AI Sales Enablement Lead

AI Sales Enablement Lead

STARK | New York, NY (Hybrid)

Build the AI tools that make sales easier.

STARK is building toward becoming an AI-native company.

We recently hired an AI Chief of Staff, and it has been a huge success. That role has focused primarily on operations, reporting, and workflow automation outside the sales organization. Now we are looking for a peer role dedicated specifically to sales.

This role is for someone who is AI-native, highly practical, and excited to make a legacy sales organization dramatically easier to operate. The goal is simple: help salespeople spend less time on computer work and more time serving clients, and help sales managers spend less time chasing information and more time coaching, supporting, and driving performance.

This is not a theoretical AI role. It is not a pure training role. It is not a traditional sales ops job.

It is a build-and-enable role for someone who can learn how work actually happens, map the friction, design better workflows, build useful internal tools, and help salespeople and managers use AI every day.

About STARK

STARK is a luxury carpet and rug company with an 85-year history and a strong reputation in the design community. We are a real company with real operational complexity, real data problems, real workflow friction, and real opportunity.

We are investing in AI because we believe the future of work is not just better software — it is better systems, better workflows, and better leverage for people.

We want to rebuild parts of our company to feel less like a traditional legacy business and more like a technology company that sells carpet.

Why This Role Exists

Our salespeople and sales managers work in an environment where:

• Systems are clunky

• Data lives in multiple places

• Activity tracking is inconsistent

• Too much time is spent on administrative work

• AI adoption is still early

• Best practices are not easy enough to follow

We want to fix that.

This role will focus specifically on making the salesperson and sales manager workflow easier, smarter, and more AI-enabled.

What You’ll Do

Learn how the sales organization actually works

A major part of this job is discovery.

Before building the right tools, you’ll need to understand how work really happens. That means:

• Interviewing stakeholders across sales leadership, showroom management, and sales support

• Shadowing sales managers and salespeople

• Mapping workflows, handoffs, pain points, and administrative burden

• Identifying where AI, automation, or workflow redesign can create the most value

• Translating messy legacy ways of working into clearer tool and workflow requirements

We do not want someone who rushes to build the wrong thing. We want someone who learns quickly, asks smart questions, and builds from real process understanding.

Build AI-native sales tools and workflows

You will design and launch practical internal tools that improve the day-to-day work of salespeople and sales managers.

Initial focus areas include:

• A CRM-light workflow layer for salespeople

• A sales manager control center

• Better customer and account search/navigation

• Easier visibility into emails, meetings, samples, quotes, and pipeline

• Tasks, reminders, and next-best-action support

• Email templates, sequences, and follow-up workflows

• Smarter activity logging and meeting capture

• Internal sales tools that simplify workflow instead of adding more noise

Help salespeople use AI every day

We want AI to become normal inside the sales organization.

You will help drive that by:

• Training managers and salespeople on practical AI use cases

• Helping users get set up with tools and workflows

• Creating reusable prompts, Claude skills, and manager workflows

• Embedding AI into sales follow-up, prep, analysis, and planning

• Making AI feel simple, useful, and relevant

Improve workflow consistency and raise the floor

Some top performers will always do things their own way. That is not the main target.

The bigger opportunity is helping average and developing salespeople operate with better structure, better follow-up, and easier access to best practices.

This role should help:

• Reduce administrative burden

• Improve activity capture

• Make manager coaching easier

• Give salespeople an “army of agents” to support their work

• Raise average sales productivity by making the right behavior easier

Collaborate with the AI Chief of Staff

This role reports to the CEO and works as a peer to our AI Chief of Staff.

That role primarily focuses on workflow automation, reporting, and AI enablement outside the sales organization. This role focuses specifically on implementing AI inside the sales organization.

