Sales Tips

Top 5 Things Enterprise Sales Needs To Know

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August 25, 2023

6 mins read

Top 5 Things Enterprise Sales Needs To Know

Top 5 Things Enterprise Sales Needs To Know

In today’s rapidly shifting business landscape, the art and science of enterprise sales is evolving at an unprecedented pace. As SVP of Enterprise Sales at Demandbase, I’ve witnessed firsthand the transformation of sales strategies, approaches, and tools over the years. However, amidst the flux, certain principles and insights stand out as paramount for success, particularly in the enterprise segment. Whether you’re a seasoned sales veteran or a newcomer looking to make your mark, understanding these crucial elements is table stakes. Dive in as I unveil the top five enterprise sales tips every enterprise sales professional absolutely needs to know and put to use.

Exceptional discovery

Do you understand the top three C-Level goals of your account or prospect? Do you know the trends in their industry at the moment, who their customers are and what their competition is doing? For enterprise companies, it’s all publicly available. Taking a first call without doing this type of pre-call planning is a call you have just wasted.

Be genuinely curious about them and confident enough to ask them thoughtful, open-ended questions about their highest level initiatives. Odds are you aren’t speaking to the CEO when calling an enterprise, but someone (or a whole Buying Group) who has marching orders to support and be in service of those CEO objectives. And going even further, that someone doesn’t always know how they are going to get there. Make the connections for them, articulate and help them visualize how your “thing” supports those initiatives, and attach your value prop to that talk track throughout the cycle, constantly reinforcing how you will get them there. To do this well and get authentic buy-in takes work. If you stop reading here, that is okay because this one has never failed me. It’s the most mission critical aspect of effective selling, and gives you the edge in an often very competitive market.

Constant momentum in long enterprise sales cycles

Move the needle every day. Every. Single. Day. Endeavor to be in contact, meet a new stakeholder, share thought leadership content, do a status call, broker a partner connection, foster executive relationships, plan on-sites, etc. for all your deals in cycle. Do whatever it takes to inch that deal forward daily.

My tactic as a sales rep was one I un-creatively referred to as the “post-it note.” The bulletin board on my wall had a collection of post-it notes each with the name of my deal that quarter and my job was to put a checkmark on that note on a daily basis. This meant that I touched them somehow that day.

Every morning I would glance at my sticky notes and it helped me prioritize while giving me assurance I was all over a deal. As a sales leader, the last thing I want to hear about a substantive deal for that quarter is a rep telling me “last call with them was two weeks ago.” At the enterprise level, it’s imperative you’re using every tool in the bag (starting with these enterprise sales tips) to keep the momentum.

Pressure-test your deals constantly

There are so many competing priorities in enterprise accounts, stakeholder politics, market changes, and savvy competitor maneuvers, that it’s a necessity to maniacally ensure your project is still tracking amidst all potential threats. Leverage your peers and sales leaders to have them unearth where you might be weak. Conduct war rooms and run DNA sessions to de-risk the risks. Knowledge is power and overcoming objections can only happen when we know what we are up against.

Evaluate every subsidiary under the parent/sister company

A unique aspect of selling to the enterprise account is that you are likely going to have multiple lines of business and potentially hundreds of subsidiaries. What separates your ‘huge earning’ years from the ‘pay-the-bills earning’ years is how you navigate large enterprises.

I have seen this work many different ways. Sometimes it’s a ground swell from enough interested subsidiaries asking their corporate parent to pull together an ELA (Enterprise License Agreement). This is an ideal scenario as you are now you are the de facto standard vendor of choice and given carte blanche to move from division to division with the best opening sentence in the world:

We are an approved vendor.” 


[That or some variation that includes being the companies’ preferred solution, having existing terms, completed clearance/vetting by security and privacy, or having gone through onboarding by procurement already.]

It feels like the gates to heaven are open. Everyone exhales at how easy it will be to do business with you and will tell their friends in other business units. I have also seen this work from the corporate parent having the initiative to establish common systems across their organization and set up an ELA to push down and out to all the children/sister companies. It’s also imperative to seek out a Center of Excellence. The most efficient technique, however, is a combo of top-down and bottom-up simultaneously. Your approach should be situational. Yes, the cycles will be longer on the front end, but the outcome is exponentially increased revenue.

This is what differentiates enterprise from the mid-market/small business sector. And we need to plan how to penetrate these often massive accounts with the end goal in mind.

When done correctly, upsells will come more frequently, more warm doors are opened for you, all the while you are fortifying retention rates as your solution is installed across many areas of their business. Ripping you out is a huge undertaking, so your future retention-minded selves will thank you for spending the time upfront driving that ELA. 

No stone left unturned

Although the title of this blog talks about five enterprise sales tips, this last point is a three-in-one package that includes a few final but equally important reminders that will come in handy in the world of enterprise sales: 

    1. There’s no getting around demonstrating ROI, but keep it simple. Something as real-time and raw as the ‘back-of-the-napkin’ can work.
    2. Qualify deals out early. Time is your most precious commodity. Don’t spin cycles where there is no real interest at the moment.
    3. Executive alignment is mission critical, and if you aren’t up-leveling inside of your accounts, trust me, others are.

These five(ish) enterprise sales tips have all been paramount to my success rates in the enterprise segment, and I have no doubt that any salesperson who implements them and keeps them top-of mind throughout their approaches will ultimately add wins to their record. 

P.S./Bonus tip: never talk SKUs or product names! Stick to their pain-points.

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Wendy Chakrin

SVP, Enterprise & Strategic Sales, Demandbase

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