Head of Marketing

Company Overview

AwardSpring is the scholarship management platform used by hundreds of colleges, universities, and community foundations to run their scholarship, financial aid, and donor engagement programs. We help higher education institutions and foundations get more of their funding into students' hands — and we're expanding into adjacent Donor Management and Advancement software categories.

We are growing fast recently recapitalized for our next phase of growth. Our product portfolio is expanding meaningfully this year — a category-defining platform story we're excited to share more about in the interview.

We move fast, ship constantly, and operate with an aggressively AI-native posture across engineering, revenue, and now marketing.

Role Overview

This is the founding full-time marketing leadership hire at AwardSpring. Today, marketing is run by a fractional lead and a paid media agency. You will own the function.

You'll arrive with a forcing function: a major platform story launching this quarter that needs a product marketing engine behind it — positioning, sales enablement, a launch campaign, demand activation, and customer proof. Multiple product lines are ramping in parallel, and a light rebrand is in flight. Your first 90 days will be dense.

You'll already operate AI-native in your personal craft (Claude, ChatGPT, Clay, Gong AI, content and image tooling, agent workflows). That's table stakes. The opportunity we're offering is the chance to design and run an AI-native marketing function at the org level — compressing the output of a traditional 3-person marketing team into a leader + agencies + AI. That part is new territory for most marketers. We're betting you can figure it out with us.

What You'll Own

Product Marketing

Own our most important product and platform launches — positioning, messaging framework, launch campaign, webinar and press activation, sales enablement

• Ongoing PMM across our growing product portfolio
• Competitive intelligence across our category

Customer Marketing

• Build a case study and reference engine from scratch at meaningful, sustained volume
• Own and grow our Customer Advisory Board, now entering Year 2
• Lifecycle communications: onboarding → release awareness → feature adoption → expansion → renewal

Brand & Thought Leadership

• Stand up AwardSpring's point-of-view on higher ed, AI, and the fund lifecycle
• Drive CEO thought leadership cadence (LinkedIn, podcast, speaking)
• Shepherd the in-flight rebrand to completion

Demand Generation (in partnership with a retained agency and RevOps)

• Direct the retained CPC agency and paid media budget
• Partner with our RevOps analyst on source attribution, funnel metrics, and pipeline contribution reporting
• Build an organic search and Answer Engine Optimization (AEO) capability — we need to show up on AI search surfaces (ChatGPT, Perplexity, Claude, Gemini) as intentionally as we do on Google

Sales Enablement

• Battlecards, demo scripts, discovery kits, ROI calculators, one-pagers
• A collateral system the AE team actually uses

Events

• Direct a significant annual events budget with an ROI discipline — sponsor vs. attend vs. skip
• Stand up a private-dinner program at priority events

Who You Are

• 4–8 years of B2B SaaS marketing experience, ideally including time in product marketing. Vertical SaaS, EdTech, or higher-education-adjacent background is a strong plus.
• Leadership Experience not necessary - you can be a strong individual contributor looking to take the next step, or an experienced leader. We're interested to explore the right candidate across the career spectrum
• Already operating AI-native in your personal craft. You default to Claude Code or Codex, use Clay or similar enrichment tools, explore agent workflows, and treat AI as a force multiplier — not a gimmick. This is not something we'll teach you.
• Product marketing fluency. You have written positioning, led a launch, built a messaging framework, and know the difference between a brief and a battlecard.
• Writer-operator. You can draft a case study, a website headline, a launch email, and a Slack post to the AE team — all on the same day.
• Comfortable with ambiguity. You'll walk into a function with no playbook, minimal systems, and a forcing-function launch. You see that as the opportunity, not the risk.
• Chicago-based and willing to be in our office 2–3 days a week.
• Bonus points: prior founding-marketer experience, higher ed or non-profit tech background, demonstrated results running paid media against measurable pipeline outcomes.

What We Offer

• Compensation Commensurate with Experience including Equity
• Hybrid work: Chicago-based, 2–3 days in office
• Full benefits: medical, dental, vision, 401(k)
• Direct CEO relationship: you report to Alex. No layers. No politics. Direct access to product, engineering, sales, and customer leadership.
• AI-native operating environment: you'll join a company where Claude, Claude Code, Gong AI, and a full suite of AI tooling is already part of how we work. We don't want you to fight for budget to use AI — we want you to lead us deeper into it on the marketing side.