Upsell Account Executive
Listed on 2026-02-16
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Sales
Sales Representative, Account Manager, Sales Development Rep/SDR, Business Development
Overview
South Key is recruiting for one of its clients!
Snapshot:
Hiring Company: Progress Learning
Position: Account Executive – Upsell & Expansion (EdTech)
Experience Level: 4+ years of closing experience
OTE: $85,000
The Role:
Looking for a seasoned Account Executive to drive expansion and upsell revenue within our existing customer base. This role is focused on uncovering growth opportunities inside districts—specifically converting single-school contracts into district-wide agreements and expanding partial subscriptions into full bundles.
This is a high-impact, outbound-driven role for someone who knows how to navigate complex accounts, build internal champions, and close multi-stakeholder deals. You’ll partner closely with Territory AEs as districts consolidate and new expansion opportunities emerge.
What You’ll Do- Own and grow revenue within an assigned territory by expanding existing customer relationships
- Lead upsell and expansion efforts from single-school contracts to district-wide agreements
- Identify and engage power users and champion schools within districts to drive adoption and expansion
- Target:
- Districts with enterprise contracts but limited rooftop subscriptions
- Non-enterprise accounts with partial or single-subject subscriptions
- Proactively source pipeline through strategic outbound prospecting (calls, email, events, and account research)
- Develop and execute a thoughtful territory and account expansion plan
- Deliver compelling virtual demos and presentations to district-level stakeholders
- Partner with Territory AEs on multi-campus and district opportunities
- Represent Progress Learning at conferences, in-person meetings, and regional events
- Accurately forecast, manage pipeline, and report progress to sales leadership
- Contribute feedback to improve sales processes, systems, and go-to-market strategy
- 4+ years of closing experience as an Account Executive, ideally in EdTech or SaaS
- Proven success managing a book of business and consistently hitting quota
- Experience selling into districts or navigating multi-stakeholder, consultative sales cycles
- Strong outbound prospecting skills and comfort owning pipeline creation
- Ability to identify champions and build consensus across complex accounts
- Familiarity with specific state or regional education markets is a plus
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