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.

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.

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.

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.

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

• 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

We want AI to become normal inside the sales organization.

• 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

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.

• Reduce administrative burden
• Improve activity capture
• Make manager coaching easier
• Give salespeople an “army of agents” to support…