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How To Scale B2B Sales; Selling To Enterprise Customers

Selling to enterprises as a start-up of 20 or fewer people is a difficult task. No doubt navigating complex enterprise buying decisions and implementing your solution successfully can be a difficult process filled with potential showstoppers, not to mention the time and effort input required to make it happen.

Over the past three years, 10to8 has scaled from working solely with SMB’s in a transactional model, through to mid-market and enterprise with a full solution sale offering. It’s been a long road but we’re getting close to having something that we can scale effectively and quickly.

As a result, I thought it may be a good idea to share some insights on how to scale B2B sales and start selling to enterprise customers. For the purposes of this article, I’ve left out lead generation and customer success as they are whole articles in themselves. I’m assuming you’ve found a way to prospect and generate leads as well as have a means of onboarding clients into the system. 


What is the difference between transactional and solution sales?

Transactional selling, in short, is a sales strategy where the main goal is a quick sale that results in a quick transaction. The value lies in your product and price is the main selection criteria. Solution sales or consultative sales focuses on unearthing the pain points of the client and offering a solution. This is a much more holistic approach, as the salesperson needs to build a relationship with the prospect, map their needs and present a tailor-made solution for them.


How to transition from transactional to solution sales?

The following points are key when moving from transactional to solution sales.

  • Have your technical team onside for InfoSec conversations 
  • Land and Expand 
  • Make sure to get a face to face meeting 
  • Be patient when it comes to contracts
  • Review, champion, and iterate 


Have your technical team onside for InfoSec conversations 

Information Security can be difficult to hurdle; if you haven’t spent the last few years becoming compliant with HIPAA, ISO27001, SOC2, GDPR, PCI-DSS, etc. then you may face some challenges in this respect.

Bringing in your technical team is a vital part of the relationship-building process. Connecting the experts to build bridges, having succinct questions and answers means that you’ve got the best people from your business connecting with the client’s team. The more customer-focused members of staff you have around the better. 


Land and Expand

Whether you can implement the land-and-expand model depends on the product offering you have but starting small and growing an account can be a simple way to win the hearts and minds of enterprises. 

At times, the sheer scale of the process that you’ll have to go through to implement the solution even for a sub $5K ACV (all-commodity volume) deal can feel large. However, if your offering is as good as you think and the clients see real value, you’ll be first in line when a suitable use case appears elsewhere within the organization. 

how to scale B2B sales with the land and expand model

Image: Hunter & Bard

As an example, at 10to8 we started with a $6k ACV for a small use case within a large US bank. We worked hard (perhaps too hard) to deliver a great onboarding process to get the client up and running and within three months they had 10X’d their contract, taking the total contract revenue to over $250k. We’re hoping to expand this further and take it to a seven-figure deal within the next 12 months, making the work we did upfront for them feel relatively small fry. 


Make sure to get a face to face meeting 

Enterprise customers buy solutions, not products and a part of your solution is the delivery team, which means building trust is always vital. 

Are you struggling to close that business-changing deal or always losing out at the point of the RFI (Request for Information)? The first thing you should be doing is getting on a flight, train or buckling up to see your prospect. It’s likely that your competitors already are. Again, this can feel like a high-risk option for a cash strapped start-up, however, the long term gains of a 3-5 year deal which represents over 5% of current MRR (Monthly Recurring Revenue) is more than worth it. Go and sit down with your prospects, deepen the relationship, build trust, and get the deal closed. 

You can close a $50k+ ACV deal over the phone, but if you want to go seven-figure-big then start getting buy-in over face to face meetings as much as possible. 

You can close a $50k+ ACV deal over the phone, but if you want to go seven-figure-big then start getting buy-in over face to face meetings as much as possible. Click To Tweet 


Be patient when it comes to contracts

You’ve shown the value, got buy-in from the decision-makers, passed the information security processes, and you’re already itching to get the team on board. But first, you need to get a contract agreed.  

A difficult part of working with enterprise customers is that they often have their own master vendor agreement which means that you’ll need to agree with their terms which will include high or even unlimited liability amongst other scary clauses. 

Agreeing, redlining and working with contracts teams can take forever. If you can build a fair internal contract that prospects are willing to check and redline then I’d highly recommend using systems such as DocuSign and Pandadoc to make the revisions processes easier. 

Contracting processes are tough but stick it out, stay the course and maintain the same energy and speed of response rates.


Review, champion, and iterate 

Your enterprise customers will know you’re small; just be honest and ask for lots of feedback. Speak to them often and ask how you can improve, iterate internally and identify champions. Champions are great as they create net-negative churn but mostly as a small business they help you win more, win bigger and win with a faster deal cycle. I’d suggest speaking to your bigger clients monthly for the first year and quarterly after their initial renewal date. 

All of this can be digested and turned into a process for future reps selling to larger organizations and not just in the enterprise but also adapted to the mid-market as well. 


Hopefully, these points will give a few small quick wins with your existing efforts and help you scale B2B sales fast. Selling to enterprise customers is tough, but the more you practice the more you learn. And putting the logos of those big names on your website will not only feel good but will also help to get more of them.

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Jacob is the Head of Sales here at 10to8, working with the ever-growing enterprise client base.

Before he joined in 2017, Jacob co-founded and worked within multiple technology start-ups.

Jacob Buckland

Head of Sales, 10to8 Appointment Scheduling Software

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