The Role

Single Grain is hiring a Head of AI-Enabled Sales to lead a revenue inflection point. This is not a sales manager role. This is a player-coach closer and revenue owner mandate.

We are at an inflection point in our growth. Founder-led sales has driven us to this stage. Now we need a revenue operator who can personally close meaningful deals, install systems discipline, and build a repeatable enterprise sales motion.

You will:

Personally close significant annual revenue
Upgrade pipeline rigor and accountability
Install CRM and conversion discipline
Embed AI workflows into the sales process
Reduce founder dependency in revenue generation

This role may evolve into leading the sales function entirely based on performance.

If you are looking to manage a team and stay out of closing, this is not the role.
If you want to own revenue, install structure, and build a modern AI-forward sales engine, read on.

Measurable revenue impact is expected within the first 6 months.

About Single Grain

Single Grain is a fast-moving, award-winning, AI-driven digital marketing agency. We’ve been helping top brands like Amazon, Uber, and Salesforce grow since 2009. We specialize in Paid Media, SEO, Content Marketing, CRO, and more, powered by a lean, high-performing team focused on smart, impactful work.

We don’t just use AI, we build it. We’ve created proprietary AI tools including Karrot.ai, an AI-powered performance marketing system that generates ads, landing pages, and campaign assets in seconds, and ClickFlow, an AI-driven SEO experimentation platform that helps teams identify content opportunities, optimize pages, and increase organic traffic through systematic testing and workflow automation.

These tools aren’t side projects. They’re embedded into how we operate and how we serve clients.

We practice what we preach. Our blog brings in over 200,000 monthly visitors, our podcast has 100+ million downloads, and more than 140,000 marketers subscribe to our YouTube channel.

We move quickly, push hard, and expect a lot from ourselves and each other. AI isn’t just a tool we use. It’s core to how we operate, from creative to strategy to execution. Our long-term vision is to build a small but elite team that stays lean, scrappy, and relentlessly focused on tech-enabled innovation and measurable business impact.

We don’t micromanage. We don’t hire people who need their hands held. But we do collaborate deeply, give honest feedback, and leave space for mistakes, growth, and iteration. No egos, no fluff, just people who care about doing great work and supporting each other.

What You’ll Do

Personally close high-value enterprise and complex service deals
Increase average deal size and improve pricing discipline
Build and enforce CRM rigor and pipeline accountability
Operate from dashboards, not instinct
Install conversion math across every stage of the funnel
Reduce founder involvement in late-stage deals
Build a repeatable enterprise sales motion
Embed AI workflows into prospecting, qualification, and deal acceleration
Improve outbound quality and strategic targeting
Increase overall revenue predictability

Non-Negotiable Requirements

Put “AI is cool” as the first line of your cover letter or subject line, or your application will not be reviewed.
Proven track record closing 6- and 7-figure deals
Must personally close $2M to $4M+ in annual revenue
Experience selling complex services such as agency, consulting, SaaS, or transformation
Comfortable selling to C-suite stakeholders
Able to defend premium pricing
Demonstrated ownership of meaningful annual revenue
AI experience is mandatory.

You must:

Actively use AI tools such as ChatGPT or Claude in your sales workflow
Be able to describe specific AI use cases
Understand how AI is changing marketing delivery
Think in leverage, automation, and process efficiency

If AI usage is surface-level, this role is not a fit.

Ideal Profile

You are:

Calm but aggressive
Analytical but persuasive
Confident but not arrogant
Structured yet fast-moving
Comfortable being measured weekly
Obsessed with pipeline math
High-agency and high-accountability

You thrive in:

Direct feedback cultures
High standards
Ownership environments
Measurable performance expectations

What This Role Is NOT

Not a sales manager who avoids closing
Not a relationship seller without pipeline rigor
Not a lone wolf closer who resists process
Not an old school sales operator
Not politically sensitive or ego-fragile
Not skeptical of AI

What Success Looks Like

Within the first 6 months:

Significant personally closed revenue
Increased deal size
Founder involvement reduced
Clear pipeline math installed

Within 12 months:

Enterprise sales motion repeatable
AI workflows embedded into sales
Revenue growth materially upgraded

Compensation & Structure

Title: Head of AI-Enabled Sales
Reports to: CEO
Target OTE: $300K to $350K