Head of Marketing / VP of Marketing

Chicago, IL (Hybrid)

Salary Not AvailableSenior LevelFull time

Posted 5 weeks ago

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Job Summary

Own and scale an AI first marketing operation with blended B2B and B2C growth, lifecycle activation, and revenue impact across segments.

  • Growth ownership: full marketing lifecycle from positioning to outbound and revenue attribution in both B2B SaaS and B2C consumer contexts.
  • AI driven scalability: deploy agents and automation to multiply output while guiding GTM strategy and field execution.
  • Market insights: lead go to market, segmentation, messaging, and sales enablement with cross functional partnership.

Job Description

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.

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.
  • Have experience marketing in the Chrome Web Store (a plus).

Benefits

  • Flexible Time Off (FTO) Policy.
  • Parental Leave.
  • 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.
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Founded in 2013
Chicago, Illinois, USA
44 employees (4 in marketing)

Traffic Signals

Monthly Visitors
6.4M
Monthly Google Ads Budget
$286
Traffic Source Mix
Search
31%
Direct
63.4%
Referral
4.9%
Social
0.4%
Paid
0.3%

Headcount Trend

Current headcount: ~44

Marketing Team

Marketing Team Size
2 (5% of company)
Marketing Roles Posted (Last 30 Days)
1