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The CEO Views > Blog > Micro Blog > Hiring a Creative Strategist: What to Look For and How to Assess It
Micro Blog

Hiring a Creative Strategist: What to Look For and How to Assess It

The CEO Views
Last updated: 2026/02/20 at 9:03 AM
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Hiring a Creative Strategist What to Look For and How to Assess It

Many will hire for “creative” and not “strategy” and get ineffective beautiful assets that don’t convert. This can be very expensive to get wrong, as cited in Who: The A Method for Hiring, estimating ~15x salary as the cost of a mishire (including opportunity cost). 

AI is also compressing the categories as targeting and production gets easier, the highest leverage hire might be the one in the middle with creative vision + data literacy + AI fluency.

What Does a Creative Strategist Do (and Not)?

A creative strategist might be more like a movie producer in retail than a designer: they orchestrate the vision, translate between concepts and insights, and validate with pattern recognition. The goal is to signal the algorithm can scale, not just good design. 

A potential metric is spend velocity: can the creatives they generate be pushed more at scale? They need to be able to “zoom up, zoom down” from positioning to hooks to pacing and iteration. They may not actually do graphic design/media buying full-time, unless you’re explicitly hiring a blended role.

Step 1: What Sort of Creative Strategist?

Mature funnels require higher intentionality; new launches need high volume to establish signal.

Pick one lane:

  1. Performance creative (paid social/conversion): Improve efficiency and scale testing roadmap, hook diagnostics, iteration plan.
  2. Brand narrative/positioning: Meaning/status, sharpening brand world messaging pillars, aesthetic direction, narrative.
  3. Lifecycle or content ecosystem: Not just email ops, but moving through the journey journey map, retention levers, expansion loops.

Step 2: Simple Scorecard so All Interviewers are Aligned

Not “job description vibes” but a scorecard with mission/outcomes and competencies. Limit competencies to 5-7, with behavioral anchors as observable evidence for consistent scoring. If you have a creative strategist agency recruiting you, this is the biggest lever to use so they align on good filter criteria and don’t keyword-match or create a “portfolio only” list.

Suggested competencies (tight and measurable):

  • Insight quality: Real objections/constraints, not demographic segmentation.
  • Concept strength: Structured persuasion.
  • Structured prioritization and iteration.
  • Measurement ethos: Documenting learnings, not just pass/fail.
  • Strong collaborator: Briefs well, reduces thrash, shares context so not siloed.

Red Flags: Generic “team player” unsubstantiated claims, nothing but pass/fail and no postmortems, and not explaining why stuff works/doesn’t.

Step 3: Portfolio Review What’s Good Versus Just “Good Design”

A strong portfolio is a silent pitch with context goal, role, impact, not just a gallery.

What to scan for as a filter:

  • Role clarity: What was owned vs. agency vs. team.
  • Decision trail: Insight to creative “what.”
  • Iteration evidence.
  • Learning capture that’s transferable.
  • Curated work that’s real and wanted.

No “why” on the creative is probably execution, not strategy.

Step 4: Interview Questions That Assess Strategy, Not Buzzwords

A structured interview with consistent questions, rating scale, and evidence-based notes creates consistent feedback and comparison which reduces bias.

Use questions like:

  1. Walk me from insight to concept to test plan: Starting with research and data, not just “I felt like…”
  2. Diagnose this video ad that isn’t working: What metrics, what do you check first, and then what fixes?
  3. Tell me about a creative direction you killed, and why: What criteria, what did you learn? (Not self-serving).
  4. What would your last boss say you’re great at, and weak at? Consistent self-modeling and allows TORC verification.

Step 5: Mini Paid Test Project Rapid Reality Check

Work samples start to be some of the best predictors, but keep it ethical as a paid test or formal short engagement.

The setup (60-120 mins): Feed them a product page and 1-2 audience segments (and ad learnings if available). The output: They produce 3 static creatives (headlines/hook/reason) and a testing plan one-pager. The grade: Grade on insight, clarity, prioritization, and how they’ll learn in week 1, not polish. Bonus points for iteration paths if the concept is flat after spend.

Step 6: Where to Find Candidates (Without Lowering the Bar)

High signal pools include referrals, niche communities, and strategists’ social media presence where they share breakdowns, not just portfolios. Specialist recruiter agencies can screen tech portfolios and use contract-to-hire to reduce risk.

If you need to move fast or want pre-vetted candidates, working with a creative strategist recruitment agency can help you reach qualified strategists sooner while still keeping your assessment process consistent.

Step 7: 30/60/90 Outcomes

Three phases: Discovery -> Activation -> Optimization.

  • 30 Days: Audit winners/losers, insight library, constraints, and offers.
  • 60 Days: Launch concept cycles, reporting, and creative lessons log.
  • 90 Days: Standardize briefing/testing, scale, and retire.

Hiring for A-Player creative strategists is about repeatable judgment, not vibes pick a lane, use a scorecard, demand portfolio evidence, conduct a mini paid test, and you’ll hire strategy, not vibes.

The CEO Views February 20, 2026
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