Breaking into IT/DevOps sales as AE

I have my eye on a couple companies and am considering what the leap from EdTech SaaS to IT/DevOps B2B SaaS might look like. I think that with my background, my ability to navigate government buying cycles and find various points of entry into an organization are strengths.

With that said, I could foresee my lack of experience selling to IT/DevOps audiences and the fact that I don't have known tech stack companies on my resume being a challenge. I also know that I'd have to learn a bit about nuances between IT buyers and my current buyers, which are K-12 Superintendents, Asst Supers, Program Directors, Coordinators, etc.

Any advice on how I can get ahead of these inevitable questions? Are there certs I should explore? What should I know about this field and these buyers? Anyone here made a similar jump?

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jefe

Arsonist

🍁

What's behind the move from EdTech to IT/DevOps?

BenitoBlanco_

Opinionated

Regional Account Executive

Great question. First, I'll say it's not a done deal - I'm always open to opportunities available to me and learning more. I'm not swearing off EdTech or anything like that.

With that said:

- In EdTech, there is a natural bias towards employees who are former educators. Teaching can be a pretty clannish occupation, and partially because it's such a difficult and underpaid job, they see themselves somewhat as martyrs for lack of a better phrase. Because of that, some of them look down on other folks who don't have an education background and think we couldn't possibly understand the job to the level they do. It's weird, because this is really only a problem with EdTech employees, and I've never had any issues with prospects/clients who are current educators.

- Employee satisfaction/approval ratings of the companies I'm looking at are through the roof. It's a personality trait of mine to find the silver lining and keep my head up through challenging times, but I've wasted more time than I'd like in the past sticking with companies where I could have been doing better, more enjoyable and lucrative work had I explored my options sooner. Doing that at a couple of my previous companies is probably my biggest regret in my professional career, so I'm making a conscious effort to always be open to what's out there. While I am not unhappy in my current role, I can't help but notice that a LOT of my colleagues are, so I'm trying to ensure I don't simply have blinders on.

- I want to expand my resume and I believe branching out into IT/DevOps Sales is a good place to be. I could also see myself potentially studying to get into a more technical sales role down the line, if I find I enjoy the work.

- I see more potential networking opportunities in this field, whereas I don't see a school district hiring me to teach or help design curriculum anytime soon. I also wouldn't be interested in a position like that.

- This may not be a good interview answer, but it's an honest one: my company is in a difficult post-merger phase right now where support for Sales teams is very behind and processes are not well thought out. I've lost a lot of opportunity this year over other teams at the company missing legislation that rules us out of competing and not having the subject matter expertise to properly compete for and win RFPs.

- I just reached a year at my company and I've already worked two different territories, and they're already talking about changing my territory again. A colleague of mine who has been here for 6 years has said the longest she has spent in the same territory is 2 years. That is particularly difficult when you are selling into government orgs that demand a high level of networking/brand-building and buying cycles are extremely rigid.

- Literally 0 reps are pacing to hit quota. I'm not aware of any reps who are even close. Just too much volatility and lack of proper planning.

- I have always been into tech and usually am the "tech guru" or nerd on my team. I'd like to lean into that and work with more like-minded folks.

That went way longer than I expected but I think you hit a nerve and words just started flowing out of my keyboard, lol.

Gasty

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BenitoBlanco_

Breaking into IT/DevOps sales as AE

3 comments

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