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Workleap
Workleap

Technical Sales Specialist - ShareGate

salesfull-timeCanada - Remote
SALARY
Not listed
WORK TYPE
remote
JOB TYPE
full-time
INDUSTRY
general
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About the role

Job Description

So, what will your new role look like?

This isn't the Technical Sales Specialist role of five years ago. We're not looking for someone who just shows up on every technical call. We're looking for a builder. Someone who knows when to jump on a call because the deal demands it, and when to instead build the system, training, or asset that lets a rep handle that same call confidently next time. When you're in a deal, you're not just validating fit. You're reinforcing value, navigating technical gaps with vision and roadmap, and helping close.

Responsibilities:

  • Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement, so reps handle the majority of technical conversations independently — without routing everything through TSS;
  • Eliminate the single point of failure on technical depth by taking real load off the existing TSS across pre-sales, expansion, and partner-led deals, so no deal stalls waiting on one person;
  • Shorten deal cycles by delivering demos that become the internal standard — the kind reps study, replicate, and learn from;
  • Drive deals to close as a technical co-closer, not just a validator — reinforcing value, navigating gaps with roadmap and vision, and keeping momentum when the answer isn't a clean "yes, today";
  • Shape product roadmap by translating field patterns into structured input PMs actually use — and closing the loop back to reps when things ship;
  • Accelerate Migrate-to-Protect attach by supporting expansion conversations with existing customers and helping AEs and AMs connect the dots between products;
  • Compound the team's technical leverage by building reusable assets and AI-powered workflows so the same problem stops landing on the team's plate twice.

A typical week? A mix of customer-facing technical sessions where your job is to move deals forward, not just answer questions. Time spent building: training modules, AI workflows, playbooks, reusable assets, so the same problem doesn't land on your plate twice. And real time with Product, surfacing the patterns you're seeing in the field and shaping what gets prioritized. The best version of this week ends with you having done less reactive deal support than the week before, because the system you built last month is now doing the heavy lifting.

What does your future team look like?

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Technical Sales Specialist - ShareGate at Workleap — Remote