Careers @ It's Tricky Tech

Sell Software.
Build a Career.

Build a career in software advisory — where deep product knowledge and honest client guidance define every engagement.

Software sales team at work

Our Sales Culture

01 / Product First

Every team member knows the products they represent, so client guidance is grounded in direct experience.

02 / Advisory Over Quota

The recommendation that fits the client — even when it's more economical — builds long-term relationships.

Open Roles

Join our sales and customer success team.
High PriorityRemote / Hybrid

Software Sales Executive

Own the full sales cycle for our software product portfolio — from prospecting to close. Ideal for someone who loves matching the right tool to the right buyer.

OpenRemote

Software Product Specialist

Become the in-house expert on a category of software products — supporting the sales team with demos, comparisons, and buyer consultations.

StrategicOn-site / Hybrid

Customer Success Manager

Ensure every buyer gets maximum value from their software purchase — driving renewals, upsells, and referrals through exceptional post-sale support.

Software sales team collaboration

Sell Products You Believe In

We represent software we'd evaluate independently for our own businesses — making recommendations credible and client relationships durable.

"We don't just sell software — we help businesses find the tools that change how they work."

diversity_3

Collaborative Team

model_training

Product Training Provided

Ready for a career in
software advisory?

If you understand software, know how to listen to buyers, and want a career built on honest advisory work — we'd like to hear from you.

Apply Now