Portfolio Management Comparison: PortfolioPilot vs Sharesight

Morningstar’s 2025 report notes that many digital-advice providers now offer account aggregation, enabling investors to link assets held outside the platform for a more complete view of their portfolios. Yet, few platforms meaningfully integrate those external assets into holistic financial planning. As portfolio tools evolve, the key question is shifting from “What’s my return?” to “How complete is my picture?”

This article compares PortfolioPilot and Sharesight - two platforms built for investors who want clear, data-driven visibility into their finances without handing over custody of their assets.

Key Takeaways

• Different missions: PortfolioPilot provides AI-driven portfolio insights and tax-aware analysis within a view of your net worth. Sharesight focuses on performance analytics, dividends, and tax reporting for detailed recordkeeping.
• Pricing models diverge: PortfolioPilot offers free tracking plus an optional flat-fee membership ($29/month). Sharesight uses tiered plans ranging from $0 to $31/month, depending on features.
• Planning depth: PortfolioPilot includes scenario modeling, diversification analysis, and ongoing recommendations. Sharesight centers on data accuracy, multi-market support, and tax reporting detail.

Core Overlap: What Both Platforms Offer

Both PortfolioPilot and Sharesight help investors understand portfolio composition, risk, and performance with modern tracking infrastructure.

Shared capabilities include:

• Account integration and automated data sync
• Manual and CSV import options
• Lot-by-lot tracking with realized/unrealized gains
• Sector, asset class, and holding-level breakdowns
• Dividend and reinvestment reporting
• Multi-asset coverage (brokerage, retirement, and cash accounts)
• Tax reporting for capital gains and income
• Regular portfolio performance updates and benchmarking dashboards
• Cloud-based data security and read-only connections
• Exportable reports for performance or tax use

So what? Both tools help turn raw account data into structured visibility.

Free vs. Paid: The Key Divide

While the overlap is significant, their pricing philosophies - and what those fees unlock - differ sharply.

• PortfolioPilot – Free net worth and portfolio tracking across all major brokerages, banks, and wallets. The optional $29/month membership adds personalized recommendations, continuous tax optimization, and scenario modeling.
• Sharesight – Free basic plan; paid tiers expand functionality:
  
  • Starter: US $7/month billed annually (US $9.33 monthly)
  • Standard: US $18/month billed annually (US $24 monthly)
  • Premium: US $23.25/month billed annually (US $31 monthly)

Distinct Advantages

Where Each Excels

• PortfolioPilot: Interesting for investors seeking actionable guidance - ongoing optimization, forecasting, and tax-awareness within a single dashboard.
• Sharesight: Ideal for investors who want precise reporting - especially for international holdings, multi-currency accounts, or dividend-heavy portfolios.

Hypothetical Example: The “Busy 40-Something”

Imagine a 43-year-old investor with a 401(k), IRA, taxable brokerage account, and rental property.

• With PortfolioPilot, they track all assets for free, run “what-if” retirement projections, and - if desired - add the premium tier for ongoing AI insights and tax optimization prompts that flag opportunities to rebalance or harvest losses.
• With Sharesight, they consolidate performance data, produce accurate tax reports, and analyze dividends and capital gains - essential for tax filing and performance attribution.
  
  

Lesson: Both systems serve diligent investors. The difference lies in whether a person wants ongoing, tax-aware guidance or precise reporting and archival clarity.

The comparison is based on publicly available information from each provider’s website as of 11/19/2025. Features, fees, and methodologies may change over time.