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DESIGN

Scaling and Getting Help

When to Bring in a Freelancer, Contractor, or Hire

You don’t need a full-time data team on Day 1. This section helps you decide when to bring in outside help, what kind of support you need, and how to make those early hires (or contracts) count.

Why it's Important
  • Avoids premature hiring (and burn) of expensive roles.

  • Helps fill expertise gaps without locking into long-term costs.

  • Enables better onboarding and data system setup early on.

  • Provides access to advanced skills like modeling or data engineering.

  • Makes sure you’re not overloading non-technical team members.

How to Implement
  • List your recurring data pain points (e.g., reports, accuracy, modeling).

  • Categorize needs: analyst, engineer, ops, visualization.

  • Decide what’s short-term (freelancer) vs. long-term (hire).

  • Budget for 5–10 hours/week of fractional support as needed.

  • Use networks, vetted marketplaces, or referrals to find talent.

  • Start with a pilot project to assess fit and impact.

  • Create SOPs or documentation as part of the deliverables.

Available Workshops
  • Data Needs Matrix: Map skills needed vs. team capabilities.

  • Freelancer vs. Hire Assessment: Role-play decision-making.

  • Pilot Project Scope: Outline a 2-week test project to de-risk hiring.

  • Tool Support Checklist: Identify tools where you need outside help.

  • Cost-Benefit Mapping: Evaluate data pain vs. hiring cost.

Deliverables
  • Data support roles definition and job briefs.

  • Shortlist of vetted freelancers or agencies.

  • Trial project brief with KPIs and budget.

  • Hiring timeline or part-time schedule.

  • SOPs created by external support (reusable post-contract).

How to Measure
  • Hours saved or errors avoided with help brought in.

  • Experiment velocity before/after data support added.

  • % of time founders spend on data pre/post support.

  • ROI of project-based work (impact vs. cost).

  • Adoption of new processes, dashboards, or models.

  • Learning transferred to internal team (via documentation).

Real-World Examples

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Calendly

Hired part-time analytics support before making their first full-time data hire.

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Figma

Used fractional help to clean and restructure their early metrics layer.

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Lattice

Embedded a contractor into the growth team to accelerate experimentation.

Get It Right
  • Define the outcome, not just the role.

  • Start small with a scoped project or retainer.

  • Look for collaborators who can teach your team, not just deliverables.

  • Use hiring as a graduation path—not the starting point.

  • Prioritize flexibility—your needs will change fast.

Don't Make These Mistakes
  • Hiring a full-time analyst when all you need is a dashboard cleanup.

  • Waiting until things are broken before seeking help.

  • Choosing talent based only on tools, not strategy.

  • Assuming the freelancer will "own the data" with no internal lead.

  • Skipping documentation and losing knowledge after the contract ends.

Fractional Executives

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