What is enterprise sales? Your definition could make or break your success.

Most definitions of enterprise sales sound something like this:


“A long sales process involving multiple stakeholders, large deal sizes, and a high perceived risk by the buyer.”


But let’s be honest… as true as that definition actually is, it doesn’t really tell you much does it?


I mean, how long is a “long sales process?” How big of a deal is “enterprise big?”


There is a lot of confusion out there as to exactly what to expect with each of these things. And unfortunately, getting something as (seemingly) simple as this wrong can have drastic, negative effects on your business.  


I’ve seen (and experienced) many businesses with huge potential in the enterprise market tank their efforts because of this.  Let alone racking up a slew of 7-figure mishiring mistakes.   


Here’s everything you need to know to set yourself up for success in enterprise sales from my 20+ enterprise sales career.


The true definition of enterprise (or complex) sales.


A big part of the reason most enterprise sales definitions end up being so vague is that it’s really tricky to nail down concretely.


For example – I’ve done 8-figure mega enterprise deals with companies of 50 that took 2 years to implement.


But I also work with clients who do true enterprise sales with F500 brands and whose deal sizes are $60,000 with sales cycles around 6 months.


That’s why I think the best way to define an enterprise deal is actually not by any particular “benchmark” but by its level of complexity and the mindset required to execute it.


“The best way to define enterprise sales is by its level of complexity and by the mindset required to execute a deal.”


To illustrate how complex is “enterprise complex,” and what the mindset of a real enterprise deal is, we need to look at the differences between SMB, Mid-Market, and Enterprise deals.


Because the things that differentiate them are critical to your success in this market.


SMB vs. Enterprise vs. Mid-Market


Each of these deal types has a varying level of complexity and a different mindset associated with executing it.


The SMB Deal.


The SMB deal boils down to “you build it, they buy it.”


Or in other words, you develop a product that solves a problem for the greater market and then work to get it into the hands of everyone who is best suited to use it.


The risk isn’t significant, the product or service isn’t sophisticated, and it doesn’t take an act of congress to get the deal done.


This deal structure is very transactional with short sales cycles (think 1-3 call close ratios). It’s typically very cut and dry and the sales process for these deals is usually all about volume and optimization.


Usually, you’re working with a single decision maker or small “buying committee” who either see the value in the product or doesn’t. While relationships always matter, they don’t materialize the same way in a “high velocity,” transactional sales motion.


The businesses you’re working with are small (or medium – hence “SMB”).


The Enterprise Deal.


Where SMB deals are small, transactional, and quick, enterprise deals are the complete opposite.


More money = greater risk = a much more sophisticated buyer journey that takes a completely different approach to getting the deal across the finish line.


It’s all about building a custom solution for individual customers, not fitting an existing product to as many buyers as possible.


This added level of complexity impacts every part of the deal:


  1. The level of discovery required goes way up – since the true solution has yet to be determined.

  2. Social proof – enterprise sales is a big, small world and you have one shot at that table. If your reputation is horrible, that will absolutely catch up like a painful boomerang.

  3. The amount of sign-off by your buyer at each step of the process increases – as do the number of people signing off typically.

  4. Your Product Team has to be ready to support the build of this new custom solution – and often more than one at a time.

  5. The deal size can be huge – big implementations for the biggest buyers can be in the 8-figure range.

  6. It’s all about security – is your buyer protected? How is the data protected and restricted between teams across the organization?

  7. The party is just getting started when the deal closes and the opportunities post-sale continue (land and expand).


And as you can imagine, the time required to close a deal like this is lengthy.


This is usually where things go awry for most startups who are just getting into the enterprise market.


They often jump in too quickly without adopting the “one-size-does-NOT-fit-all” mindset. And as a result, they don’t do the work required (or put in the time) to be successful.


Ultimately, you must seek to understand first. Discovery and re-discovery is your best friend in enterprise sales.  It’s about working with a variety of people every step of the way (multi-threading) to architect a solution that helps the buyer:


  • Solve problems
  • Reach goals
  • Get better


The Mid-Market Deal.


Mid-Market deals are a very tough, grey area to define.


They are often similar to SMB in that they can be about finding the buyers who are the best fit for your existing product.


But occasionally they’re like Enterprise deals in the sense that you’ll need to tweak your product for your buyer as well.  Discovery and delivery start to become a priority.


From my perspective though, the real differentiator for Mid-Market is deal size.


They are typically smaller deal sizes than enterprise but high enough that a transactional approach won’t work.


