cawolf / learn

Staying up to speed on how code is delivered

learn

Hi, my name is Josh and I specialize in selling early-stage, mostly unproven (at least commercially) technology. Self-promotion has never been a strong suit for me, so you're probably not going to see me plastered across the internet. The bulk of my reputation has come from building upon sales experience after sales experience by seeking out uncomfortable and somewhat ambiguous sales roles with steep learning curves where resourcefulness and "figuring it out" have been crucial to success.

After more than 10 years in sales, I've realized that being a do-er across industries, segments, deal sizes, and company stages has provided me with a unique perspective available to help others seeking to have more success in tech sales. I enjoy being a part of even the earliest transactions, as every interaction has the potential to inform what is needed to scale.

Why I decided to create this repo

1. Sales is really hard these days. Sales reps that have repeated success in tough accounts or with highly complex technologies are rare. The best reps know that their value is not in their rolodex, but in their ability to consume more information than they're customers, gathering wider context on the problems customers like them are trying to solve. It's not always about the depth, but the ability to connect the dots and clear the path. For someone entering sales in this industry, that is a daunting task...where do I start? How do I keep up? They'll see right through me.
2. Technical cofounders building enterprise technologies have it hard. Many times, they're learning to build a company and a product simultaneously. Even with deep expertise in the problem space and product, it's still not enough. Early sales requires knowledge and process. Knowledge has many dimensions, well beyond the technology alone. Process is what creates predictability, even in those first few deals.
3. Regardless of the role, everyone I've ever worked with has had to own an outcome. It can be as local as making an individual decision and implementing it. Othertimes, it can be as global as a key organizational change where hundreds or thousands may be impacted. Communicating context and creating a narrative are crucial in driving influence, but most are forced to learn each lesson on their own. That's not ideal, especially as the radius of the impact of these decisions grows throughout individual's careers.

Where to start

I originally wrote the Getting Into Sales doc to learn Git and markdown, and provide a place for my peers to discover and access content I was absorbing regarding software development trends. It became a tool to onboard new reps and set expectations around the types of knowledge they would need to have to build credibility with prospects.

For you founders out there, I jotted down a few thoughts on earning those first few deals in the Startup Sales Primer.

The Business Value Template came from a talk I gave at Kubecon EU to help technology practitioners in influencing management to support their use of open source software.

Knowledge and Process provides a checklist for what a founder should know going into their first prospect engagements, and how to structure them to have the best chance for sales success.

Yeah, your probably thinking, this isn't just a repo...it's a monorepo! I have a few dad jokes too.

In all seriousness, enjoy the content, make suggestions, ask me questions.

I can be reached via twitter, linkedin, or email