I started my sales career like many do, making small transactional sales. It was all about the emotional appeal of the sale, the need to drive urgency. This type of deal lives mostly at the top of the funnel and you have lots of levers you can pull during these conversations. With so many at-bats, it’s a great place to start building up your sales knowledge.

Today, I’m an enterprise sales rep. I’m responsible for managing stakeholders through longer sales cycles. I need to identify my customer champion and decision-maker. This type of sale homes into the bottom of the sales funnel. It’s definitely a more complicated and refined sales experience. 

I made the transition to enterprise selling because I felt like I could bring my authentic self to sales calls. I have the opportunity to earn my customer’s trust and respect by being open and honest, not focused on the pressure to close a transactional deal. I can put on my sales hat for some calls, and put on my strategy hat for others. Enterprise selling is all about building a true partnership with your customers. 

Planting the seed

At my first job, I had a wonderful mentor who really opened my eyes to the world of sales; not everything was about driving urgency, split decisions, and short deal cycles. There’s a world where you can be consultative and sell by being a problem solver. 

After three years in SMB, I was tired of transactional sales. Sometimes it felt like I was forcing deals when what I really wanted to do was partner with my customers and develop relationships with them. I felt that I would get so much more energy and satisfaction from that type of sales. 

Having a mentor, who gave me insight into what a career in sales could look like, led me to start thinking about enterprise sales very early in my sales career. I wanted to be able to say that I closed a 6 figure deal and I wanted to tie my business impact directly to winning large amounts of revenue. 

I was lucky to get a taste of what enterprise sales could be at my SMB job. Instead of a spray and pray approach, I was targeting and reaching out to specific accounts. I was ready to transition into enterprise. I was given the opportunity at the same company, but unfortunately, I’d have to start over as a BDR – and take a pay cut. 

So for me, I needed to leave that company to get into enterprise sales. But if you have the opportunity to level up in your current company, take it. You’ll know the product already, the company will already value your work, and it's a more logical transition that sets you up for success. 

The core competencies of enterprise sales

If you’re looking to make this same move, start by building up your enterprise sales competencies. In SMB, it’s about the volume of deals and being courageous in your work. But there’s a lot more to enterprise sales. 

You’ll need to get creative, especially when putting together a proposal that helps everyone feel like they’re winning. You can’t just give the customer what they want to close the deal and move on. Learn how to negotiate, otherwise, you’ll never get to your number. 

Enterprise clients tend to be educated buyers. They know which systems and processes they need in place. It’s up to the sales rep to show buyers the benefits that come with making big changes. Be patient and willing to work with your prospect through the evaluation. Your job is to get them to commit to making these changes.

My advice to sellers who want to transition to enterprise

Take time to learn about sales methodologies like BANT, MEDDIC, etc. 

• You need to understand that there’s a strategy that makes for successful sellers. You can’t make it in enterprise sales with just resilience and hard work.

Think of yourself as an investigator and information gatherer, not just a seller. 

• For example, I had a champion say to me, “our IT specialist doesn’t make the best purchasing decisions.” It was clear to me that I needed to talk to this guy and make sure I covered everything with him.

Understand your motivation. 

• What inspires you? What do you want to achieve? Maybe you want to make the most sales and be at the top of the leaderboard. In that case, SMB is a good fit for you. In enterprise, it’s the thrill of closing a seven-figure deal after months of work. 

There are no quick wins.

• You won’t get a daily dopamine rush in enterprise. You need to have faith in yourself that things will materialize over months, even if you go a whole quarter without closing a deal. Don’t let it get you down, just keep your eye on next quarter.  

Be comfortable not knowing all the answers. 

• When I was an SMB seller, I never needed a solutions engineer or CSM to answer questions. I knew everything about the product. But in enterprise sales, there’s no way to know everything. Lean on your resources, don’t overwhelm yourself trying to learn every detail about the product. It will only hinder your productivity. It’s okay to say, “I don’t know. I’ll get back to you with an answer after the call.” 

Always have a next step planned with a follow-up. 

• Ask yourself, how do I get them on the phone again? It may be a month before your next meeting is scheduled so keep yourself top of mind by providing value throughout the entire evaluation.

Make friends with other departments. 

• Enterprise selling is a team game. Cultivate relationships with the experts in your organization and ask for time on someone’s calendar. Learn what they want to achieve and help them succeed with you. Get people in your corner so you can lean on these relationships when working with customers.

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Transitioning into an enterprise sales role was a perfect opportunity for me to button up my sales skills and learn the “second half” of what makes someone a great seller. It’s like moving from checkers to chess. If you want to become a strategic seller, enterprise is for you.