • More relationship-driven deal (i.e. you need to build strong professional and “personalized” relationships over the longer time frame)
  • Need to find more leverage and use your own execs to get in there – you coach your execs more on the deal, you create a lot of asset value and ROI for the buyer
  • “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
But there are also some similarities – you do these in both Enterprise sales and Mid-Market sales too:
  • 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