You will collaborate on:

• Shared data and reporting foundations

• Internal applications built on common infrastructure

• Intersections between sales workflow and broader operational workflow

• Identifying where sales needs overlap with automation opportunities elsewhere in the company

What Success Looks Like

In the first 90 days, success likely means:

• Interviewing stakeholders and mapping key sales workflows

• Identifying the highest-friction opportunities in the salesperson and manager workflow

• Launching a functional v1 of a CRM-light workflow system for pilot users

• Helping implement a sales manager control center

• Delivering a few practical workflow wins that make managers and salespeople feel the benefit immediately

• Beginning to build real excitement inside the sales organization around how AI can help them

At 6 months, success means:

• The pilot users are genuinely excited about the tools

• AI is becoming part of daily sales workflow

• Sales managers have better visibility and better prep

• Salespeople are doing less manual admin work

• The sales organization feels meaningfully easier to operate

What This Role Is Not

This role is not:

• A traditional sales manager role

• A people management role

• A pure trainer or facilitator role

• A deep data engineering or infrastructure role

• A back-office ops automation role unrelated to sales workflow

• A generic executive assistant

There may be some administrative responsibilities related to the sales organization, such as goal tracking, meeting support, communication support, or follow-up around sales leadership workflows, but only where those responsibilities improve sales operations and can be systematized or automated over time.

Who You Are

You might be a fit if you are:

• AI-native and think AI-first about workflow design

• A builder with an operator mindset

• Practical, not theoretical

• Energized by simplifying messy, clunky systems

• Strong at translating business pain into usable tools

• Humble, curious, and eager to learn process before forcing solutions

• Comfortable working directly with senior leaders

• Able to move quickly without overcomplicating things

• Excited by helping a legacy company become AI-native

Skills and Experience

We care more about capability than pedigree, but strong candidates will likely bring some mix of:

• Demonstrated ability to build practical internal tools, automations, or lightweight apps

• Strong fluency with AI tools and workflows

• Ability to conduct stakeholder interviews and process mapping

• Good workflow design instincts and user empathy

• Ability to work with data using tools such as SQL, Power BI, Power Automate, data warehouses, or similar

• Comfort training and enabling non-technical users

• Strong written and verbal communication

• Bias for simplicity, usability, and speed over overengineering

Helpful backgrounds might include:

• AI-native operator with sales enablement instincts

• Sales ops or revenue ops person who became AI-native

• Builder who understands CRM workflow and manager needs

• Early-career, unusually high-output operator with strong learning velocity

Compensation

This role is designed for a high-upside builder/operator profile, and compensation will reflect that level.

Why Join Now

This is a chance to help define how a real sales organization evolves into an AI-native one.

You won’t be writing a strategy deck about the future. You’ll be building the future here, in a real company, with real users, real friction, and real stakes.

If that sounds energizing, we’d like to hear from you.

Benefits:

• Health Insurance

• Dental Insurance

• Vision Insurance

• Supplemental Benefits

• Great Paid Time Off Policy

• 401k match

COMPANY INFO

About Us:

With more than 80 years of industry expertise, STARK is the discerning designer’s go-to source for luxurious custom carpet and rugs.

Our Mission: To live our mission of helping create world class experiences, we believe our first responsibility is making design industry professionals the heroes in their projects because supporting businesses helps to preserve craftsmanship and enable unique and specially designed spaces to exist. In meeting their needs, we must continue to deliver peace of mind service while offering an expansive, diverse, and innovative product assortment that is accessible and convenient.

Our Heritage: Established by Arthur Stark and his wife Nadia in 1938, the foundation of STARK was always to provide the very best products to our customers. With a rich history, third generation owners Chad Stark, as CEO, and Ashley Stark, as Creative Director, bring the STARK legacy into the new century by staying true to their founding principles. To seek out the best craftsman and methods of manufacturing for the most innovative and beautiful designs.

STARK is a certified Great Place to Work® (June 2026– June 2027) — and that comes straight from our people. 85% of our employees say STARK is a great place to work, 28 points above the typical U.S. company. See our full certified profile and what our team says about working here: greatplacetowork.com/certified-company/7023725

Stark Carpet Corporation provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws.