Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work — investigating, resolving, and acting on every signal across every channel that matters. We're backed by a16z, BCV, General Catalyst, and Y Combinator, and more than 1,500 companies including Linear, Cognition, Modal Labs, and Incident.io run their support and customer success workflows on Pylon.

We're looking for a Head of Marketing to own how Pylon positions, tells its story, and drives growth. This is a leadership role, not an execution-only one. You'll set the product marketing and messaging strategy that anchors everything else, run point on pipeline as a company-level number, and lead a team that already covers product marketing, brand, content, events, and performance, sharpening how they work together along the way. You'll work directly with our CEO and leadership team on go-to-market strategy at a company that's already proving out product-market fit and scaling fast.

What You'll Do

• Own product positioning, messaging, and narrative: translate what Pylon actually does into a story that differentiates us against competitors and resonates with buyers, reps, and the board.

• Drive launches end-to-end: set go-to-market plans for new products and features, arm Sales with enablement and competitive intel, and track how positioning moves pipeline and win rates, not just awareness.

• Elevate brand and messaging with a growth lens. Every PMM and brand initiative should tie back to the pipeline, not exist in a vacuum.

• Lead a team of six: a Product Marketing Manager, Lead Brand Designer, Events Marketer, Content Marketer, and two Performance Marketers. You're not just managing outputs, you're leveling up how each function operates and connects to the pipeline, with product marketing as the throughline.

• Build and execute the company's overall marketing strategy aligned to business and revenue goals.

• Set marketing OKRs and report on performance to the executive team and board.

• Own pipeline generation strategy and be the person in the room who can defend that number to the CEO and to Sales.

• Set and run the multi-channel demand gen strategy, including paid (LinkedIn/Google), events, content, and inbound, and know which levers actually move pipeline versus which just look good in a deck.

• Partner closely (dotted-line) with Marketing Operations. You own the strategy, they own the systems.

• Partner with Sales on GTM strategy, pipeline, and demand generation to align on delivering against goals. Define marketing ROI and attribution across channels, kill what isn't working, and double down on what is.

• Build the team further as we scale: identify gaps, make the case for headcount, and hire people who raise the bar.

What You've Done

• 8+ years in B2B software marketing overall, including 2+ years leading a multi-functional marketing team (brand, content, product marketing, or performance), not just running a single channel.

• 3+ years in product marketing, owning positioning, messaging, competitive strategy, or product launches, at a B2B software company, ideally with additional exposure to brand, content, or demand gen.

• Excellent storyteller with proven ability to turn a complex product into a narrative that a buyer, a rep, and a board member all understand, and to translate that narrative into sales enablement and launch plans.

• Built or scaled a marketing function at a fast-growing startup (Series A-C preferred), including hiring and developing managers or senior ICs.

• Working understanding of how positioning and messaging affect pipeline and demand generation, and how to influence pipeline metrics through levers beyond just channel spend.

• Comfortable operating at the executive level: you can walk a CEO or board through what's working, what isn't, and why.

• Strong analytical instincts, comfortable in Salesforce, attribution tooling, and funnel reporting, and you use data to make the call, not just report on it.

• Hands-on when it matters: you can jump into a launch, a piece of positioning, or a campaign directly, not just direct from above.

Why Join Pylon

• Join as marketing leader at a high-growth startup

• Work directly with founders on go-to-market strategy

• Join a strong in-person culture in San Francisco

• Comp package includes competitive salary, equity, and benefits

Our perks

🏥 Fully covered medical, dental, and vision insurance for employees

🏦 401(k) retirement plan

🚆 Commuter benefits

🌱 Parental leave

🏝️ 14 company holidays + unlimited PTO

🗺️ Annual offsite

🍽 Lunch, dinner, and snacks at the office

🏋️ Fitness stipend