A Practical Guide to Closing More SaaS Deals

(This post first appeared March 21st on my SaaS Sales Blog: QuotaClimb)

I’ve been managing sales reps for 13 years now and helping them win deals is obviously a significant part of my job. When they succeed, I succeed! There are lots of ways managers go about helping their teams achieve success. One of the most common strategies in SaaS is a periodic event called a “Deal Review”. The idea behind a deal review is an open and honest dialogue about all the particulars of a key opportunity the sales rep is pursuing. Some managers do deal reviews during 1:1 time, some do them ad hoc via email, others do them quarterly in a big dog and pony show while others just don’t do them at all :)

I’ve learned a lot in the field with live fire. I’ve also been fortunate to have worked for companies like SuccessFactors, Periscope Data, Envoy & Box where sales training is a regular part of the annual cadence. These organizations believed that investing in their talent with high quality training was a pillar of long-term success. (It’s no secret we adopted this philosophy via the cross-pollination of best practices from the SaaS godfather Salesforce.com). I’ve taken a lot of what stuck in real deals plus the various training classes and created a deal review framework of 4 quadrants that just about any sales manager or sales rep can use to “review” any key opportunity they are working on.

My framework was particularly useful in 2011 when I had 16 direct reports. Yes, 16 front line reps reported to me! @Box we were scaling like mad and I had to come up with a way to scale myself. When I first created the framework I would lead the sessions in a conference room with 3 or 4 reps at a time. Each taking a turn reviewing their largest deal. I would stand at the whiteboard and go trough the quadrants, ask a bunch of questions and document all the next steps and gaps in “Quadrant 4” aka “What’s Missing?”. If you’ve ever been in a review with me you know my favorite 2 questions are “Why?” and “Did they tell you that or is that what you assume?” I would also encourage each of the reps to ask questions of their colleague and give feedback on where they saw gaps. Eventually the team of 16 was able to be split into 4 teams with rotating captains and they would run the reviews themselves. After their independent sessions they would take pictures of the whiteboard and upload it to Box for posterity. Then during the next review they would talk about the same opportunity and learn from one another on ways to move deals forward.

Below is a light rundown of the framework as well as a sample document you can use yourself to run a review on an opportunity you are working on right now!

*I really enjoy doing the deal reviews early in a sales cycle then coming back some period of time later to see what progress was made and what evolved along the way.*

The framework has 3 principles:

1) Our primary goal is to find numerous gaps in the opportunity & identify our next steps to fill those gaps. Filling gaps helps you learn more and communicate exactly how your solution is the best possible fit to solving the customer’s problem. Its ok to not know. Its not ok to not know that you don't know :)

2) We only talk about things we know for certain. Such as verified facts via personal research or statements validated by the buyer. No guessing, no company value prop stuff. Only what the buyer admits they care about. (Important in 3 of the quadrant to be VERY honest).

3) This is a creative exercise and meant to find holes. Be genuinely curious. Every opportunity has gaps. Even a bluebird, hot lead, 1 call crush opp. There are no right or wrong questions or answers. It’s a map of where we are today and several paths to get where we want to go! I want Quadrant 4 to have lots of things in it for us to work on together!

The information we discuss and gather is organized into quadrants:

1) All about them: Who are they? What are they trying to accomplish as a company?

2) All about the sales/decision process: How will they pick a vendor?

3) All about the pain and business benefit we are providing: What are we helping them with? How are we unique?

4) All the stuff we are missing: How will we lose? What do we need to fix/find out to win?

Here is a sample document I made to show one way of slicing the 4 quadrants. It also has some sample questions to ask in each section during your review session. I promise to add more to this concept in future posts!

* You can learn more about Rocky Paap on his Linkedin page or on his Twitter feed *

* If you see an acronym or word anywhere on this blog post that you haven't seen before, I might have posted an explanation at my SaaS Sales Blog: QuotaClimb. If not tell me and I'll add it!*