AI GTM Expert - Enterprise Sales

Overview

You're building the enterprise GTM motion from the ground up at ImagineArt, an AI image/video creation platform that bootstrapped to $30M+ ARR selling to individual creators. Now they want to move upmarket to sell to creative teams at agencies, marketing departments, and media companies. You'll work directly with CEO Ahmed Abubakar to figure out what enterprise positioning actually resonates, build your own pipeline, close deals yourself, and document what works so it can be repeated.

Role Snapshot

Company Context

Stage: Bootstrapped, $30M+ ARR (no VC funding)

Size: 191 employees

Growth: Proven product-market fit with creators, now experimenting with enterprise

Market Position: Strong in consumer/prosumer AI creative tools, unproven in enterprise

GTM Reality

Pipeline Sources:

• 90% Outbound - You're building lists, doing cold outreach, testing messaging
• 10% Inbound/Referrals - Occasional enterprise user who asks about team plans
• 0% SDR Support - You're doing your own prospecting

Current State: They have 30M+ ARR from individual creators paying $10-100/month. Enterprise is a hypothesis. The product wasn't built for team collaboration or enterprise security requirements. You're selling what exists today while influencing what gets built next.

SDR/AE Structure: No SDRs. You source and close everything yourself.

SE Support: No dedicated SEs. You demo the product yourself or pull in a PM if deeply technical questions arise.

Competitive Landscape

Main Competitors: Midjourney (for image generation), Runway (for video), Adobe Firefly (for enterprise creative teams), Canva Enterprise (for design teams)

How They Differentiate: Strong consumer product with 30M ARR proves the tech works. Lower price point than Adobe/established players. More flexible than Midjourney's Discord-only model.

Common Objections: "We already have Adobe/Canva," "Is this secure enough for our IP?", "Can our whole team use this?", "What happens to our data?", "How do we manage licenses and access?"

Win Themes: Speed of creation, cost efficiency vs hiring designers/agencies, proven consumer product, flexible APIs for custom workflows.

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (30%) | Strategy/Internal (30%)

Key Activities

• Building target lists: Identifying creative teams at agencies, marketing departments, media companies who could use AI content tools. You're figuring out who even has budget for this.
• Cold outreach: LinkedIn messages, emails, asking for intros through your network. Testing different angles - cost savings vs creative agencies? Speed for social media teams? Custom content for media companies?
• Discovery and demos: Getting on Zoom with creative directors, marketing VPs, agency principals to understand their workflow. Showing them the product and seeing where they get excited vs where they say "but we need X."
• Internal strategy work: Weekly syncs with CEO and product team. You're feeding back what enterprise buyers actually need (SSO, team collaboration, usage analytics, security compliance). Influencing roadmap. Documenting what positioning works. Building the sales deck and pitch as you go.

The Honest Reality

What's Hard

• The product was built for individual creators, not enterprise teams. You'll hear "we need SSO" and "where's the admin dashboard" constantly. You're selling the roadmap as much as the product.
• No established enterprise positioning or case studies yet. You're figuring out the messaging through trial and error.
• You're doing everything yourself - prospecting, demoing, negotiating contracts, managing deals. No SDR to book meetings. No SE for complex demos. No CSM to handle onboarding.
• Bootstrapped company means slower product development than VC-backed competitors. Enterprise features get prioritized against consumer features that drive current revenue.
• Most of your early deals will be smaller tests ($20-50K) not the big logos you're hoping for. You need to close those to earn credibility for bigger swings.
• You're based in SF/NY/LA and expected to be in-person frequently with the CEO. This isn't a remote role.

What Success Looks Like

• You close 5-10 enterprise deals in year one ($500K-1M in new enterprise ARR)
• You document a repeatable playbook: target personas, messaging, demo flow, pricing tiers, common objections and responses
• You identify the 2-3 enterprise features that unlock bigger deals and get them prioritized on roadmap
• You build a pipeline of 20-30 active enterprise opportunities at various stages

Who You're Selling To

Primary Buyers:

• Creative Directors at agencies (50-500 person shops)
• VP/Director of Marketing at mid-market companies (need content at scale)
• Heads of Creative/Content at media companies

What They Care About:

• Cost: Can this replace some freelancer/agency spend?
• Speed: Can their team produce more content faster?
• Quality: Is AI-generated content good enough for their brand?
• Control: Can they manage team access, usage, brand guidelines?
• Integration: Does this fit their existing creative workflow and tools?

Requirements

• 5+ years in B2B SaaS sales, with at least 2 years selling to enterprise creative/marketing/media buyers
• Experience building GTM motions from scratch - you've been the first enterprise seller or early GTM hire before
• Deep knowledge of AI tools landscape (you use these tools, you understand the technology, you can speak credibly about LLMs and image generation)
• Comfortable with ambiguity - there's no playbook, you're writing it
• Strong product intuition - you'll influence what gets built based on what buyers need
• Self-sufficient - you prospect, demo, close, and problem-solve without needing a support system
• Based in or willing to relocate to SF/NY/LA with expectation of regular in-person work with CEO