Enterprise Sales Leadership: Perception vs. Reality


Recently, I had a conversation with a sales leader whose #1 goal was to hire a BDR leader for the team.  The thing is, he’d been through one already and the rest of the team keeps churning… 


So I threw up the white flag to understand the situation and asked:


  • Why didn’t they work out?
  • Who’s your buyer?
  • What’s your expectation for your BDR team for when you want to see production?


Then the red flag started to wave –– his answers didn’t match up!  


My point is that enterprise sales is not easy, it’s not transactional, it’s not a one-size-fits all game, and it takes time to learn and perfect an enterprise sales process.  Do you think there’s a magic wand you’re going to wave and suddenly these great results are going to pour in?  Not a chance!


Unfortunately, this is a common misconception that can have devastating consequences.  If you try to dive headfirst into enterprise sales without understanding the market, your buyer, and the steps you need to take to succeed, you’re in for a rough ride.  


A failed enterprise sales function can send a ripple effect throughout your company and cause potentially irreparable damage.  It’ll turn off your potential buyers (good luck getting that door to open again), can cause your best employees to leave, and leave you scrambling to pick up the pieces.  


Unlike SMB sales, enterprise sales is an intricate and complex beast.  So being a great enterprise sales leader requires a specific skill set and a deep knowledge of that segment.  


Don’t take a short-term approach to a long-game scenario.


I’ve said it before, but it bears repeating… SMB sales success does NOT translate directly to enterprise sales success.

This is one of the biggest problems I see when companies try to transition into the enterprise market.  They think that what worked for them in their SMB sales process is just going to simply carry over.  


The fact is, you have to account for a transition period if you’re looking to get into the enterprise market.  You can’t just keep the same team, with the same skill set, and the same sales process, and expect to succeed with enterprise buyers.  


Enterprise sales is complex.  The buyer journey is longer, the process is more intricate, and it involves building deep relationships with a variety of people among all the moving parts involved.  


As a leader, it’s essential that you’re tuned in to the ins and outs of what’s involved and what’s at stake.  If you don’t understand it, how on earth can you properly comprehend the buyer journey to coach and lead your team? 

Simply put: if you’re the type of person who’s always looking for immediate results or shortcuts, then enterprise sales is NOT for you.  


True story… One of my biggest enterprise deals took two years to complete.  The only reason I even got a seat at that table was because I’d spent the first 18 months doing business with all of their field offices and absorbing all of that priceless intel like a sponge.


I was collecting data, looking for themes, solving their problems, and helping them navigate difficult situations.  From that initial legwork, I created a network of mega fans who loved the work we did and how we did it and weren’t afraid to scream it from the mountaintops on my behalf.


Only then was I able to leverage all of that work to get a seat at the table with the COO to present an informed pitch that pushed all the right buttons.  


Know what you’re working with from the get-go.


This should go without saying, but so many enterprise sales leaders miss this.  


As you’re evaluating enterprise sales leadership roles, it’s critical to get the full lay of the land –– i.e. what kind of budget and organization do you have to support you?


Has the sales team worked in the enterprise market before?  Is the budget aligned with the long-term vision for the company?  How do budgeting decisions get made by the company?  What’s the post-sales strategy (when the deal closes, that’s when the party really gets started)?  Is the product team ready and able to support customizations and integrations?

Knowing your budget and the bureaucracy surrounding what needs to happen to get it right for your buyers means knowing how and what you’ll need to make an enterprise function work.  


I can’t stress this enough: you need to have the courage to ask these questions at the beginning of the process.  This is your career after all!


Without this knowledge, you’ll never know if there’s true alignment and will be setting yourself up to flounder in the market.  


Remember, enterprise sales is complex and requires a more significant investment upfront and a longer timeframe for that investment to pay off:



Most importantly, beyond knowing your budget and what’s in store as you get your enterprise function going, the most critical piece of the puzzle is knowing your buyers, what’s important to them, how they buy, and why they buy. 

