Head of Marketing

Role Overview

• Drive both B2C brand perception and B2B sales growth
• Architect and drive growth across both B2C (app downloads, influencer marketing, consumer brand) and B2B (cold lead generation, community building, sales enablement) channels
• Develop unified marketing strategy across B2C and B2B channels
• Create clear, simple product marketing that makes complex offerings digestible
• Stay on the pulse of cultural trends to position Checkmate as the "cool" choice in savings and marketing tech
• Generate cold leads beyond our current agency-dependent sourcing
• Create viral-worthy content from conferences, partnerships, and B2B events (LinkedIn, podcasts, etc.)
• Build B2B community through experiences, dinners, and thought leadership
• Develop product marketing materials (decks, videos, guides) that clearly communicate value
• Help with the overhaul of our website to better align with the B2B/B2C strategy you set
• Support sales, partnerships, and customer success with quality lead gen
• Execute social media strategy focused on amplifiable moments
• Develop TikTok strategy around savings hacks and relatable content
• Turn UGC, influencer partnerships, and power users into compelling ads and organic reach
• Design community moments (events, giveaways, surprise and delight) that create content opportunities
• Build relationships with trending brands and influencers
• Own the product narrative so brands and consumers quickly understand what Checkmate does and why it matters
• Scale from individual activations to a must-attend community ecosystem
• KPIs: deals sourced, deals closed, upsells, social engagement

Requirements

• 5-8 years in growth marketing or product marketing at software/SaaS startups
• Second-in-command experience (reporting to a CMO/SVP/VP as a Marketing Director, Head of Growth, etc.) with proven execution ability
• Ecommerce tech or B2B/B2C hybrid background preferred
• Track record of building brand while driving measurable outcomes
• Strategic but hands-on: you’re a doer, not just a delegator
• Culturally tuned-in with pulse on trends and what makes brands "cool"
• Content creator mindset that turns moments into amplifiable content
• Data-driven with ability to set KPIs and optimize
• Product marketing expertise: you excel at distilling complexity into simplicity
• High social EQ: you know how to build meaningful relationships before selling
• Growth marketer mentality: you’ve done a bit of everything and know how to prioritize
• What "Cool" Means: Association with trending brands and respected people, elevated exclusive experiences, on-trend opinions, relationship-building over hard selling, and smart positioning with marketing expertise.

Benefits

• Competitive salary + equity
• Healthcare + dental + vision
• 401(k)
• 4 weeks PTO + health days
• Gym membership reimbursement
• US Remote-friendly, with hubs in NYC and LA
• Regular offsites and team retreats