Sales Director (Player-Coach, AI-Native)

Read This Before Applying

This is a high-bar role. We are looking for a builder, not a traditional sales manager. You will carry a personal quota, lead a team, design outbound systems, and implement AI workflows across the revenue organization.

If your experience is primarily:

• Managing pipelines

• Running weekly sales meetings

• Relying on founder-driven deals

• Hiring large teams before proving process

…then this likely isn't the right role.

Strong candidates for this role typically have:

• Personally closed $3M+ revenue in a year

• Built or rebuilt a sales system from scratch

• Used AI and automation in their sales workflow

• Led a team while still carrying meaningful production

If that excites you, keep reading.

Build the Revenue Engine for an AI-Native Growth Company

Single Grain is not a traditional agency. We're a digital growth company operating at the intersection of services, software, and AI.

Our portfolio includes:

Single Grain Agency

Enterprise digital marketing services including:

• SEO

• Paid media

• Creative

• CRO

• AI-driven growth strategy

Our clients include companies looking for serious, scalable growth, not basic marketing support.

ClickFlow

Our AI-powered content optimization platform. ClickFlow helps companies unlock hidden growth from their existing content by identifying high-impact SEO opportunities and improving rankings with AI insights.

Karrot

A LinkedIn advertising and landing page platform built specifically for B2B companies running demand generation programs. Karrot helps companies scale LinkedIn campaigns with better targeting and conversion infrastructure.

We are actively evolving into a tech-enabled services (TES) company where software, automation, and services combine to create leverage.

Our CEO Eric Siu hosts the Leveling Up podcast and co-hosts Marketing School with Neil Patel, reaching millions of marketers and founders every month. This brand ecosystem gives us reach most agencies don't have.

But brand alone doesn't build a revenue engine. That's where you come in.

The Role: Player-Coach Sales Architect

This is not a traditional Head of Sales role. This is a player-coach role where you will:

• Carry a personal revenue quota

• Lead and level up a small sales team

• Build the sales systems that drive predictable pipeline

• Implement AI across the sales workflow

• Help scale our transition to tech-enabled services

You are not here to manage a pipeline. You are here to build the revenue machine.

What You'll Own

Personal Revenue

You will actively close deals across the full portfolio:

• Enterprise marketing retainers

• SaaS products

• Hybrid services + software solutions

Our deals often involve multiple stakeholders and complex problem-solving, so consultative selling is essential.

Sales Systems

We care about systems more than heroics. You will:

• Improve pipeline structure and forecasting

• Install CRM discipline and reporting

• Create repeatable sales playbooks

• Document processes that make the team faster

If something can be systematized, you systematize it.

Outbound Growth

Historically, our pipeline has leaned heavily inbound. You will help design a repeatable outbound engine, including:

• ICP definition

• Messaging frameworks

• Multi-channel outreach

• AI-assisted prospect research

• Automated sales workflows

The goal isn't more activity. The goal is predictable pipeline generation.

AI-Native Sales

Single Grain is an AI-forward company. Every department uses AI daily. Sales leaders here are expected to:

• Use AI for prospect research and list building

• Automate repetitive workflows

• Analyze call transcripts and pipeline data

• Improve forecasting and reporting

• Identify new tools that increase team leverage

If your AI strategy is "write better emails," this is not the role for you.

Team Leadership

You'll inherit a small but capable sales team. Your role is to:

• Coach reps through complex deals

• Improve performance standards

• Increase accountability

• Identify process gaps or talent gaps

Great sales leaders build systems that make their teams better.

What Success Looks Like

Within your first year:

• You're consistently closing meaningful revenue

• Pipeline visibility and forecasting accuracy improve dramatically

• Outbound becomes a predictable pipeline source

• Agency clients begin adopting our software products

• AI workflows make the team significantly faster

• Sales playbooks and systems are documented and repeatable

In short: The machine runs better because you built it.

Who This Role Is Perfect For

You'll likely thrive here if you:

• Have built or rebuilt a sales engine

• Have carried quota while leading others

• Are comfortable selling both services and SaaS

• Think in systems and metrics

• Use AI tools regularly in your workflow

• Prefer building infrastructure over managing large teams

Who This Role Is Not For

This role is not a fit if you:

• Depend on large teams before proving process

• Avoid AI or automation

• Rely heavily on founder-led selling

• Prefer maintaining existing systems instead of building new ones

• Default to generic sales playbooks

Our Hiring Process

After an initial screen, select candidates will complete a Sales Leadership Challenge.

This challenge evaluates:

• Strategic thinking

• Sales system design

• AI fluency

• Understanding of Single Grain's market

• Communication clarity

We will compare your thinking against AI outputs for the same challenge. Generic answers will not pass.

One More Thing

Strong candidates typically research before applying. Before applying, we recommend exploring:

• Eric Siu's Leveling Up podcast

• Our product ecosystem: Single Grain, ClickFlow, Karrot

• The evolution of tech-enabled services

If you move forward in the process, you'll participate in a sales leadership challenge designed to evaluate how you think about building revenue systems in an AI-first company.

Apply

Submit your application at: singlegrain.com/apply and select "Sales Director 010"

If you’re excited about building a high-performance, AI-native sales organization, we’d love to hear from you.

Benefits

• Medical, dental and vision insurance after your first month of employment

• 401k with 100% match up to 4% of your salary

• $50K life insurance policy, paid 100% by the company

• 12 weeks of paid family leave, effective after the first year of employment

• Flexible Unlimited Paid Time Off

• $100 utilities stipend paid out as an extra $50 per paycheck

• $60 UberEats credit each month

• A Macbook, keyboard plus mouse

• $500 WFH Office Reimbursement