Founding Creative Strategists / Chief of Creative Strategy (AI-first)

About Upspring.ai

Upspring.ai is an AI-first creative intelligence platform that helps performance and creative teams understand exactly what worked in their ads - across their own campaigns and competitors - and turn those learnings into better creative, faster. We translate creative performance signals into clear, actionable direction so teams can ship more winning ads with less iteration and drive measurable lift in ROAS and efficiency.

Built by serial entrepreneurs from the industry, Upspring already works with leading brands and agencies such as Fashion Nova, Jackpot.com, Timberland, Brand.Co, and OneBone. On average, customers see +21% higher ROAS and +33% faster campaign execution.

We’re building a company with a simple belief: AI should not be a feature - it should be the operating system. We move fast, we take ownership, and we hold a high bar.

The Role

We’re hiring a Chief of Creative Strategy to own everything related to creative strategy across customers and products. You will set the standard for how Upspring translates creative intelligence into decisions, and you’ll shape how our product thinks about creative - from “what works” all the way to a high-end content and strategy layer that teams can act on immediately.

This is a hands-on role - we’re a small team operating like a big one, and we’re looking for someone who’s excited to build, do, and lead from the front.

You’ll work directly with top clients and strategic partners, lead high-stakes strategic engagements with brands and agencies, and influence the roadmap significantly. If you’re looking for a role where you can define a category, move fast, and win in the AI era - this is it.

What You’ll Do

Customer-facing strategy (external)

• Own the strategic layer of customer outcomes - the part that turns insights into clear creative direction.
• Lead creative strategy sessions with performance teams and agencies: audits, diagnosis, opportunity mapping, and action plans.
• Build repeatable frameworks: briefs, testing roadmaps, learning loops, and “what to do next” playbooks.
• Build and own Upspring’s “high-end content layer”: translate what works into world-class outputs (creative strategy, angles, hooks, briefs, scripts, variations, and testing plans) that teams can execute quickly.
• Operate AI-first to scale your impact: use AI to accelerate analysis, generate sharper hypotheses, and deliver better strategic output - while keeping quality and correctness at a high bar.
• Become a trusted thought partner to customers: performance reviews, strategic planning, and executive-level guidance.
• Train the team on creative strategy, frameworks, and how to communicate it.

Product-facing strategy (internal)

• Be the voice of “creative truth” inside Upspring - translate what you see in the market into product direction.
• Define the creative ontology: what we measure, how we label, how we explain “why it worked,” and how we recommend “what to do next.”
• Shape the AI behavior and outputs: AI Settings, prompts, agent flows, scoring logic, and how we present recommendations so they feel tailored, opinionated, and useful.
• Define what “great” looks like for insights, creative briefs, scripts, strategic outputs, and the overall content layer - then push the bar continuously.
• Create internal knowledge assets: guidelines, best-practice libraries, competitive tear-downs, and vertical playbooks (eCom, apps, subscription, etc.).

Content and market authority

• Build external-facing assets that showcase strategic depth: case studies, teardown writeups, webinars, talks, and practical frameworks that performance teams actually use.
• Help position Upspring as the category leader in creative intelligence and AI-driven creative strategy.
• Treat Upspring’s own marketing like a performance org: run continuous creative experimentation, test hooks/angles/channels, and package learnings into repeatable acquisition plays.

Leadership

• Own a function, not a task list. This role will evolve into leading a team as we scale.
• Set the tone: high standards, clarity, pace, and customer obsession.
• Partner closely with founders on strategic decisions across product, customers, and positioning.

Who We’re Looking For

You’re likely a fit if you are:

• Senior and proven: you’ve led creative strategy or performance creative at a high level and have real wins behind you.
• Comfortable with intensity: Upspring is growing fast. We move quickly, and this role is built for someone who wants that.
• Deeply fluent in performance creative: you understand Meta and modern paid creative systems - testing, iteration, angles, fatigue, hooks, UGC, statics vs video, and creative production workflows.
• Strong on “what works” depth: you can explain why creative worked, what signal matters, and how to translate that into repeatable wins.
• AI-native: you understand what AI can and can’t do today, you use it daily, and you’re excited to build with it at the pace the market is moving.
• Analytical and structured: you can turn messy creative performance data into a clear narrative, decisions, and next actions.
• Strong communicator: you can run exec-level sessions, write crisp frameworks, and simplify complexity.
• High ownership & Bias for Action: you don’t wait to be told what to do - you build, ship, and iterate fast.

Experience that helps (not required, but a plus)

• Creative strategist / creative director in performance environments (brands or agencies)
• Head of Creative Strategy / Head of Performance Creative / Growth Creative Lead
• Experience with DTC/eCom brands, subscription, mobile apps, or performance-heavy categories
• Familiarity with creative intelligence tools, measurement, and experimentation systems
• Experience working closely with product teams (especially AI products)

What Success Looks Like

• Customers consistently translate Upspring insights into better briefs, better tests, and better creative decisions.
• Upspring becomes known for “creative truth” - clear, credible, and actionable strategy, not generic advice.
• The “content layer” becomes a flagship: fast, high-quality, and clearly better than what teams can generate on their own.
• Product outputs feel smarter, more tailored, and more useful - because you shaped the underlying logic.
• Internal teams level up: CS becomes sharper, faster, and more strategic.
• You build repeatable playbooks that scale across verticals and customer segments.

Why Join

• Work directly with 2Xpost-exit founders and influence product strategy.
• A category-defining role with direct ownership over how Upspring wins on the creative side.
• Join a fast-growing company already working with some of the world’s leading brands and agencies.
• Build in an AI-first environment where speed, quality, and ownership are the culture.
• Big surface area: customers, product, strategy, frameworks, content, and market authority - all in one role.