Understand your buyers before you do anything!


Buyers care about three things: getting better, solving problems, and reaching goals.  That’s it.  If you’re not able to help them achieve any or all of these, you’re in for a rude awakening and a weak pipeline.


Sophisticated buyers need a lot of hand-holding and guidance throughout the process.  For my big $26M deal (referenced above) I met the buyer where they were at.  NOT where I wanted them to be.


I went to their conferences and events to listen and learn and take that priceless knowledge to connect their dots and provide value.  I didn’t just invite them out to dinner or ask for 30 minutes of their time so I could talk at them with a lame pitch.

The process of getting to know your buyer is a cumulative one that transpires over a long period of building and nurturing the relationship.  That’s the only way to fully understand them and give them exactly what they want. 

The best enterprise sellers realize that it’s not about their sales process, it’s about their buyers and what’s important to them.  


To be clear, this doesn’t mean that your buyers are always right or that you can’t challenge them.  Ultimately, it’s up to YOU to connect all the dots and sell them on the big picture.  


So before you try to sell anything in the enterprise market, take a page out of my friend Sam McKenna’s book:  ‘show them you know them’ by putting in the effort to get to know your buyers as deeply, intricately, and personally as you can.  


Remember, you’re not trying to bring them to you.  You’re meeting them right where they are.  And when you do that, watch the magic happen.


Think about how magnetic it is for a buyer to know that they’ve been truly heard and understood.  Especially in a world where nobody has the patience to give anyone the light of day…  


It always goes back to reaping what you sow.  Take the time to know your buyers, be patient, do the right work consistently and you’ll put yourself and your team in a great position to build strong pipelines with real opportunities for the short, near, and long term.  And when that happens, say bye bye to chasing your tail or resorting to icky sales tactics that come back to haunt you later.


Enterprise sales is a team effort that starts from the top.

It takes a village as they say and when you take care of your team and your buyers, they’ll take care of you.  No matter how skilled you are, or how many connections you have, or how confident you are coming into the enterprise market, remember, you can’t do it alone. 

Sales leaders who try to be a lone wolf while alienating everyone else that can help push the boulder up the hill, don’t stand a chance.  


Enterprise sales is a team sport and takes a well orchestrated team effort to succeed.  The sooner you come to this realization, the better off you’ll be in the long run.  


However, in enterprise sales (especially in a startup) you can’t be sitting up in the luxury box calling the shots –– you need to be your team’s quarterback, right on the field in the thick of the action.  

A leader is one who knows the way, goes the way, and shows the way.”  — John Maxwell


Great leaders lead by example.  Make no mistake, this is absolutely essential in enterprise sales.  How you approach and interact with your buyers informs how the rest of your team will. 


This is true regardless, but it takes on another level of importance when the team you’re managing is still getting their feet wet. 

As a leader, it’s critical to understand your team like the back of your hand while knowing how to utilize them to the best of their ability.  If you’re not connected to your team, and deeply knowledgeable about what makes them tick to make sure the right people are in the right roles doing the right work, it’s not going to translate into success for the long haul.

Because enterprise sales is a whole different ball game you’ll need to have your whole team on the same page if you’re going to succeed.   


There are at least 6-10 people involved in the enterprise buyer journey. If those people are getting treated differently by different members of your team, it’s going to turn off your buyers and you’ll be back to square one.  


Don’t make that mistake.  Get your team in sync with each other, lead by example, understand your marketplace, seek to understand (internally and externally) and remember your buyers hold the keys to the castle… always.


Wrapping Up


Transitioning into the enterprise market is tough for any sales leader, regardless of your prior experience.  


But with the right foundation around you, a cohesive hard-working team, and a relentless commitment to your buyers’ needs, you can make it happen!  


Also, I recently joined forces with Sam McKenna, Dalton Van Hatcher, and Sara Lash a la The Revenue Collective to talk about this and then some.

You can find the full conversation here if you’re interested in diving deeper into this topic.  Enjoy!