Head of Marketing / VP of Marketing

Well, hello there 👋 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. About this role 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. What you’ll do: Go-To-Market & Demand Generation 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. B2C Business Ownership 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. AI-Enabled Marketing Workflows & Agents 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. Product Marketing 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. Leadership, Planning & Reporting 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. You’re perfect for this role if you: 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. Have experience marketing in the Chrome Web Store (a plus). This is a Chicago-based position with 3 days a week in the office. Working at Castify We are results-focused, fast-moving, and here to change how the world communicates and learns through video. We value accountability, speed, and people who take ownership end-to-end. We love a challenge, a good problem, and teammates who bring both creativity and follow-through. Rule #1: Be a good person. Compensation The expected annual base salary for this role is anticipated to start at $165,000 with an annual performance bonus. Final compensation may vary based on experience and qualifications. Competitive Compensation. We take a data-driven approach to our compensation strategy so all employees are paid competitively and fairly. 401(k) & Annual Performance Bonus Opportunity. We want to invest in present you and future you, which is why we offer a 401(k) match + Annual Performance Bonus opportunity. Flexible Time Off (FTO) Policy. We recognize that time off to rest and recharge is important. The Flexible Time Off Policy (FTO) is designed for our employees to do just that -- balance work and life while maintaining well-being. Parental Leave. Generous paid time off for parents to bond with the newest addition to their family! Medical, Dental, & Vision Insurance. We offer comprehensive health benefits, including medical, dental, and vision insurance. Plus, all employees receive a free One Medical membership. Divvy Bike Membership. If you’re in Chicago, take advantage of an annual Divvy membership -- on us. At Castify, we foster an inclusive, supportive, fun, and challenging team environment. We value having a team that is made up of a diverse set of backgrounds and respect the healthy expression of diverse opinions. We embrace experimentation and the examination of all kinds of ideas through reasoning and testing. Come join us as we continue to change the world through video. Castify is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender, sexual orientation, national origin, age, genetic information, gender identity, disability, Veteran status or any other characteristic protected by federal, state or local law.