Account Executive - Enterprise

Overview

You sell Mac, iPad, iPhone, and related enterprise services to mid-to-large companies in the Cincinnati/Pittsburgh territory. Most of your accounts already have some Apple presence—you're expanding deployments, displacing Windows/PC equipment, and selling the total cost of ownership story. You work with IT leaders, procurement, and occasionally C-suite on larger strategic deals.

Role Snapshot

Company Context

Stage: Public (Fortune 10)

Size: 170,000+ employees

Growth: Steady enterprise push; Apple has been investing heavily in B2B over the past decade

Market Position: Premium brand leader in consumer, growing challenger in enterprise where Windows/PC still dominates most corporate IT

GTM Reality

Pipeline Sources:

• 40% Existing accounts - renewals, expansions, new projects within installed base
• 35% Outbound - you identify companies using competitor hardware, target growth companies with younger workforce
• 15% Inbound - marketing generates some leads, but this isn't a high-volume MQL engine
• 10% Partner/Channel - Apple resellers and IT service providers bring opportunities

SDR/AE Structure: No dedicated SDRs - you source your own pipeline and work existing accounts

SE Support: Shared Solutions Engineer pool for technical demos and large deals; you need to prove deal size/likelihood before getting SE time

Competitive Landscape

Main Competitors: Dell, HP, Lenovo (hardware); Microsoft Surface; Google Chromebooks in some segments

How They Differentiate: Premium hardware, ecosystem integration (iPhone/iPad/Mac), security features, lower TCO story (fewer help desk tickets, longer device life), employee satisfaction/retention angle

Common Objections: "Too expensive", "We're a Windows shop", "IT doesn't support Macs", "Our software only runs on Windows", "Leadership won't approve premium pricing"

Win Themes: Employee preference (especially for recruiting/retention), security posture, total cost of ownership over 4-5 years, creativity/productivity tools, seamless mobile integration

What You'll Actually Do

Time Breakdown

Account Management (35%) | New Prospecting (30%) | Active Deals (25%) | Internal (10%)

Key Activities

• Account mapping and planning: You maintain 40-60 named accounts. You research org charts, budget cycles, current hardware refresh timelines, and identify expansion opportunities within your territory.
• Outbound prospecting: Cold calling CIOs, IT Directors, and COOs. Most already know Apple but haven't considered it for enterprise. You're booking discovery calls to understand their environment and pain points.
• Discovery and demo cycles: You run 5-10 active opportunities at once. Lots of calls with IT to understand their infrastructure, security requirements, and application compatibility. Arranging SE support for technical deep dives and POCs.
• Multi-threading and stakeholder management: Deals involve IT, finance (for TCO analysis), procurement (for enterprise agreements), and sometimes HR (employee satisfaction angle). You're coordinating meetings, sending follow-ups, and chasing approvals through procurement cycles.
• Negotiating and closing: Working through enterprise purchase agreements, volume pricing, and service packages. Procurement will push back on price—you need to justify premium pricing with TCO models and business value.

The Honest Reality

What's Hard

• You're fighting Windows inertia: Most enterprises are deeply entrenched in Microsoft. IT teams are comfortable with Windows management tools. You're asking them to support a new platform, which means change management, training, and perceived risk.
• Price objections are constant: Apple hardware costs 50-80% more upfront than comparable PC equipment. Even when your TCO model shows savings over 4 years, procurement sees the sticker price and pushes back. You'll lose deals on price.
• Long procurement cycles: Even when everyone agrees Apple is better, enterprise buying takes forever. Budget approvals, multiple stakeholder sign-offs, legal reviews. Deals you think are closing this quarter slip 2-3 times.
• Limited SE resources: You can't bring technical support to every deal. You need to qualify hard and choose which opportunities get SE time. Smaller deals you handle solo.
• Internal complexity: Apple is a massive organization. Finding the right internal resources, getting marketing support, navigating partner relationships—there's bureaucracy.

What Success Looks Like

• Landing 2-3 new enterprise logos per year with $200K+ initial deployments
• Expanding existing accounts by 20-30% annually through refresh cycles and new use cases
• Hitting 90-110% of annual quota ($3-5M depending on territory)
• Building a pipeline with 3-4x coverage (because deals slip and procurement is unpredictable)

Who You're Selling To

Primary Buyers:

• CIO / IT Director (technical decision maker)
• CFO / Finance Director (economic buyer, cares about TCO)
• VP of Operations / COO (business sponsor for strategic deals)
• Procurement (contract negotiator)

What They Care About:

• IT: Can we manage this? Is it secure? Will it integrate with our systems? What about Active Directory, MDM, application compatibility?
• Finance: What's the total cost? How does it compare to Dell/HP over 3-5 years? What's the ROI on employee productivity claims?
• Business Leaders: Will this help us recruit and retain talent? What's the user experience improvement? How does this impact security posture?

Requirements

• 3-5 years of B2B sales experience, ideally in hardware, software, or IT solutions
• Experience selling into IT organizations; you need to speak credibly with technical buyers
• Proven ability to manage complex, multi-stakeholder sales cycles
• Comfortable with territory management and self-sourcing pipeline
• Strong business acumen—you'll build TCO models and ROI analyses
• Located in or willing to relocate to Cincinnati/Pittsburgh area (this is a field role with regular customer visits)
• Ability to work independently without heavy SDR or SE support on every deal