As a result, you’ll still have things like:


  1. More stakeholders that need to sign off
  2. Higher perceived risk
  3. Customization requests


And the sales cycles will take longer than a transactional sales model.


Enterprise sales benchmarks to use for planning.


Ultimately, the approach required to be successful is the most important thing when you’re defining what is enterprise sales and what is not.


So I hope you understand why I haven’t thrown out numbers around sales cycles, deals sizes, etc. yet (as most people do).


The last thing I want you to do is to take a bunch of numbers as gospel and then get it wrong  (very costly)!


That said, here is a brief overview of benchmarks you can use to set your expectations correctly if you’re considering taking the plunge into the enterprise market:


what is enterprise sales


Again, these are just here to help you plan. The truth is, you’ll have to define each of these things for your business (and each individual deal for that matter).


So focus less on these numbers and more on the process required to get a successful deal closed. The best way to do that is to spend time with your buyers, listening to them versus assuming what you think they need, immersing yourself into the marketplace, looking for the themes, and adjusting as necessary.


If you’re a startup Founder trying to make heads or tails out of the enterprise sales market, I’ve broken down 17 resources to map it all out for you.


But wait, there’s more!


Here is the exact process I’ve used for enterprise sales that has generated more than 9-figures over the course of my 20-year enterprise sales, startup career.


My enterprise sales process and strategy.


Hopefully, you have a good grasp on the mindset required to play in the enterprise market (as well as the work that it takes to really do it well).


That’s step one and the most important part!


Next, I use the process below that has yet to fail me.


1. Calculate your Total Addressable Market.


This is exceptionally important and deserves an article all by itself. Read this to learn how to calculate your TAM.


To give you a quick high-level overview, there are three primary ways to calculate your TAM:


  1. By using industry research and reports that are available to you.
  2. By getting out in the market yourself and seeing how it responds.
  3. By making educated guesses about a buyer’s willingness to pay.


Each of these has its merits. Full disclosure, I prefer to use all three together to get the most accurate picture.


2. Start with the accounts that are the best fit.


The power of a pipeline is fierce in enterprise sales and trumps all. You want a robust pipeline filled with short-term, near-term, and long-term opportunities.


Enterprise sales is a long game scenario, so it’s important to prioritize your time accordingly with the accounts that are the best fit from the beginning and be prepared to put a lot of irons in the fire all at once.


Personally, I prefer to do this by testing the market and refining over time.  Pay attention to where you do your best work and go from there.


Know your ICP (ideal customer profile) like the back of your hand and then it’s just a matter of scaling from there once you have a good sense of what works best.  When you know your ICP you’re spending time on the right deals versus chasing your tail with the wrong buyers that will cost your business over time.


3. Get deep inside your prospects’ world.


Once I have my prioritized list of key targets to go after, I set up alerts on company and industry news for each.


You want to be looking for things like acquisitions, announcements, changes, new business, and more.


In Enterprise Sales you must ask yourself:

  1. What’s happening in the marketplace?
  2. What challenges are they facing?
  3. What are the common themes for different segments or verticals?
  4. What do LinkedIn Sales Navigator, G2, 6sense, Lead411, Apollo, Owler, Crunchbase, Pitchbook, D&B Hoovers, their annual report, earnings calls, etc. say about them?
  5. What does their roadmap look like?
  6. Understanding how to communicate with your buyers is just as important as all of the bits and pieces outlined above. I can’t live without tools like Crystal Knows and Lavender.


Clearbit is one of my personal favorites for automating the process of staying on top of what’s happening with my contacts and their businesses.


4. Map out the organization and engage the decision makers.


First things first… figure out who you think will be involved in the buying process, who your buyer will be, who your influencer will be, etc. Having a framework will create intentional efficiency to make sure you don’t miss key factors of the enterprise sales buying journey.


Once you have a good feel for who those people are, it’s time to start engaging them!


For some creative ways to do this, this article contains the tactics and strategies that have served me best.


5. Consult… don’t sell!


“Good salespeople sell lots of product, but great salespeople make lots of customers successful.”


Mark Birch


Enterprise buyers have competing priorities and are getting approached ALL the time.


So once contact is made, you need to find new and different ways to add value to what they’re trying to achieve and stand out from the crowd in the process.


This is where your mindset and approach is SO important. This is about co-creating the best solution together – not selling.


Great questions and thorough discovery are key at this stage so make them count. Then listen, adjust, pivot, and respond in earnest to hit the nail on the head!


Look for the space in between that nobody else would pick up on and use that fill the gaps they have.


