Securing The Five-Figure Sale

Learn How Your Business Can Successfully Enter the Enterprise

You’re here because you know you can handle this.

You’re here because you’re ready to go after the enterprise sale and land some five-figure customers.

I’ve spent the last decade selling to enterprise customers against huge public companies and well funded startups with HelpSpot.

Selling to enterprises doesn’t have to be expensive or time consuming.

You CAN do it profitably without cold calling sales people and fancy steak dinners (optional).

In fact, selling to the enterprise is more about understanding their internal processes than it is about “selling”.

Securing The Five-Figure Sale explains:

  • What enterprise buyers need from your website
  • What to do with RFPs
  • How to run demos
  • Manage contact relationships
  • How your pricing impacts enterprise sales
  • Understanding how to get paid
  • How to avoid getting trapped by customers who are “too big to lose”

Securing The Five-Figure Sale lays out the framework we’ve used at HelpSpot for the past 12 years so you can hit the ground running in these key areas.

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Table of Contents

  • Approaching the Five-Figure Sale

    • Should You Sell to Enterprise Customers?
    • Why Enterprise Customers are Worth the Extra Effort
    • The Right Level of Enterprise Sales to Pursue
  • Capturing Leads – And Knowing What To Do With Them

    • A Note on RFPs
    • What Your Website Needs to Pursue Enterprise Sales
    • Website Tools To Consider
    • Why Demos – And Who’s Running Them?
    • Timing (for Trials) is Everything
  • Communicating with Your Contacts

    • Managing Outbound or Direct Sales Processes
    • Responding to & Navigating Pre-Sales Inquiries
    • Following Up for Customer Retention & Expansion
    • Move Beyond Automated Emails
    • Understanding the Support & Sales Overlap
    • Assisting Contacts & Facilitating Their Purchasing Processes
  • Exploring Pricing Models & Payment Systems

    • Pricing Model Considerations
    • Key Software Pricing Models (Not Software? Still Read!)
    • Negotiations
    • Payment System Adjustments for the Enterprise
    • The Nuts & Bolts of Getting Paid
  • “Too Big to Lose:” The Risks of the BIG Client

    • How Far Will You Go For That Big Client?
    • Avoid Factoring Large Clients Into Long-Term Planning
    • Customizations & Implementations: Doing What It Takes To Close the Deal
  • It’s Time To Sell