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CHERRYPICKER

Student consulting & product research

Cherrypicker Challenge

Student teams investigate real problems at the intersection of academic planning, product strategy, technology, and student behavior — then turn their findings into evidence-backed recommendations.

The Cherrypicker Challenge brings together small student teams to complete short-term strategy and product consulting cases exploring the business and technical sides of academic planning. Students work in teams of approximately five, supported by one project manager, to investigate a defined case over 4–6 weeks before presenting their findings and recommendations.

  • Teams of ~5
  • 1 project manager
  • 4–6 weeks
  • Final presentation
  • Research + strategy
  • Resume-ready work
Explore casesApply to a case

8 cases open · Applications reviewed on a rolling basis

One case, start to finish

  1. QuestionA defined case
  2. ResearchInterviews, surveys, data
  3. AnalysisModels, rankings, frameworks
  4. RecommendationA presented point of view
  5. ImpactMay inform the product

Strong recommendations may inform a future product decision. None are guaranteed to ship — the reasoning is the deliverable.

The format

How the Challenge works

One question, a few weeks of real research, and a recommendation somebody actually reads.

  1. Choose a case

    Select an open product, research, strategy, or analytics problem from the cases below.

  2. Investigate

    Conduct interviews, surveys, competitive research, data analysis, market research, or user testing — whichever the case actually calls for.

  3. Build the recommendation

    Turn the findings into a polished consulting-style presentation, framework, model, or prototype.

  4. Present

    Teams present their findings and recommendations at the end of the 4–6 week case.

  5. Potential product impact

    Strong recommendations may contribute to future Cherrypicker product decisions, experiments, or beta features.

Featured case

What a Challenge case can become

Case A started as a research question about how students plan together. It is now a feature students use.

SolvedProduct ResearchCase A

Plan with friends

How might academic planning become more collaborative without making the planning experience more complicated?

  1. Question

    A student and product research question, not a feature request: could planning become more collaborative without becoming more complicated?

  2. Research

    Student interviews and observation of how people already coordinate academic decisions — with friends, classmates, study groups, people taking the same prerequisites, and peers targeting the same universities.

    • How students coordinate classes with friends, classmates and study groups
    • Where schedule sharing already happens, and where it breaks down
    • When students actually want to know what their friends are taking
    • Friction in collaborative academic planning
    • Competitive and product research into existing planning tools

  3. Product concept

    The findings turned into a product question rather than a wish list.

    • Whether collaborative planning was genuinely useful, or merely appealing
    • Which collaboration behaviors mattered most
    • How it could fit inside Cherrypicker without becoming a social network
    • How students should invite and connect with people
    • What information should — and should not — be shared

  4. Live feature

    The research contributed to Plan with friends — a real Cherrypicker feature. Students create a temporary planning group, choose their own sharing scope, and get schedules built around the group. It is documented as Friend Mode in the privacy policy and terms, and nothing about another member is visible until they have explicitly accepted.

Research from a case can move beyond the presentation stage. Strong ideas may influence how Cherrypicker evolves — and the person behind the original Plan with friends concept was later hired by Cherrypicker.

The cases

Open cases

Choose a problem worth investigating. Every case below is a real open question about how students plan their transfer — and one of them is already answered.

  • Case ASolvedProduct Research

    Plan with friends

    How might academic planning become more collaborative without making the planning experience more complicated?

    • Coordination behavior
    • Schedule sharing
    • Sharing boundaries

    OutcomeBecame a real Cherrypicker feature.

    View case study — Plan with friends
  • Case BOpenStrategy

    Cherrypicker's next campus

    Which California community college should Cherrypicker support next, and what makes it the strongest opportunity?

    • Enrollment and transfer volume
    • UC / CSU transfer orientation
    • Market attractiveness
    • Academic planning gaps

    Expected outputsSchool comparison dataset, weighted scoring model, ranked recommendation.

    Apply to this case — Cherrypicker's next campus
  • Case COpenProduct Strategy

    What is worth paying for?

    Which academic-planning capabilities do students perceive as valuable enough to pay for, and why?

    • Student interviews and surveys
    • Feature preference ranking
    • Willingness-to-pay research
    • Student segmentation

    Expected outputsSurvey analysis, student segments, feature-value matrix.

    Apply to this case — What is worth paying for?
  • Case DOpenProduct Research

    Why do plans get abandoned?

    Why do students stop using academic plans after creating them, and what would make those plans stay useful all quarter?

    • Student interviews
    • Journey mapping
    • Habit formation
    • Planner benchmarking

    Expected outputsBehavioral journey, drop-off analysis, recommendation deck.

    Apply to this case — Why do plans get abandoned?
  • Case EOpenProduct Analytics

    Designing better product experiments

    How should Cherrypicker determine whether a change to the student experience actually makes the product better?

    • Funnel modeling
    • A/B test design
    • Engagement and retention metrics
    • Sample-size reasoning

    Expected outputsExperiment framework, metrics hierarchy, measurement plan.

    Apply to this case — Designing better product experiments
  • Case FOpenProduct / Trust

    Why should students trust a recommendation?

    What information makes students trust an academic recommendation enough to act on it?

    • Source transparency
    • Requirement explanations
    • Confidence and verification
    • Information overload

    Expected outputsTrust survey, trust-factor ranking, recommendation framework.

    Apply to this case — Why should students trust a recommendation?
  • Case GOpenStudent Research

    Comparing transfer schools

    How do community-college students actually decide which universities to target?

    • Major availability and requirements
    • Cost, location, prestige
    • Time to transfer
    • Articulation complexity

    Expected outputsDecision framework, preference ranking, comparison prototype.

    Apply to this case — Comparing transfer schools
  • Case HOpenProduct Research

    Exploring majors

    How should students explore majors they may not already know to search for?

    • Career-first vs subject-first discovery
    • Which information students weigh
    • Related-major paths
    • Competitiveness and difficulty

    Expected outputsResearch deck, discovery framework, information-priority ranking.

    Apply to this case — Exploring majors
  • Case IOpenProduct Strategy

    What happens when a student changes their mind?

    What should an academic planning tool do when a student changes their major, university target, or transfer goal?

    • Requirement overlap
    • What-if planning
    • Decision friction
    • Comparing alternate paths

    Expected outputsDecision journey, requirement comparison model, prototype recommendation.

    Apply to this case — What happens when a student changes their mind?

Have a different question worth investigating?

Students may also propose an original Cherrypicker Challenge case involving academic planning, transfer, student behavior, product strategy, research, or technology.

Pitch a case

Send your proposed case to admin@cherrypickerapp.net

What you leave with

Work you can actually talk about

Challenge participants leave with a defined problem, a research process, an analysis, a final recommendation, and a presentation they can discuss in recruiting and interviews.

  • User research
  • Product strategy
  • Market analysis
  • Data visualization
  • Experiment design
  • Competitive research
  • Survey design
  • Consulting presentations

Strong work may influence future Cherrypicker features, experiments, or product decisions. No case guarantees that a recommendation is implemented — which is exactly why the recommendation itself, and the reasoning behind it, is the deliverable.

Applications

Apply to a case

Choose a case and tell us what immediately stands out to you.

No case chosen yet — pick one below, or press Apply to this case on any open card.

Required

Not your school email — we need to reach you after the term.

Kept private. Used only to verify your application.

Only open cases can be applied to.

What immediately stands out to you? What would you want to investigate, and why does this case interest you?

2,500 characters left

Participation in the Cherrypicker Challenge is subject to the applicable participant agreement. Cherrypicker retains ownership of its platform, software, confidential information, and related intellectual property. Participants may describe approved non-confidential contributions in resumes and portfolios.