The better you do this, the more eager they will be willing to engage! Remember, your buyers, especially in enterprise sales want to be seen, heard, and understood with no BS solutions that can move their needle. When you get over your agenda and wrap your arms around theirs, watch enterprise sales magic happen.


6. Land and expand.


Many enterprise sales functions will start with smaller, more approachable deals (like a pilot or a proof of concept trial) to reduce upfront risk and barriers to entry.


While this is effective for getting your foot in the door, it often means that there is a ton of opportunity left out there with each buyer. Especially for global companies that have a plethora of different business units operating under their own P&L.


In fact, sometimes going from pilot to full-size deal can take years.


That’s why the best enterprise sellers know the hard work isn’t over once a contract is signed. There is often so much more opportunity for further growth that is left untapped through even further expansion of the solution you can provide!


To do enterprise sales well for the long haul, you must stay on top of changes in their marketplace and in their trajectory. Be that trusted confidant they can come to when they have questions or the proverbial @#!$ hits the fan.


Even better, keep yourself top of mind by taking a proactive approach to helping them uncover potential blind spots and opportunities. Good begets good… always.


A quick note for businesses with a Customer Success team…


It’s pretty common to turn the buyer over to your Customer Success team once the deal is done these days.


That’s totally fine! But whether it’s the Customer Success team or the rep, make sure you’re keeping your buyer engaged at all times just like you do in the sales process. Remember, you’re there to help them to make it refreshing to do business with you.


The best way to do that is to partner with Customer Success to architect a plan where both parties are working together to keep the customer successful while uncovering opportunities. This is how you reduce the churn margin for error to boot.


The last thing you want is for it to feel like the only time you reach out to them is for a renewal or upsell discussion. So if there is a Customer Success team, have them join forces with your reps to execute a strategy that delivers meaningful outcomes versus ‘touch points’ (which is often what happens post-sale).


Stay in front of them, stay valuable, connect the dots, and focus on helping them make the most out of their investment at all times.


How to prepare your business for the enterprise market.


First and foremost, it’s that you as the leader of your business are ready to support your team in execution.


Again, this is why mindset is so important here!


That said, these are additional key details needed to put in place before you take the leap into the enterprise market.


  1. Ensure you have enough runway to support an enterprise team.  As I mentioned above, it’s unlikely you’ll be seeing a major stream of revenue from your first efforts in this market for the first 12-18+ months. I’ve seen many businesses build an enterprise team only to realize too late that they didn’t have the $$ to support them. This creates a bad market reputation and has led to many companies being shut out of this market! If you don’t have enough time or money to support a 12+ month ramp time, it’s time to reconsider getting into this market. Remember, the first year is the build year.

  2. Hire sales leaders and salespeople with a true enterprise mindset. Your team has to be aligned with everything in this article if you want to succeed in this market. More on this in the next section!

  3. Be ready to iterate on your product. Again, enterprise sales is about “custom solution for a single buyer.” Make sure your product team is ready to support custom builds for multiple potential buyers at once. And be prepared to constantly be looking in the rearview mirror to learn and grow.

  4. Prepare to support post-sale. Enterprise clients take a lot of resources to support once the deal is done and the solution is implemented. It’s 10x harder to get a new client than to keep an old one, so make sure your Customer Success team is poised to deliver!


The critical qualities to look for when you’re ready to hire.


If you’ve made it this far and you’re ready to hire… Congrats! That’s a huge step.


However, the complexity of defining what enterprise sales is and isn’t can still rear its ugly head at this stage.


How do you know which sales leader or enterprise sales rep is right for your business? After all, there are 48 different kinds of VPs of Sales swirling around in the marketplace. Do you know the differences and what’s right for your business and stage of startup?


While it’s nice to have industry experience, connections, previous success in sales, etc. to help you get started quickly there are qualities beyond those that you should prioritize.


 What is enterprise sales


Special considerations for any enterprise sales leaders you hire.


Any sales leader you hire should embody the qualities above as well along with a clear understand of what they do best aka their sales leadership superpower.

On top of that, it’s essential that they’ve done the job themselves too. It’s the only way they’re going to know how to break apart deals, manage up to set realistic expectations, and help your team think through how to win them on a strategic level.


Without this experience, the risk of doing major damage exponentially increases.


Questions about enterprise sales?


Enterprise sales in startups is my first business love and helping startups get it right the first time around is my life’s work.


If you have questions about any of this or want to talk shop about anything related to enterprise sales, my hotline is always on with an ear to listen and a mind to brainstorm!


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