Product Marketing Manager, Letter Compass

Letter AI, Inc.; Chicago (IL); Hybrid; USD 110,000 - 145,000; Full time

Benefits offered by this job

Letter stock options

Medical, dental, and vision coverage

401(k) with company match

Commuter benefits

Daily lunch in Chicago and SanFrancsco

Job summary

Letter AI, Inc. is hiring a Product Marketing Manager for Compass in Chicago. You’ll own positioning, messaging, launches, and sales enablement, collaborating with Product, Sales, Customer Success, and Demand Generation, while engaging with customers and prospects to shape RevOps-driven go-to-market strategies.

This high-ownership role involves shaping how the market perceives Compass, working with cross-functional teams, and driving adoption and expansion across Letter’s customer base.

Qualifications

• 3 to 5 years in product marketing at a B2B software company.
• Experience leading product launches in fast-moving environments.
• Ability to turn complex technical concepts into clear messaging.
• Strong cross-functional collaboration with Product, Sales, Customer Success and Marketing.
• Skill at turning customer insights into messaging and campaigns that drive pipeline.
• Self-directed and able to work in a fast-paced startup.
• Bonus: experience marketing to RevOps or Sales leaders.

Responsibilities

• Own Compass messaging and positioning.
• Lead go-to-market launches with Product, Sales, Customer Success, and Marketing.
• Build a deep understanding of the buyer and market through interviews, feedback, and data.
• Lead competitive intelligence to differentiate and guide sales.
• Shape the product roadmap with customer and market findings.
• Enable the field with pitch decks, battlecards, and talking points.
• Drive adoption and expansion across Letter’s customer base.

Skills

B2B SaaS marketing

Product launches

Storytelling / messaging

Cross-functional collaboration

Customer insights

Ownership / self-driven

RevOps / Sales marketing familiarity

Job description

View all jobs Product Marketing Manager, Letter Compass Chicago Marketing Hybrid Full-time

About Letter AI

Letter AI is the world’s first revenue enablement platform powered natively by AI. We’re reimagining the end-to-end revenue journey by turning real customer conversations and account data into actionable insights, personalized coaching, meeting prep, and next steps. Revenue teams aren’t asking for more content or tools. They’re asking for better outcomes. Letter does just that, empowering them to learn faster, sell smarter, and win more. We recently raised a $40M Series B and are already helping leading companies like Adobe, Lenovo, and Figma transform how their teams work. We 10xed our revenue last year and are looking for the best of the best in Chicago to help us build on that momentum.

About Letter Compass

The most important signals in a deal don’t live in the CRM. They live in customer conversations. Compass captures and analyzes those conversations, but it doesn’t stop at what was said. It connects those conversations with CRM data and buyer engagement to understand the full deal. Built into Letter’s best-in-class content and learning platform, Compass also understands your business and how you sell, from your products and messaging to your sales frameworks. Compass turns that context into action. It helps reps understand what matters, what to do next, and quickly create on-brand, deal‑specific content. At the same time, leaders get visibility into deal risk, seller execution, and where to focus across the pipeline. The result is stronger seller execution, deeper buyer engagement, and teams that win more deals, faster.

The Role

As the dedicated Product Marketing Manager for Compass, you'll own positioning, messaging, launches, and sales enablement for the product. You'll work closely with Product, Sales, Customer Success, and Demand Generation, and you'll spend real time with customers and prospects to understand how RevOps and Sales leaders buy. This is a high-ownership role at a fast-moving company: you'll shape how the market understands Compass and how our sellers win against incumbents.

Responsibilities

• Own Compass messaging and positioning. Build and maintain the Compass value narrative, tying what the product does to the problems Sales and RevOps leaders need to solve, and keep it current as the product and market change.
• Lead go-to-market launches. Plan and run Compass launches with Product, Sales, Customer Success, and Marketing so that internal teams are ready on day one and the launch reaches the right buyers.
• Build a deep understanding of the buyer and market. Gather insight from customer and prospect interviews, sales feedback, product usage data, and market research, and use it to shape go-to-market strategy.
• Lead competitive intelligence for Compass. Monitor the market and equipping Sales with clear differentiation, competitive insights, and guidance to win.
• Shape the product roadmap. Bring customer and market findings into product planning, help validate new concepts, and contribute to naming, packaging, and pricing decisions.
• Enable the field. Create pitch decks, demo narratives, battlecards, objection handling, and talk tracks for Sales, Solutions Engineering, and Customer Success.
• Drive adoption and expansion. Partner across Demand Generation and Customer Success to drive Compass adoption and expansion across Letter’s customer base.

Qualifications

• B2B SaaS product marketing experience. 3 to 5 years in product marketing at a B2B software company.
• Launch track record. Experience leading product launches in fast-moving environments, with the ability to create the process, align cross-functional teams, and drive measurable results.
• Clear communication. Strong storyteller who can turn complex technical concepts into clear, compelling messaging for both business and technical audiences.
• Cross-functional partnership. Strong cross-functional collaboration skills, with experience partnering closely with Product, Sales, Customer Success and Marketing.
• Customer insight into messaging. Skill at turning what you learn from customers into messaging and campaigns that drive pipeline and adoption.
• Ownership. Self-directed and comfortable with ambiguity, ability to work in a fast-paced startup environment and manage multiple priorities.
• Bonus points. Experience marketing to RevOps or Sales leaders and familiarity with conversational intelligence, revenue intelligence, or sales enablement products.

How We Operate

• Customer-obsessed : Make your customers unreasonably happy and everything else will fall into place
• Ambitious yet practical : Set big goals, but stay grounded with disciplined execution and ruthless prioritization
• Direct yet kind : Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
• Driven yet humble : Push for excellence and deliver fast, but keep your humility

What's In It For You?

• Compensation: $110-145k base salary, depending on experience, expertise, and expected impact
• Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
• Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
• Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
• Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
• Build with us: Join a fast-growing startup where you’ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter