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Upsell Account Executive

South Key, Plano, Texas, us, 75086

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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

What We’re Looking For

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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