Airing some dirty laundry on our sales process

April 25, 2017 Roy Raanani

Guest blog post by Jerry Pharr, Director of Field Readiness at

Note: This post includes a bit of airing our own dirty laundry. We share this because we value transparency -- and because we all benefit from learning from one another’s mistakes. Feedback welcome!

At Outreach we’ve built a $10M+ ARR business in two years by drinking our own champagne -- using the power of our own platform to rapidly ramp and support the most productive and successful sales team around. Not surprisingly, we think a lot about repeatability and scalability, not only because it makes good business sense, but because it helps our reps be successful while creating a better buyer experience. See this article by our CEO Manny on the importance of improving reps in the middle of the pack.

Since I joined Outreach to lead Field Readiness, we’ve doubled down on our sales process investment, down to the types of conversations we want our sellers to be having. Like most successful sales organizations, we find it helpful to define what a “great” discovery meeting should look like, specifically highlighting the themes we want our sales team to explore on every call.

In principle, this makes sense. During discovery, it’s essential to consistently ask questions that help you understand as much as possible about the prospect’s situation and pain. Moreover, when you’re growing, it’s powerful to look a new hire in the face and say “If you follow this process, you will close business. If you’d like to deviate from it after you’re ramped up, that’s up to you - but this is proven to work.”

In practice, it’s tricky. Among the bigger challenges is knowing if a process is being followed, and if it is or isn’t working. This is especially important if you’re trying to understand why reps aren’t ramping as successfully as expected. We solved this for workflows (because of our own product), but had little visibility into what was happening during customer facing meetings.

Because we're a distributed team, I needed a way to do that without sitting in on every meeting. We started using to automatically record and transcribe the meetings, and then decided to use it to instrument our sales process.

What does that mean? We have specific language we use to discuss each of the four themes in our discovery process. Using their AI, we know which themes were or were not discussed, can quickly listen to specific parts of a meeting, and can tie adherence to our sales process to the advance rate of our opportunities. With this data, we can increase adoption by rep through personalized coaching.

There were 3 takeaways when we looked at Chorus’s insights:

  1. The more themes we covered in discovery, the more likely an opportunity was to advance. A good thing. When we stick to our process, deals advance.

  2. We rarely covered all 4 themes.  Expected, to some degree. This is a new framework and we knew adoption wouldn’t be perfect. Admittedly, though, we were surprised that it was less than 10%.

  3. We advanced over 50% of opportunities where only one of four themes was discussed. A bad thing, but a big insight.

#3 has two big implications, so I’ll focus there:

  • We are potentially wasting our team’s time. It’s somewhere between possible and likely that we’re moving deals into the pipe that shouldn’t be there, because we haven’t done sufficient discovery. More follow-up. More emails. More scheduling. More meetings. More manager time. Internally you spend time discussing those deals. In theory we should not advance any opportunities where only one theme was discussed.

  • We lose “the answers to the test” that help us down funnel. Discussing these themes help us position our value and need for our product to other stakeholders, and help us through the inertia of a B2B sales process. Without it, sales cycles are longer and it’s harder to maintain urgency and justify pricing.

Like with any process, the most important thing is to define what’s important, measure it and improve it. This is a starting point for us to instrument and improve our team’s conversations and create great experiences for Outreach buyers at scale.

I’d love to hear how you think about creating repeatable, high quality interactions with your teams. Let us know in the comments!

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