Morgan Mackles
Sep 25, 2018 · 4 min read

It’s no secret that selling to the enterprise is a particularly daunting task. As an enterprise technology venture fund, Work-Bench is constantly pinged for advice on sales. The challenges around enterprise sales are practically universal within the community of early-stage enterprise tech startups in NYC. To help alleviate this critical need, Work-Bench developed the Enterprise Sales Guide, a series of tactical playbooks and templates to help you crush enterprise sales.

My own contributions to the Work-Bench Enterprise Sales Guide playbook were born out of 15+ years of personal sales experience — the good, the bad, and the ugly!

As I climbed up the ranks over those many years, I’ve spent my entire career in a never-ending cycle of learning, testing, iterating, failing, winning deals, losing deals, iterating again.

I think I’ve personally lived the pain of nearly every sales-role that exists: the daily grind of cold-calling from never-ending lists as an outbound SDR, the frantic pace and frenetic energy I felt as a quota-obsessed Inside Account Exec, the manic swings and inherent isolation of Enterprise Field-Sales … and I’ve loved every minute!

Where my personal sales narrative becomes interesting and applicable for Startup Founders is this: from my very first VP role leading sales at, I’ve become obsessed with the goal of building scalable and repeatable sales processes for VC-backed Startups.

Since becoming addicted to building out sales processes, I’ve been honored to work closely with dozens of amazing VC-backed SaaS Startups in my capacity as Program Advisor for the Heavybit and Work-Bench venture funds in San Francisco and New York City respectively.

I’ve also had the privilege of refining my processes in real-world Advisory and Consulting roles with some of the most exciting SaaS startups in the industry, working collaboratively with rising-star CEOs such as Fred Stevens-Smith at RainforestQA, Edith Harbaugh at LaunchDarkly, and Dennis Pilarinos from BuddyBuild.

In summary, I’ve built and led sales teams, advised and consulted for top-tier startups, spent countless hours learning best-practices from best-in-class mentors and sales-leaders, and now I’m eager to share some of my sales-learnings with the Work-Bench community.

And so, without further ado, I’m excited to contribute my “Sales Process Playbook” and “Customer Evaluation Document” templates to this edition of the Work-Bench Enterprise Sales Guide!

Sales Process Playbook

The Sales Process Playbook was born out of my personal philosophy that scalable-and-repeatable sales methodologies are more about science than art. While there may still be a bit of magic in developing solid rapport with a key decision-maker or art in a negotiating a perfect win/win volume discount, a completed sales playbook should look and feel much more like a simple, plug-and-play, checklist-style resource. The key to a truly scalable playbook is in the clarity and the simplicity it creates for your team to move sales opportunities from stage to stage.

This version of the “Sales Process Playbook” template provides a solid starting-point by detailing ten specific, tactical stages of an Enterprise sales process, guiding you from raw lead to POC to closed/won. Each of these ten steps dives deep into the desired outcome to keep you focused on the goal of each stage, a detailed checklist of each member of the sales team and their unique deliverables at each stage, as well as examples of the tools your reps will need to move forward from stage to stage.

Customer Evaluation Document

The Customer Evaluation Document zooms in on the vital “Evaluation Phase” of an Enterprise sales opportunity. Often referred to by Enterprise customers as a “Pilot” or a “POC,” this is one of the subjects that Startup Founders ask me about most often. Therefore, I wanted to provide a complete and detailed example template to help get you started on the right track.

This version of the Evaluation Document is intended to be shared in a collaborative manner with your prospect’s champion — a core stakeholder at the buyer’s company who help you sell our service to their colleagues. Your Evaluation Document should be delivered prior to kick-off, and should clearly outline the objectives and deliverables, pre-evaluation activities, evaluation schedule, post-evaluation activities, pricing, terms, and contact information.

The key objective of this collaborative document is to ensure that both parties are on the exact same page when it comes to every detail of the process — even before kicking off the evaluation itself. If this document seems like overkill to you, trust me that true Enterprise buyers actually appreciate the level of detail and professionalism your Evaluation Document will bring to the table.

As a part of the Work-Bench Enterprise Sales Guide, I hope these documents provide a helpful starting point as you constantly work to iterate and improve your commercial processes and ultimately CRUSH ENTERPRISE SALES!

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Morgan Mackles is VP Sales at Work-Bench portfolio company, the market leader in artificial intelligence scheduling software.


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement.

Morgan Mackles

Written by

Morgan Mackles is VP Sales at, the market leader in artificial intelligence scheduling software.


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement.

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