AI Implementation Strategist (Boston)

Remark; Boston (MA); Hybrid; USD 85,000 - 135,000; Full time

Benefits offered by this job

Hybrid work with WFH 2 days a week

Full healthcare benefits

Flexible PTO

Company retreats

Annual fitness reimbursement

Job summary

Remark is the AI client advisor for elevated brands, partnering with names like J.McLaughlin, Veronica Beard, Ariat, and Backcountry to bring the in-store advisor experience online. The role focuses on designing and building how each brand's advisor operates, from contract to live conversations, crafting prompts, knowledge, and AI behavior to fit the brand voice and product line.

You will own launches end-to-end, tuning workflows, integrations, and the advisor's responses, then measure

Qualifications

• Hands-on AI building with prompts to guide LLMs.
• Solutions-oriented mindset for platform configuration and integrations.
• 3+ years running multiple launches in parallel.

Responsibilities

• Own the launch from contract to go-live and manage milestones.
• Architect the brand setup: knowledge base, intents, integrations, automations.
• Build the advisor: write prompts, tune knowledge and logic, test and iterate.

Skills

AI building

Technical mind

Automation fluency

Ownership

Clear communication

Ambiguity tolerance

Tools

SQL

Excel

APIs

Zapier/Make

Job description

Join us at Remark

Remark is the AI client advisor for elevated brands. We work with 70+ of them, including J.McLaughlin, Veronica Beard, Ariat, and Backcountry, to bring the in-store advisor experience online: collection expertise, curated edits, virtual try-on, and guidance from consideration to decision.

The problem we're solving is simple. A great boutique converts around 30% of the people who walk in. The same brand's website converts about 2%. The difference is the advisor. For decades luxury was sold through guidance, trust, and taste, and online most brands got the same flat storefront as everyone else. We're fixing that.

We started as Outdoorly, a marketplace of outdoor product experts. Their 60,000+ advisor conversations became the training data behind Remark's AI. We've raised about $27M from investors including Stripe and Inspired Capital, and we're a team of technologists, operators, and people with real taste who care as much about how an experience feels as whether it works.

What this role is

The title says strategist. The job is building. You design how each brand's advisor should work, then you build it yourself, from signed contract to a live advisor handling real client conversations.

You'll own each launch end to end, but most of your time goes to the build itself: architecting the brand's setup across the platform, designing automations in our workflow builder, wiring integrations, and shaping the AI. You'll craft the prompts, knowledge, and logic that turn a general model into that brand's own expert advisor, one that speaks in its voice, knows the collection cold, and guides clients with taste. Then you'll measure it and tune it until it performs.

No two brands are alike, so no two builds are. When a brand needs something the platform doesn't do out of the box, you engineer the way to make it happen.

If you're technical, endlessly resourceful, and energized by using AI in ways most people haven't tried yet, this is a rare chance to build the systems behind how the world's most discerning brands show up online.

What you'll do

• Own the launch. Be the brand's primary contact from contract to go-live. Run the plan, the milestones, and every dependency on both sides.


• Architect the setup. Translate the brand's goals into the right configuration of Remark: knowledge base, intents, integrations, automations, and advisor behavior.


• Build the advisor. Write and tune the prompts, knowledge, and logic. Decide what a great answer sounds like for that brand, test against it, and keep iterating until the advisor gets there.


• Engineer the hard fits. When defaults don't match, design the workaround: a custom integration, a data transform, a workflow that does something we haven't done before.


• Measure what matters. Every launch is judged on client engagement, conversion, and revenue. You'll watch those numbers from day one and tune toward them.


• Set the brand up to succeed. Train their team, set expectations, and document how and why the build was configured so Merchant Success inherits a strong foundation.


• Shape the product. Bring what you learn from real launches back to Engineering and Product. Your builds are the best signal we have for what the platform should do next.

What you'll bring

• Hands-on AI building. You've written and iterated on prompts to get precise, reliable behavior from an LLM, and you have a point of view on how to test whether it worked. Experience with evals, RAG, or agent tooling is a strong plus.


• A technical, solutions-oriented mind. You learn a platform's full toolkit fast and design the right configuration, automation, and integration for each situation. You're comfortable with APIs, data models, and tools like SQL and Excel.


• Automation fluency. Real comfort with workflow tools (Zapier, Make, or similar), or the aptitude to pick them up in a week.


• Ownership across multiple launches. 3+ years running several demanding projects in parallel and getting each one over the line without details slipping.


• Clear communication. You set expectations with brand teams and engineers alike, especially when things are moving fast.


• Comfort with ambiguity. Our process is still evolving. You pair discipline with the flexibility to fill gaps and keep moving.


• Boston or Denver, in person. We're in the office 3 to 5 days a week.

Bonus points if

• You've built something clever in a no-code or automation tool just for the satisfaction of it


• You've shipped an LLM agent to production, or built one on the side


• You have strong opinions about what makes an experience feel effortless


• You've worked in or around e-commerce, fashion, or luxury retail


• You notice the details other people walk past

Benefits

• Hybrid work with the flexibility to WFH 2 days a week


• Full healthcare benefits (medical, dental, vision)


• Flexible PTO (we recommend at least 15 days a year)


• At least one company retreat a year


• $500 annual reimbursement for fitness and outdoor recreation

Compensation

$85K–$135K base, depending on experience.

Ready to join?

We'd rather meet you than miss you.

Remark is an equal opportunity employer. We're building a workplace where everyone can belong, and we encourage applicants from all backgrounds.

Requirements

• Able to work from our Boston, MA or Denver, CO office at least 3 days a week


• Must be a U.S. resident