Account Executive - Course Sharing

Overview

You're selling Course Sharing—a product that lets institutions share course content across their network—to K-12 districts, colleges, and potentially business/government accounts. You'll split time between expanding existing Canvas customers (upsell motion) and hunting net-new accounts that might buy Course Sharing as an entry point into the Instructure ecosystem. Most of your buyers are instructional designers, academic VPs, or district curriculum directors.

Role Snapshot

Company Context

Stage: Public company (KKR-owned after going private in 2020, 2,000+ employees)

Size: 2,166 employees

Growth: Mature core product (Canvas), expanding into adjacent products and new markets (Course Sharing, business/government)

Market Position: Category leader in higher ed LMS (Canvas has dominant market share), now trying to monetize the install base with additional products and crack new segments

GTM Reality

Pipeline Sources:

• 30% Inbound - Existing Canvas customers expressing interest, marketing-generated leads from webinars and product releases
• 50% Outbound - Cold prospecting into K-12 districts, colleges without Course Sharing, competitive accounts using Blackboard/Moodle/D2L
• 20% Internal referrals - Canvas AMs flagging upsell opportunities in their accounts

SDR/AE Structure: Likely self-sourcing for this newer product line—Jake's team is just expanding, so you probably won't have dedicated SDR support initially

SE Support: Shared SE pool for technical demos and POCs when needed, but you'll do most first calls yourself

Competitive Landscape

Main Competitors: Other LMS add-ons, homegrown content-sharing solutions, open-source alternatives, bundled features in competing LMS platforms (Blackboard, D2L, Moodle)

How They Differentiate: Integration with Canvas ecosystem, network effects if multiple institutions use it, Instructure brand credibility in EdTech

Common Objections: "We already share content manually," "Is this really worth the cost vs free tools?" "We need to see other schools using it first," budget constraints in education

Win Themes: Time savings for faculty, quality control for shared content, integration with existing Canvas workflows, data/analytics on content usage

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Internal Coordination (25%)

Key Activities

• Cold outreach to new districts/institutions: You're researching schools, finding the right contacts (not always easy in education—lots of committee decision-making), and doing cold calls and emails to book discovery calls. Response rates are low—education moves slowly.
• Discovery and demo calls: You're walking through how Course Sharing works, trying to uncover pain points around content duplication and faculty efficiency. You'll need to understand their current LMS setup and explain integration.
• Multi-stakeholder navigation: Education deals involve curriculum directors, IT, procurement, sometimes faculty committees. You're scheduling and running meetings with multiple people, building consensus.
• Internal coordination: Working with the Canvas AM if it's an existing customer, pulling in SEs for technical questions, coordinating with implementation teams on timelines, getting pricing approvals for non-standard deals.

The Honest Reality

What's Hard

• Education buying cycles are tied to budget years (often July-June) and academic calendars—deals slip all the time because "we'll revisit next fiscal year"
• Committee-based decision making means you need 5-8 people to say yes, and any one person can stall the deal
• Course Sharing is a "nice to have" product, not a must-have, so it often loses out to budget priorities
• You're selling something relatively new, so there aren't a ton of case studies or reference customers yet
• K-12 deals can be $15-30K but take 6 months; higher ed deals are bigger but even slower

What Success Looks Like

• Closing 8-12 deals per year in the $25-75K range
• Building a pipeline that's 3-4x your quota because of the slip rate
• Getting repeat business or expansions in year 2 as schools see value

Who You're Selling To

Primary Buyers:

• Chief Academic Officers, VPs of Instruction (higher ed)
• District Curriculum Directors, Instructional Technology Coordinators (K-12)
• Sometimes: CIOs or IT Directors (if integration/security is a concern)

What They Care About:

• Faculty time savings and reducing duplicated effort creating course content
• Quality control and standardization across courses/campuses
• Data on what content is being used and how effective it is
• Budget justification—clear ROI or cost avoidance story
• Ease of integration with Canvas (or effort required if they're on a different LMS)

Requirements

• 2-3+ years in B2B SaaS sales (EdTech experience is a plus but not required)
• Experience with consultative, multi-stakeholder sales cycles
• Comfortable with self-sourcing—this isn't an inbound lead machine
• Understanding of education market dynamics helpful (budget cycles, procurement processes, committee decision-making)
• Willingness to learn a newer product and help shape the sales playbook
• Remote role, US-based