About Gladly:

Gladly, the customer-centered AI customer support platform is built around people, not tickets. Unlike traditional ticket-based customer support solutions, our software helps brands deliver radically personal service at scale by integrating every channel—voice, email, SMS, chat, social messaging, and self-service—into a single, lifelong conversation stream. Companies like Allbirds, Bombas, Crate & Barrel, and Warby Parker use Gladly to create exceptional customer experiences, transforming everyday customer interactions into lasting connections.

Gladly is a fully distributed company that embraces remote work and believes in flexibility, innovation, and inclusivity. We foster a collaborative, inclusive culture that prioritizes growth, DEIB, and meaningful connections. At Gladly, people are at the heart of everything we do.

The Team

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At Gladly, we’re building the customer service platform of the future; one that’s human-first, AI-powered, and built for the next generation of customer experiences. As we evolve our internal operations to match the intelligence we offer externally, we’re hiring a GTM Engineer to help bring the power of applied AI to every corner of our Revenue organization.

You’ll be part of the Revenue Operations team and report to the Director of RevOps. You’ll work closely with our GTM leadership, AI-forward vendors, and the broader Gladly team to identify high-impact opportunities for intelligent automation, copilots, and synthetic data workflows.

The Opportunity

You’ll sit at the center of Gladly’s AI transformation, taking ideas from prototype to production across one of the most data-rich, process-heavy parts of the business: revenue operations. You won’t just be generating insights, you’ll be creating intelligent systems that act on them autonomously.

This is not a traditional analyst or operations role. While data fluency is critical, your primary responsibility will be the design, deployment, and scaling of AI-powered workflows that improve how we sell, service, and grow. You’ll play a hands-on role in embedding AI into everyday tools and processes - accelerating prospecting, elevating insights, and transforming the employee experience across Sales, Marketing, and Customer Success.

What You’ll Do

Operationalize AI use cases across Revenue teams—from prompt chaining to embedding models to smart copilots that automate repetitive tasks.
Build and maintain intelligent data pipelines that feed LLMs and AI tools with context-rich, structured inputs (enrichment, summarization, normalization).
Partner with vendors like Clay, N8N, Gong, Outreach, and ZoomInfo to prototype and validate new AI features, driving adoption across GTM teams.
Translate team workflows into AI-native automations (e.g. lead prioritization, customer health prediction, call summarization, meeting prep).
Create internal AI training and enablement materials, turning complex models and tools into everyday accelerators for the team.
Identify and surface gaps in current data availability that block key AI workflows, influencing the internal analytics engineering roadmap.
Support the executive team with AI-enhanced narrative reporting for fundraising, board updates, and strategic planning.

What We’re Looking For

3-5 years in a fast-paced, b2b software startup; bonus points for prior experience in training & enablement, or prospect-/customer-facing experience
Have hands-on experience working with LLMs, prompt engineering, or generative AI tools in a business setting, a plus if you have LangChain, LlamaIndex experience.
Have experience building out scaled outbound campaigns use workflow tools like Clay, N8N, or Make.
Have worked with (or evaluated) AI-forward tools in the GTM space—e.g. Lan Gong’s AI warnings, Outreach’s smart sequences, Salesforce Einstein, etc.
Are fluent in data architecture (SQL, dbt, or equivalent), but always thinking about how to turn data into action through automation or AI
Have a strong understanding of B2B SaaS revenue workflows and can identify high-leverage points for AI intervention
Have experience initiating and leading organization-wide change leveraging business intelligence systems, training, and cross-functional influence
Are a systems thinker who’s obsessed with identifying inefficiencies and automating them away with precision
Excellent written and verbal communication skills, seamlessly aligning Exec-level leadership, mid-level managers, and individual contributors
Are excited to build in a fast-moving environment where you might be the first person doing this kind of AI ops work

Compensation

Compensation for this role is $130,000-$160,000 per annum + Equity + Benefits

The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Gladly's bonus plan for eligible roles. In addition to cash compensation, all Gladly's employees are eligible to participate in Gladly's equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job-related reasons.

Why Join Gladly?

At Gladly, we’re not just building software—we’re transforming an industry. We take a people-first approach, both in our product and our culture. When you join us, you’ll enjoy:

Competitive salaries, stock options, and comprehensive benefits
Generous paid time off, parental leave, and home office stipends
A fully remote work environment with opportunities for in-person team gatherings
A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive

At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer-first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.