Head of Marketing / VP of Marketing

Screencastify • Chicago, IL

10h • Hybrid

About The Position

Castify (Creators of Screencastify) is a leading video technology company helping teachers scale their impact and improve student outcomes across K-12, post-secondary education, and corporate markets. With 15M+ users and growing, we are seeking a Head of Marketing / VP of Marketing to lead our next stage of growth. We are also actively expanding into new and exciting markets outside of K-12 including bringing our tested solution into companies and organizations. We are evolving from a widely-used screen recorder into an AI-first learning and collaboration platform, and we need a marketing leader who can own the full picture. This role spans B2B and B2C, demand generation and product marketing, and AI-enabled marketing operations. You will report directly to the President, GTM, lead one individual contributor, and be deeply hands-on yourself. The right person sees a lean team plus smart AI tooling as an advantage, not a constraint.

Requirements

• Have driven measurable growth across both B2B SaaS and B2C consumer products.
• Have thrived in early-stage or growth-stage startups (under 50 people) where you had responsibility to lead the marketing function.
• Are hands-on with AI marketing tools and have deployed agents or automated workflows in a real marketing context.
• Have built demand generation engines that connect marketing activity to pipeline and revenue.
• Bring strong GTM partnership experience working closely with Sales.
• Have deep product marketing chops: positioning, messaging, segmentation, and go-to-market execution.
• Are a player-coach who sets strategy and then executes it yourself.

Nice To Haves

• Have experience marketing in the Chrome Web Store

Responsibilities

• Own the full marketing lifecycle across B2B and B2C; strategy through execution.
• Drive pipeline and revenue growth in close partnership with Sales.
• Leverage the B2C user base to fuel B2B acquisition (PLG motion).
• Build a consistent outbound motion and convert marketing activity to closed revenue.
• Own B2C marketing end-to-end: acquisition, activation, retention, and upsell.
• Run lifecycle marketing programs (email, in-product, push) to convert free users and reactivate dormant ones.
• Build community and content strategies to grow organic reach.
• Track B2C KPIs: MAU, conversion rate, churn, and B2C ARR.
• Design and deploy AI agents across marketing functions: content, lead scoring, personalization, SEO, and reporting.
• Build automated, intelligence-driven programs that scale output without scaling headcount.
• Stay at the forefront of AI marketing tools and codify workflows on which the team can iterate.
• Model what AI-first marketing operations look like for the rest of the organization.
• Own positioning, messaging, and segmentation across all customer segments.
• Create sales enablement materials, customer-facing content, and internal training resources.
• Conduct user research to inform go-to-market strategy and surface actionable market insights.
• Represent Castify at conferences, events, and customer meetings.
• Lead and coach one marketing IC while remaining deeply hands-on yourself.
• Use AI tooling to multiply team capacity, enabling two people to operate like many.
• Establish KPIs across B2B and B2C and provide regular performance reporting.
• Work with the executive team on strategic planning and market expansion into new segments.

Benefits

• 401(k) match
• Annual Performance Bonus Opportunity
• Flexible Time Off (FTO) Policy
• Generous paid time off for parents to bond with the newest addition to their family!
• Comprehensive health benefits, including medical, dental, and vision insurance.
• Free One Medical membership.
• Annual Divvy membership

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed