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Raspberry AI

Enablement Lead

New York, NY, United States

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Job details

Posting language: English
Posted: Nov 6, 2026

Original job description

ENABLEMENT LEAD - JOB DESCRIPTION

WHY RASPBERRY AI

Raspberry AI is building the agentic platform transforming how fashion and retail is created and brought to market. Raspberry brings AI into the center of their process - connecting design, product development, merchandising, marketing, ecommerce, and wholesale teams in one platform.

Our customers use Raspberry to move from an idea to production-ready designs, assortments, campaigns, ecommerce imagery, and sales materials in a fraction of the time. Today, some of the world's leading fashion brands and retailers - including SKIMS, Fabletics, Under Armour, Oscar de la Renta, Walmart, rag & bone, Kate Spade, Savage x Fenty and more - are using Raspberry to rethink how their teams work.

We're backed by a16z and recently raised $29M to keep building.

THE ROLE

We're hiring our first Enablement Lead to head-up the two teams that sit between our product and our customers: AI Implementation Specialists and Solution Engineers. Together they win deals, get brands live, and make sure Raspberry becomes part of how fashion teams actually work.

Today these teams have no dedicated manager. You'll build the function around them: one operating rhythm, shared playbooks, clear handoffs from presales to onboarding to adoption, and a hiring plan that scales with our customer base.

This is a player-coach role. You'll lead the team and the program, and still get hands-on with our most strategic accounts and deals.

WHAT YOU'LL DO

Lead and build the team

Manage AI Implementation Specialists and Solution Engineers weekly 1:1s, goals, performance, and career growth.
Hire for the next stage. Define the profile for each role, run interviews, and onboard new team members fast.
Set the operating rhythm: capacity planning, account coverage, and how work is assigned across presales and post-sales.

Own the customer journey from demo to adoption

Design clean handoffs between Sales, Solution Engineering, Implementation, and CS so no customer context gets lost after signature.
Own how every enterprise customer is onboarded: kickoff, workflow mapping, training, and go-live.
Build the enablement program: onboarding playbooks, role-based training for design, product development, merchandising, and ecommerce teams, office hours, and certification.

Support revenue

Partner with Sales leadership and the AE team so Solution Engineers are on the right deals at the right time: discovery, tailored demos, proofs of concept, and technical evaluations.
Make sure what we show in presales matches what we deliver in implementation.
Use adoption data to spot expansion opportunities and flag churn risk early.

Bring fashion expertise into everything

Lead the Implementation Specialists who show brands what's possible: creative workflows, model outputs, and real use cases by team.
Turn customer wins into reusable demo assets, case studies, and templates.
Feed what customers need back to Product and Engineering with clear, prioritized input.

Measure and improve

Define and report on team metrics: time-to-first-value, activation, adoption by team, presales win rate, and training satisfaction.
Stay ahead of Raspberry's product releases and the broader generative AI landscape so the team sells and trains on what's next.

WHO YOU'LL LEAD

Your Solution Engineers own presales. They work alongside our AEs on technical discovery, tailored demos, proofs of concept, and evaluations, showing brands exactly what Raspberry can do for their workflows. Once a deal closes, your AI Implementation Specialists take over. They onboard new customers, train design and product teams, and build Raspberry into the way those teams work day to day, carrying each account from go-live through full adoption.

WHAT WE'RE LOOKING FOR

7+ years across solutions engineering, implementation, enablement, or customer success, including 3+ years managing a team.
Have led both presales and post-sales people, or a mixed team where one hands off to the other.
Have built an onboarding or enablement program from scratch, not just run an existing one.
Comfortable in front of enterprise customers: you can run a discovery call, lead an executive demo, and rescue a stalled implementation.
Hands-on with AI and creative tools. You use generative AI in your own work and can explain it to designers who are skeptical.
Operate with data: you've set team metrics, built the dashboards, and used them to make staffing and process calls.
A clear writer and communicator who works well with Sales, Product, and Engineering.

Nice to have

Background in fashion, retail, apparel, or footwear, especially design, product development, or merchandising.
Experience at a Series A or B startup where you built the function as it scaled.
Familiarity with PLM, 3D, or creative tools used by fashion teams (Centric, Browzwear, CLO, Adobe).
Experience supporting both US and UK/EU customers.

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Skills

Merchandising
Sales
Workflow
Onboarding
Leadership
Manage a team
PLM

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