Account Executive

Overview

You sell EdSights' AI-powered student engagement platform (EdSights Admit and EdSights Retain) to universities and colleges. You're talking to VPs of Enrollment, Deans of Students, and Retention Directors about using SMS chatbots and analytics to improve student persistence. You run the full sales cycle from prospecting to close, navigating academic bureaucracies and competing with legacy systems or doing-nothing-at-all.

Role Snapshot

Company Context

Stage: Late-stage growth (just raised $80M Series C/Growth from JMI Equity in Sept 2025)

Size: 65 employees

Growth: Recently welcomed new sales hires (Sean and Roy in May 2025), expanding team post-funding. Ranked #6 fastest-growing education company in America.

Market Position: Category leader in AI-powered student engagement - competing against legacy retention platforms, point solutions, and the "we'll just use our existing tools" mindset.

GTM Reality

Pipeline Sources:

• 30% Inbound - conferences, word-of-mouth in higher ed circles, content marketing. Quality varies - some tire-kickers, some genuine RFPs.
• 60% Outbound - you're calling/emailing into universities cold. Higher ed has publicly available org charts, so targeting is easier, but gatekeepers are real.
• 10% Referrals - existing customers connect you to peers at other institutions.

SDR/AE Structure: You'll have BDR support (they're hiring one now), but expect to do significant self-sourcing, especially for target accounts. BDRs will book initial meetings, but you'll need to develop your own pipeline too.

SE Support: Likely shared pool or you run demos yourself. Product is relatively straightforward (SMS chatbot + dashboard), so not always SE-heavy, but implementation conversations might need technical resources.

Competitive Landscape

Main Competitors:

• Ocelot (comprehensive student engagement platform)
• AdmitHub (SMS-based enrollment chatbots)
• Legacy CRM/retention systems already in place (Ellucian, Salesforce Education Cloud)
• "We'll just have our staff text students directly"

How They Differentiate:

• AI that actually works (not just keyword matching)
• Real-time intervention data and student voice scoring
• Purpose-built for higher ed (not adapted from corporate tools)
• Track record with retention/persistence outcomes

Common Objections:

• "We already have [legacy system] we're not replacing"
• "Students won't engage with a chatbot"
• "Budget is allocated for next fiscal year, come back in 6 months"
• "We need IT security review" (adds 2-3 months)
• "Can this integrate with our 15-year-old student information system?"

Win Themes:

• Demonstrable ROI on student retention (every retained student = $20-50K+ in tuition)
• Benchmarking data across institutions
• Ease of implementation vs building in-house
• Purpose-built for higher ed compliance/privacy needs

What You'll Actually Do

Time Breakdown

Prospecting (30%) | Active Deals (45%) | Internal (25%)

Key Activities

• Prospecting and Territory Planning: Research universities in your territory, identify the right contacts (usually VP Enrollment, Dean of Students, Director of Retention), send personalized outreach. You're competing with 100 other vendors for their attention. Expect 1-2% response rates on cold outreach.

• Running Discovery and Demos: Lead 45-60 minute calls walking through the platform. You're diagnosing their retention challenges, showing how the AI chatbot surfaces at-risk students, and quantifying potential ROI. Most demos involve 3-5 people from the university side. You'll do 5-10 demos per week.

• Navigating Multi-Stakeholder Buying Committees: Higher ed decisions involve enrollment teams, IT, legal/compliance, sometimes provosts or VPs. You'll schedule meetings, send follow-ups, and wait weeks between conversations. Chase people down after summer break, winter break, and during busy enrollment periods.

• Building Business Cases and Proposals: Create ROI models showing retention impact, respond to RFPs (if they issue formal procurement), negotiate contract terms, get through legal review. Expect 2-3 rounds of revisions and weeks of radio silence.

• Internal Coordination: Weekly forecast calls with leadership, updating Salesforce, working with customer success on handoffs, product feedback sessions. Standard sales admin that takes more time than you'd like.

The Honest Reality

What's Hard

• Academic calendar constraints: Universities make budget decisions on fiscal year cycles (often July 1). If you miss their window, you're waiting 12 months. Summer and winter breaks stall deals for weeks. Enrollment season (spring/fall) means your champions are too busy to talk.

• Slow, consensus-driven buying: Even after a verbal "yes," you'll wait on IT security reviews, legal contract redlines, and budget approval committees. Deals that should close in 90 days take 6-9 months. Your pipeline will slip quarters regularly.

• Competing with inertia: Many schools know they have retention problems but struggle to prioritize a new tool. You're often selling against "we'll figure this out internally" or "let's wait until next year." Budget constraints are real in higher ed.

What Success Looks Like

• Closing 6-10 new university accounts per year
• Building a pipeline that's 3-4x your quota (because of long cycles and slippage)
• Developing champions who advocate internally and provide references to other institutions
• Renewals and upsells from your accounts (if comp includes expansion)

Who You're Selling To

Primary Buyers:

• VP of Enrollment / Chief Enrollment Officer
• VP of Student Affairs / Dean of Students
• Director of Retention / Director of Student Success
• Provosts or Academic VPs (for larger deals)

What They Care About:

• Proven impact on retention rates (ideally case studies from similar institutions)
• Student data privacy and compliance (FERPA, accessibility requirements)
• Integration with existing systems (SIS, CRM, LMS)
• Implementation timeline and staff training burden
• Cost per student vs retention ROI
• Peer institution adoption ("who else like us is using this?")

Requirements

• 3-5+ years full-cycle SaaS sales experience
• Track record closing $50K+ ACV deals with 3-6 month sales cycles
• Comfortable navigating complex, multi-stakeholder sales (higher ed, government, or enterprise experience helpful)
• Self-starter who can build pipeline through outbound prospecting
• Experience selling into higher education is a plus but not required
• Ability to articulate ROI and build business cases
• Comfortable working remotely and managing your own time
• Willingness to travel occasionally for conferences or on-site meetings